Autumn Along the Connecticut River — Seen from Mount Sugarloaf across the Connecticut River, the town of Sunderland, Massachusetts, is nestled amid a carpet of fall color.
*Photo Credit : Carl Tremblay*

“Long Tidal River” the region’s NativeAmericans called it when they first explored the“Connecticut” (a Colonial variation on an Algonquian name) thousands of years ago. And indeed it is long, trickling from humble origins 300 yards below the Canadian border, then plunging 410 miles through four states before emptying into Long Island Sound. From mid-September through mid-October, this verdant landscape, the very core of New England, wears the vibrant colors of autumn, as a spectacular panorama of foliage lights up the valley.The itineraries that follow—just a small sampling of the valley’s many opportunities for exploration—will give you a feel for the river along the way, each week a mini-season all its own. From the Great North Woods to the Tidelands, we feature four distinct stretches—one each within the valley’s four major regions. Each trek can be a destination in itself, or you can spin them all into one of the most memorable autumn outings anywhere, as you watch the color riding the river on its sinuous north–south plunge.

NORTHERN EXPOSURE | THE GREAT NORTH WOODS

Third and Fourth Weeks of September

Our Connecticut River Valley adventure begins close to the Canadian border, in the farthest reaches of New Hampshire’s Great North Woods, then heads south through the remote Connecticut Lakes region and our base in the town of Pittsburg. We’re in the heart of “Moose Alley,” a stretch of U.S. Route 3 that will take us through some of the most beautiful territory in all of New England, where pristine lakes and tumbling waters feed the Connecticut River, cradled amid imposing mountains.

Bill Bernhardt is the head guide for The Cabins at Lopstick in Pittsburg, New Hampshire, and designs many of the flies sold in Lopstick’s shop.
*Photo Credit : Carl Tremblay*

Three peaceful tributary streams—Perry, Indian, and Halls—burble along to the west. In 1832, however, armed rebellion was in the air here, when this little corner of New England produced the secessionists of the Indian Stream Republic (p. 94). Today it’s home to rustic camps, woodsy resorts, and all the outdoor recreation any hiker, paddler, or fisherman could wish for. We’ll visit a handful of these storied wilderness lodgings, but first let’s take in a few unique North Country sites. From Pittsburg, take Route 145 South through Clarksville into Stewartstown Hollow to stop at Poore Farm Historic Homestead & Museum (get there before the September 30 close), a unique early-19th-century settlement and a venture into bygone days. A bit farther south on 145, pull over at Beaver Brook Falls, one of those surprising, beautiful sights that seem to just appear along the roads here. A few minutes more and the “big city” of Colebrook (pop. 2,300) emerges, with a café, a tavern, a nifty arts-and-crafts shop—and Le Rendez Vous, a bakery so beloved by townspeople that their victorious fight in 2009 to keep it open when the State Department didn’t renew its French owners’ visas brought the New York Times to town. Now let’s travel U.S. Route 3 and find a couple of those classic lodgings that pulse with the flavor of the North Country. Tall Timber Lodge, on Back Lake, started life as a sporting camp in 1946. The Caron family took it over in 1982, and their descendants run the operation today. Cindy Howe (née Caron) creates the hearty breakfasts, while her brother, David Caron, is maestro of the Rainbow Grille (try the Woodsman Steak, Filet & Crab, or One Fat Fish for world-class wilderness dining). Tall Timber offers 26 cabins and eight individual rooms in the lodge itself. You’re here for the outdoors, and Tall Timber provides its guests with canoes, paddleboats, and kayaks; you can rent a fiberglass fishing boat (or a family-size pontoon boat), or meet up with a professional fly-fishing or birding guide. Nearby are The Cabins at Lopstick. Begun as the Currier Camps in the 1920s, Lopstick is a complex of more than 50 fully equipped cabins spread out around First Connecticut and Back lakes, along the Connecticut River, and on nearby Perry Stream. Lopstick is an official Orvis-endorsed fly-fishing outfitter; its guides can teach you technique and steer you to the best spots.

