14 Fun Things To Do On Shelter Island

Shelter Island is a gorgeous island located off the eastern end of Long Island, New York. The island is full of activities and attractions, making it an ideal spot for a fun and relaxing vacation. From exploring the island’s beaches and nature trails to shopping, dining, and more, there is something fun for everyone on Shelter Island. Here are 14 of the most fun things to do on Shelter Island.

Shelter Island Town Beach

Go Fishing: Fishing is one of the most popular activities at the beach. Whether you’re a beginner or an experienced angler, you’ll find plenty of opportunities to catch some of the local fish. You can rent a fishing rod at the beach or bring your own.

Swim: The crystal clear waters of Shelter Island Town Beach are perfect for swimming. Whether you’re looking to cool off in the summer or take a dip in the winter, the beach offers plenty of options for swimmers of all ages and abilities.

Snorkel: The waters around Shelter Island Town Beach are full of colorful coral and sea life. Snorkeling is a great way to explore the underwater world and get up close and personal with some of the area’s most beautiful creatures.

Hike: The beach is also home to several hiking trails that offer stunning views of the island and the ocean. Whether you’re looking for an easy stroll or a challenging hike, there’s something for everyone.

Kayak: Kayaking is a great way to explore the waters around the beach. You can rent a kayak at the beach or bring your own. Kayaking is a great way to get some exercise and take in the stunning scenery of the island.

Visit the Beach Cafe: The Beach Cafe is a popular spot for locals and visitors alike. The cafe has a wide variety of food and drinks, as well as live music on the weekends. It’s the perfect spot to relax and enjoy a refreshing beverage while watching the sunset.

Visit a Museum: Shelter Island Town Beach is home to several museums, including the Shelter Island Historical Society and the Shelter Island Maritime Museum. These museums offer a great way to learn about the island’s rich history and culture.

Whether you’re looking for some relaxation or an adventure, Shelter Island Town Beach has something for everyone. From fishing and swimming to kayaking and hiking, there are plenty of activities to keep you busy. And with its stunning views and vibrant culture, it’s no wonder why Shelter Island Town Beach is one of the most popular destinations on Long Island.

Mashomack Preserve

The preserve features miles of trails with varying terrain, including grassy fields, woody forests, and rocky cliffs. Whether you’re looking to explore the coast or venture deep into the woods, Mashomack Preserve has the perfect trail for you. There are also numerous opportunities for wildlife viewing, such as bird watching and observing the local plants and animals.

For those looking to take a more leisurely approach, there are plenty of activities to enjoy in Mashomack Preserve. The beach is a great spot for swimming, sunbathing, and beachcombing. There is also a picnic area where visitors can enjoy the views and have a snack. For the more adventurous, there are kayaking and canoeing activities available.

One of the best aspects of Mashomack Preserve is its sheer beauty. The views are breathtaking, with lush vegetation, rolling hills, winding trails, and majestic wildlife. On a clear day, visitors can even see the distant skyline of Manhattan.

No visit to Mashomack Preserve would be complete without exploring its history. There are numerous historical sites throughout the area, including an old Native American fort and a colonial-era cemetery. For a truly unique experience, visitors can join a guided tour to learn more about the area’s past.

No matter how you choose to spend your time in Mashomack Preserve, you’re sure to have an unforgettable experience. As the late naturalist John Muir famously said, “In every walk with nature, one receives far more than he seeks.” Come experience the beauty and serenity of Mashomack Preserve for yourself.

Crescent Beach

One of the best things to do at Crescent Beach is to take a walk along the shore. The sand is soft and the views are breathtaking, making it a perfect spot to relax and watch the waves roll in. You can even spot some of the local wildlife, including the seals that often come ashore. The beach is also a great spot for shell collecting, so keep your eyes peeled for the perfect souvenir.

If you’re looking for something a bit more active, Crescent Beach is a great spot for swimming and surfing. The beach is known for its waves, providing plenty of opportunities for those looking to practice their surfing skills. There are also plenty of places to rent kayaks, paddleboards, and other beach gear, making it easy to explore the calm waters of the beach.

Fishing enthusiasts will also find plenty to do at Crescent Beach. The waters are filled with a variety of fish species, making it a perfect place to catch dinner. There are also plenty of charter boats available to take you out on the open sea.

No trip to Crescent Beach would be complete without a trip to the Shelter Island Lighthouse. This historic beacon has been guiding ships since the 1800s, and can be seen from nearly any point on the beach. Take some time to explore the lighthouse museum and learn more about the area's maritime history.

In addition to the activities mentioned above, Crescent Beach is also a great spot to stargaze. With the beach being so far away from light pollution, you can see the night sky in all its glory. Pack a blanket and enjoy the peaceful atmosphere of the beach at night.

