Things to Do in Shelter Island & Greenport
Discover the best things to do in Shelter Island and Greenport with this insider’s guide to Long Island’s North Fork. Explore beaches, historic sites, wineries, dining, outdoor adventures, and unforgettable sailing trips aboard SailSelinaNY’s classic 1926 wooden yacht. Perfect for weekend getaways, family vacations, and romantic escapes on the East End.
Top Things to Do on Long Island’s East End
Welcome to New York’s East End — where small-town charm, coastal beauty, and American maritime history come together. Whether you’re planning Long Island travel for a romantic weekend, a family vacation, or a quick coastal retreat from the city, there’s no shortage of things to do in Greenport and Shelter Island.
For travelers comparing Long Island sailing tours, SailSelinaNY offers a uniquely intimate experience, combining classic yacht charm with small-group sails around Greenport, Shelter Island, and Long Island Sound.
If you’re searching for Greenport things to do beyond the usual beach day, this guide will help you discover sailing adventures, hidden trails, historic sites, and unforgettable food and wine experiences.
At the heart of it all is SailSelinaNY, offering private sailing experiences aboard a lovingly restored 1926 wooden yacht, built right here in Greenport at Sweets Shipyard. Before or after your sail, discover the best of the North Fork activities— from family-friendly adventures and local museums to waterfront dining and world-class wineries.
North Fork Vacation Ideas for Long Island Travel
Family-Friendly Adventures
Explore beaches, lighthouses, sailing excursions, nature preserves, wildlife viewing, and kid-approved activities like pirate lore, treasure hunting spots, local playgrounds, the carousel and hands-on maritime experiences.
History-Rich Experiences
Visit historic estates, Native American heritage sites, the first U.S. production of Peter Pan, vintage boatyards, Captain Kidd treasure legends, the Grand Sachem’s domain, and waterfront towns filled with centuries-old stories.
Outdoor Activities
Enjoy scenic bike rides, hiking trails, paddleboarding, kayaking, beachcombing, farm tours, vineyards, and sunset sailing on Peconic Bay, Shelter Island Sound, and Greenport Harbor. Book a Greenport yacht charter with SailSelinaNY for sunset sails, day trips, or family outings — one of the top ways to explore the North Fork from the water and one of the best Shelter Island boat tours for hands-on sailing and wildlife spotting.
Family-Friendly Adventures & Outdoor Fun
Create memories your kids will talk about for years with a day of outdoor exploration. Sailing with SailSelinaNY is one of the most unforgettable Shelter Island activities for visitors looking to explore the East End from the water and experience the island’s coastal beauty up close.
SailSelinaNY Family Sailing Adventure – Step aboard our vintage yacht for a private hands-on sailing tour. Kids can help raise the sails, take the helm, or just enjoy spotting ospreys and sailboats on The East End.
Greenport Antique Carousel – Built in the 1920s, this waterfront carousel in Mitchell Park delights riders of all ages with hand-carved horses and bayfront breezes.
Mashomack Preserve (Shelter Island) – Explore over 2,000 acres of preserved coastline and woodlands. Easy trails make it ideal for strollers and small adventurers.
67 Steps Beach (Greenport)– A favorite local spot for beachcombing, photography, and family picnics.
Historic Sites & Museums
The North Fork’s maritime legacy is woven into every dock and boathouse. Dive into local history at these nearby museums:
East End Seaport Museum (Greenport) – Discover shipwreck artifacts, lighthouse history, and Greenport’s role in America’s boatbuilding past.
Railroad Museum of Long Island – Climb aboard vintage railcars and explore interactive exhibits that bring Long Island’s train history to life.
Sylvester Manor Educational Farm (Shelter Island) – Part farm, part museum, part cultural center — this 17th-century estate tells stories of history, agriculture, and community.
Greenport Village Historic District– Wander past 19th-century homes, charming boutiques, cafés, and galleries that blend the village’s working waterfront roots with modern-day charm.
Waterfront Dining & Local Favorites
Greenport and Shelter Island are packed with delicious dining options — from casual dockside bites to elegant farm-to-table cuisine.
Greenport Restaurant Guide
Claudio’s Waterfront – A Greenport institution since 1870. Fresh seafood, classic cocktails, and harbor views.
Noah’s – Upscale yet relaxed, known for small plates featuring seasonal North Fork ingredients.
PORT Waterfront Bar & Grill – Family-friendly with great service and an unbeatable sunset view.
Shelters Island Restaurant Guide
1901 Grill (Shelter Island) – Classic American coastal fare in a casual, welcoming atmosphere. Perfect for family-friendly dining, outdoor seating, and crowd-pleasing comfort dishes after a day on the water. 631-749-5466 • the1901grill.com
Léon 1909 (Shelter Island) – Mediterranean-inspired dishes served in a cozy, beautifully restored farmhouse. Known for its warm ambiance, creative cocktails, and elegant Middle Eastern + French flavors. 917-734-3471
SALT Waterfront (Shelter Island) – An island favorite for seafood and sunsets, with dock-and-dine access for boaters. The waterfront views, live music, and fresh raw bar make it the perfect summer dining vibe. 631-749-5535 • saltshelterisland.com
The Eccentric Bagel (Shelter Island) – Your go-to spot for breakfast or an energizing start before exploring the island. Bagels, breakfast sandwiches, and locally loved quick bites in a cheerful café setting. 631-749-5363 • eccentricbagel.com
Vine Street Café (Shelter Island) – A Shelter Island dining treasure offering elevated seasonal dishes featuring local produce and seafood. Refined yet welcoming, perfect for a romantic dinner or special night out. 631-749-3210 • vinestreetcafe.com
Seasonal Events & Festivals
Add some local flavor to your visit by timing your trip with one of Greenport’s or Shelter Island’s beloved annual events.
Greenport Maritime Festival (September) – Tall ships, seafood tastings, crafts, and live music fill the harbor.
Harborfrost (February) – Celebrate winter with fireworks, ice sculptures, and seaside festivities.
North Fork Crush Wine & Artisanal Food Festival (June) – Sip, sample, and mingle with winemakers from across the region.
Shelter Island Farmers Market (Summer Saturdays) – One of Shelter Island attractions they offer Local produce, flowers, baked goods, and more.