The Most Charming River Towns In Connecticut

The best days in Connecticut's river towns happen right at the water's edge. You can catch a steamboat at Essex or a musical over the swing bridge at East Haddam. Kent Falls tumbles down toward the Housatonic and Deep River fills Main Street with fifers every July. The old mills and warehouses along these banks turned into galleries and theaters instead of falling down. Each town charms you in its own key. What they share is a river that never stopped mattering.

Essex

The Connecticut River borders Essex along its western edge, where historic Steamboat Dock sits near the foot of Main Street beside the Connecticut River Museum. The museum occupies a former 1878 steamboat warehouse and maintains exhibits focused on navigation, shipbuilding, and commerce along the river. Docks beside the museum accommodate seasonal excursion vessels operating on the Connecticut River during the warmer months. The waterfront sits just a short walk from downtown, and marinas and boatyards fill the shoreline south of it. North of the town's center, the Essex Steam Train & Riverboat combines rail excursions through the lower Connecticut River Valley with a cruise on the river itself.

Chester

Main Street concentrates much of Chester's arts community within a short stretch of storefronts surrounding the town green. Ceramica specializes in imported European pottery and ceramics, while neighboring galleries and studios display paintings, photography, and mixed-media work.

Pattaconk Brook passes through the center of Chester before joining the Connecticut River south of town. During the nineteenth century, water flowed through the brook-powered mills operated along its banks. Now, shops occupy the historic buildings. The Norma Terris Theatre occupies a converted factory building near the center of town and has long operated as the second stage of Goodspeed Musicals, where new productions undergo development before moving to larger venues. Programming should be checked season to season.

Old Lyme

The Lieutenant River passes through Old Lyme before entering Long Island Sound through broad tidal marshes south of the village center. Along its banks stands the Florence Griswold Museum, occupying the former home of Florence Griswold and the grounds that became associated with the American Impressionist movement in Connecticut. Artists including Childe Hassam, Henry Ward Ranger, and Willard Metcalf worked from the property during the late nineteenth and early twentieth centuries. Painted doors and wall panels created by resident artists form part of the museum collection, with galleries on the grounds exhibiting works connected to the Lyme Art Colony and later American art movements.

South of the museum, the Lieutenant River widens toward the marshes surrounding Long Island Sound and the shoreline at Sound View Beach. Lyme Street holds galleries, studios, and historic buildings within a short distance of both the river and coast.

Westport

The Saugatuck River cuts straight through the middle of Westport on its way to Long Island Sound, and the town grew up on both banks of it. The Route 136 bridge that carries traffic across the river dates to 1882 and still swings open by hand for boats, which makes it the oldest working movable bridge in the state. Before the bridge, a ferry had been crossing the same spot since 1746. The river is the reason the town is here at all.

The west bank around the Post Road and Riverside Avenue crossing is the old Saugatuck shipping village, now the National Hall Historic District, where eleven Federal and Italianate buildings survive from the days when local captains sent produce and lumber down to New York. On the east bank sits the Levitt Pavilion, an outdoor stage under sail-shaped canopies that has run free summer concerts since the 1970s. A brick RiverWalk connects it to the library and follows the water south past the marsh. Downtown Main Street runs right alongside the river, so the shops and cafes look out over the same current the shipyards once used.

East Haddam

The Goodspeed Opera House stands beside the Connecticut River, at the eastern end of the East Haddam Swing Bridge. Built in 1876, the theater hosts musical performances throughout the year within a Victorian riverfront building overlooking one of the lower Connecticut River's principal crossings. The Swing Bridge links East Haddam with Haddam on the opposite bank, one of the busiest crossings on the lower river.

South of the town center near Hadlyme, Gillette Castle State Park occupies the high ground above the Connecticut River. Actor William Gillette designed the stone residence, completed in 1919, with built-in furnishings and rooms connected by narrow passageways. Trails throughout the park lead toward overlooks facing the river below.

Deep River

The Deep River Ancient Muster takes place each July and brings fifers and drummers to Main Street from organizations across New England and the eastern United States. Marching units assemble throughout the center of town for parades and performances associated with military music traditions dating back several centuries. A short distance downhill, Deep River Landing meets the Connecticut River with public docks and waterfront access beside the lower end of the business district. During the nineteenth century, the river supported shipping and manufacturing activity tied to the town's prolific ivory industry. The Deep River Historical Society maintains collections documenting that period from headquarters in the Stone House on West Elm Street. Exhibits include photographs, tools, documents, and household objects connected with Deep River's industrial development and the businesses that operated along the riverfront.

Kent

The Housatonic River runs along the western side of Kent, while Kent Falls Brook descends from the hills east of town before joining the river below. Kent Falls State Park follows the brook through a series of cascades dropping more than 250 feet over exposed rock ledges. Trails climb beside the water toward upper viewing areas, with a covered footbridge crossing near the base of the lower falls.

South of the park, Main Street occupies a narrow section of the Housatonic valley between the river and the surrounding hills. Morrison Gallery exhibits contemporary painting and sculpture from a large exhibition space within the town center, with works ranging from monumental outdoor pieces to smaller studio paintings.

Collinsville

A stone dam spans the Farmington River through the center of Collinsville beside rows of brick factory buildings constructed for the Collins Company. Water from the river powered manufacturing machinery throughout much of the nineteenth and twentieth centuries, with edge tools and axes produced in the village for more than a century. Retaining walls and sections of the former factory complex span the waterfront through the center of town. Several segments of the industrial district now house local businesses, including the Collinsville Axe Factory Antique Center operating within the old manufacturing spaces.

Below the dam, the Farmington River broadens through the center of the village before continuing downstream toward Canton. Paddlers launch from the waterfront near Collinsville Canoe & Kayak, while anglers and recreational users set up along the riverbanks and the calmer waters immediately upstream of the dam.

Connecticut's River Town Charm

The thread running through all of these towns is water that used to do work. The Farmington turned the machinery that made Collins axes. The Connecticut carried Deep River's ivory downstream to the Sound. Deep River still musters its fifers and drummers every July, and Old Lyme still keeps the painted doors the Impressionists left behind. The mills went quiet a century ago, but the theaters, galleries, and paddling put-ins that took their place give these riverbanks a second life worth knowing.