On The Water | The Connecticut Lakes

Here’s a 14-mile drive to give everyone, from the avid outdoorsman to the casual nature lover, a taste of the river system near its source. If you don’t have your own equipment, local inns, lodges, and outfitters can lend a hand with rentals. Start just a half-mile south of the Canadian border (and tiny Fourth Connecticut Lake) along U.S. Route 3 at Third Connecticut Lake, a mile long and a half-mile wide; a boat launch lets paddlers and trout fishermen enjoy these intimate waters. For walkers, a stone path hugs the shore on either side of the water for much of the way; look back at majestic Salmon Mountain,rising 3,364 feet to the east. Continue on to Second Connecticut Lake—1,200 watery acres for paddlers and fishermen. Three more miles south and there it is: magnificent First Connecticut Lake, more than five miles long and two-and-a-half miles wide. Magalloway Mountain, at 3,360 feet, towers over the eastern shore, showing off its fall color. Paddle over to Picnic Island, a delightful spot to spend a few hours. And the chain of lakes continues: Although not officially one of the Connecticuts, Lake Francis (manmade in 1940) is nonetheless a part of the river. The state park here offers campsites and canoe and kayak rentals.

Local Secret | Indian Stream Republic

In 1832 a lot of people in what became Pittsburg weren’t happy with one another or pretty much anyone else. So, on July 9, a 250-square-mile area between Halls Stream and the Connecticut Lakes (including Indian Stream and Perry Stream) declared itself a sovereign republic, independent of both the U.S. and Canada, which were engaged in a double-team taxation-without-representation maneuver. Thus, as all rebels do, they fought a war (a short one with Canada) and then defended themselves (against the New Hampshire militia). Order was eventually restored and the “Streamers” ultimately returned to the fold—although if you see people around here celebrating wildly on the 9th of July, don’t assume they were simply five days late remembering the 4th. Nearly a century later, this area was once again involved in anti-government doings—as a conduit for illegal booze shipped from Canada to the U.S. during Prohibition. Two miles up Indian Stream Road, look for a clearing called “the old holding place,” where a cache of alcohol was diverted during transport from Quebec and is, supposedly, still buried. On Tabor Road you’ll find Indian Stream Cemetery, where some of the 19th-century rebels and 20th-century bootleggers are said to be buried together. Old habits die hard.

Home Away From Home | The Glen at Bear Tree

Inhaling the deep, refreshing aroma of sawn pine, we wound our way up a stout timber stairway to our log-walled room in the lodge at The Glen in Pittsburg. Just below us, double doors led to a spacious, Adirondack-style porch. In front of us lay First Connecticut Lake in all its blue tranquility, with Magalloway Mountain overlooking the scene.

“At Bear Tree” is the official name of an assortment of lodges, lakeside and woodland cottages, and guest rooms at a yellow-clapboard inn, home to Murphy’s Steakhouse. However, the heart of this operation, in our minds at least, is The Glen: the lodge and seven sweet cabins dotting the lakeshore below. It’s the site of what was perhaps this region’s most iconic sporting camp, established in the late 19th century. Current owners John and Georgie Lyons took over in 2012, carrying on from the previous owner of more than 50 years, Betty Mae Falton, a North Country legend for her hospitality and hearty cooking.

At around 10:30 p.m. on this cloudless night, we were sitting on the porch watching the near-full moon as it hung over the lake, Magalloway’s faint purple outline in the background. An eclipse stole slowly across the scene, turning the moon a dusky red before finally snuffing it out like a smoky candle. Then a thousand stars popped against the sky’s black velvet curtain … A once-in-a-lifetime show—one for which we, lucky devils, had front-row seats.

PICTURE PERFECT | THE UPPER VALLEY

Last week of September/first week of October

From the verandah of the “Little Studio” at the Saint-Gaudens National Historic Site in Cornish, New Hampshire, we’re staring at a perfectly framed view of Mount Ascutney across the Connecticut River in Vermont. We’ve followed the river 150 miles south from Pittsburg, and here on rural Route 12A, we’ve happily left civilization behind. In Cornish, the renowned sculptor’s former summer estate is replete with blooming gardens, nature trails, and stop-and-stare views of the surrounding valley. Civil War buffs (and fans of the movie Glory) won’t want to miss the Bowling Green, which contains the final casting of the stirring bronze Shaw Memorial that graces Boston Common.

