The Connecticut River's headwaters are way up near the Canadian border in New Hampshire. Still, the development of towns along New England's longest river began in the south, along the Connecticut's final run to its meeting with Long Island Sound. The fertile Lower Connecticut River Valley remains remarkably rural; its towns delight visitors with their surviving Colonial-era and 19th-century structures and walkable village centers, their green spaces for recreation, their historic inns, and chef-owned restaurants, and their cultural attractions. Plan a day trip or weekend getaway to one of Connecticut's top river towns, or extend your stay and see them all.
Established as a colonial outpost at the mouth of the tidal Connecticut River in 1635, Old Saybrook is known for its breezy shoreline beaches and bustling Main Street business district: home to restaurant's like Liv's Oyster Bar, where chef-owner John Brescio's menus celebrate local seafood, and casual Jack Rabbits, where you can sample an only-in-Connecticut treat: lobster hot dogs. This is also where you'll find The Kate, a theater named for Katharine Hepburn, the town's most legendary former resident. Non-residents pay a premium for parking, but summer days at Harvey's Beach are worth the investment. For history, head to Saybrook Point, where you can see remnants of Connecticut's first military fortifications and also play a round of mini-golf at a waterside course that features miniature replicas of local landmarks. Saybrook Point Resort & Marina, one of Connecticut's most complete and most eco-conscious lodging properties, is also here, offering River Valley visitors an elegant yet relaxed place to stay, dine, and indulge in spa treatments.
Opposite Old Saybrook, on the east bank of the Connecticut River, the coastal town of Old Lyme came to prominence at the turn of the 20th century, when American Impressionist artists discovered the beauty and hospitality that awaited at Miss Florence Griswold's boarding house. Her art-filled home is now the centerpiece of the multi-building Florence Griswold Museum, where you're encouraged to not only view Lyme Art Colony masterpieces and other exhibited works but to set up an easel or bring a sketchbook to create artwork of your own. You can also picnic on the grounds beside the Lieutenant River. Pick up sandwiches up the road at The Hangry Goose. Head to the Old Lyme Historic District, centered around Lyme Street, to see fine examples of American Colonial architecture, shop, and savor a cone at Old Lyme Ice Cream Shoppe. For nature lovers, the ultimate Old Lyme experience is renting a kayak or SUP from Black Hall Outfitters to paddle out among the eagles, egrets, and osprey that inhabit the 500-acre Great Island salt marsh. Overnighting? Try to score a room at the Old Lyme Inn, known by music lovers for its Side Door Jazz Club.
Moving up the Connecticut River's west bank, lively Essex is one of New England's best-preserved towns from before the Revolutionary War. You'll find nostalgia in abundance, whether you hop aboard the Essex Steam Train & Riverboat for a scenic rail and river ride, visit Main Street shops like Emmy's on Main tucked inside antique buildings, or spend a night at the Griswold Inn, which opened its doors to Connecticut visitors in 1776. The Tap Room at "The Gris" is even older: It was built as a schoolhouse in 1735 and attached to the inn in 1801. It's filled with maritime art, firelight, and live music. Devote some time to visiting the Connecticut River Museum, where you'll learn about the river's natural and human history and can take a boat tour: Eagle Cruises are popular in the winter months. And be sure to allow Chef Colt Taylor and his team to cook you a memorable meal at The Essex, where the emphasis is on seasonal, farm-to-table fare.
Community spirit is alive and well in Deep River, just north of Essex on the Connecticut River's west side. Stay at the Riverwind Inn, an 1854 Federal-style home that is now one of the coziest, best-run B&Bs in the state, and you'll not only enjoy blissful slumber and homecooked morning meals, but you'll also be a short walk to restaurants, shops, and craft beer maker High Nine Brewing. The inn building dates to an era when Deep River was a wealthy center of the ivory trade. Deep River Landing is now a pretty park and the spot where Essex Steam Train passengers board the Becky Thatcher riverboat. You'll find a used book store and an old-school hardware store in the heart of town, plus stylish boutiques for women and men: Compass Rose and Anchor & Compass. The town may be best known for the Deep River Ancient Muster, America's longest-running and largest gather of fife and drum corps, held annually on the third Saturday in July.
