10 Perfect Fall Weekends in New England

Vermont invented “Foliage Season” just after World War II, launching it with full-color spreads of ruby-and-gold–colored hills in the first issues of Vermont Life.Until then, no one had thought of inviting visitors to come see colored leaves. Today, all of New England is a mecca for leaf peepers and autumn’s color show is generally billed as running from mid-September into late October.

Which is to say, there is no single peak foliage moment across New England. Instead, it moves like a spotlight, highlighting one part of New England after another. The show starts with the burning red of the early swamp maples in Maine and in the mountains of Vermont and New Hampshire, and it continues throughout the region for more than a month. When the trees are nearly bare in the north, there remain the last colors on the southern coast of Connecticut. Anyone who has witnessed New England’s annual procession of fall color, even just one time, never forgets it.

To help you get a jump on the color, we’ve put together our picks for the best fall weekends in New England. They’re presented sequentially, beginning in northern Vermont and ending in Connecticut and Rhode Island. Together, they offer the perfect primer on how to make the most of this brief but brilliant season.

Mid-September Through the First Week of October

Vermont’s St. Johnsbury Region

Color in the Kingdom

“St. J” is the largest town in Vermont’s Northeast Kingdom, the high-elevation, secluded northeastern corner of the state. Its museums are a year-round draw, but fall is its prime time. Foliage festivals begin in mid-September and multiply into the first weekend in October. Make St. Johnsbury your hub as you explore the surrounding, usually sleepy villages.

What to See

In St. Johnsbury, the handsome, Victorian Fairbanks Museum and Planetarium (802-748-2372) and the St. Johnsbury Athenaeum& Art Gallery (802-748-8291) are legacies of the Fairbanks family, inventors of the platform scale. The museum displays thousands of vintage stuffed animals and birds, local flora and artifacts collected from around the world. The Athenaeum includes an 1870s gallery hung with works by period painters, including Albert Bierstadt’s epic “Domes of the Yosemite.”

Great Vermont Corn Maze (802-748-1399) North Danville

Here, visitors can spend hours exploring this mammoth agricultural construction. For the impatient types, there are “cheater poles” along the way to permit a quick exit. There’s also a barnyard nature center and a smaller maze geared for younger children. Everyone who finds this place is enthusiastic about it, just beware: GPS is not always reliable in Vermont. Begin at the blinking light on Rt. 2 in Danville and head north. It’s wise to download the map from the website.

Kingdom Trails (802-626-0737) East Burke

Take in the 100-mile network of mountain ridge and valley trails for riders of all abilities. You can find lift-assisted trails accessible on weekends in Burk Mountain Bike Park (802-626-7300) where a chairlift runs from the base lodge to mid-mountain.

Cabot Creamery (802-563-3393) Cabot

Vermont’s major cheese producer maintains an inviting visitors’ center. Frequent tours include plenty of samples but you may wish to call ahead if you want to actually see the cheese being made.

Where to Stay

The Wildflower Inn (802-427-3333) Lyndonville

The inn sits amid 300 acres, high on a ridge with panoramic views and direct access to hiking/mountain biking trails. This is a welcoming, family-owned resort with varied lodging, and bountiful breakfasts and dinners—with a view—at the inn’s Juniper’s restaurant.

Village Inn at East Burke (802-626-3161) East Burke

A hospitable and affordable bed & breakfast with seven comfortable guest rooms and a three-bedroom apartment, the Village Inn features plenty of common space, including a guest kitchen, a weather-proof hot tub, and riverside grounds. Don’t miss the standout breakfasts, such as caramelized pear crepes, prepared by chef/owner Chris Willy.

Where to Eat

Bailiwicks (802-424-1215) St. Johnsbury

Head for the tables on the deck, high above the river. This converted mill building also offers a formal pink- and green-walled formal dining room and an informal pub area with an extensive beer and cocktail list. Try the basil cucumber martini.

Dylan’s Café (802-748-6748) St. Johnsbury

The café makes its home in a 1920s post office building.The result: A spacious, cheery restaurant, hung with bright art, filled with tables and booths garnished with fresh flowers. A blackboard menu lists locally sourced greens, made from scratch soups, pastries, and dinner specials. Don’t pass on the flourless chocolate cake or sweet potato fries.

Cantina di Gerardo (802-748-0598) St. Johnsbury

A family-owned Italian restaurant that serves up authentic southern Italian fare, classic red sauce dishes, pizzas, and pastas.

Insider’s Tip: Extend your stay and take a few extra days to time your visit with the Northeast Kingdom Foliage Festival(Sept. 26–Oct. 2 this year).For more than 60 years, seven small towns have taken turns hosting visitors over seven days, each feeding and guiding them over dirt roads to covered bridges, farms, and other places worth finding. Proceeds from the church suppers, concerts, and back road bus tours benefit local causes.Profits from the sale of knitted items, handmade puzzles, toys, and the like go to the people who made them.

Mad River Valley, Vermont

Visit, if you can

Walled to the west by the Green Mountains and to the east by the Roxbury Range, this wide, magnificent valley features the Mad River running down its center.It’s a layout seemingly designed to display fall colors and there are an unusual variety of high vantage points—ski lifts, ridge trails, gliders, and high mountain roads—all perfect for spectacular overviews.Covered bridges, as well as distinctive dining and shopping, round out the autumn experience.

