Note: Why pay for parking in New York City? Leave your car
at Old Saybrook train station where parking is free and these towns are just a
short drive. Take the Metro-North train from Grand Central Station to New Haven’s
Union Station and transfer to the Shoreline East train to Old Saybrook or take
Amtrak from Penn Station directly to Old Saybrook.
TOWNS ON THE WEST SIDE OF THE CONNECTICUT RIVER
Essex
Essex is a postcard-perfect town on the Connecticut River,
known for its historic charm, colonial architecture, and nautical heritage. Its
Main Street leads down to a scenic harbor and is lined with boutiques,
restaurants, and galleries. Popular attractions include the Essex Steam Train
& Riverboat, the Griswold Inn, and waterfront parks. With a strong cultural
scene and timeless atmosphere, Essex is both a tourist favorite and a
sought-after place to live.
Chester
Chester is a small, artistic town tucked into the hills near
the Connecticut River. Its walkable village is full of galleries, artisan
shops, and upscale restaurants, many housed in 19th-century buildings. The town
is known for its creative community, local events, and the Chester-Hadlyme
Ferry that crosses the river to Gillette Castle State Park which has been operating continuously since 1769 (the boat is a more recent vintage). Chester combines
rustic charm with a cosmopolitan flair.
Deep River
Deep River is a quiet, close-knit town that borders both
Chester and Essex, with easy access to the Connecticut River. Its compact
downtown features locally owned shops, cafés, and a classic town green. The
Deep River Landing offers a boat launch and access to the river, and the town
shares in the region’s strong sense of history and natural beauty. It’s a
peaceful residential community with small-town warmth.
TOWNS ON THE EAST SIDE OF THE CONNECTICUT RIVER
Lyme
Lyme is a rural, picturesque town known for its rolling
hills, preserved woodlands, and classic New England farms. It’s ideal for those
seeking privacy and natural beauty, with hiking trails, horse farms, and scenic
drives. The town borders the Connecticut River and is home to several nature
preserves, including the Nehantic and Selden Neck State Forests. Lyme has no
commercial center, emphasizing open space and tranquility.
Old Lyme
Old Lyme is both a coastal and cultural destination, famous
as the birthplace of American Impressionism. It offers beautiful beaches on
Long Island Sound, as well as galleries, historic homes, and the Florence
Griswold Museum. Old Lyme blends seaside living with artistic heritage, and
features a charming village center, waterfront neighborhoods, and easy access
to I-95.
East Lyme
East Lyme includes the villages of Niantic and Flanders, and
offers a mix of shoreline charm and suburban convenience. Niantic is a lively
waterfront district with a boardwalk, beaches, shops, restaurants, and a
year-round calendar of community events. The town also features parks and marinas. East Lyme is popular with families, vacationers, and
commuters alike, with a relaxed coastal lifestyle and easy highway access.
Thinking about a second or weekend home in Connecticut? I'm here to help. The search for a home is more than a transaction—it’s a journey, and I’d be honored to take it with you. Let's start with a visit. Hop on the train at Grand Central Station and two hours later I'll meet you in New Haven for an area tour. There's no better way to start.
Let’s talk.