From Cornish, a happy choice awaits: Continue south along the Connecticut’s eastern bank to explore New Hampshire’s farm country, or head west to Vermont over the much-photographed Cornish–Windsor Bridge (longest wooden covered bridge of its vintage in the U.S., at nearly 450 feet) to chase outdoor adventure? On the New Hampshire side, off Route 12 just outside tree-lined Walpole, we’ve made Valley Farms our base (p. 101). Across the road is 450-acre Alyson’s Orchard, a must visit for its 50 varieties of classic and heirloom apples and its breathtaking views. On a smaller scale, along River Road South lies Boggy Meadow Farm, on land worked by the same family since the mid-1600s. Their Fanny Mason cheeses, made in the original 18th-century barn, are the real deal. (Still more 18th-century history awaits along Route 11 at Charlestown’s Fort).

On the Vermont side, off U.S. Route 5, intrepid travelers should head north to Great River Outfitters in Windsor (p. 98)—or visit nearby Artisans Park, where you’ll find Harpoon Brewery, with its impressive array of craft beers and ales paired with hearty lunch fare. While at Artisans, you can also walk Great River’s sister operation, the inspiring Path of Life Garden, on 14 landscaped acres. You may well be tempted to camp overnight here in one of two roomy Native American tipis. Don’t leave this area without visiting Mount Ascutney State Park. Buckle up, because the nearly four-mile summit road, although completely paved, will make you feel like a competitor at Le Mans. Your reward is an impressive view to your right just beyond the three-mile marker, then an even more eye-popping one at the summit parking lot to your left. If you hike the 0.7-mile summit trail, you’ll marvel at the knockout panoramic view of the entire region in glorious fall color from the observation deck.

On the Water | Great River Outfitters

Offering kayaks, canoes, and big family rafts, Great River Outfitters in Windsor, Vermont, will strap your choice of vessel to a carrier, put you on their shuttle bus, and take everyone to the launch five miles upriver, just below Sumner Falls. Flanked by fall scenery on both banks, it’s a leisurely three-hour trip downriver, with dramatic views of Mount Ascutney in front of you. Below the rapids, the Connecticut is classified as “moving flat water,” which means that it’s more like a lake, with a gentle current propelling you downstream.

You might also opt for a longer half- or full-day trip, traveling farther downriver and under the Cornish–Windsor Bridge. Stop at any time to do a little fishing; or to let your kids take a turn on the rope swing on the Vermont side, just off the old railroad bridge; or to picnic on Chase Island in the middle of the river, south of the covered bridge; or maybe to just kick back and observe the waterfowl and other birds.

Local Secret | The Fort at No. 4

Though not as widely known as some other restored settlements, such as Old Sturbridge Village, The Fort is an equally worthy site: a historically accurate reproduction of the fortified stockade built in 1744 to safeguard the people of Charlestown, then known as Plantation No. 4, the northwesternmost British settlement in the American colonies at the time. Protecting the first settler families became a pressing issue when the Brits had to contend with some pushy French elements, allied with various Native American tribes, who were looking to stop “New England” from consuming “New France.” In 1747, militia captain Phineas Stevens repelled a raiding party of French and Indians who had devastated the British frontier during the winter of 1746–47; Colonial hero Major Robert Rogers found safety here when hurriedly retreating from his attack on the French-supporting Abenaki at St. Francis in Quebec.

Later, during the American Revolution, General John Stark massed forces at No. 4 to deploy at the decisive Battle of Bennington in August 1777, and again before the crucial Battle of Saratoga. You, as a visitor, can witness a reenactment of General Stark’s exploits on Revolutionary War Weekend, October 1–2 this year. Other fall events include “Women of the Fort,” “Pickpockets, Rogues, and Highwaymen,” “Native Heritage Weekend,” and the festive November “Harvest Dinner.”