What to Do

Sugarbush Resort (800-537-8427) Warren

The Super Bravo Chairlift hoists passengers and bikes up to Gad Peak, and visitors to Mad River Glen (802-496-3551) in Waitsfield can take the Single Chair to the 3,637-foot summit of Stark Mountain for a view of both the Mad River and Champlain Valleys.

Riding the Gaps

Two high passes, Lincoln Gap at the southern end of the Valley and the Appalachian Gap to the north, climb up over the Green Mountains and down into the Champlain Valley, arguably Vermont’s most scenic and adventurous circular route. From Rt. 100 in Warren, the 10-mile long Lincoln Gap Road climbs so steeply up a shoulder of Mt. Abraham that locals sled down the three-mile stretch that’s closed in winter. From the tiny village of Lincoln, the descent to Rt. 116 in Rocky Dale is relatively gentle and the 16-mile road back begins just two miles north. Route 17 spirals easily up through the 2,356-foot Appalachian Gap and past the Mad River Glen base lodge, sloping the last few miles to Rt. 100 in Waitsfield.

Hiking

The Monroe section of the Long Trail runs along the Green Mountains’ ridges, connecting with the two Gap roads, as well as with the two ski lifts. The shorter but more demanding hike north from Lincoln Gap to Mt. Abraham yields a 360-degree view of both the Champlain Valley and New York’s Adirondacks region. A shorter but still strenuous hike leads south from Lincoln Gap to Sunset Ledge.

Vermont Icelandic Horse Farm (802-496-7141) Waitsfield

Brought to Iceland by the Vikings, these strong, pony-sized mounts are used for one- and two-hour, half- and full-day trail rides.

Soaring at Sugarbush-Warren Airport (802-496-2290) Warren

Go easy on the legs but still take in the high views from one of the airport’s short, scenic plane rides.

Where to Stay

Pitcher Inn (802-496-6350) Warren

Considered the Valley’s premier lodging destination. Each of the Inn’s nine guest rooms was created by a different designer or architect to evoke an aspect of the town’s history. Our favorite suggests a Masonic Lodge with its midnight-blue ceiling studded with stars, and the obelisk-shaped bedposts. In the elegant dining room, the locally sourced menu changes daily.

Sugarbush Resort (800-537-8427) Warren

This popular stopping point offers varied lodging: condo-style units in all sizes at Claybrook, the base area centerpiece; traditional rooms at the Sugarbush Inn; and 100 or so condos, all with access to the resort’s sports center and indoor pool.

Mad River Barn (802-496-3310) Waitsfield

Innkeepers Heather and Andrew Lynch have taken this legendary Civilian Conservation Corp ski lodge down to the studs and put it back together with a fresh feel. The 18 uncluttered rooms range from family suites to bunk rooms geared toward singles. Stop by (4pm–9pm) for warm pretzel sticks and a local brew in the iconic pub with its massive stone hearth and adjacent old-style game room.Dining is open to the public too; family-style at long tables and a menu that ranges from burgers and pork belly tartar to roast lamb. A robust kids’ menu is also offered.

Millbrook Inn (802-496-240) Waitsfield

This hospitable bed & breakfast offers seven inviting guest rooms and exceptional food. Once a popular local dining spot, the Millbrook continues its foodie heritage as innkeeper/chef Joan Gorman offers four-course dinners to inn guests. A full breakfast is included with every stay.

Wilder Farm Inn (800-496-8878) Waitsfield

Inside and out, there’s plenty to please at this 1850s farmhouse with attractive common spaces, guest rooms, and grounds. Your host, Luke Iannuzzi, is a professional potter, as well as an avid beer connoisseur and mountain biker, who is happy to steer guests to the area’s best trails and brews.

Where to Eat

Peasant (802-496-6856) Waitsfield

Warm red walls and friendly service define the experience at the Peasant in Waitsfield, a family-owned and -run restaurant. The menu features pan-European comfort food, all locally sourced. Try the traditional white bean cassoulet with chicken, sausage, and pork. Just be sure to leave room for the house-made ice cream.

American Flatbread (802-496-8856) Waitsfield

The menu offers distinctive, thin-crusted pizza baked in a primitive, wood-fired oven, heated to 800 degrees. The results are nationally distributed, but if you want the true flavor of its famous pizzas, you’ll need to eat one at the restaurant’s iconic home base.

Warren Store (802-496-3864) Warren

Breakfast on fresh, flaky croissants or bagels. Or select lunch from the blackboard menu, with its diverse selection of deli food and sandwiches. Tables inside and on the deck overlook a small waterfall. Climb the stairs to The More Store, one of the Valley’s hidden gems, with an eclectic mix of clothing, jewelry, and other giftware favorites.

Insider’s Tip: Visit the Waitsfield Farmers’ Market on the Mad River Green on Saturdays 9am–1pm. It’s one of the liveliest in all of New England, with local produce, cheese, maple products, brews, and live entertainment.

The First Two Weekends of October

Mount Washington Valley

Above It All

Literally the high point of New England, 6,288-foot Mount Washington has been scaled since the 1860s on the east by the “Auto Road” and on the west by the world’s first Cog Railroad. In fall, the view from the peak’s summit building is a seemingly endless sea of rolling color. Down below, on less elevated ground, the offerings also seem endless. Begin in North Conway, the hub of the Mount Washington Valley, where serious climbers and hikers rub shoulders with hard-core shoppers and leaf peepers. Don’t miss Jackson, a small gem of a village, cradled in the high, horseshoe-shaped Wildcat River Valley, accessible through a covered bridge.