Whether you’re looking for a relaxing getaway or a day filled with adventure, Crescent Beach has something for everyone. With its stunning views and wealth of activities, it is easy to see why this beach is one of the most popular destinations on Shelter Island.

South Ferry

The South Ferry to Shelter Island is a popular destination for visitors looking to explore the beauty and charm of Long Island. With a variety of activities and attractions available, it's easy to find something to do on Shelter Island. From beaches to hiking trails, there is something for everyone.

If you're looking for a unique experience, the South Ferry offers a variety of guided tours. From exploring the coastal bluffs to kayaking in the harbor, you can take in the sights and sounds of the island from the comfort of a tour boat. There are also guided fishing trips available, allowing you to catch your own dinner.

Shelter Island is also home to some of the best beaches on Long Island. Spend a day relaxing on one of the sandy beaches, or take a dip in the turquoise waters of Crescent Beach. For a more adventurous experience, take a hike on the Montauk Point State Park trails. You can also explore the nearby Mashomack Preserve, where you can spot a variety of wildlife such as deer, foxes, and even eagles.

If you're looking for a unique dining experience, Shelter Island has a variety of restaurants to choose from. From award-winning seafood restaurants to cozy cafes, you can find something to suit your tastes. The island is also home to a number of wineries, offering tastings of locally produced varietals.

If shopping is your thing, Shelter Island has plenty of shops to explore. Whether you're looking for souvenirs or art galleries, you can find it all on the island. You can also find unique handmade items in the local craft shops.

For a unique experience, be sure to check out the historic South Ferry terminal. The terminal has been in operation since the 1800s and offers a glimpse into the island’s past. It's also home to a variety of events throughout the year, including a farmers market, art shows, and live music.

Shelter Island is a great place to explore and experience all that Long Island has to offer. The South Ferry is the perfect way to get to the island and start your adventure. With its variety of activities, attractions, and restaurants, you’re sure to find something to do on Shelter Island.

Sylvester Manor Educational Farm

Characteristic	Description
Name	Sylvester Manor Educational Farm
Type	Farm in Shelter Island Heights, New York
Website	Go to website
Rating / Review count	4.3 / 36
Address	80 N Ferry Rd, Shelter Island, NY 11964
Phone	(631) 749-0626
Profiles

One of the farm’s most popular activities is its farm-to-table dinners. The farm’s chefs prepare a sumptuous meal featuring local, seasonal ingredients from the Sylvester Manor fields. Guests can enjoy this delicious meal while taking in the breathtaking beauty of the farm and the surrounding area.

Another popular activity is the educational programming offered at the farm. Visitors can learn about sustainable agriculture practices, wildlife conservation, and the history of Sylvester Manor. A variety of classes, workshops, and tours are available that focus on a range of topics.

The farm also offers unique experiences such as hayrides and stargazing. The hayrides take visitors through the farm’s fields and pastures, while the stargazing events provide an opportunity to learn about the night sky and identify constellations.

In addition to its activities, the farm also offers a variety of special events throughout the year. These events range from live music performances to art workshops to farm tours.

Ram Island Park

Families can spend their days exploring the nature trails, where they will find an abundance of wildlife. There are numerous birds to watch, and the park also has a nature center where visitors can learn about the local wildlife. Additionally, the park has a playground area for the little ones, as well as a picnic area for the whole family.

For those interested in fishing, Ram Island Park has plenty of opportunity. The park is well-known for its striped bass and bluefish fishing, but anglers can also try their luck with other types of fish. The park also has a boat launch, so visitors can bring their own boats to explore the area.

Kayakers can make their way around the beautiful waters surrounding Ram Island Park. The water is generally calm, and there are plenty of spots for snorkeling and scuba diving. There are also several kayaking tours that lead visitors to the nearby East End Lighthouse.

Hikers will love the trails at Ram Island Park. The trails are easy to navigate, and they lead through some of the most beautiful areas of Shelter Island. There are also several viewpoints along the trails providing a great place to take in the sights.

If visitors need some downtime, they can relax on one of the many beaches. There are several stretches of beach perfect for swimming, sunbathing, and beachcombing. Many visitors also like to spend time beach fishing, or collecting shells on the shoreline.

Havens House Museum

The museum is divided into several galleries, each highlighting a different aspect of Shelter Island’s history. The main gallery is the Maritime Gallery, which displays artifacts related to the island’s fishing, boatbuilding, and sailing industries. Visitors can explore the nautical history of the island, and gain insight into the lives of the fishermen and other islanders who lived and worked on the island.

The museum also has a gallery dedicated to the island’s industrial heritage. This gallery features artifacts from various industries, such as the iron works, the oyster beds, and the shipbuilding industry. Visitors can learn about the changes in technology and industry that took place on the island over the years.

The Havens House Museum also offers a variety of educational programs for children and adults. These programs include interactive activities, such as museum tours, hands-on workshops, and storytellers, which help visitors learn more about the island’s history. Visitors can also join in on guided hikes, which provide an opportunity to explore the island’s natural environment.