Home Away From Home | The Inn at Valley Farms

There are two ways to enjoy your stay at this 105-acre farmstead in Walpole, New Hampshire, set amid surroundings so beautiful you may never want to leave. Two tastefully appointed guest rooms and a spacious suite, all on the second floor, are as charming as they are comfortable. Downstairs you’ll find a sitting room, library, and elegant dining room, where innkeeper Jackie Caserta serves sumptuous three-course farm-to-table breakfasts. Out the back door are a terrace and gardens with views of the rolling hills beyond. Or, if you’ve come en famille, two guest cottages (with fully stocked kitchens) and Sunnyside Farmhouse, a splendid retreat, are available.

But best of all is the farm itself. Wander around and enjoy the fields, and visit the expansive barn, which dates back more than 100 years. Come with a cooler so that before you leave you can visit the farm store and extend your experience for a few extra days back home.

HEART OF THE REGION | THE PIONEER VALLEY

Second Week of October

We’re standing on an 1889 iron bridge (long closed to cars) across the narrow run of the Millers River just before it enters the main event near French King Gorge. On this spectacularly beautiful early October day, downstream and some 200 feet above us soars one of the most imposing sights on the entire Connecticut River: the graceful 800-foot span of the French King Bridge, linking the towns of Erving and Gill in western Massachusetts. Next door is Cabot Camp, purportedly the site of a rollicking tavern that served log drivers, stagecoach drivers, and river rats of all stripes nearly two centuries ago. However did we find this place?

Kicking off our 40-mile jaunt through the lush Pioneer Valley earlier that morning on Route 63, we’d boarded the Quinnetukut II at Northfield Mountain for a don’t-miss river excursion. Later, back on shore, we discovered by chance a hidden dirt road hugging the water, leading to Cabot Camp, where we stopped for a picnic and a poke around the ruins of that old-time watering hole, Durkee’s. Cabot Camp, like Durkee’s before it, has long since beaten a retreat back to nature.

Pushing on west and then south on U.S. Route 5, a few miles’ trek brings travelers to an ideal overnight base, the gracious Deerfield Inn (p. 104), just steps from the colonial houses of Historic Deerfield. While here in the valley, be sure to take a detour up the access road to Mount Sugarloaf State Reservation. From the top, you’ll be treated to wide-open vistas of the river, the Holyoke and Mount Tom ranges, and the entire Pioneer Valley. Head east over the river on Route 116 to Sunderland; pick up Route 47 to follow the river though the valley’s most fertile farmland. Nothing says fall more than a New England farm stand, and they appear one after the other: Warner on your right, then Riverland; on your left, Millstone, Smiarowski’s, and finally North Hadley Market & Sugar Shack.

Make time to visit the Porter–Phelps–Huntington House Museum in Hadley, too. This historic “River God” home dates from 1752, on land laid out in 1659. No structural changes have been made since 1799; its collections of original furnishings, quilts, and paintings rival any in New England.

South of Hadley, we reach the end of this leg. But we’ve saved the best for last: views of the valley from Skinner State Park, home of Mount Holyoke and its fabled Summit House. From the second-floor porch, look west to the dramatic curve of artist Thomas Cole’s Oxbow, a horseshoe-shaped pond that was once a 360-degree bend in the river before floodwaters in 1840 cut a new channel—still today an arresting sight.

On the Water | Quinnetukut II

If one could travel only seven miles of the river’s 410, our vote would go here, to this stretch between Northfield Mountain and Barton Cove in Gill. The compact Quinnetukut II takes you on a narrated, 90-minute cruise; in the fall, the foliage-rich banks on either side of the water are aglow in shades of red and gold.

Captain Scott Brennan is a genial sort and a born yarn spinner; first mate Kim Noyes is a learned naturalist. You’ll be riveted by their true-life tales: of the Squakheag people, here when the first Europeans came (Quinnetukut means “long tidal river”); of 19th-century log drivers, ferry captains, stagecoach drivers, and flatboatmen (who probably delivered rum to Durkee’s Tavern); of the river’s rich wildlife, including bald eagles; of geological formations like French King Rock, the “Horserace,” the Dinosaur Track Quarry, and “King Philip’s Abyss,” the deepest spot on the entire river and home to unique underwater invertebrate habitats.