What to Do

Conway Scenic Railroad (603-356-5251) North Conway

Three different excursions are offered from North Conway’s 1870s rail station: There’s the shorter journey to Conway and back; a slightly longer trip up through Crawford Notch in Dome cars (daily Oct. 10–23); and always a favorite, the longer “dining on the rails” package.

The Mount Washington Auto Road (603-466-998) Pinkham Notch

A 12-person wagon pulled by six horses began carrying passengers up the mountain from Pinkham Notch in 1861. The current 8-mile road climbs steadily at an average 12 percent grade. It’s open to passenger cars, but we recommend a guided tour of the road via a 1.5-hour, narrated van tour.

Mount Washington Cog Railway (603-278-5404) Bretton Woods

In 1869, this was such a novel idea that its creator was told he might as well “build a railway to the moon.” We’re glad Sylvester Marsh continued on with his dream. Today, the world’s most iconic cog railroad is still operating with steam engines angled for the steep (average 25% grade), 3.25-mile climb from Crawford Notch to the summit.

Mount Washington State Park (603-427-3347) Sargent’s Purchase

This famous park features a two-story visitors’ center atop the famous summit, with views from inside as well as out. You can also tour the former Tip-Top House next door, built as a hotel in 1853. Don’t miss the Extreme Mount Washington museum at the Mount Washington Observatory, which explores the nitty-gritty of the mountain’s subzero, hurricane-force drama.

Bretton Woods Scenic Lift Rides (603-278-3320) Bretton Woods

The best view of Mount Washington, with its namesake hotel at the base, can be enjoyed from a deck half way up Mt. Rosebrook, across Crawford Notch. The Express Quad chairlift hoists you up from the Bretton Woods base lodge to this area, part of Latitude 44° Restaurant, which serves lunch and snacks. Take the chairlift back or walk down a ski trail.

Destination Shopping in North Conway

Begin with New Hampshire’s zero sales tax, then add 70 national brand name outlets within Settlers Green and Settlers Crossing, and you have good reason to move on up Rt. 16 to North Conway Village and park. The few surrounding blocks are studded with independently owned shops. Don’t miss Zeb’s General Store (603-356-9294), with its 67-foot-long candy counter, some 5,000 New England products, and plenty more treasures upstairs. The 5&10 Cents Store (603-356-3593) is the real thing, under the same family ownership since 1931.

Where to Stay

Omni Mount Washington Resort (603-278-1000) Bretton Woods

Picture a vast, grand hotel moored like a white cruise ship in a sea of fall color at the base of Mount Washington. Facilities include a spa, 27-hole golf course, mountain bike trails and hiking paths, as well as a zip line and the chairlift ride at the nearby Bretton Woods Ski Area (603-278-3320).

AMC High Huts, Highland Lodge at Crawford Notch, and Joe Dodge Lodge at Pinkham Notch

Since its 1876 founding, The Appalachian Mountain Club (617-523-0655) has been involved with blazing and maintaining hiking trails, and creating shelters in the Presidential Range of the White Mountains. Fall is peak hiking time so it’s wise to snag a bunk or bed as early as possible in any of these great facilities.

Eagle Mountain House (603-383-9111) Jackson

Smaller and less stuffy than a grand hotel but sensitively renovated to preserve its 1916 ambiance.The 90 rooms and suites are furnished in country pine and cheery prints. The immense veranda overlooks the mountains across narrow Carter Notch and there’s a satisfying dining room, and pub, plus a 9-hole golf course.

Where to Eat

Inn at Thorn Hill (603-383-4242) Jackson

The many-windowed dining room, with its ambiance and views, is the setting for an elegant night out. Begin with the lamb lollipops, glazed with balsamic vinegar and served with a mint yogurt sauce, then dine on grilled veal Porter House.

Moat Mountain Smokehouse (603-356-6381) North Conway

Heaping plates of BBQ and a choice of the house microbrews are the draw at both the original Rt. 16 restaurant overlooking the Moat Mountains or in the restored Limmer Barn in Intervale.

Insider’s Tip: Avoid Rt. 16 traffic through North Conway by taking the scenic West Side Road.

Bethel, Maine

It’s Not Just About the Snow

Known better as a summer and ski resort, Bethel is a hiker’s heaven in fall, with dozens of well-trod trails in the neighboring Mahoosucs and White Mountains, which provide sweeping valley views.For the less strenuously inclined, the ski lifts at Sunday River Resort ease the way to the top of North Peak. There are also ample mountain biking trails as well as scenic golf links. Down in the Androscoggin Valley, Bethel is a draw for strollers and shoppers.

What to Do

Sunday River Resort (207-824-3000) Newry

For the ride to North Peak, you can choose between an open chair orgondola. The resort also offers 20 miles of lift-accessed mountain bike trails, zip line tours, and the opportunity to play at the 18-hole Sunday River Golf Club.

Hiking

For years, seasoned hikers have flocked to the rugged summit trail up 4,180-foot Mount Spec at Grafton Notch State Park in Newry; gentler paths lead to Screw Auger Falls and Mother Walker Falls. In Bethel, look for the 3.25-mile Mount Will Hiking Trail, which loops up over ledges for a panoramic view of the Androscoggin Valley. Pick up maps to local trails at the Bethel Area Chamber of Commerce (207-442-5826).

