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Wades Beach is considered Shelter Island’s most family-friendly beach, located on the south side of the island with calm, gentle waters, lifeguards in season, and restroom facilities. The beach is less crowded than Crescent Beach and offers a quieter, more relaxed experience. A parking permit is required in summer — available from the Town Clerk’s Office. Read more...Address: 114 S Midway Rd
Shelter Island
New York
11964
United States -
Crescent Beach is one of Shelter Island’s most popular and beautiful beaches, located on the northwest shore near Shore Road. With calm, protected waters, soft sand, a lifeguard on duty in season, and restroom facilities, Crescent Beach is ideal for families and swimmers. The beach faces west, making it one of the best spots on Shelter Island for spectacular sunsets. Read more...Address: 35 Shore Rd
Shelter Island Heights
New York
11965
United States -
Whale’s Tale is a beloved Shelter Island institution offering classic soft-serve ice cream and a fun mini golf course. A perfect stop for families visiting Shelter Island, open seasonally throughout the summer. Read more...Address: 3 Ram Island Rd
Shelter Island
New York
11964
United States -
Paard Hill Stables, run by Ellen Lear (daughter of TV producer Norman Lear), offers horseback riding lessons for all levels on Shelter Island. A unique and memorable activity for visitors of all ages. Read more...Address: 41 Ram Island Rd
Shelter Island
New York
11964
United States -
Shelter Island is one of the best cycling destinations on Long Island, with quiet roads, gentle terrain, and stunning scenery. Bicycle rentals are available seasonally near the North Ferry. The island’s compact size makes it ideal for a half-day cycling tour. Read more...Address: 177 N Ferry Rd
Shelter Island Heights
New York
11965
United States
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