Old Saybrook sits right at the mouth of the Connecticut River, which gives it a mix of beach town and river town. It is compact, easy to get around and makes a relaxing two or three night stay.
Day one: Main Street and The Kate
Start on Main Street, a walkable stretch of shops, galleries and cafés. In the evening, catch a show at The Kate, the Katharine Hepburn Cultural Arts Center, which hosts concerts, comedy, films and theater in the town’s historic former town hall. There is also a small exhibit about Hepburn, who spent much of her life in town.
Day two: the water
Spend the morning at Harvey’s Beach, the town beach on Long Island Sound, known for calm, shallow water that is great for younger swimmers. In the afternoon, head to Saybrook Point for marina views and mini golf, and walk Fort Saybrook Monument Park, a waterfront park with signs that tell the area’s colonial history.
Day three: across the river
Old Lyme is just across the bridge. Visit the Florence Griswold Museum, home of the Lyme Art Colony and its American Impressionist painters, then walk the gardens along the Lieutenant River. Nature lovers can also explore The Preserve, a large coastal forest with miles of trails on the Old Saybrook, Essex and Westbrook line.
Old Saybrook, Westbrook & Clinton homes
Beachfront homes and private beach access along the shore.
Getting here
Old Saybrook is a stop on Amtrak and Shore Line East trains, so it is one of the easiest shoreline towns to reach without driving. A car is still the best way to explore the nearby beaches and towns.
Hours, seasons, passes and event dates change from year to year, so check each venue’s website before you go. Questions about where to stay? Email str@pmisoutheastct.com or call 860-451-9101.