Local Secret | Historic Deerfield

What distinguishes Historic Deerfield from other “museum villages” is that this one is part of a real village: 12 museum houses interspersed among private homes along Old Main Street, where the 18th century blends seamlessly with the 21st. An admission fee lets you tour the interiors—but there’s no charge if you want to just walk around and take in the surrounding farmland and meadows the way they might have looked 250 years ago. This now-serene place, first settled as a frontier town in 1669, was once witness to decisive events in New England’s battle-scarred colonial history: Native attacks in 1675 during King Philip’s War; the bloody reprisal by Colonials the next year at a Native refugee camp near the Great Falls (where the river forms the Turners Falls/Gill border today); and the infamous 1704 “Raid on Deerfield,” when the French and their Indian allies killed 47 settlers and kidnapped 112, marching them 300 miles to Canada. Visit the Old Burying Ground at the end of Albany Road, where those who perished lie together in a mass grave, today a gentle grass-covered mound of earth. If you’re into artifacts and antiques, the museum’s Flynt Center of Early New England Life features thousands of objects, many of which are housed in a transparent storage area, making the “Museum’s Attic” visible to all. Historic Deerfield engages with many communities, from those of New England’s earliest ancestors to the people who live right here, right now, in this timeless corner of the Connecticut River Valley: Fall programs include open-hearth cooking and historic-trades demonstrations; the ADA/Historic New England Antiques Show; and Archaeology Day.

Home Away From Home | The Deerfield Inn

Of all the tributaries in this watershed, the Deerfield River may be the most scenic, descending southeast for some 75 miles from Vermont’s Green Mountains through the Berkshires to join the Connecticut where the towns of Deerfield and Greenfield meet—just a few miles from where we’re sitting now, out on the porch of the 132-year-old Deerfield Inn. Innkeeper Jane Howard calls it “our own made-in-America Brigadoon”—but then, she’s British. (The inn, fittingly, has a “Beehive Parlor,” a warmly enveloping space done up in buttery hues, where afternoon tea, with honey and cookies—Jane would call them “biscuits”—are served daily.) It sits at the midpoint of mile-long Old Main Street, surrounded by a phalanx of Colonial-era houses, including the carefully preserved homes of Historic Deerfield; Pocumtuck Valley’s Memorial Hall, another outstanding regional history musem; old churches; the iconic campus of Deerfield Academy; and majestic trees lining this road the way many Main Streets were a century ago.

There are 24 guest rooms, 11 in the main building and 13 in the adjoining carriage house. Homemade breakfast comes from local sources; the same philosophy informs the menu at the inn’s restaurant, Champney’s, when you head down for lunch or dinner. Inn guests also receive discounts at Historic Deerfield and its gift shop. Most important of all, when you ask about reservations and specials, tell them “Jack” sent you. This sweet-faced black Lab is the inn’s “marketing manager.” He’s often off somewhere else with his posse of other rescued pups, but when in residence he’ll give away the whole place for a few tummy rubs and a well-placed pat on the head.

SOUTH TO THE SOUND | THE TIDELANDS

Second and Third Weeks of October

Fifteen miles below Hartford, Connecticut, the river turns sharply at Middletown before its final, tidewater run southeast to Long Island Sound at Saybrook Point. From our base in the town of Deep River (p. 107), we’re chasing the water along lovely Route 154 down to Essex, a gemlike inland seaport with a downtown so compact you can walk its entirety in less than an hour. Take in the sailboats in the harbor, bobbing up and down next to the Connecticut River Museum (p. 107). Or board an antique railcar and a Mississippi-style riverboat for an escape into the past (p. 107). Later, head to the 240-year-old Griswold Inn and choose one of the “historic rooms” as your dining spot while perusing bookshelves, antique weaponry, or maritime artworks. Visit the Tap Room with its lively music, or try the elegant Wine Bar—but after a glass or two, don’t stare too long at the full-width riverboat mural behind the bar—it moves like the real thing and you might just turn “a whiter shade of pale.”

