Lower Connecticut River Valley: Paddle Boarding, New England Towns and the Annual Tree Swallow Migration

A breathtaking aerial ballet of half a million migrating tree sparrows, jaw-dropping foliage and quaint historical towns await visitors in autumn.

If you’ve never heard of this area of New England, you’re in for a beautiful outdoor treat, especially if visiting during the fall. Early autumn brings a spectacular aviary event and invites water-based outings on the river, on boats, kayaks, canoes and SUPs. The later weeks of the fall season deliver the magnificent orange, red and yellow foliage that the New England region is known for, along with exquisite water views. And whenever you visit, the charming historic towns on or near the Connecticut River, from Old Lyme and Chester to Haddam and East Haddam, promise to steep you in historical architecture, captivating artworks and fun activities, from shopping to dining.


Old Lyme – Small Town Charm

Start your fall trip through the lower Connecticut River Valley in Old Lyme, located on the east bank of the Connecticut River where it merges with the Long Island Sound. During the summer, this coastal community’s lovely Sound View beach and other beaches are a huge draw, but the town’s rich artistic heritage and historic flair entice year-round right along with the nearby rolling fields and rocky shores — a magical mix!

Old Lyme was at the center of the American Impressionism movement in the early 1900s and that creative vibrancy can still be experienced today. Visit the Florence Griswold Museum, which housed the Lyme Art Colony, the hub of American Impressionism, for over a century. Or check out the Lyme Art Association, where the original Lyme Art Colony artists sold their work and where current members of the association still show and sell their creations. Beyond museums and associations, there are plenty of art galleries to explore including The Cooley Gallery and Studio 80+ Sculpture Grounds.

Stop by these attractions as you stroll down Lyme Street, the town’s main street, in the historic village center. This area is also filled with Colonial and Federal-style homes, some of which were once the residences of sea captains. Visit boutiques and antique shops and grab a handcrafted treat at the local ice cream parlor, Old Lyme Ice Cream Shoppe.

When it comes to food, there are plenty of delectable stops. Grab a gourmet deli sandwich and coffee at Coffee’s Country Market. For delicious seafood and stunning views of the spot where the Connecticut River meets Long Island Sound, head to upscale Fresh Salt in nearby Old Saybrook — patrons rave about their lobster roll, oysters and clam chowder as well as the soaring stone fireplace and romantic atmosphere. Indulge in contemporary New England fare or afternoon tea on the patio at the gracious Old Lyme Inn. For a more casual option, Hideaway Restaurant & Pub is great for American faves, like burgers and steaks.

Old Lyme’s thriving arts and culture scene extends to live music performances as well. If you’re a jazz lover, visit the Side Door Jazz Club, located in the historic Old Lyme Inn, to hear world-class jazz musicians. Or listen to a mix of genres, from soft rock to the blues, at Nightingale’s Acoustic Cafe, an intimate venue with a laid-back coffeehouse vibe.


Connecticut River and Goose Island

Migrating Tree Swallows in Flight.
Migrating tree swallows in flight.

In the closing week of August through late September (and sometimes early October), you can see the annual tree swallow migration over Goose Island, a small land mass in the Connecticut River that’s easy to reach by boat or paddling. Old Lyme is the perfect place to rent a kayak, canoe or SUP and paddle out on the river to witness the phenomenon. There’s a small launch site at the end of Pilgrim Landing Road, off Route 156 less than a mile north of the Baldwin Bridge. Goose Island is less than a mile north of the launch.

“I have seen a million flamingos on the lakes of East Africa and as many seabirds on the cliffs of the Alaska Pribilofs, but for sheer drama, the tornadoes of tree swallows eclipsed any other avian spectacle I have ever seen.”

Roger Tory Peterson

During the annual tree swallow migration that takes place from late summer to early fall, from half a million to one million tree swallows flock to the island to roost in the reeds along the riverbanks. Every evening around sunset, the swallows soar up together into the skies over the Connecticut River and fly in swirling, looping patterns that some have described as an ‘avian ballet.’ With standout blue and green feathers, even a single tree swallow is beautiful to behold. But the mass of birds that swoop and dive in unison to form spinning tornado-like funnels over Goose Island is simply jaw-dropping. The seemingly coordinated flights can last as long as twenty minutes. The birds also perform the dance at dawn, providing a second opportunity to watch if you’re willing to get out on the river before sunrise.

The late Roger Tory Peterson, one of the country’s most renowned naturalists, ornithologists, artists and bird guide authors, once said: “I have seen a million flamingos on the lakes of East Africa and as many seabirds on the cliffs of the Alaska Pribilofs, but for sheer drama, the tornadoes of tree swallows eclipsed any other avian spectacle I have ever seen.”

Another excellent way to see the birds ‘perform’ is to take a guided 3-3.5-hour Tree Swallow Sunset Cruise with RiverQuest (based in nearby East Haddam) from late August through the end of September, or a Swallow Cruise with The Connecticut Audubon Society in September. Be sure to reserve a spot well in advance of your trip as these cruises book up very quickly. You’ll likely spot bald eagles and great egrets along the way, too, as many other species migrate through the region in early fall.

