Blake Walsh

20 Best Things to Do in Shelter Island, NY

  • Published 2022/11/17

Charming, vibrant, and utterly beautiful—these are words that come to mind when trying to pinpoint what makes this island town in Suffolk County so special.

Shelter Island boasts several scenic natural spots and historical places that’ll surely keep your trip brimming with new experiences.

From expansive nature preserves to beaches, there’s truly something for all the adventures you seek!

Are you planning a trip to this island town soon?

If so, here are the 20 best things to do in Shelter Island, New York:

Get Lost in Nature at Mashomack Preserve

Body of water at Mashomack Preserve

Maria T Hoffman /

If you’re looking to add some thrill and exciting adventure on your trip to Shelter Island, then you should visit the Mashomack Preserve.

This expansive nature preserve spans more than 2,000 acres of natural land, featuring scenic woodlands, marshes, and creeks.

The nature preserve was established for public use in 1980 dedicated to preserving natural lands in Shelter Island.

Hike the scenic trails that will lead you to the breathtaking natural vistas and see the rich flora and fauna of the area with a plethora of species.

If you’re going on an adventure with the entire family, don’t forget to pack some snacks and have a picnic under the canopies of the trees.

Mashomack Preserve is a must-visit if you’re an adventure seeker or you simply want to have some time away from the hustle and bustle of your daily cares.

Wade the Beach of Wades Beach

A trip to Shelter Island won’t be complete without spending a day out in the sun.

So make sure to pack your beach essentials and head out for a vibrant day at Wades Beach!

This white sandy beach is the perfect destination to wade the waves, try water recreation activities, and search for precious rocks and seashells.

Wades Beach offers pristine ocean views, where you can bask under the shore and enjoy the glistening blue waters reflecting from the sun.

The beach access is located along Midway Road in Shelter Island, with plenty of parking space perfect if you’re driving with the entire family.

Wear your sunscreen, pack your beach balls, and don’t miss out on a vibrant time by the beach on your trip to Shelter Island.

Get a Glimpse of History at Havens House Museum

Whether you’re a history geek or simply curious about the history of the town, you’ll surely enjoy a visit to the Havens House Museum.

The historical center features a collection of historical displays that showcase the island’s history.

You’ll get to see tons of exhibits ranging from art pieces, photographs, archives, and fascinating artifacts.

The museum is located along South Ferry Road, where you can learn and join educational programs to learn about the island’s history.

This gem is a must-visit in Shelter Island that’ll take you on a trip back in time.

Take a Ferry Ride with North Ferry Company

Take a relaxing ferry ride to Shelter Island or other nearby cities and marvel at the beautiful ocean views.

The North Ferry Company connects Shelter Island with Greenport and the North Fork offering short, smooth trips throughout the day.

Enjoy the warm sea breeze as you traverse through the sea, marvel at the stunning sights, and relax as you smoothly sail the calm waters.

Whether you’re heading out to the city or you simply want to enjoy a round-trip to have a nice, relaxing experience, then you should be aboard North Ferry Company.

So make sure to enjoy the experience as you aboard the ferry, and don’t forget to breathe in the warm sea breeze and breathe out your stresses.

Book Your Tee Time at Shelter Island Country Club

Name sign of the Shelter Island Golf Club

DanTD, CC BY-SA 4.0, via Wikimedia Commons

Head out for a game at Shelter Island Country Club.

The course is located at Sunnyside Avenue, covering over 2,500 yards of scenic, hilly terrain.

Shelter Island Golf Club is a historic golf course established in 1901, featuring the pioneering design of early golf layouts, and it was added to the National Register of Historic Places in 2009.

A restaurant in Shelter Island Country Club

DanTD, CC BY-SA 4.0, via Wikimedia Commons

The fairways feature a nine-hole course where you can tee off and enjoy a bit of challenge like it’s the old days.

The golf club also features a clubhouse, driving range, and maintenance facility that has all your needs covered.

Don’t forget to stop by the clubhouse to get some grubs and cold drinks for an energy boost before or after your tee time.

Go Kayaking at Taylor’s Island

Exterior of Smith-Taylor Cabin on Taylor's island

Darshanbib, CC BY-SA 4.0, via Wikimedia Commons

Take your trip up a notch by going on an exciting adventure where you paddle the waters of the sea and enjoy a day surrounded by the sea at Taylor’s Island.

This secluded area in Shelter Island is where you can find the historic Smith-Taylor Cabin built around the 1900s.

Taylor’s Island is a tombolo in Shelter Island, where a cabin was built dedicated to the recreation and enjoyment of the general public.

Join fun events, learn about the history of the place, or go kayaking in the waters.

There are plenty of things to do on Taylor’s Island, so you can also book your stay in the cabin if a day isn’t enough to enjoy the fun offerings of the area.