Our final 10-mile stretch leads to Saybrook Point and the mouth of the Connecticut. From the boardwalk, far in front of us across a cove sit two historic structures: lovely Lynde Point Light (a.k.a. Saybrook Inner Light) and the iconic Saybrook Breakwater Light out on its stone jetty. And so, the Connecticut’s 410-mile journey ends here. Look up, out, and around: You’re at the very place where the mighty river empties into Long Island Sound. And what an awesome sight it is: this big, wide, magnificent water, the lifeblood of New England, rolling on into the infinite sea.

On the Water| Essex Steam Train & Riverboat

For our final expedition, we first boarded an antique Pullman car, pulled by a vintage locomotive out of historic Essex Station, heading north to Deep River through rich marshland. Valley Railroad president Kevin Dodd and chief mechanical officer J. David Conrad between them have worked every job up and down the line during their careers, and their passion and knowledge ensure an unforgettable experience for visitors.

In Deep River, our train met up with the triple-deck Becky Thatcher riverboat. From here Captain Paul Costello took us on a 75-minute narrated cruise upriver to view sights that you just can’t experience from the land in quite the same way. One showstopper is Gillette Castle, looming from its clifftop perch over the river at East Haddam, the legacy of famed early-20th-century stage actor William Gillette, the wildly popular embodiment of the storied Sherlock Holmes. In retirement, he designed a 24-room fieldstone replica of a medieval castle, with trails, walkways, and even a narrow-gauge railroad with tunnels, trestles, and a station. Now part of its own state park, this huge stone construction is open to the public. From the water, it looks like an impossible illusion, sure to disappear if you blink in the shimmering sunlight.

Local Secret | Connecticut River Museum

If you were to simply walk up the three-story staircase on one side of the building and then down the staircase on the other side, your trip to the Connecticut River Museum in Essex would be a thoroughly enjoyable, informative experience. Although, of course, there’s a lot more to it than that. On your right as you ascend the steps inside this expansive 1878 white clapboard building, artist Russell Buckingham has created a colorful, whimsical, three-story vertical mural depicting the entire length of the Connecticut River from south to north. Then, upon your return journey—down the stairway at left—you encounter the same scenes and sites, north to south, in the form of striking aerial photos by Tom Walsh. Inside, enthralling exhibits beckon. The coolest for kids is an interactive model of America’s first submarine, the Revolutionary War Turtle. Outside, moored at the CRV wharf is the sleek 1906 schooner Mary E, aboard which the museum schedules daily cruises into October. Plus, a “Paddle Explorations” program offers staff-led tours and classes and self-guided canoe and kayak trips. The guided Swallow Paddle (September 15 this year) is the hit of the early-fall season—letting you witness the aerial ballet of tens of thousands of tree swallows soaring and swirling high above in their premigration choreography. This is a fun and amazing place—and by visiting it you’re helping to protect New England’s most cherished common resource: its “Great River.” As executive director Chris Dobbs notes, “The river [is] a unifying force. It symbolizes our past, our present, and our future.”

Home Away From Home | The Riverwind Inn

Riverwind, with seven beautiful guest rooms, has been in Elaine and Leo Klevens’ care since 2005. It seems that Elaine had acquired so large a collection of beloved antiques beforehand that she “simply had to open a B&B, with so many things and no place to put them!” The front half of the house, including a lovely dining room with fireplace and front guest rooms upstairs, dates to 1854. The back half is a more recent addition, but so tastefully done—using original foundation stones for the fireplace and local antique timber for ceilings and corner posts—that we thought it was the older part of the house. Elaine’s delicate stenciling graces the guest rooms and staircase, enhancing the home’s Early American spirit. We rose early and headed for coffee in the upstairs sitting room. En route, with no one else astir, we were mesmerized by both the enchanting aroma of fragrant spices and the subtle twinkling of tiny white lights throughout the house. The effect was magical. Then Elaine served a filling breakfast of homemade rolls and sizzling herbed frittatas: a delicious start to our final day following the Great River, at home in the heart of the valley’s historic Tidelands. MORE CONNECTICUT RIVER: The Connecticut River in Autumn | Photographs

Eileen Terrill

30 Days of Wonder | Autumn Along the Connecticut River