Venture west from Deep River on Connecticut's Route 80 and discover the open spaces and growing places that make Killingworth a worthy destination. Lavender Pond Farm, New England's largest lavender grower, has really put Killingworth on the map with its fragrant fields of purple flowers, train rides around the pond and over a covered bridge, solar SunFlower, and adorable store filled with lavender gifts galore. Other farm stops include Bitta-Blue Farm for organic produce and goat's milk bath and body products; Parmelee Farm, a 132-acre town-owned property with dog-friendly walking trails; and Chatfield Hollow Farm, where edible and medicinal shiitake mushrooms are grown using small-scale forest mushroom cultivation techniques originated in Japan. Stay at the on-site Chatfield Hollow Inn, with its glammed-up rustic styling, and you'll love visiting the property's black swans and peacocks and savoring a bountiful breakfast spread made with eggs and other farm-harvested ingredients. Adjacent to the farm, 412-acre Chatfield Hollow State Park offers a freshwater swimming beach and miles of trails to hike.
Just north of Deep River on the Connecticut River's west side, Chester is a town for those with elevated tastes in food and art, where some residents trace their ancestry back to the town's 17th-century settlers, and others are newcomers seeking a quiet retreat from the pace of New York City or Boston. Pattaconk Brook, a Connecticut River tributary, flows right alongside the town's architecturally rich Main Street, where out-of-towners love wandering in and out of upscale shops and art galleries. Don't miss seeing the enormous, vibrant canvases inside Leif Nilsson Spring Street Studio and Gallery and the Chester Gallery's latest exhibition. Visit multi-artist gallery, The Space, too. It's near Lark, a popular gift shop. The Chester Sunday Market adds even more to shop for along Main Street. Foodies make their way to Chester to dine at what many consider to be Connecticut's finest Italian restaurant. At Chef Joel Gargano’s Grano Arso, in an old 1902 bank building, New England-grown grains are milled in-house to make fresh pasta and bread. More down-to-earth eats here have just as many devotees. Try the spicy fried chicken and French bistro fare at Hot French Chix and the wood-fired pizzas at Otto.
When the Chester-Hadlyme Ferry is operating (typically April through November), there's no more historic and scenic way for you (and your car) to get across the Connecticut River. This ferry route has been operated since 1769, and supplies were ferried at this crossing throughout the Revolutionary War. You'll have East Haddam's most famous attraction in view on your short voyage east. Gillette Castle is a magnificent stone mansion built in 1919 for Hartford-born actor William Gillette. He may have been rather eccentric, but Gillette made an excellent decision to bequeath his riverview estate to the people of Connecticut when he died. It is now one of Connecticut's most popular state parks. While you're in East Haddam, you may also want to see Chapman Falls, a picturesque waterfall just inside Devil's Hopyard State Park. The town is also home to Goodspeed Musicals, a Tony Award-winning musical theater company that stages productions in a riverside Victorian opera house. Dine and perhaps even spend a night at the neighboring Gelston House, which has an elevated patio overlooking the Connecticut River.
Farther north on the Connecticut River's eastern shore, just minutes south of Hartford, you won't want to miss the opportunity to poke around in Connecticut's oldest town. Main Street in Old Wethersfield is a veritable museum of distinctive homes from the Colonial and Federal periods. There are a few Victorians around town, too, most notably the magnificent Second Empire-style Silas W. Robbins House, built in 1873 and now a bed & breakfast with five guestrooms. If the inn looks familiar, you may have seen it, along with other scenes from Wethersfield, in the 2018 Hallmark Channel movie, "Christmas on Honeysuckle Lane." While you're in Wethersfield, stop into Comstock, Ferre & Co., America's oldest seed company, not only to purchase heirloom vegetable and flower seeds but to enjoy a light breakfast or lunch handcrafted with local ingredients at the Heirloom Market. Down the street, pop into the Old Wethersfield Country Store for local souvenirs before touring the Webb-Deane-Stevens Museum's three pre-Revolution homes. Travel even farther back in time by driving to Cove Park, where a circa 1690 warehouse looms over a protected cove with direct access to the Connecticut River. Then, you can kick back and enjoy a meal indoors or out at Revolutionary War captain Elijah Wright's home, now The Charles restaurant.