FOUNDED IN 1635 and known as one of the oldest settlements in Connecticut, the quaint seaside town of Old Saybrook, 27 miles west of Mystic, sits where the Connecticut River meets the Long Island Sound. Saybrook Point was the site of a prominent fort and an important coastal trade center during the 1700s and 1800s for vessels from river boats to ocean ships. Present day Old Saybrook is as charming as ever, dotted with clapboard houses, boutiques, antique stores, galleries, and cafes that brim with history.
Old Saybrook is proud to have been the home of legendary film star Katharine Hepburn. In 2009, the town opened “the Kate,” otherwise known as the Katharine Hepburn Cultural Center, which hosts theater productions, screenings and lectures about her life.
The town’s coastal location affords ample opportunity for water activities. To the southwest is Harvey’s Beach, a perfect spot for the entire family to cool off on a hot day. Kayakers will love exploring the North Cove and South Cove, both very protected.
And there’s plenty of non-water fun to be had too. In this bike-friendly town, cycle along the 10-mile loop out to Saybrook Point for breathtaking views, meandering along Long Island Sound as you go. Be sure to make a detour to check out Lynde Point Lighthouse, which sits at the mouth of Connecticut River. Ready for a game of golf? Stop by the Fenwick Golf Course, completed in 1896, to play a round. The waterfront Mini-Golf at Saybrook Point will make everyone in the family happy.
If you are in town during the last weekend of July, be sure to visit the 51st Annual Arts & Crafts Festival, which features more than 150 artists and crafters. And every Wednesday at 7 p.m. throughout the summer, Main Street hosts Concerts on the Green, a series of live music.
Where to Dine
- Fresh Salt (2 Bridge St., 860-395-2000) offers locally inspired dishes and handcrafted cocktails, all while overlooking the picturesque views of the Connecticut River and Long Island Sound.
- Liv’s Oyster Bar (166 Main St., 860-395-5577) Whether you dine in the main room, at the bar, or on the patio, Liv’s is a locals’ favorite for seafood dishes emphasizing local ingredients.
- Penny Lane Pub (150 Main St., 860-388-9646) is an English-style pub offering go-to’s such as half-pound burgers and shepherd’s pie, plus live entertainment.
Where to Dock
- Saybrook Point Inn & Spa (860-395-3080, saybrook.com) is a full-service resort is located at the mouth of the Connecticut River that accommodates boats up to 200 feet. New for the 2016 season is the environmentally-conscious marine fueling system and four new transient floating docks. Other amenities include indoor and outdoor heated pools, the Sanno Spa (facials, massage therapy, body wraps, manicures and more), a complimentary shuttle, fitness club, high-speed fueling, marine supply store and Fresh Salt, the onsite restaurant.
- Brewer Ferry Point Marina (860-388-3260, byy.com) is a full-service boatyard located three miles north of Long Island Sound. The marina has 130 seasonal slips with amenities including picnic areas, laundry and shower facilities, a swimming pool, WiFi, pump out, fuel and a ship’s store.