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

St. Johnsbury, Vermont

“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.

St. Johnsbury Attractions

Fairbanks Museum and Planetarium, St. Johnsbury

It’s a window on the wider world, Victorian-style. The Romanesque Revival building boasts an astoundingly eclectic hoard of natural science, ethnology, and Vermont-history treasures—an old-style “cabinet of curiosities” writ large. Upstairs, the state’s only public planetarium offers state-of-the-art star shows.

Great Vermont Corn Maze, 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.

Dog Mountain, St. Johnsbury

Since it opened in 2000, no place in America—and likely the world—pays greater homage to the bond between dogs and humans than these 150 mountaintop acres created by artist Stephen Huneck and his wife, Gwen. Though the Hunecks have both passed on, their legacy continues. Leashes are optional as dogs romp across fields and swim in ponds. Be prepared: The tiny dog chapel adorned with photos and remembrances of pets will bring both wonder and tears.

Kingdom Trails, 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 Burke Mountain Bike Park, where a chairlift runs from the base lodge to mid-mountain.

Where to Stay in St. Johnsbury

The Wildflower Inn, 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, 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.

St. Johnsbury Dining

Boule Bakery, St. Johnsbury

It pays to drop in early to this corner bakery before their sourdough breads, baguettes, and croissants sell out, which they often do. If so, sourdough cardamom buns, cinnamon knots, or espresso shortbread cookies make worthy consolation prizes. The superlative baked goods are not the only draw, though; breakfasts and lunches here are elevated by small gestures, such as house-made syrups for coffee (using beans from a West Burke roastery) and house mayo on sandwiches. Laptop warriors can linger at the rustic wooden counter while watching passersby.

Mad River Valley, Vermont

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.

Mad River Valley Attractions

Sugarbush Resort, Warren

The Super Bravo Chairlift hoists passengers and bikes up to Gad Peak, and visitors to Mad River Glen 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.

Waitsfield Farmers’ Market, Waitsfield

Held on the Mad River Green every Saturday from 9 to 1 from mid-May to mid-October, rain or shine. It’s one of the liveliest in all of New England, with local produce, cheese, maple products, brews, and live entertainment.

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 Adirondack region. A shorter but still strenuous hike leads south from Lincoln Gap to Sunset Ledge.

Vermont Icelandic Horse Farm, Waitsfield

Easy to ride, the Icelandic horse is a breed known for its good nature and small stature. It was bred to carry riders over challenging terrain, and at this farm and inn, horse lovers can choose from rides of varying lengths, from hourlong jaunts to multiday excursions, that take them into the heart of the Mad River Valley.

Warren Store, Warren

Perched on a ledge above the Mad River, this deli-bakery offers an easy stopover for a breakfast burrito or a midday meal. For lunch, grab a hefty sandwich stuffed with local smoked turkey and bacon layered between slabs of house-baked bread, or warm up with the daily soup. Browse crafts and clothing by local artisans in the boutique upstairs, then head home with a bottle of wine or fresh IPA from hometown brewery Lawson’s Finest Liquids. Staying nearby? The store also offers catering to go.

Mad River Valley Lodging

The Pitcher Inn, 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. There are also two spacious, family-friendly, two-bedroom suites in the Red Barn. In the elegant dining room, the locally sourced menu changes daily.

West Hill House B&B, Warren

At just nine guest rooms, West Hill House may be small, but it’s thinking big about global warming. All the electricity at this renovated 1850s residence comes from solar power, which also helps to cover two-thirds of the property’s water heating. (There is complimentary EV charging, too.) Other eco-friendly touches abound, including coffee from the nation’s first roastery powered by 100 percent renewable biogas.

Mad River Lodge, Waitsfield

This renovated barn blends minimalist design with understated comfort across its apartments and studios (some with kitchens, all with private bathrooms) for under $200 a night, depending on the season. Amenities are simple—think coffee, laundry facilities, and a breezy common room—but the location is hard to beat: right in the heart of the Mad River Valley, minutes from the Mad River Glen ski area, the village of Waitsfield, and a patchwork of restaurants, breweries, trails, and swimming holes.

Mad River Valley Dining

Canteen Creemee Company, Waitsfield

When chef Charlie Menard ditched his longtime gig at the upscale Inn at Round Barn Farm to open a creemee stand, he wasn’t looking to sling premade ice cream and frozen hot dogs. At Menard’s year-round snack bar, the handmade dairy confections range from basic flavors—chocolate, vanilla, maple, lemon—to exotic cones topped with extravagant clouds of maple cotton candy. Our pick? The chocolate-dipped banana-cream waffle cone sundae—with or without hunks of cocoa-covered bacon and banana chips.

Green Rabbit Bakery, Waitsfield

Suzanne Slomin’s solar-powered bakery began years ago to supplement her farm business at Warren’s Kingsbury Market Garden. In 2014, she moved operations to a dirt-road homestead in Waitsfield. There, at the edge of the forest, in the shadow of Mount Alice, she and her tiny crew blend organic grains with salt, sourdough starter, water, and time. Her burnished, split-eared loaves come studded with olives and rosemary, Jack cheese and chives, cinnamon and raisins. For those living in the bakery’s Vermont delivery radius, the breads offer a regular taste of mountain living at its finest.