Finding Gems

Locally found gems include amethysts, topaz, and tourmalines. In Bethel, The Maine Mineral and Gem Museum (207-824-3036), a decade in the making, is still not fully open, but its preview exhibit is worth a stop and (through Columbus Day) Maine Mineralogy Expeditions (207-824-4224) sells bucket-sized loads of mine tailings for those seeking a shot at fortune.

The Bethel Historical Society (207-824-2908) Bethel

Located on the common, this surprisingly fun destination is lively, free, and currently featuring a major exhibit on the history of skiing in Maine.

Where to Stay

The Bethel Inn Resort (207-824-2175) Bethel

Despite its size (just 49 rooms), this inn packs the feel of a grand old hotel with gracious common spaces, an 18-hole golf course, indoor/outdoor pool, tennis, and a boathouse on Songo Pond. Lodging options include traditional rooms in the main inn and annexes and multi-bedroom condos in the town houses.

Mill House Inn (207-824-3241) Bethel

Tucked at the end of a quiet street near the common, this nicely renovated carriage barn–turned-inn offers six comfortable rooms and two suites. The dining room is open to the public Thursday–Sunday. Studio Bistro & Bar specializes in tapas-inspired small plates and craft beers.

Holidae House Bed and Breakfast (802-824-3400) Bethel

A gracious, turn-of-the-century Main Street home built by a local lumber baron features seven freshly refurbished guest rooms and a common space furnished with comfortable antiques.

Bethel Village Motel (207- 824-2989) Bethel

An affordable, 10-unit, middle-of-the-village, old-school motel that offers comfortable, spotless rooms with A/C, coffee, and a friendly welcome.

Sunday River Resort (207-824-3000) Newry

Discover 210 rooms in the condo-style Grand Summit Hotel and 135 in the Jordan Hotel; in addition, there are hundreds of slope-side condominiums available.

Where to Eat

S.S. Milton (207-824-2589) Bethel

For locals, this Main Street Gingerbread house is a favorite dining out spot.Lunch and dinner are served up, inside and out. Seafood is the house specialty, along with pies, which are best eaten with the restaurant’s Irish coffee.

22 Broad Street (207-824-3496) Bethel

Gracious ambiance defines the dining room of this 1840s mansion on Bethel’s common. The dining room features a wood-burning fireplace and a classic, Italian menu. Favorites include the Beef Carpaccio, Shrimp Scampi Pasta, and the Tuscan Porterhouse. Check out “The Godfather” (Scotch and Amaretto with a lemon twist) in the restaurant’s martini bar.

Suds Pub (207-824-6558) Bethel

Located downstairs in the back of the Sudbury Inn, this is the town’s gathering place for beer (29 taps), pub food, and pizza.

DiCocoa’s Market & Bakery (207-824-6386) Bethel

Stop by for a breakfast espresso, almond granola, or daily-baked bagels and croissants. Lunch options include delicious veggie soups, stews, and wraps.

Insider’s Tip:Bonnema Potters (207-824-2821) in Bethel is home to Garret and Melody Bonnema, arguably Maine’s most distinguished potters. They don’t sell their wares online and the couple’s Bethel studio/store is filled with lamps, dinnerware, and tiles streaked with colors evoking local landscapes.

Manchester, Vermont

Where History and Foliage Meet

Since the Civil War, tourists have descended on Manchester and skiers began visiting in 1939, the year Bromley opened. But autumn is truly the best time to visit. Spectacular views are easily accessed from the top of Mt. Equinox, just west of town, while the sights are equally breathtaking from both Bromley and Stratton ski resorts. In town, a delightful mix of shopping, culture, and dining give this southern Vermont town a vibe all its own.

What to Do

Hildene (802-362-1788) Manchester Village

Many presidents have visited Manchester over the years, but it was Lincoln’s family who made the village a second home. A visit here must include a stop at the 412-acre estate created by Robert Todd Lincoln, the president’s only son to live to adulthood. Plan to spend several hours between the visitors’ center, the 24-room mansion and gardens, Hildene Farm, and the 12-plus miles of walking trails. Bring a picnic.

Southern Vermont Arts Center (802-362-1405) Manchester

The Wilson Museum is a work of art in itself with soaring, light-filled galleries housing changing exhibits. Currently on display, “Quixotic Encounters,” is a retrospective of painter David Brewster’s Vermont landscapes. The 180-acre, sculpture-spotted campus also includes Yester House, home to more art, and Sora Café, which specializes in homestyle Japanese lunch (Thurs.–Sun.) and offers dinner before weekend concerts in the Center’s Arkell Pavilion.

The American Museum of Fly-Fishing (802-362-3300) Manchester Village

For anglers, Manchester is a bucket list destination. The Battenkill, beloved by fisherman and canoeists, running south from Manchester through Sunderland and Arlington, has been the subject of more than a few trout obsessed writers. It’s also here that Manchester native Charles Orvis perfected the ventilated reel and opened his first store in 1856.The rest is fly-fishing history. At this wonderful museum, see rods and reels built by famous makers and owned by such iconic Americans as Bing Crosby, Ernest Hemingway, and Presidents Hoover and Eisenhower.

