One of the best ways to experience the natural beauty of Shelter Island is by visiting the Mashomack Preserve. This 2,039-acre nature preserve offers miles of scenic hiking trails, birdwatching opportunities, and stunning views of the surrounding wetlands and woodlands. Be sure to keep an eye out for osprey, deer, and other wildlife during your visit.
Crescent Beach is a favorite spot among locals and visitors alike for its soft sandy shores and calm waters. Pack a picnic, bring a good book, and soak up the sun on this picturesque beach. You can also rent kayaks or paddleboards to explore the waters around Shelter Island.
For a taste of Shelter Island's history and agricultural heritage, take a guided tour of Sylvester Manor Educational Farm. Learn about the estate's 17th-century origins and its role in the development of the island. You can also participate in workshops and events focused on sustainable farming practices and local food production.
Shelter Island is home to several boutique vineyards that offer wine tastings in scenic settings. Spend an afternoon sampling local wines while overlooking the vineyards and the Peconic Bay. Many vineyards also host live music events and food trucks, making for a fun and relaxing outing.
Take a stroll through Shelter Island Heights, a charming Victorian-era village with historic architecture and quaint shops. Stop by the Perlman Music Program campus to catch a concert or explore the various art galleries and boutiques in the area. Don't forget to snap a photo of the iconic Heights Dock at sunset.
End your day in Shelter Island by dining at one of the island's waterfront restaurants. Enjoy fresh seafood, locally sourced ingredients, and stunning views of the water. Whether you prefer fine dining or a casual seafood shack, you'll find plenty of options to satisfy your taste buds.