Lawson’s Finest Liquids, Waitsfield

The liquid here is beer—the kind to rival cheese and maple as Vermont’s star commodity. In the heart of the Mad River Valley, where cyclists and skiers work up a mighty thirst, Lawson’s cozy taproom serves a heady array of IPAs, Pilsners, stouts, and porters with light fare to match, and a side of jazz, blues, and folk. Check the schedule for occasional beer-themed dinners

The First Two Weekends of October

Mount Washington Valley

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.

Mount Washington Valley Attractions

Conway Scenic Railroad, 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, 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, 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, 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.

Zeb’s General Store, North Conway

Named after an early 1900s schooner boat captain, Zebulun Northrop Tilton, Zeb’s is a multi-floor tour of nostalgia and homegrown fare. Amid the store’s antique fixtures, discover an array of penny candy, Moxie soda, and more—including the largest collection of New England–made specialty foods—at this White Mountains bucket-list stop in the heart of downtown North Conway.

Mount Washington Valley Lodging

Omni Mount Washington Resort, 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.

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

Since its 1876 founding, The Appalachian Mountain Club 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, 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.

The Inn at Thorn Hill, Jackson

The bar for luxury is set high at this inn, but if you want a true heart-to-heart escape, book a stay at one of the rustic cottages on the property. These two tiny homes are private and peaceful, yet mere steps from the main lodge, and both feature gas fireplaces, screened-in porches, and private baths, including a two-person spa hot tub in the aptly named Trailside cottage.

Mount Washington Valley Dining

Moat Mountain Smokehouse, 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.

Thompson House Eatery, Jackson

Jeff and Kate Fournier first earned acclaim as Boston restaurateurs, but when they pulled up stakes for a 200-year-old property in the White Mountains, their talents came into full bloom. In the past couple of years, they’ve added greenhouses to extend their growing season and expanded their farm stand into a well-stocked year-round market featuring local meats, cheeses, produce, and sweets. Best of all: the house-made pasta Bolognese and grilled Mexican-style corn alone are worth the drive.

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

Bethel, Maine

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.

Bethel, Maine, Attractions

Sunday River Resort, Newry

For the ride to North Peak, you can choose between an open chair or gondola. 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).

Maine Mineral & Gem Museum, Bethel

Despite a rocky start (it debuted a few months before the shutdown, then suffered a bout of flooding after reopening), this 15,000-square-foot museum has established itself as one of Maine’s most fascinating attractions. At the core of its assemblage of treasures dug out of the earth is the Perham Collection, accumulated by a century-old Maine rock shop. Here you will also discover a world-class display of extraterrestrial minerals, including a 32-pound rock from Mars; an array of meteorites, and the five largest pieces of the moon to be found this side of, well, the moon.

Bethel, Maine, Lodging

The Bethel Inn Resort, 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, 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, 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, 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, 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.

Bethel, Maine, Dining

Gemini Café & Bakery, Bethel

Anna Sysko and Nicole Pellerin chose the name Gemini for their cozy in-town café, located in a former bank, because they worked together like the fabled twin constellation, and it has become a bright star in this western mountain town. Locals linger over coffee drinks and sweet and savory baked goods, including flaky croissants, crunchy-chewy bagels, and pastries worthy of a British baking show. For a heftier meal, opt for a breakfast or lunch sandwich, such as pastrami on rye, jambon beurre, and the always-popular peanut butter and jam.

Le Mu Eats, Bethel

Word of mouth from hungry Sunday River skiers and foodies alike has propelled this Laotian-Southern hybrid from humble beginnings in 2018—as a little blue takeout shack next to Steam Mill Brewing—to a sit-down restaurant of its very own, opened late last year. The cult-favorite Angry Rooster sandwich (fried chicken with chili aioli) and superlative banh mi are still there, alongside elevated, dine-in-only new offerings like khao piek sen, a chicken soup swarming with thick and chewy hand-rolled tapioca-rice noodles.

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.

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.

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.

Manchester, Vermont, Attractions

Hildene, Manchester Village

One summer sojourner lured by southwestern Vermont was Robert Todd Lincoln, Abraham Lincoln’s son. The railroad car executive chose Manchester as the site for Hildene, his 1905 neo-Georgian retreat. Unlike many mansions of the era, this one seems cozily livable. It’s furnished in period style, from parlors to servants’ quarters, and is graced by formal gardens. A sumptuously restored 1903 Pullman sleeping car is preserved on-site.

Southern Vermont Arts Center, Manchester

Treasures from the American Regionalist movement have no better home than this 120-acre museum complex, created by and for Vermont artists. Ten galleries in a 1917 mansion show off a permanent collection of 1,000-plus paintings, etchings, and sculptures. The center also hosts rotating exhibitions, concerts, and theatrical performances and maintains the largest sculpture garden in Vermont. svac.org

The American Museum of Fly-Fishing, 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, 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.

