Nestled between the North and South Forks of Long Island, Shelter Island is a hidden gem waiting to be explored. This charming island, spanning just 27 square miles, offers a tranquil escape from the hustle and bustle of city life, all within a 90-mile drive from NYC.
With nearly one-third of the island preserved in its natural state, Shelter Island is a paradise for nature lovers and outdoor enthusiasts. The island’s intimate size, coupled with its unpretentious atmosphere, makes it an ideal destination for those seeking a relaxed, fun-filled getaway on the East End.
From pristine beaches and hiking trails to historical sites and culinary experiences, there’s no shortage of things to do on Shelter Island. Whether you’re looking for adventure or simply a chance to unwind, this article will guide you through the top activities and hidden gems that make Island Heights and beyond a perfect spot for your next fun escape.
Discovering Shelter Island: A Hidden Gem Between the Forks
Tucked away between the North and South Forks of Long Island, Shelter Island is a serene escape waiting to be explored. This charming island offers a unique blend of natural beauty, outdoor adventures, and cultural experiences that make it an ideal destination for travelers.
Location and Getting There
Shelter Island is strategically located between the North and South Forks of Long Island, making it easily accessible by ferry. You can reach the island via the North Ferry from Greenport or the South Ferry from North Haven. Both ferry rides offer a scenic 15-minute cruise, providing a picturesque introduction to the island.
To plan your trip, it’s essential to know the ferry schedules and costs. During peak summer months, ferries run frequently, and reservations are recommended to ensure a smooth journey. The North Ferry and South Ferry services are the lifelines connecting Shelter Island to the North and South Forks, facilitating easy access to this hidden gem.
When to Visit Shelter Island
The best time to visit Shelter Island depends on your preferences. The summer season, from Memorial Day to Labor Day, is ideal for beach activities and water sports. In contrast, the shoulder seasons of spring and fall offer a more relaxed atmosphere, with spring bringing blooming gardens and fall showcasing vibrant foliage.
For those who enjoy kayaking or paddleboarding, the Marine Water Trail offers a unique way to explore the island’s perimeter and harbor areas. Regardless of the season, Shelter Island’s natural beauty and charm make it a perfect destination for a weekend getaway or a week-long vacation.
Beautiful Beaches of Shelter Island
Shelter Island’s 20 miles of coastline are home to six unique beaches, each offering a distinct experience. Whether you’re looking for family-friendly swimming spots or secluded stretches for quiet contemplation, Shelter Island’s beaches have something for everyone.
Crescent Beach (Sunset Beach)
Crescent Beach, also known as Sunset Beach, is a favorite among visitors and locals alike. Its half-moon shape and magnificent sunset views make it a perfect spot for both families and those looking for a more sophisticated atmosphere. As the day progresses, the beach transforms into a lively scene with a touch of European vibes.
Wade’s Beach
Wade’s Beach is a haven for families, offering calm, shallow waters that are perfect for young children. The beach is well-maintained, with clean facilities, a covered gazebo for picnics, and tidy restrooms, making it an ideal destination for visitors with kids.
Shell Beach
Shell Beach is a narrow stretch of beach that offers breathtaking 360-degree views of the surrounding water. It’s a great spot for shell collectors, with an abundance of shells scattered along the shore, some even perched on tree branches. The gentle bay waves add to the serene ambiance of this beach.
Hay Beach and Reel Point
For a quieter beach experience, Hay Beach is the locals’ choice, perfect for swimming, snorkeling, and dog-friendly outings. It’s also a great spot for picnicking in more secluded areas. Reel Point, located on Ram Island, is a fragile sand peninsula that serves as an important wildlife habitat, featuring American beach grass, seaside goldenrod, and bayberry that attract migratory birds and butterflies.
When visiting Shelter Island’s beaches, it’s worth noting that vehicle parking permits are required during the summer months, available for $70 for the season. This helps maintain the beauty and accessibility of these wonderful beaches.
Outdoor Adventures and Natural Wonders
With nearly one-third of the island preserved in its natural state, Shelter Island is a paradise for nature lovers. You can explore the island’s diverse ecosystems, from forests and meadows to tidal creeks and salt marshes, making it an ideal destination for outdoor enthusiasts.
Mashomack Preserve Hiking Trails
The Mashomack Preserve is a 2,000-acre sanctuary that covers one-third of the island, offering diverse hiking trails ranging from 1.5 to 11 miles. You can explore the preserve’s natural beauty, spotting ospreys and other bird species along the way.
Water Activities: Kayaking and Paddleboarding
You can experience the beauty of Shelter Island’s waterways through kayaking or paddleboarding. The Coecles Harbor Marine Water Trail offers a serene paddling adventure, exploring the island’s calm creeks and harbors while observing marine life.
Shelter Island Country Club (Goat Hill)
The Shelter Island Country Club, also known as “Goat Hill,” is a public nine-hole golf course covering 2,512 yards of varying terrain. You can enjoy scenic views of the Peconic Bay and Dering Harbor while playing golf or simply relaxing at the course.
Whether you’re hiking through the Mashomack Preserve, paddling through the water trails, or golfing at the Shelter Island Country Club, Shelter Island offers a wide range of outdoor adventures for everyone to enjoy.