Take a Trip Back in Time at the Sylvester Manor

Gateway of Sylvester Manor

DanTD, CC BY-SA 4.0, via Wikimedia Commons

Explore the historic Sylvester Manor that started as a plantation in 1652 in North Ferry Road.

Since it was developed, this historic site has been passed on the long family line.

The manor is famous for its rich history and remarkable archives that date to nearly 400 years of American life.

Stone pillar of Sylvester Manor's gateway

DanTD, CC BY-SA 4.0, via Wikimedia Commons

The Sylvester Manor features the historic home set in the expansive grounds with a beautiful garden.

The windmill built in the 1920s remains in Sylvester Manor, set in a 4-acre field overlooking the Manwaring Road.

A trip to Sylvester Manor offers plenty of enriching experiences like educational tours, farm tours, hunting programs, and so much more.

Get Active at Fiske Field

Are you looking for a place on Shelter Island where you can enjoy a sunny afternoon out in the fields?

If so, you should visit the Fiske Field in Shelter Island, where you can enjoy some fun time out in the open field.

Take a relaxing run if you want some time to yourself, watch baseball games, or simply enjoy your time outdoors.

The field features an expansive open area with ball courts surrounded by lush trees where you can have a relaxing time under the shade.

Fiske Field is located along Bateman Road, the perfect spot if you want to kill some time but don’t want to stay in your hotel room.

Have an Old-Fashioned Dining Experience at Shelter Island Heights Pharmacy

If you want to try a unique dining experience, then head out for some grubs at the Shelter Island Heights Pharmacy!

The pharmacy features an old-style dining counter with the classic soda fountain, which gives out that traditional retro experience.

This quaint pharmacy slash diner offers a classic short order menu that’ll surely fill your tastebuds with delight.

Shelter Island Heights Pharmacy has been in business since 1883, located along Grand Avenue in Shelter Island.

Make sure to stop by this charming time capsule pharmacy and diner to experience what it’s like to dine in the old times.

Book Your Stay at The Chequit

If you’re looking for a place to rest your weary feet and have a good night’s sleep after your adventures, then you should book your stay at The Chequit!

This chic 4-star hotel is located along Grand Avenue overlooking the Peconic River Harbor and is close to the beach and ferry station.

The Chequit was established in 1872, featuring comfortable accommodation in Shelter Island, a cozy cafe, and a world-class restaurant.

This charming hotel has a lovely ambiance that’ll surely keep you relaxed and comfortable during your stay.

The Chequit combines the historic charm with modern comforts, making the ideal weekend getaway in Shelter Island.

Shop and Dine at Downtown Shelter Island

A weekend getaway won’t be complete without a bit of splurging and lots of dining, so make sure to head out to downtown Shelter Island.

Whether you’re searching for a vintage item, a souvenir, or something unique, there are plenty of quaint boutiques and specialty stores to choose from in downtown Shelter Island.

Stop by the restaurant to get some hearty grubs and appreciate the charm of Shelter Island by spending some time relaxing in a cozy cafe.

A trip downtown allows you to get acquainted with the community, meet the locals, and get a glimpse of the daily life on this charming island.

Make sure to take a little stroll and be on the lookout for interesting stuff at downtown Shelter Island!

See What’s Currently on Tap at Shelter Island Craft Brewery

Shelter Island Craft Brewery is a reputable, comparatively modest craft brewery that specializes in drinks produced using locally sourced components.

Have a taste and discover how every single brew is meticulously created and prepared by the proprietor, Jim Hull, a professional brewer.

Their staple selection of beers is supplemented with an ever-changing selection of seasonal beers.

Chocolate Stout, Firefly Rosé, Old World Pilsner, Raspberry Ale, and 114, their flagship IPA, are currently on tap.

Shelter Island Craft Brewery is operational Saturdays and Sundays from noon to sunset and is located in Shelter Island, NY, among both the North Fork and the Hamptons.

Watch the Sunrise at Shelter Island House

Shelter Island House was established in 1945 and has kept its traditional historic architecture while infusing a distinct touch of trendy and contemporary features.

The cozy Shelter Island House has nicely proportioned rooms with luxuries and features such as spa baths, robes, flat-screen televisions, wireless internet, trendy decor, and notable local artworks.

You may select between rooms on the first or second floors with garden views to enjoy nature as you sleep.

Begin and then plan your day by the porch while relaxing, sipping your morning coffee, or spending time at the beach.

Rent a bike and go sightseeing while feeling the breeze in the air if you want to break a sweat and get some exercise for the day.

Before heading to the pool for an evening plunge, you may enjoy cocktails or other beverages at the pavilion.

Dine at Vine Street Cafe

They manufacture food with authenticity by beginning with the best ingredients and eliminating shortcuts, whether crafting a meal or designing a new item for their marketplace.

Vine Street Cafe builds products from the ground up, carefully honing taste layers until they are flawless.

Their local producers, fisherman, and winemakers provide them with a bounty.