Kimpton Taconic Hotel, Manchester Village

You, the kids, and even your Great Dane will be pampered at this four-story luxury hotel. After settling into lodgings that offer a modern take on Vermont’s grand inns, you can relax on the sweeping porch overlooking the mountains, take a fly-fishing course at the Orvis school, or shop up a storm at the nearby outlets. 

The Dorset Inn, Dorset

Vermont’s oldest hostelry in continuous operation has welcomed guests since 1796. Several of the 24 rooms and suites are located in the original building facing the village green. Many have gas fireplaces, four-poster beds, and whirlpool tubs. Breakfast and dinner, served indoors or on the patio, reflect the inn’s membership in the Vermont Fresh Network, committed to forging relationships between farmers and chefs.

Where to Eat

The Little Rooster Café, Manchester

A favorite spot for locals and visitors alike, this cheery diner near the outlet malls is the place to fuel up for the rest of your day’s ramble. Hearty is the word here—look for stacks of pancakes with Vermont maple syrup, corned beef hash with béchamel sauce, and sandwiches including a terrific Reuben. Facebook

The Silver Fork, Manchester

Like a beloved book re-read through the years, the Silver Fork, first opened in 2011, is the kind of culinary destination that demands revisiting. You never know what global inspiration chef Mark French will be channeling—German, Caribbean, Turkish, Baltimorean—or what creative, locally flavored libations his wife and co-owner, Melody, will have on offer. Even more reason to return? The restaurant’s über-stylish new home in a former library, where soaring windows and midcentury-modern panache are the backdrop for a storybook night out that you’ll never want to end. 

The Yard at The Crooked Ram, Manchester

The synergy between 24-hour-fermented crust, San Marzano tomatoes, and fresh basil makes for transcendent Margherita pies at The Crooked Ram, while the wood-fired Valoriani oven lends charred edges and oozing middles. Other seasonal pizzas might be topped with Calabrian salumi, spinach-mascarpone fonduta, or simply mushrooms and fontina. Seasonal is the operative word, as these pies are served only in The Yard, a patio behind The Crooked Ram proper that’s open from May to October and usually feels like a garden party.

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, 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, 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, Williamstown

It’s not what or where it used to be: Williams College built a modern replacement for its on-campus hotel in 2019 in a central location that’s ideal for visiting parents and museum- and theater-bound tourists, too. Cool, calm hues and energy-saving green features characterize all 64 thoughtfully designed rooms and suites. Common areas and the Barn Kitchen & Bar have more rustic warmth, but on balmy nights, the ahi tuna nachos and local craft beers taste best outdoors, fireside. 

The Guest House at Field Farm, 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.

Where to Eat

Mezze, Williamstown

With its refined wood-beamed interior and white table linens, Mezze is the go-to for Williamstown Theater Festival patrons and fans of dramatically good bistro fare, presented here with Mediterranean flair. Owner Nancy Thomas founded Mezze in 1996 and keeps it in the culinary vanguard with off-season “R&D” menus and creative pop-up events. 

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 Preserve allows 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.

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 the two 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

Shelburne Falls Coffee Roasters, multiple locations

Founders Kathy Lytle and Curtis Rich planted their roots in Shelburne with this small roastery/bakery/café along the Mohawk Trail in 1991, and it’s since grown into a Western Massachusetts mini chain. And a true family affair, too, with daughter and general manager Annabelle serving up hand-blended coffees, espresso, chai, and seasonal lattes at the Shelburne headquarters. Local flavor abounds in the lineup of egg sandwiches named after surrounding towns; for our money, you can’t go wrong with the signature Shelburne Falls, a combo of egg, prosciutto, Brie, tomato, and pesto. Pair it with a cup of First Light, the roastery’s bold and fruity signature blend, and you’ve got a perfect start to the day.

Blue Rock Restaurant and Bar, 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, 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.

Columbus Day through late October

Kent, Connecticut

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. Backcountry Outfitters (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 Association is home to several collections, including the Connecticut Museum of Mining 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

The Kent Collection, Kent

Choose from three unique and fully renovated landmark properties. The Firefly Inn (formerly the Starbuck Inn) and The Victorian are perfect for a countryside getaway. Meanwhile, The Garden Cottages, with fully equipped kitchens and private outdoor lounging, offer the comfort of home away from home.

Fife’n Drum, 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 with updated baths.

Where to Eat

Ore Hill, Kent

If you’ve followed Tyler Anderson’s meteoric career and perhaps, like Sir Paul McCartney, traveled hours to dine at one of his restaurants, then heads up: The celebrity chef is hanging out on the Connecticut–New York line these days, serving as culinary director for the only Connecticut restaurant to make The New York Times’s current list of America’s 50 best restaurants. The building, a revamped 18th-century farmhouse, is as stunning as the tasting menu plates crafted with meticulously selected, just-harvested produce from farms on both sides of the border. Whether or not you opt for paired wines, it’s a tipsy treat to dine this well so far from city lights. 

Gifford’s, 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, 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, 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.

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.

Herreshoff Marine 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.

Mount Hope Farm, 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!

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