Amelia Clark on the Shelter Island Ferry and More

Amelia Clark Practically Grew Up On The Shelter Island Ferry

If there’s one person you could consider the eyes and ears of Shelter Island, it might be Amelia Clark. The college junior was raised on Shelter Island and is part of the legendary Clark family that’s run the South Ferry since the 1800’s. She and the rest of her Clark crew work hard year in and year out making sure everyone coming from the Hamptons gets on and off the island as efficiently and safely as possible. To say she and her family are the heartbeat of Shelter Island would be an understatement.

Amelia Clark | Photograph provided by Amelia Clark

When she’s not issuing tickets on the ferry, you’ll find Amelia working at Shelter Island’s most high-end restaurant 18 Bay, babysitting some local kids, and even popping her head in at Seven! So naturally, we had to find out Amelia’s top Shelter Island picks and what she loves most about this magical place. 

Tell us about your family and the Shelter Island ferry…..

I believe we are the oldest family run ferry company on the East Coast, but it’s always been our family that ran it on Shelter Island. The house I grew up in was the original ferry house, and right outside our house is where the ferries dock at night, right on the beach. 

My grandfather and his brother run the ferry together. Before that it was their dad. My dad is the scheduler for the ferry. He’s worked there ever since we’ve lived there. My mom worked on the ferry when she was pregnant with me. I started training to work there over winter break.

How did that go?

It was really fun. There’s a lot of technicality to it. When you’re charging people, you have to go by different prices, sizes, lengths, and how many people are in the car. You have to take all of that into account. So there are a few different formulas. I’ll probably have to get retrained for summer because going back to school fills my brain back up, but it’s really fun. People who work there are so nice. We’re big on having a positive attitude and always being kind to everyone. Who would want to work somewhere that’s not a positive environment? No one wants that reflected onto them.

Is there ever any friendly competition with the North Ferry service?

18 Bay | Shelter Island Restaurant | Photography by Doug Young*

I don’t think about it as competition. They take people to the North Fork and we take people to the South Fork. Typically people will go through both of us depending on where they’re going, so I don’t think of it in a competitive way. I believe the North Ferry is a corporation. They do things differently. They are advancing more technologically, for example they have scanners. We haven’t gotten there yet, but I’m not sure we feel like we need to. 

Tell us about the training process….

It’s really hands-on. When you’re training, they have a trainer with you. So first you’re walking around with him or her for a bit to see what they do. Slowly, they implement different tasks, at first you’re loading and unloading and opening the gates. Then once you have that down, it’s OK, now you’re going to go to the windows, get money and click tickets. OK that sounds like a plan. I got that down. Then you keep doing it over the course of a week, and your trainer is there to let them know if you need any help with anything. I won’t know everything right away because there’s so much to remember and recheck up on. But everyone’s so nice and so helpful about it. A lot of people come across with a commuter or resident pass, so if you know the price of a car typically then you’re fine. 

What’s life on Shelter Island like now compared to when you were growing up?

Shelter Island Ferry | Photograph by Doug Young

I feel like it’s changed a little bit. The North Fork is getting “hamptonized,” so to speak. I can almost see it in some cases and feel it coming to us, just the people and the changing of businesses and the new businesses that come around in the summer. It’s like when I used to go to Sag Harbour as a child, it was very similar to Shelter Island. They were two small towns, but the vibe has gotten different as I’ve gotten older and it feels like it’s spreading through to here, too. I think we have a doctrine that we can’t have chains or fast food, but I can feel it spreading in different ways.  

What was it like to grow up on Shelter Island?

Shelter Island Ferry Captain | Photograph by Doug Young

I loved it. It can be complicated in some ways. There were small classes, I mean 23 kids were in my graduating class senior year. But it’s like a little family inside a bigger family. The population all year ‘round is not very big and you’re surrounded by the same kids your whole life. So their parents are your pseudo parents and they check up on you and support you. You always see your teachers around. You see them in the summer on the beach. But you can have amazing experiences because the classes are so small. You get to go on a Schooner trip in seventh grade. We went to Disney World in eighth grade. We get to go see Broadway shows fairly regularly. We also just feel like we have a lot of support that makes itself available to us.

Do you think you’ll stay on Shelter Island?

As nice as I think it would be to raise kids on Shelter Island, at some point I’d like to go away for a bit. I plan to summer here myself, and I’ll probably move back when I’m older, but I’ve always enjoyed big cities and really crowded places. I actually like background noise when I sleep. Shelter Island is eerily quiet at night for most of the year, so that’s made it difficult for me to sleep. My parents crack up. They used to take me to music festivals in New Orleans and Austin, and the noise would always help me go to bed. That was not the case for them. I’ve always felt comfortable with more people. I’m going to try to embrace that more.