The museum also offers a variety of special events throughout the year. These events include lectures, performances, and art exhibitions. Visitors can enjoy a variety of activities, including a movie night and a family day.

The Havens House Museum is located in the heart of Shelter Island and is open year-round. Visitors can explore the museum on their own, or join a guided tour led by a knowledgeable guide. With its engaging and educational programs and activities, the Havens House Museum is a great place to explore the history and culture of Shelter Island. As a local resident, or a tourist, the museum is sure to provide an unforgettable experience.

In the words of a local guide, “At the Havens House Museum, you can explore the history and culture of Shelter Island through the eyes of the people who lived and worked here. It’s an amazing experience.”

So if you’re looking for a fun and educational day trip, the Havens House Museum is the place to go. With its engaging and interactive activities, the museum offers a unique and enjoyable experience that will stay with you for years to come.

Shell Beach

The beach itself is relatively small, but there is plenty to do while spending the day here. Visitors can relax on the beach, go for a swim in the crystal-clear waters, or explore the many tide pools located nearby. There are also plenty of activities and amenities available to keep visitors of all ages entertained.

Perhaps the most popular activity at Shell Beach is the collection of shells. The beach has a variety of shells of all shapes and sizes that can be collected and taken home as souvenirs. There are also plenty of unique rocks and fossils that can be found along the shoreline.

For those looking for a more active adventure, there are plenty of activities available at Shell Beach. Visitors can go kayaking and explore the nearby coves and inlets. The beach is also a great spot for stand up paddleboarding. There are also some great hiking trails in the area to explore.

For those looking to relax, Shell Beach is the perfect place to do so. There are plenty of beach chairs and umbrellas available to rent, as well as cabanas where visitors can enjoy some peace and quiet. There are also food and beverage vendors located around the beach, making it easy for visitors to grab a bite to eat or a cold drink.

Crescent Beach Park

One of the most popular activities at Crescent Beach Park is swimming. The beach is lined with a pristine white sand, and the gentle waves of the Atlantic make it an ideal spot for a cool dip in the summer months. There are lifeguards on duty during the summer, so it’s a safe place to take a dip. Additionally, the beach is equipped with showers and changing rooms so that you can freshen up after a swim.

Fishing is another popular activity at Crescent Beach Park. Fishers of all skill levels can find something to do here, from casting off the beach to deep-sea fishing charters. The waters around Shelter Island are teeming with a variety of fish, including striped bass, fluke, and bluefish.

For those looking for a more active day, there are plenty of water sports to enjoy. Kayaking is a great way to explore the coastline, and there are plenty of rental shops nearby that offer everything from single kayaks to entire fleets. Stand-up paddle boarding is also popular, and can take you to some of the most secluded spots along the beach.

For visitors who are looking for a bit of history, there are a number of historic sites located nearby. The Shelter Island Historical Society operates a museum right next to the beach, where visitors can learn about the island’s history and culture. Additionally, there are numerous lighthouses located around the island, most of which are open to the public.

Sunset Beach

When it comes to activities on Sunset Beach, visitors will find plenty to do. Swimming, sunbathing, and kayaking are all popular activities, and there are also a range of beach-related activities, such as beach volleyball and beachcombing. The beach also has a variety of restaurants and bars, perfect for enjoying a meal while watching the sunset.

For those looking to explore the area further, there are plenty of options. Visitors can visit the nearby Greenport Village, which is a bustling port town with a variety of shops, restaurants, and attractions. There is also the Shelter Island Historical Society, which offers visitors the chance to learn more about the island’s rich history.

If you’re looking for a chance to relax and take in some beautiful scenery, a visit to Sunset Beach is a must. The sunsets on the beach are truly breathtaking, and visitors can enjoy a peaceful evening under the stars. Additionally, visitors can take advantage of the nearby hotels and resorts that offer comfortable accommodations, perfect for a weekend getaway.

Finally, for those looking for a truly unique experience, Shelter Island is home to a number of festivals throughout the year, such as the Shelter Island Music Festival and the Shelter Island Brew Fest. There is also the annual Shelter Island Spring Celebration, which is a great chance to sample the island’s local cuisine and explore the island’s culture.

Whether you’re looking for a relaxing beach vacation, a chance to explore the island’s history and culture, or a unique experience, Sunset Beach on Shelter Island is the perfect destination. With its stunning sunsets and plenty of activities to keep you entertained, it’s the perfect spot to enjoy a memorable getaway.

Dering Harbor Marina

For the sailing enthusiast, Dering Harbor Marina offers a variety of sailboats to rent. From dinghies to larger vessels, there is a craft to suit any size group of sailors. Whether you’re a novice sailor or an experienced skipper, the marina has all the equipment and instruction you need. There’s even a sailing school on-site, so you can brush up on your skills before setting out.

