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Ferries loaded with coolers, bikes and beach chairs leave Bay Shore all summer long for the car-free villages of Fire Island, making this South Shore hamlet the main mainland gateway to the barrier beach. Bay Shore lies on the Great South Bay in the Town of Islip, about 50 miles east of Manhattan.
In the late 19th century wealthy New Yorkers built summer estates and hotels along the bay here, and a few traces remain, from the colonial Sagtikos Manor, where George Washington slept in 1790, to the Spanish-style home of the architect Rafael Guastavino Jr. The town later grew into a busy commercial center for Suffolk County.
Today visitors come for the ferries to Ocean Beach and Kismet, dinner and drinks along a revived Main Street, shows at the Boulton Center and quiet walks in Gardiner County Park. The grand estates of Bayard Cutting Arboretum and the beaches of Heckscher State Park are a short drive east.
Fire Island Ferries leave from the docks off Maple Avenue for Ocean Beach, Kismet, Saltaire, Fair Harbor and other western Fire Island communities, a crossing of about 30 minutes. A taxi or shuttle links the dock with the Bay Shore train station. Arrive early on summer Fridays, when boats and parking fill up.
The liveliest village on Fire Island, reached by ferry from Bay Shore, with a wide ocean beach, boardwalks, wagons instead of cars, and casual seafood spots and bars. Day-trippers can swim, walk the sand and return on an evening boat. Note the village's strict local rules, including bans on eating on the beach and alcohol in public.
The westernmost community on Fire Island, a short ferry ride from Bay Shore, with sandy lanes, small cottages and a relaxed bar scene facing the bay at sunset. From here you can walk west along the beach toward the Fire Island Lighthouse. Bring supplies, as there are only a couple of places to eat and shop.
A Suffolk County park on Montauk Highway in West Bay Shore, with easy trails through woods and meadows that lead to views over the Great South Bay. Horseback riders and dog walkers share the paths, and birds are plentiful in spring and fall. Entry is free and the trails are flat, ideal for a short morning walk.
About five miles east in Great River, this former estate of William Bayard Cutting has walking paths through pinetum, rhododendron and azalea gardens and wildflower meadows along the Connetquot River. The Tudor-style mansion has a cafe. Spring bloom in May is spectacular; there is a vehicle fee in season.
A large state park in nearby East Islip with calm bay beaches, campsites, picnic groves and wooded trails where deer are often seen. It is busy on summer weekends but rarely crowded on weekdays. Bring bikes for the park roads, and pay the vehicle fee at the entrance in summer.
A manor house begun around 1697 in West Bay Shore, where George Washington stayed during his 1790 tour of Long Island. Owned by Suffolk County and run with a historical society, it has rooms furnished across three centuries and gardens. Tours run on limited summer days, so confirm the schedule before visiting.
The Spanish Revival home built for himself by Rafael Guastavino Jr., the architect famous for the tile vaults of Grand Central Oyster Bar and many New York landmarks, is listed on the National Register of Historic Places. It is a private home, so view it respectfully from the street.
An intimate theater on Main Street run by the YMCA, presenting concerts by touring musicians, tribute bands, comedy and community theater throughout the year. With a few hundred seats, every seat is close to the stage. Combine a show with dinner at one of the nearby restaurants on Main Street.
Bay Shore's Main Street has become one of the South Shore's busiest dining strips, with seafood houses, Latin and Italian kitchens, gastropubs and cocktail bars a short walk from the marina. Summer evenings bring sidewalk tables and live music. Weekend reservations are wise, and free municipal lots sit behind the stores.
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