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.
If you're reading this, chances are you've already imagined life with a weekend home. The only question is where. You've probably considered the Hamptons, the North Fork, or the Catskills. For many buyers, though, Connecticut turns out to be the sweet spot: charming shoreline towns, historic villages, scenic countryside, remarkable value, and an easy drive or train ride from New York.
For nearly twenty years, I've helped people discover that the best weekend home isn't necessarily the farthest away. It's the one that's close enough to become a habit.