They use these wonderful ingredients and time-tested cooking methods to produce meals inspired by the seasons.

Co-owners, cooks, and companions in life and business Terry Harwood and Lisa Murphy have developed a system fueled by their love of the little things and hands-on dedication to everything.

Host your large gatherings and special occasions at Vine Street Cafe.

Make Use of the Amenities at the House on Chase Creek

Your weekend retreat is in the middle of Shelter Island Heights, House on Chase Creek.

The area is genuinely attractive, and there are fun things to do close by.

They are the ideal home center for outdoor exploring since they are close to the North Ferry port, the railway, bike rentals, nature trails, the beachfront, restaurants, and more.

Its original pinewood flooring and antiques have a timeless appeal, but they also have all the contemporary facilities and conveniences you want.

They offer a peaceful, tranquil ambiance, so visitors can sleep well.

House on Chase Creek is an excellent place to explore all year round due to the spring blossoms, the vibrant hues of fall, and the quiet of winter.

Have a Fun-Filled Day at Shelter Island Whale’s Tale

A nice and friendly whale once decided to take a trip to Shelter Island.

Following the 18 holes of the miniature golf courses will put you on the same enjoyable voyage that brought this charming whale to this lovely island.

Their buddy whale met several wonderful pals and visited some breathtaking sites while on their amazing tour.

From dolphins, penguins, tortoises, lighthouses, and boat anchors!

As you embark on this voyage with him, their whale would want you to indulge in his preferred ice cream flavors and his two favorite leisure moments, golf and video gaming.

The Whale’s Tale is a fantastic venue for your next entertaining event.

All-age birthday celebrations, family reunions, fundraisers, youth organizations, and more!

Other Things to Do Nearby

Take a Boat Ride Going to Long Beach Bar Lighthouse

Exterior of Long Beach Bar Lighthouse

Aleksandr Dyskin /

If you’re fascinated with charming lighthouses and their rich history, then head out on a boat ride to Long Beach Bar Lighthouse!

This historic lighthouse was first lit on December 1, 1871; it is dedicated to guiding the fishers and sailors of the sea.

Far view of Long Beach Bar Lighthouse

Aleksandr Dyskin /

The lighthouse is a white structure with a keeper’s dwelling; its early appearance as a screw-pile structure gave it the nickname “Bug Light.”

Marvel at the charming structure of Long Beach Bar Lighthouse and be delighted with the stories you’ll discover in this lovely spot.

A 10-minute boat ride to Long Beach Bar Lighthouse is worth it once you see the structure at its best.

A boat passing in front of Long Beach Bar Lighthouse

Laura Stone /

Ride the Antique Carousel

Exterior of Antique Carousel

Leonard Zhukovsky /

Nothing beats the classic fun of riding a carousel where you go in circles and up and down surrounded by glimmering lights.

This Antique Carousel captures all the classic fun of riding a carousel that’s sure to bring out the kid in you.

The Antique Carousel is located in Greenport, just a 10-minute ferry ride from Shelter Island, and it’s just a few minutes away from the ferry dock.

The carousel in Antique Carousel

Leonard Zhukovsky /

Prepare to be delighted with the intricate fixtures of this antique carousel that’ll make you feel a rush of nostalgia.

A carousel ride is sure to delight the youngsters and the young at heart, so make sure to bring out the kid in you and have the best time!

Antique Carousel

Leonard Zhukovsky /

Discover Maritime Stories at the East End Seaport Museum and Maritime Foundation

A boat at the side of East End Seaport Museum and Maritime Foundation

Leonard Zhukovsky /

Get a glimpse of history and learn about the maritime industry at the East End Seaport Museum and Maritime Foundation.

This charming museum is located in the heart of Greenport, which is just a 10-minute ferry ride away from Shelter Island.

The museum features a collection of artifacts and exhibits that showcases local stories in Greenport.

Aside from strolling through the museum, you can also join educational events that’ll let you delve deeper into the region’s maritime history.

The museum also arranges lighthouse cruises that’ll take you on a journey on the waters and give you a glimpse of the breathtaking scenery of the lighthouses.

Spend the Night under the Stars at Eastern Long Island Kampground

Take a break from your daily cares and enjoy the serene atmosphere tucked away from the bustling community.

The Eastern Long Island Kampground offers the best camping experience brimming with fun adventures in a serene location.

The campground features different camping sites with a range of glamping opportunities; you can stay in a cabin, a yurt, or a nice safari tent.

There’s also a pool, an archery range, a playground, and a basketball court that you can use during your stay.

The combination of the serene atmosphere with the modern comforts is sure to delight your senses.

Eastern Long Island is located in Greenport, just a 10-minute ferry ride away from Shelter Island tucked near downtown Greenport.

Final Thoughts

Shelter Island combines a rich history and breathtaking natural sceneries perfect for filling your getaway with many experiences.

Make sure to bookmark this list if you’re planning a trip to this charming island town soon!

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