Best Things to Do on Shelter Island for History and Culture Lovers
As you explore Shelter Island, you’ll uncover a rich tapestry of history and culture that spans centuries. This charming island is home to numerous historical landmarks and cultural attractions that are sure to captivate anyone interested in the past.
Sylvester Manor Educational Farm
Sylvester Manor Educational Farm is a 243-acre historic plantation and nonprofit educational farm that offers a glimpse into the island’s rich history. This former 17th-century provisioning plantation has evolved into a center for historical research and education, engaging visitors of all ages in farm-based programs.
The farm stand is a must-visit during the season, offering organic homegrown produce and artisan delights. Explore the grounds to discover the windmill, burial grounds, and archaeological sites, which provide a unique insight into the lives of the people who lived and worked on the plantation.
Havens House Museum and Historical Society
The Havens House Museum is a fascinating glimpse into early Shelter Island life, managed by the Shelter Island Historical Society. The museum features exhibits on local history and the Havens Store, which offers books by local authors, unique locally-made merchandise, nautical maps, and more.
This cultural hub also hosts various events, including the seasonal farmers market, antique car shows, and children’s time travelers program, making it a great place to experience the island’s culture firsthand.
The Perlman Music Program
The Perlman Music Program is a cultural highlight on Shelter Island, offering evening concerts under a tent near Crescent Beach. Gifted young musicians and faculty from around the world perform during the summer season, providing a dose of culture on this picturesque island.
This premier cultural institution on the East End brings world-class classical music to the island, making it a must-visit for music lovers. The program’s reputation as a leading cultural institution is a testament to the island’s commitment to preserving and promoting the arts.
Family-Friendly Activities on Shelter Island
Shelter Island is a haven for families, offering a diverse range of activities that cater to all ages. From outdoor adventures to entertainment centers, there’s something for everyone on this beautiful island.
Whale’s Tale Mini Golf and Arcade
Whale’s Tale is a family entertainment center that features an 18-hole mini-golf course, arcade games, and a beloved ice cream shop serving Hershey’s ice cream. It’s a great place to spend a cloudy day or after dinner, enjoying air table hockey and old-school pinball games. Please note that Whale’s Tale is cash only.
Taylor’s Island Adventure
For a unique excursion, families can kayak to Taylor’s Island, accessible via the Coecles Harbor Marine Water Trail. Explore the historic Smith-Taylor Cabin, built around 1900, and enjoy a picnic in a scenic setting.
Kid-Friendly Beaches and Activities
Wade’s Beach is a favorite among families, with its calm, shallow waters perfect for young swimmers. The beach offers clean facilities, a covered gazebo for lunch breaks, and opportunities for shell collecting and sandcastle building. You can also bring your own kayak or paddleboard for an added adventure.
In addition to these activities, families can visit Camp Quinipet for summer programs, explore the child-friendly trails at Mashomack Preserve, or participate in the children’s time travelers program at the Historical Society. Shelter Island’s small size and minimal traffic make it safe and easy for families to explore by bicycle, with rental options available for all ages.
Dining, Shopping, and Nightlife
Shelter Island’s dining, shopping, and nightlife scene is a surprising blend of casual charm and sophisticated elegance. You can enjoy a wide range of activities, from dining at top-rated restaurants to shopping at unique boutiques and enjoying the evening entertainment.
Top Restaurants and Eateries
Shelter Island is renowned for its farm-to-table dining culture, with many restaurants offering seasonal menus that showcase fresh produce from local farms and the day’s catch from surrounding waters. Some top recommendations include 18 Bay, known for its husband and wife team offering special menus sourced from local farms on the East End, and Shelter Island Heights Pharmacy, an iconic soda shop serving classic breakfast and famous milkshakes. You can also enjoy a great lobster roll at Salt Restaurant.
Unique Shopping Experiences
Whether you’re looking for antiques, souvenirs, art, or fashion, Shelter Island has something for everyone. Marie Eiffel Boutique offers internationally acclaimed designers and custom fashion, while Finlay’s Fiction and Black Cat Books are must-visits for book lovers. Finlay’s Fiction specializes in new releases, and Black Cat Books is a vintage shop with over 20,000 titles. You can also find seasonal organic produce at Sylvester Manor’s farm stand and marine supplies at Preston’s Chandlery.
Evening Entertainment and Nightlife
The evening entertainment on Shelter Island is just as vibrant, with spots like Sunset Beach offering European-inspired cocktails while you enjoy the sunset. You can also head to Shipwreck Bar for live music and casual drinks or attend one of The Perlman Music Program’s summer concerts. The dining and entertainment scene changes with the seasons, with many establishments offering special events and themed dinners throughout the year.
Planning Your Perfect Shelter Island Getaway
To make the most of your Shelter Island getaway, plan ahead and consider the season. Optimal trip durations vary; a long weekend is ideal during summer for beach activities, while a mid-week stay during shoulder seasons offers a more relaxed experience.
Choose from various accommodations, such as boutique hotels like The Chequit in Shelter Island Heights, vacation rentals, and B&Bs. Booking in advance is recommended, especially for summer stays. Bringing a car via the North or South Ferry is advisable for exploring the island.
For a memorable trip, combine beach time, outdoor adventures at Mashomack Preserve, and cultural experiences at Sylvester Manor Educational Farm. Don’t miss the top restaurants and consider seasonal activities, like hiking in the fall or visiting during the spring for blooming gardens.
