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The railroad remade the town's geography in 1873, when the Shore Line route and the Connecticut Valley line met at a junction here, and the shoreline that had launched ships began receiving summer visitors instead. Cottage colonies spread along the beaches, and on the peninsula between South Cove and the Sound the borough of Fenwick took shape in the late nineteenth century — shingled houses, a small golf course, and families who returned every summer for generations, the Hepburns among them from 1913.
The colony's first years were hard ones — Saybrook Fort stood under siege through the winter of 1636-37 during the Pequot War, and the settlement that survived grew slowly outward from the fort into a farming and seafaring town. By the eighteenth and nineteenth centuries Old Saybrook was a working port: shipyards on the coves, oyster beds in the rivers whose names still say so, and captains' and merchants' houses rising around the green — the Hart House of 1767 and the James Pharmacy of 1790 among the survivors, and the South Green itself now a National Register district of that prosperous port century.
Why People Visit Old Saybrook Connecticut
- Relax at Harveys Beach, shallow waters and soft sand for easy family time on Long Island Sound.
- Walk Fort Saybrook Monument Park, interpretive signs marking the 1635 fort site near the marsh and the river mouth.
- Tour the General William Hart House (1767), a Federal-era home with period rooms and gardens reflecting eighteenth-century town life.
- Stroll Saybrook Point, boardwalks and marinas with views to Lynde Point Lighthouse (1803) at the river mouth.
- Visit the Katharine Hepburn Cultural Arts Center on Main Street, an intimate restored theater hosting year-round performances.
- Drive across the causeway to Fenwick borough, a quiet shoreline community of shingled houses on the peninsula between South Cove and the Sound.