Mount Equinox (802-362-1114) Sunderland

The toll road climbs 5.2 miles to the 3,824-foot summit and a viewing center maintained by the Carthusian monks who own most of the mountain. Pick a clear day, otherwise your drive may be mostly in the clouds.

Bromley Mountain’s Adventure Park (802-824-5522) Peru

Take the chairlift to the summit view; also check out the zip line and Giant Swing. Stratton Mountain Resort (800-787-2886), accessed from Rt. 30 in Bondville, offers gondola rides to a summit for a four-state look at the color.

The Manchester Designer Outlets number 40 mostly high-end brand stores clustered downtown. Shops and small shopping centers also line Main Street (7A) as it climbs a hill to the flagship Orvis Retail Store (802-362-3750) in Manchester Center.

Where to Stay

The Equinox Resort & Spa (802-362-4700) Manchester Village

Vermont’s most historic hotel has grown incrementally over the centuries, beginning in 1769 with a tavern and ballooning into a white-columned grand hotel by the time Mrs. Abraham Lincoln vacationed here. The current 200 guest rooms range from comfortable to luxurious; amenities include dining at a choice of five restaurants, and access to a full spa and a prestigious 18-hole golf course.

The Inn at Ormsby Hill (802-362-1163) Manchester Village

Set amid flower gardens, rolling lawns, and mountains, it’s among Manchester’s most historic mansions and retains the feel of a gracious home. The eight rooms and two suites feature fireplaces, four-poster beds and whirlpool tubs. A full breakfast is served in the light-drenched dining room.

Wilburton Inn (802-362-2500) Manchester

The highlights: A 30-acre, secluded hillside estate with a Tudor-style mansion at its center plus a variety of scattered buildings. The grounds include a tennis court and working farm.

The Dorset Inn (802-867-5500) Dorset

This classic Vermont village inn, operating continuously since 1796, still offers genuine hospitality and good food. When the temperature drops, sit by the grand fireplace in the front parlor. When it inches back up again, take a seat on one of the front porch rockers.

Where to Eat

The Silver Fork (802-768-8444) Manchester

The hottest spot in town. Menu choices are surprisingly varied for just six tables and include dishes like wiener schnitzel with house-made spätzle, and an abundant selection of imaginatively prepared seafood. Reserve if you can.

Ye Olde Tavern (802-362-0611) Manchester Center

Oldie New England atmosphere in a 1790s inn with a large menu that includes some innovative as well as traditional fare. Dine on classic Yankee pot roast or roasted duck with rosemary and garlic sauce. Friday features venison prepared in a variety of ways.

The Perfect Wife Restaurant & Tavern (802-362-2817) Manchester

Options are in abundance. Take a seat in the reasonably priced tavern or make your way to the upscale cobble-walled dining room or the nicely lit greenhouse terrace. Signature favorites include sautéed crab cakes served with remoulade on mixed greens, and the seared tuna served over stir-fried vegetables.

Insider’s Tip: If the foliage season crunch has left limited availability at the local hotels and inns, check out the ski condos at Stratton and Bromley.

Williamstown, Massachusetts

College Town Color

No town embodies the beauty of the Berkshires like Williamstown. Walled by the Taconic Mountains to the west and overlooking massive Mt. Greylock to the southeast, the town has been home to Williams College since 1791, and village and campus are closely entwined. It’s also been a tourist destination since the mid-19th century, when large summer homes and hotels began sprouting up in and around the town center. Today, outdoors life and a strong cultural base make Williamstown and the surrounding area worth more than just a quick stop.

What to Do

Clark Art Institute (413-458-2303) Williamstown

Few American museums rival the Clark’s permanent collection of French impressionist and 19th-century American artists as well as its medieval works and paintings by grand masters. Enter the original museum through the dramatic new Clark Center and climb the hill behind to the Lunder Stone Hill Center for more galleries and a café overlooking the valley. The 140-acre museum grounds are webbed with gorgeous walking trails.

Massachusetts Museum of Contemporary Art (413-443-0188) North Adams

More than 100 large-scale wall drawings designed by artist Sol LeWitt are a must-see extravaganza of pattern and color at this bold museum that has transformed old brick mill buildings into a dynamic center for contemporary art. Leave time to explore the entire complex, where gigantic gallery spaces let artists unleash their creativity through often fascinating installations.

Mount Greylock

This is a state reservation, accessible from Rt. 2 in North Adams and Rt. 7 in Lanesboro, site of the visitors’ center (413-499-4262). The highest point in Massachusetts (3,491 feet) Greylock has views that encompass five states. Food and lodging are available at Bascom Lodge (413-743-1591), which was built by the Civilian Conservation Corps in the 1930s.

Where to Stay

The Williams Inn (413-458-9371) Williamstown

A 124-room motor inn with colonial reproduction furnishings, restaurant, and welcoming common spaces where locals frequently love to congregate.

The Orchards (413-458-9611) Williamstown

Walled off from a commercial strip, the 45-room inn faces inward on a landscaped courtyard. The feel is that of a small, elegant, slightly faded European country hotel.

The Guest House at Field Farm (413-458-3135) Williamstown

Set on 316 upland acres with a magnificent view of Mount Greylock, this exceptional house (five guest rooms) is owned by the Trustees of Reservations and represents prime mid-century design.

