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A 7-minute ferry ride brings you to the island between the forks.

Where Is Shelter Island and How to Get There

Shelter Island is a peaceful, 27-square-mile island nestled between the North and South Forks of Long Island. It's just a seven-minute ferry ride away from either Greenport on the north side or North Haven on the south side. 

Getting to Shelter Island is easy and scenic. It’s sort of a planes, trains, and automobiles travel situation, but you’re using your car -- or feet and a ferry. Visitors can drive or take the Long Island Rail Road to either ferry terminal, then enjoy a quick ferry ride to the island. Whether you're coming for a day trip or a weekend getaway, Shelter Island offers a perfect escape from the hustle and bustle. 

Top Things to Do on Shelter Island with Kids

1. Shelter Island Heights Pharmacy

Once you’ve arrived on the island, Shelter Island Heights Pharmacy on Grand Avenue is a good first stop for last-minute sunscreen, gum, or other trip necessities. They have old-school counter-service meal options for breakfast, lunch, and dinner, and also offer take-out. Pick up a free map of the island then venture on! You can easily navigate the roads with your vehicle, and parking lots are ample.

2. Piccozzi's Bike Shop

If you're on foot or want to explore at a slower pace, pop into Piccozzi's Bike Shop for a rental and zip around the island on two wheels instead of four. With rental options by the hour, half-day, or day, this bike shop also offers kid-sized bicycles and baby seat add-ons.

3. Kayaking

Yet another way to explore this island, kayaking offers a sweeping water vantage point. Kayak Shelter Island has rentals for self-guided, as well as two-hour guided tours. Head out in a single or double kayak or opt for a stand-up paddleboard. 

RELATED: 25 Great Things To Do with Kids in Montauk

Discover the wildlife that calls Mashomack Preserve home. 

4. Mashomack Preserve

Located three miles from the south ferry, Mashomack Preserve boasts 11 miles of coastline and acres of creeks, woodlands, and fields. Start out at the field house for interactive exhibits of the ecosystem on site. There are several trail options, from one to 10 miles, so choose wisely as to which you think your brood will handle best. We managed to do two miles with my boys, who were 8 and 10 during our last visit. The terrain was steep at times and bumpy, so tread carefully. Be sure to catch the bird feeding area inside as well. Trails are open dawn to dusk, seven days a week. Visitor Center bathrooms open 8am to 5pm, seven days a week, and Visitor Center exhibits open 10am to 3pm, Thursday through Saturday.

5. Sylvester Manor Farm

Sylvester Manor is a historic farm on Shelter Island that offers a unique opportunity for families to explore the island’s rich past. With its rolling green fields, centuries-old buildings, and a classic windmill, it’s a beautiful place to step back in time. From the 1810 windmill to the lush gardens to the 1737 Manor House, you'll be engaged at every turn here. As of publication, the Manor House is closed to the public while the house is undergoing refurbishment and restoration.  (Inside, the archaeology display is filled with fascinating artifacts, including Native American tools and pottery, early European coins and pipes, and even building materials from the island’s Dutch and English settlers, offering a glimpse into life hundreds of years ago.) Be sure to pop into the on-site farm stand where you can purchase a variety of tasty treats, including quiches, pocket pies, pesto, salsa, breads, and even lasagna! 

6. Mini-Golf

The Shelter Island Whale’s Tale Dessert Cafe & Miniature Golf Course is an 18-hole mini-golf course. It's rather simple, yet the design reminds you of a simpler time. There's a large water feature, but no mechanical or moving holes. Fiberglass figures of mermaids, turtles, and a water-spouting whale greet you at various holes. There are cute wooden cut-out photo booths on site, too. It also has picnic tables with umbrellas and a full Hershey's ice cream shop inside, as well as only 8 frozen yogurt, pies, frozen lemonade, and some retro video games. This recreational spot is open seven days a week, seasonally. 

7. Hit the Beach 

Beaches are located all along the island's coastline, and there is even an inland beach at Fresh Pond. A resident beach sticker is required for any vehicle that parks at a town beach between May 15 and September 15. Since 2015, $25 daily beach passes have been available for purchase online. Crescent Beach (a.k.a. Louis' Beach) is closest to the north ferry. Southold and Greenport on the North Fork serve as a backdrop to this beach. Wades Beach, near the south ferry, is the most popular for families. On our first trip in 2014, we opted to head southwest to secluded Shell Beach. A hook-shaped, one-lane dirt road leads to panoramic 360-degree views of West Neck Harbor and Shelter Island Sound. It's a great place to picnic and collect shells, as well as swim. However, there are no lifeguards on duty. Most recently, we visited Reel Point Preserve in Ram Island County Park. Located at the easternmost tip of the island, this beachy peninsula is laden with rocks and shells ripe for the picking. We were able to amass a sweet collection of jingle shells. You'll also see osprey, piping plovers, Monarch butterflies, and more.

RELATED: Family-Friendly Hotels on Long Island's East End

Grown-ups can enjoy an adult beverage at Shelter Island Craft Brewery, while adjacent Maria's Kitchen serves up tacos for the family.

Family-Friendly Shelter Island Restaurants

8. The Islander

This resident-tourist spot is perfect for family-friendly meals. Breakfast is served all day long, so my boys enjoyed French toast and Oreo pancakes for lunch. You can also eat outside, and we all know dining al fresco makes the meal extra tasty. Hit their takeout window for a to-go meal or see when their food truck is operating. 

9. Maria's Kitchen

Got a hankering for more roadside grub? Maria's is adjacent to the brewery and serves up tacos, burritos, nachos, and salads, as well as vegetarian options. It's perfect for a quick pit stop to or from the ferry. Opt for a seat in the garden to make this meal more memorable. 

10. Shelter Island Craft Brewery

This craft brewery is located on the same site as Maria's, so 'rents can grab a mug of suds while the kiddos wolf down tacos. The charming tasting room has beer, wine, and cider on tap, as well as non-alcoholic drinks. 

11. Salt

Sit harborside at the Island Boat Yard and marvel at the boats puttering in and out. There are plenty of shaded tables, and the menu is coastal-inspired cuisine in a cozy setting. This is ideal for seafood and raw bar lovers, as well as a kids' menu for your wee ones.

Where to Stay on Shelter Island with Kids

12. The Pridwin Hotel & Cottages

The Pridwin Hotel & Cottages is a historic waterfront resort offering elegant accommodations, a private beach, outdoor pool, tennis courts, spa, and water-sport rentals. Think vintage charm with modern family amenities. From pickleball to paddleboarding, it would be tough for kids to cry "I'm bored: here. Plus, kids love the outdoor movie nights and BBQ events. Families can also take advantage of a boat cruise on Fred's Folly.  

13. Seven  Shelter Island

A warm, comfortable boutique bed & breakfast nestled near Stearns Point, Seven Shelter Island offers family‑size rooms, lush gardens for morning relaxation, bikes for exploring, and a heated pool for swimming. Here, families can be quiet and beautiful with a hint of luxury at a moderate price. 

14. House on Chase Creek

This tranquil, eco-conscious inn offers rooms and a shared breakfast area in a historical setting within walking distance from the North Ferry port. While it is among the most affordable stays on Shelter Island, the House on Chase Creek offers thoughtful touches and easy access to nearby nature and attractions. 

A version of this article was posted in 2014. It was updated in August 2025.

Photos by the author