What do you love most about Shelter Island?

The sense of community. It’s always been the best thing. I’ve always felt taken care of. Everyone looks out for you. I was so involved at school so I was my cousins’ TA in their art classes. When my cousin was in kindergarten, I was a TA in that class, too. And just even the involvement of babysitting. I babysat so many of those kids I’m a junior in college, so these kids I babysat are getting into middle school and high school, and I’ve watched them, all of them. All their parents know me.

Amelia Clark with family and friends at Shelter Island’s South Ferry | Photograph provided by Amelia Clark

Amelia’s Shelter Island picks:

Maria’s: “I love Maria’s. That’s always been my favorite place to go if we wanted to get food after school. The food is great, and in the summer it’s awesome to sit outside. Maria is a sweetheart. I went to high school with both of her kids. She always talks about her kids when I come in, and asks me how I’m doing. She always checks up on me.

The beaches: “Shelter island has the best beaches. Crescent Beach is awesome. The sand is less rocky. If you get there earlier, it’s really great. And everywhere is so safe. Our joke is that we don’t have a key to our house. We don’t lock our car doors. The beaches are also so safe.

18 Bay:  “Jimmy is the manager and Chef Adam and Elizabeth are the sweetest people. I’ve worked there since I was 16. They’re my other family. They check up on me all the time and are so supportive. The food is so good, too, and the menu changes every week. Sometimes they let me eat there.

Greenport: “There are so many cute shops and places to eat. I really like this one little shop called Tea and Tchotchkes. They sell crystals and really cute clothes and self-help books and tarot cards. I love going in there. I’ll go once a week to stand around and get crystals and a necklace or something.

Grindstone Coffee and Donuts, Sag Harbor: This place is so good. On Shelter Island we don’t have a lot of fast food. There’s no Dunkin Donuts etc. I’m not even a big donut person, but I love going in. It’s also across the street from Whites Apothecary, which has so many nice skincare and makeup brands. I love going in and debating whether I can afford to buy anything.

Stars Cafe: I love that place so much. They’ve got the best muffins and bread every morning, especially in the summer. They also make the best breakfast wraps and sandwiches. Right door is the pharmacy, which is really the pinnacle place on Shelter Island. The milkshakes are top tier.

Read more about the top things to do in Shelter Island here.

*View more photographs by Doug Young here.

The Top 25 Things To Do in Shelter Island

There’s no shortage of things to do in Shelter Island, New York. From the gorgeous beaches to the incredible expanses of nature to some of the best culinary outposts on Long Island, Shelter Island is a gem set in the middle of the East End with plenty of activities for people of all ages. We’re giving you an overview of all the fun you could possibly have on Shelter Island, whether you’re jonesing for a perfect day at the beach, an on-water adventure or some relaxing shopping in town. Shelter Island has it all.

Perfectly situated between the North and South Forks of Long Island, Shelter Island is one of the most beautiful islands on the entire East Coast. Whether you choose to visit on a crisp fall day or in the height of summer, there are so many things to do that you can simply take your pick. The island is surrounded on three sides by the Shelter Island Sound and on the fourth side by Gardiner’s Bay. That means that outside of swimming in fabulous beaches or setting sail on the bay, you’ll do well dining at any of the island’s restaurants, as they’re always sourcing ingredients from the best farms for local produce and the freshest catch of the day.

If you come visit us at Seven on Shelter Island, you can essentially design a daily itinerary that’s perfect for you. With so many things to do in Shelter Island, it might appear overwhelming, but we’re breaking down the essential list so that you can maximize your stay and enjoy our little slice of paradise.

shelter island ny sylvestor manor
The Sylvester Manor
Salt Restarant Bar and Grill
Black Cat Books

We obviously think Shelter Island is fantastic, but why should you visit Shelter Island? Well, aside from all the things to do, you’ve got the perfect combination of quaint vibes with a strong dose of style from the nearby Hamptons. Only on Shelter Island, there are no velvet ropes or waiting lists. It’s a come as you are, picture perfect place.

*All photography in this article is by Doug Young.

