Old Saybrook

We arrived in Old Saybrook by accident, really — a wrong turn off Route 1 that dead-ended at Saybrook Point, where the whole town seemed to exhale toward the water. Lia and I sat on a bench near the marina watching the Connecticut River widen into Long Island Sound, sailboats threading past two small lighthouses guarding the channel like punctuation marks. It is an old town, founded in 1635 as the first English settlement on the river, but it wears its history lightly, more interested in tide charts than plaques.

Saybrook Point and the lighthouses

From the point, we could see both Lynde Point Light, still active and privately owned, and the smaller Saybrook Breakwater Light standing on its pier out in the river mouth — a squat cast-iron tower that has guided boats home since 1886. We rented kayaks from a shop near the marina and paddled out along the breakwater, the current picking up as freshwater met salt, ospreys circling overhead from nests on channel markers. It is the kind of unfussy maritime scene that towns further up the coast have long since converted into something more manicured.

Main Street and Kate’s ghost

Old Saybrook’s Main Street is short and unhurried, anchored by the Katharine Hepburn Cultural Arts Center, a converted 1911 town hall named for the actress who spent decades summering nearby in Fenwick. We ducked into the Acton Public Library archive room, where a modest collection of Hepburn memorabilia sits alongside local shipbuilding history, then had fried clams at a counter that has apparently not changed its recipe since the Eisenhower administration. Lia declared it the best chowder of the trip, high praise after Boston.

Getting There

Old Saybrook sits roughly two hours from both New York City and Boston via I-95, making it an easy stop along the Connecticut shoreline. Amtrak’s Northeast Regional and Shore Line East trains both serve the local station, and once in town, everything from the marina to Main Street is within easy walking distance.