House on Main Street (413-458-3031) Williamstown

This village house melds several styles of architecture, suggesting its long history, dating back (in part) to the 1700s. In 1914, it hosted President Woodrow Wilson for Thanksgiving dinner. Convenient to the college and downtown, it was a guesthouse for many decades and is now a welcoming B&B with five comfortable rooms and hospitable hosts serving full, family-style breakfasts.

Where to Eat

Mezze Bistro & Bar (413-458-0123) Williamstown

Mezze owner Nancy Thompson is the area’s farm-to-table pioneer and her charming bistro serves up a highly seasonal a la carte menu. In fall, you might begin with a pumpkin soup, then dine on heritage breed pork loin with turnips, mushrooms, and green garlic. The bar features small batch micro-brews, locally distilled spirits, and small production wines.

Hops & Vines (413-884-1372) Williamstown

In the casual “Hops” side, the focus is on local brews while the formal “Vines” side is decidedly first-class, with a menu that includes Maine oysters and locally sourced lamb burgers. Delicious veggie options, too. Wash it all down with something from the affordable wine list.

Spice Root (413-458-5200) Williamstown

Lunch on the bargain-priced buffet or on mulligatawny soup and honey sesame naan.The contemporary Indian cuisine, creative cocktails, and attractive mid-village setting also make this a popular choice for dinner.

Cozy Corner Restaurant (413-458-3854) Williamstown

Family-owned and affordable, Cozy Corner is a go-to place for Greek comfort food like eggplant and Mediterranean-style cod.

Insider’s Tip: Check the Bascom Lodge calendar for special sunset hour programs and prix fixe dinner.

Damariscotta Area, Maine

At Water’s Edge

World-known for its oysters, Damariscotta is the lively hub of quiet lakes, tidal rivers, and nearly 100 miles of coastline, most of it meandering around the neighboring Pemaquid Peninsula. There’s a special fall beauty to this mix of land and water that is punctuated by a lively downtown village.

What to Do

Pemaquid Point Lighthouse, Damariscotta

Pemaquid Point is pictured on the Maine quarter because it looks just like a lighthouse should.Built in 1824 atop dramatic but climber-friendly rocks, it’s open to the public, along with the Fisherman’s Museum (207-677-2423), which makes its home in the former lightkeeper’s quarters.

Hardy Boat Cruises (207-677-2926) New Harbor

The 60-foot vessel with plenty of inside and outside seating offers 1.5-hour autumn tours of Muscongus Bay as well as ferry service to Monhegan Island—ten miles offshore and known for its high cliffs and 17 miles of hiking trails.

Damariscotta River Cruises (207- 563-1393) Damariscotta

Narrated tours aboard this former navy launch are the best way to explore the ten-mile tidal river with its birdlife, seals, and oyster farms.Check out the evening oyster and wine–tasting cruises.

Damariscotta River Association (207-563-1393) Damariscotta

The organization maintains 33 miles of trails at more than a dozen area properties it has preserved. At its Salt Pond Farm headquarters, hay fields, salt and fresh water marshes, and woods are laced with paths, while a meandering trail at Dodge Point Preserveallows for an easy walk along the river.

Damariscotta Pumpkinfest & Regatta

This year’s event is Oct. 8–10 and marks the 10th anniversary of this colorful festival. Don’t miss the always creative regatta of boats made from pumpkins.

Renys (207-563-5757) Damariscotta

Damariscotta is home to Maine’s quixotic and most beloved department store chain. Check out both the original store and the “Underground,” where visitors will find linens, packaged food, electronics, and clamming and camping gear, among so many other items.

Where to Stay

Bradley Inn (207-677-2105) New Harbor

The area’s only full-service inn, it’s an easy bike ride (bikes are complimentary) from Pemaquid Point. The shingled, turn-of-the-century inn features 16 comfortable rooms and suites, as well as a spa and two attractive dining rooms decorated in nautical antiques.

Mill Pond Inn (207-563-8014) Damariscotta Mills

Nicely sited on a pond with kayak and canoe access to the big lake, Mill Pond is a thoroughly hospitable and affordable bed & breakfast with five individually decorated and shaped rooms and suites. Innkeeper Bobby Whear enjoys turning guests on to the best the area has to offer.

Newcastle Inn (207-563-5685) Newcastle

Just across a bridge from downtown Damariscotta, this gracious bed & breakfast offers 14 luxurious rooms. More than half have gas fireplaces and the grounds overlook the Damariscotta River.

Where to Eat

Damariscotta River Grill (207-563-2992) Damariscotta

A brick-walled, two-story, middle-of-town gem. Head upstairs to a seat by the window or at the copper bar. Begin any meal with oysters on the half shell, served with the house horseradish. The big menu features creatively prepared local seafood and produce.

King Eider’s Pub (207-563-008) Damariscotta

A favorite local gathering spot, the menu includes boutique brews and crab cakes as well as oysters.

Schooner Landing (207-563-7447) Damariscotta

Calling all oyster lovers: Kick back by the river and feast on oysters every which way. This is also a good choice for brews and pub food.

Larson’s Lunch Box (207-563-57550) Damariscotta

A favorite choice among locals for clam and/or lobster rolls as well as from-scratch chowder.

Insider’s Tip: Check out Damariscotta Pottery (207-563-8842), located behind the Courtyard Street shops. Watch the Majolica ware being shaped and painted in bright floral designs. Open every day but Sunday.