If you’d rather stay closer to shore, the Marina also offers fishing charters and kayak rentals. The tranquil waters of the harbor are teeming with fish, making it a great spot for anglers of all abilities. For the more adventurous, kayaking around the harbor is an excellent way to explore the area.

The Marina also offers swimming for guests who want to cool off. With a variety of amenities, such as a beach area with lounge chairs and umbrellas, and a picnic area, Dering Harbor Marina is perfect for a day of relaxation and fun.

For those who enjoy the nightlife, Dering Harbor Marina has plenty of opportunities for entertainment. There are two restaurants on-site, as well as a bar and lounge, giving visitors plenty of options for a night out. The marina also offers live music and other entertainment on the weekends, making it a great way to spend a summer evening.

No matter what you’re looking for, Dering Harbor Marina has something for everyone. With its peaceful setting, variety of activities, and excellent amenities, the Marina provides an enjoyable experience for all. Whether you’re interested in sailing, fishing, swimming, or just relaxing, Dering Harbor Marina has something for everyone.

Sylvester Manor Gardens

One of the most popular activities at the manor is a guided walking tour. Tour guides will take visitors through the grounds and explain the history of the estate, as well as the many features, gardens, and structures that have been preserved over the centuries. Visitors can also take a self-guided exploration of the grounds, which includes a number of nature trails, ponds, and wooded areas.

Bird-watching is another popular activity at Sylvester Manor Gardens. The estate is part of the Shelter Island National Wildlife Refuge and is home to a variety of species, including hawks, owls, woodpeckers, and songbirds. The manor also offers a variety of educational programs, such as workshops on bird-watching and guided walks to learn about the local flora and fauna.

For those looking for a more laid-back experience, the manor also hosts a variety of events throughout the year. From concerts to lectures to art shows, there is always something to do at the manor. The manor is also a popular wedding and event venue, with a variety of indoor and outdoor spaces available for special occasions.

Additionally, the manor is home to a number of historic artifacts and documents, which can be seen in the library and archives. The historic documents include manuscripts, maps, photographs, and other materials related to the manor's history.

For those looking for a unique experience, Sylvester Manor Gardens is the perfect place to visit. From walking tours to bird-watching to educational programs, there is something for everyone, and the manor offers a chance to learn about the past and explore the natural beauty of Shelter Island. As one of the oldest estates in the country, it is a must-see for any traveler. As the late great author and Shelter Island resident, Tom Wolfe said, “Shelter Island is a place of beauty, a special spot in the universe.”

Gardiners Creek Park

At Gardiners Creek Park, visitors can explore a number of trails, ranging from easy to moderate hikes. The park is home to a variety of wildlife, including deer, foxes, rabbits, and a variety of bird species. Visitors can also spot a variety of plant life, including native wildflowers, shrubs, and trees. For those looking for a more adventure, the park also offers kayak and canoe rentals, allowing visitors to explore the creek and nearby rivers.

Fishing is also a popular activity at Gardiners Creek Park. Visitors can take part in catch-and-release fishing, as well as trolling for large-mouth bass. There are also plenty of other fish species in the park’s waters, including trout, catfish, and sunfish. The park is also home to a number of freshwater ponds, where visitors can try their hand at fly fishing.

For those looking for an educational experience, Gardiners Creek Park offers a number of educational programs. Visitors can learn about the area’s natural history and environment through guided tours, field trips, and workshops. The park also offers a number of bird-watching programs, allowing visitors to observe a variety of species in their natural habitat.

Mashomack Golf Course

The course is designed to challenge players of all levels, from the beginner to the professional. It features an 18-hole championship course, complete with bunkers, water hazards, and a variety of challenging holes. The course also features a 9-hole par 3 course, perfect for beginners and those who want to practice their short game.

For those interested in more than just golf, the course also offers a wide variety of activities. There are tennis courts, a swimming pool, and a restaurant. The restaurant offers breakfast, lunch, and dinner, and is also a great place to grab a drink after a long day on the course.

The course also offers a variety of packages for groups and individuals. Whether you want to play a round by yourself or with a group, there is a package that will fit your needs. The course also offers lessons, so you can get some help from a professional if you need it.

In addition to the golf course, Shelter Island also offers a variety of other activities and attractions. From beaches and hiking trails to biking paths and fishing spots, there is something for everyone on the island. There are also a number of restaurants and bars, offering a variety of local cuisine.

For those looking for a unique and unforgettable experience, a trip to Shelter Island is a must. Not only is the course a great place for a round of golf, but it also offers a variety of other activities and attractions, making it a great place for a weekend getaway. So, if you’re looking for a great golf experience and a chance to explore an amazing island, Mashomack Golf Course of Things to Do on Shelter Island is the perfect destination.

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