RiverQuest pioneered the concept of the sunset tree swallow cruise and offers near-perfect views of the event, but the company also operates other tours on the lower Connecticut River year-round and at all times of day. Go on one of them and you’ll learn about the local history, ecology and wildlife and see a fair amount of beauty no matter when you choose to visit.


Cruise the Connecticut River & Drive Through the Lower Valley

The spectacular gold and claret hues that unfold in the trees along the lower Connecticut River provide an excellent excuse to hop into your car and spend time in the area’s towns and on its local waters. The river is crystal clear as first frost hits, and you’ll be able to spot legions of blue crabs heading downriver as the foliage reaches its peak.

Chapman Falls in Devil's Hopyard State Park, Connecticut.
Chapman Falls in Devil’s Hopyard State Park, Connecticut.

Explore On the Water

For a unique vantage point on the beautiful fall foliage, get out onto the river. One way to do this is to book RiverQuest’s Fall Foliage Cruise. In addition to gorgeous leaf-powered views, you’ll see a flurry of local and migrating wildlife and various historical sights. Black Hall Outfitters, based in Old Lyme, offers paddling Eco Tours and Sunset Paddle Tours in the Great Island salt marsh (located near the coast where the Long Island Sound gives the river high-powered salt infusions) as well as kayak, canoe and SUP rentals so you can explore the autumn splendor on your own.

Drive From Town to Town

From Old Lyme, head up to Chester, a quaint rural town with an enchanting village center that exudes historic charm (it was settled in 1692 and was a former shipbuilding and milling town) and has long been known as an artists’ enclave for painters, photographers, sculptors and printmakers. The picturesque winding Main Street is lined with old 19th-century buildings that house art galleries stocked with local art creations, chef-owned restaurants and independent boutiques with unique wares (Lark, which carries gifts, jewelry, clothing and home goods, is nearly a block long). To explore the town with a Historical Society expert, consider taking a walking tour with Chasing Squirrels.

From Chester on the west side of the Connecticut River, ride the Chester/Hadlyme ferry (the second oldest operating ferry in the U.S.) to the east side of the river from April 1 to November 30. The views along the way are wonderful and when you reach the other side, you can readily visit one of the area’s top attractions in East Haddam: historic Gillette Castle, a 24-room granite mansion resembling a medieval castle that was the home of actor and playwright William Gillette. Guided tours are available — it’s best to reserve your tickets in advance through Reserve America. For sure, Gillette Castle will intrigue you, but the fall colors shimmering in the adjacent river waters will wow as well.

Another historic site in Chester that’s worth a look is the Chester Museum at the Mill, an 1860s mill overlooking a dam and the Pattaconk Brook. It’s open on weekends from June through October or by appointment. Located near the center of Chester, the museum features both permanent and changing exhibits that tell the story of Chester over time.

Covered bridge crosses stream at Devil’s Hopyard State Park.

To soak up the fall colors on land, hike or bike through the foliage in Cockaponset State Forest — the state’s second largest state forest.

When you’re in need of eats, hit up The Wheatmarket for yummy homemade deli options; Brushmill, a local landmark overlooking a waterfall that dishes up American cuisine up in a building that was a grist and saw mill in the 1800s; and Pattaconk 1850 — an old tavern on Main Street serving pub classics and beer on tap and cocktails. When your sweet tooth begs for a treat, indulge it with the mouthwatering, if unusual, ice cream and sorbet flavors served at Honeycone Craft Ice Cream. How do Rosemary Olive Oil, Sweet Corn Blueberry and Sage Candied Pecan sound?

From Chester head north to Haddam, a vibrant town with historic architecture that’s just a 25-minute drive away. The top attraction here is the Thankful Arnold House. Built from 1795 to 1819, it gives visitors a sense of daily life during that era.

Dine at Blue Oar, ideal for any river rat because it overlooks the Connecticut River. Feel the breeze, listen to the reggae and savor creatively cooked meat and seafood dishes (the menu changes daily).

From Haddam, cross over to the east side of the Connecticut River to East Haddam.

In addition to the previously mentioned Gillette Castle and RiverQuest, the town offers the Goodspeed Opera House, an acclaimed performance hall for musicals housed in a majestic white Gothic-style manse located at the edge of the river. Theater-lovers should catch a musical during Goodspeed’s fall season, which extends from the end of September through November.

Visitors to East Haddam can also see colorful foliage and incredible birds along the network of scenic trails in Devil’s Hopyard State Park, one of the best birding spots in the whole state. The park’s main feature is Chapman Falls, which cascades more than 60 feet down a series of steps. Numerous perfectly cylindrical potholes in the stones near the falls add to their scenic beauty and covered bridges punctuate the lovely nature with man-made charm.

History lovers will want to stop by the red single-room Nathan Hale Schoolhouse on Main Street, where teacher-turned-spy Nathan Hale (who was caught and hanged by the British for espionage activities during the American Revolution) once taught.

Staehly Farm Winery produces numerous fruit wines made from locally grown berries and other fruits — visit the winery to buy some of their stellar wines. And sample the wine an hard ciders (made with East Haddam-grown apples) at the farm’s Yankee Cider Co.


Taughannock Falls State Park.
Taughannock Falls State Park. Photo credit: @jamiemalcolmbrozn.

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