Old Saybrook, CT
Old Saybrook’s history begins at Saybrook Point, which was inhabited by the peaceful Algonquin Nehantic Indians until 1590, when, along with other Algonquin tribes, they were conquered by the hostile Pequots from the north.
In 1623, Dutch traders established a village at Saybrook Point, hoping to lay claim to it before English settlers did. But the settlement lasted only a short time, and soon after the English, by way of the Council for New England, were granted title to the land, with John Winthrop Jr. appointed its first governor.
Upon learning that the Dutch were planning a return to Saybrook Point, Winthrop dispatched a vessel and 20 men to build a fort equipped with two cannons, as well as a small village. Naming the settlement Saye-Brook after two British members of the Council, that small fort with its two cannons fended off both the Dutch settlers, as well the Pequot Indians, during the Pequot War of 1636 to 1638. In time, Saye-Brook became Saybrook, and in 1854, it was formally incorporated as Old Saybrook.
Since then, the town has evolved into one of The Shoreline’s most popular places to live and vacation. Visitors often wonder how this charming little town has avoided the industry, wharves, and warehouses common to similar ports, given its spectacular location at the mouth of the Connecticut River. But the answer is quite simple — indeed, no deeper than the vast natural sandbar that has prevented navigation inland from Colonial days to the present.
Main Street is home to intriguing restaurants and stores, including Mirsina’s, a favorite breakfast/luncheon spot; The Paperback Café, a quaint eatery & coffee shop; Liv’s Oyster Bar, a superb little place; and the Penny Lane Pub, well-known for its great “pub grub.” Likewise, shoppers enjoy Saybrook Home’s tasteful home furnishings and apparel; Pearls & Plaid, a delightful women’s clothing boutique; and Driftwood of Old Saybrook, with its unique gifts and decorative items.
And Main Street is also home to the General William Hart House & Exhibit Gallery, a gem on the National Register of Historic Places; the Katharine Hepburn Cultural Arts Center, a town icon usually referred to as simply The Kate; and the Old Saybrook Arts & Crafts Festival held each October on the Saybrook Green.
Heading north on Main to the Boston Post Road promises some wonderful antiquing at Re-Unique Antiques or The Trove — and more great dining at the Parthenon Diner; Nancy’s Rosemary & Sage — a stylishly relaxed bistro and bar offering contemporary American cuisine; or Little Pub, a cozy, rustic tavern!
Beyond the town center are scenic side roads leading to charming homes and breathtaking views of the marshes and the sea. On Bridge Street are Harbor One Marina, a premier yachting center, and Liv’s Shack, where the lobster rolls are amazing. And at the end of College Street are the parks at Saybrook Point, Captain Pete’s Sea Sprite Sport Fishing charters, and Saybrook Point Resort & Marina, featuring sumptuous food, luxury lodgings, superb year-round spa services, and an impressive seasonal marina. It’s award-winning restaurant, Fresh Salt, is beyond excellent.
Nearby is Fenwick, where actress Katharine Hepburn spent a great deal of time at her family’s “cottage” — and playing golf at Fenwick Golf Club, a 9-hole course that wends its way through the borough and welcomes visitors to sign up for a tee time!
Continuing westward on Route 154 takes one through more lush neighborhoods to a glorious panorama of sea and sky, while Great Hammock Road wanders its way through the golden marshes and tidal estuaries that make Old Saybrook one of the Nature Conservancy’s Last Great Places on Earth.
North of town, Route 154 and Essex Road stretch past the Otter Cove neighborhood, revealing more beautiful homes, plus exceptional views of the river.
And north of Route 1 on Ingham Hill Road is Great Cedars Conservation Area, a peaceful site with marked trails open to the public — all adjacent to a pristine woodland tract that is among the very few intact coastal forests in New England.