Shelburne Falls & the West County Hill Towns

Mountains of Color

Usually rivers divide towns, but in the case of Shelburne Falls, the Deerfield and its two bridges—one a blaze of blooms—unite thetwo downtowns to form a single, lively village.A popular stop on the Mohawk Trail, Shelburne Falls also serves as the dining and shopping hub for the “Hill Towns,” a region of abrupt hills, cupping small villages.

What to Do

The Bridge of Flowers, Shelburne Falls 

Originally built to carry trolleys, this New England icon now serves as a unique common for the village of Shelburne Falls. Shops on both sides of the river showcase quality works by area craftspeople, and on weekends (through Oct.), a restored 1896 trolley makes short runs from the Shelburne Falls Trolley Museum.

Zoar Outdoor (800-532-7483) Charlemont

Talk about a memorable way to see the color. Zoar offers rafting on a 10-mile stretch of Class II and III whitewater on the Deerfield River. Kayaking, zip line canopy tours, camping, and lodging are also available.

The Conway Festival of the Hills, the first weekend in October, and the Ashfield Fall Festival, on Columbus Day Weekend, are two of the oldest and most colorful fall festivals in New England.

Where to Stay

The Warfield House (413-339-6600) Charlemont

A hilltop farm with great views across the valley to Berkshire East Mountain. Two clapboard guest houses offer a total of nine rooms and a continental breakfast.

Bird’s Nest Bed & Breakfast (413-625-9523) Buckland

Three pleasant upstairs guestrooms in an 18th-century house are sited on the common of a quietly beautiful hill town.

Brandt House (413-774-33290) Greenfield

The Brandt’s new owners offer a warm welcome to guests at this gracious mansion, set in a quiet neighborhood high above downtown. The nine guest rooms vary in size but not comfort and there are spacious common spaces.

Where to Eat

West End Pub (413-6225-6216) Shelburne Falls

Overlooking the west end of the Bridge of Flowers, West End is a special spot with good, locally sourced, reasonably priced fare. Try the house-made crab cakes. Open for lunch and dinner.

Blue Rock Restaurant and Bar (413-625-8133) Shelburne Falls

Heavy on greens and grains, light on the wallet, favorites include Grandma Jo’s enchiladas, Java-rubbed baby back ribs, and marinated grilled cauliflower steak.

Pine Hill Orchards (413-624-3325) Colrain

This country oasis is a great breakfast and lunch stop, known for its fruit and cream pies, fresh-pressed sweet cider doughnuts, and freshly made soups and sandwiches on house-baked bread. The farm stand features local hard cider, beer, and maple syrup as well as a large selection of apple varieties. Check out the pot-bellied pigs and miniature donkey in the barnyard and the ducks by the pond.

Gould’s Sugar House (413-625-6170) Shelburne

Family-owned for generations, Gould’s features a rustic dining room set high above the Mohawk Trail (Rt. 2) with views of the surrounding hills. Open only during sugaring and foliage seasons, the restaurant specialty is—you guessed it—pancakes with house-made maple syrup.

Insider’s Tip:Elmer’s Store (413- 628-4003) in Ashfield has served as the heartbeat of the village since the 1830s. It’s a great source for general store basics plus local crafts, cheese, art, and live music.

Columbus Day through late October

Kent, Connecticut

Best Foliage Town

Praised by Yankee in 2010 as New England’s number one foliage town, Kent sits in the heart of Connecticut’s spectacular Litchfield Hills. North of town, a trail leads to the top of the state’s highest waterfall, while in South Kent, you can drive through a vintage covered bridge. Home to prestigious Kent School, the tidy village is studded with art and antique galleries, specialty stores, and restaurants.

What to Do

Kent Falls State Park

A bench-spotted trail winds up the slope beside Kent Falls, where visitors can take in a series of cascades and pools. Park facilities include picnic tables and grills.

Hiking

Appalachian Trail thru-hikers will tell you that one of the most beautiful and least demanding stretches in the AT’s 2000+ miles is the 4.8-mile river walk north from Kent village through woods and fields bordering the Housatonic. A more demanding riverside trail begins by the waterfall and covered Bulls Bridge and climbs gradually to meet the AT with views of the river far below. BackcountryOutfitters (860-927-3377) is the village link with the AT, the place hikers stop for local transport and mail, not to mention gear, locally sourced ice cream, and chocolate.

Museum Mix

Don’t pass on the unlikely grouping of museums north of the village. The Sloane Museum (860-927-8349) houses the studio, works, and extensive antique tool collection of painter Eric Sloane (1905-1985), known for his skillful depiction of iconic New England buildings.The adjoining tree-shaded campus of the Connecticut Antique Machinery Associationis home to several collections, including the Connecticut Museum ofMining and Mineral Science (860-927-0050). This is itself a hidden gem, as it traces the state’s iron mining history and geological formation. Exhibits feature unexpectedly stunning minerals—marble, sparkling quartz, and geode-embedded garnets.

The Housatonic River is well known for trout and fall is prime time for fly-fishing. Check out Rip Lips Fishing (860-927-0090) for flies, tackle, and guiding.

Shopping

Main Street is known for galleries and antiques shops, as well as an eclectic assortment of special shops. Favorites include House of Books (860-927-4104), a serious independent bookstore, as well as a great source of cards, puzzles, and artist’s materials. Foreign Cargo Ltd. (860-927-3900) is filled with an impressive array of handcrafts, antiques, arts, and jewelry collected by the owner over years of traveling in the Far East.

Where to Stay

Starbuck Inn (860-927-1788) Kent

Park your car and take advantage of Starbuck’s in-town location. The six guest rooms offer comforts like fine linens and the living room is stocked with enticing books. Rates include tea and an exceptional breakfast.

Fife’n Drum (860-927-3509) Kent

Housed in a converted carriage house, the Fife’n Drum offers 13 moderately priced, individually decorated rooms on two floors. Décor varies, but all have been thoughtfully, comfortably furnished and the baths have recently been updated.

Inn at Kent Falls (860-927-3197) Kent

A handsome bed & breakfast dating back to 1741, the inn makes its home near the expansive grounds of Kent Falls State Park and features a mix of antiques and modern comforts. Check out the spa, and don’t miss the breakfasts.

Where to Eat

Gifford’s (860-592-0262) Kent

The ambiance is elegant and contemporary, as Culinary Institute of America–trained chef and co-owner, James Neunzig, takes pride in his from-scratch, New American cuisine. Don’t miss the signature fried chicken breast with Belgian waffles.

Kingsley Tavern (860-592-0261) Kent

A middle-of-the-village gathering spot for local families as well as visitors, Kingsley offers up a menu that’s locally sourced to the max. Try the pan-seared yellowfin tuna steak.

Hopkins Inn (860-868-7295) Warren

The dining room in this 19th-century inn, specializing in Austrian dishes, overlooks Lake Waramaug and the hills beyond. Weather permitting, reserve a table on the terrace.

Insider’s Tip: Check out the locally made truffles at Kent Coffee & Chocolate Co. (860-927-1445).

Bristol, Rhode Island

Between Mountain and Water

Sandwiched between Providence and Newport and occupying a narrow strip of land between Mt. Hope and Narragansett Bay, Bristol is a special place in its own right. Gracious, Federal-era captains’ homes evoke the town’s glorious seaport days and vast gilded-era mansions recall its second coming as a summer resort.Fall is a quieter time to explore the town’s waterside trails, expansive preserves, museums, walkable waterfront, and downtown.

What to Do

Blithewold Mansion (401-253-2707) Bristol

The 45-room, Tudor-style mansion is set on 33 landscaped acres that include a sweeping stretch of lawn from the front steps to Narragansett Bay. Bench-spotted paths wind between late-flowering beds and between literally thousands of trees, while the property’s arboretum is home to hundreds of species, including a 90-foot Sequoia. A perfect place to put away your smartphone and just wander.

Coggeshall Farm (401-253-9062) Bristol

Famed for its mid-September Harvest Fair, this 1790s saltwater farm is a favorite for photographers well into October, when marsh grass in the Mill Gut turns bronze and the maples still glow. Staff in period dress work inside and out and mind the heritage breed sheep, cows, and multi-colored “Dung” chickens.

HerreshoffMarine Museum (401-253-5000) Bristol

Boat lovers can’t get enough of this place, which showcases dozens of sleek yachts, thousands of which were produced here between 1863 and 1945, including eight America’s Cup defenders.

The 14.5-mile East Bay Bike Path from Providence ends at Independence Park on Bristol’s downtown waterfront, and links to bike and walking paths that cut through the 464-acre waterside Colt State Park.

Where to Stay

Bristol Harbor Inn (401-254-1444) Bristol

This newly renovated, 40-room boutique hotel overlooks the harbor and is just steps from the center of town.

Point Pleasant Inn (401-253-0627) Bristol

Built by a local textile mill owner, this family-owned mansion sits on Poppasquash Neck, a finger of land dividing Bristol Harbor from Narraganset Bay. Set on 25 acres overlooking the harbor, Point Pleasant offers seven guest rooms, which vary widely in price and size. The choices include a two-room suite with shared bath. Among the amenities are a fitness room, sauna, tennis courts, and bikes.

The Governor Bradford House at Mount Hope Farm (401-254-1745) Bristol

This is a popular wedding venue with a dozen gracious rooms divided between the main house, which dates in part from 1745, and several guesthouses. The 200-acre “farm” is the former Haffenreffer family estate with walking trails down to Mount Hope Bay.

William Grant Inn (401-253-4222) Bristol

A centrally located, 1808 Federal home with five guest rooms, private baths, and a full breakfast.

Where to Eat

Bristol Oyster Bar (401-369-5820) Bristol

A downtown favorite: No views to celebrate, but the kitchen churns out the area’s freshest oysters and little necks.

DeWolfe Tavern (401-254-2005) Bristol

Housed in a vintage, harborside, stone warehouse, DeWolfe is known for its big, varied menu of Indian specialties.

Le Central (401-296-9965) Bristol

A moderately priced restaurant with a menu of wonderful French-flavored dishes, like coq au vin and steak frites.

Redlefsen’s (401-254-1188) Bristol

Known for German specialties, beers, and lively Octoberfest celebrations. Try the lunch salads and Jonah crab cakes.

Quito’s Seafood Restaurant (401-253-4500) Bristol

A seasonal, popular waterside spot for seafood like crab lump meat sandwiches, Rhode Island clam chowder, and of course, stuffed quahogs.

Insider’s Tip: Don’t miss the boardwalk through fresh and saltwater marshes down to Narragansett Bay. It’s part of The Audubon Society of Rhode Island Environmental Education Center (401-245-9339).

What tops your list for the best fall weekends in New England? Let us know in the comments!