The Top 25 Things to do in Shelter Island

A. Beach/Swimming/Boating:

  1. Crescent Beach
  2. Hay Beach
  3. Shell Beach
  4. Wade’s Beach
  5. Reel Point

B. Sightseeing/Hiking:

  1. Shelter Island Kayaking
  2. Mashomack Preserve
  3. Shelter Island Country Club
  4. The Sylvester Manor
  5. Bootleggers Alley

C. Indoor Activities:

  1. Finlay’s Fiction
  2. Black Cat Books
  3. Shelter Island Brewery
  4. White Oak Wine Garden
  5. Shelter Island Pilates & Barre

D. Family-Friendly:

  1. Whales Tale
  2. Wade’s Beach
  3. Peconic Water Sports
  4. Camp Quinipet
  5. HiBerry Beach Lane

E. 21+/Adult Activities:

  1. Shipwreck Bar
  2. Sunset Beach Bar
  3. The Perlman Music Program
  4. 18 Bay Bar
  5. Salt Restaurant Bar & Grill

A. Beach/Swimming/Boating:

things to do shelter island ny wades beach
Wade’s Beach
  1. Crescent Beach: Known for its magnificent sunsets and halfmoon shape, this beach is the perfect combination of family-friendly and adult-oriented. Kids will enjoy swimming in the gentle, calming waters without gigantic waves or you can all rent paddle boards together without the fear of getting lost at sea (though there is a bit of a current, so stay close to shore). For the 21 and over set, Sunset Beach is the official party spot of the island, where a DJ spins beach tracks all day and the rosé starts popping by early afternoon. Think European vibes right here on Shelter Island. As its name suggests, sunset hour is the perfect time to pull up to this beach and take in all of the magic, and spotting the yachts that pull up is an added bonus. We love how close it is to Seven, just one block away!
  2. Hay Beach: For a quieter beach experience, head to this locals-only beach
    that’s perfect for swimmers. Grab your flippers and masks for a fun snorkel
    outing or bring your pup, as this beach in particular is very dog-friendly. We
    love packing up a picnic lunch and finding a spot that’s entirely our own for a
    sublime afternoon in the sun. You might also spot a few fishermen catching the
    day’s specials.
  3. Shell Beach: This narrow stretch of beach makes for some pretty epic 360-degree views of the water. If you investigate, you’ll find trees with shells perched on the branches like Christmas ornaments. Kids will love collecting all sorts of shells that decorate the sand as well. There are gentle bay waves here, which lends it a family-friendly feel, and this beach is the perfect place to plant your umbrella and chill out for the day. It’s also quite pup-friendly as well, making it one of the most popular things to do in Shelter Island.
  4. Wade’s Beach: This popular sunning spot is where the locals descend when
    they’re seeking a day at the beach. Bring your kayak, wind surf board or paddle
    board and get out on the water and enjoy. We love this beach for its covered
    gazebo, especially when you want to picnic in the shade, as well as its super tidy
    public restrooms. If you want to be truly adventurous, get a license and go
    clamming. The local hardware store in town sells the tools and shovels you’ll
  5. Reel Point Beach on Ram Island on Shelter Island: This fragile sand peninsula
    offers a beautiful wildlife habitat at the tip of Ram Island. You’ve got a mix of
    American beach grass, seaside goldenrod and bayberry, making it a haven for
    migratory birds and butterflies, like osprey, piping plovers and Monarchs. If you’re
    a nature lover, bring your binoculars and join the fun. Just note that vehicle parking
    permits are required at all Shelter Island beaches. They go for $70 in the summer

See Ana Gambuto’s Top 5 Beaches on Shelter Island here.

B. Sightseeing/Hiking:

  1. Shelter Island Kayaking: These kayak tours are fun for the entire family and give
    you a glimpse into Shelter Island, as only experienced from the water. Head out
    with a guide or explore on your own along the breathtaking Mashomack Preserve
    or head into nearby West Neck creek.

80 Burns Rd, Shelter Island, NY 11964
(631) 749-1990

mashomac shelter island hiking
  1. Mashomack Preserve: This massive preserve covers one-third of Shelter Island and offers various trails in difficulty levels to enjoy with a group or on your own. Mind the colored markers of the trail and set out exploring. If you love to bird watch, you could catch some wonderful beauties out there, or just take a walk in the incredible meadow. Be sure to meet the guide in the museum and have a quick chat before you set out. This landmark area of Shelter Island is protected by the Nature Conservatory and is one beautiful place to visit. Please note that there are no dogs, bikes or jogging here.

79 S Ferry Rd, Shelter Island, NY 11964
(631) 749-1001

  1. Shelter Island Country Club: Also known as Goat Hill, this club right across the street from Seven is a public, nine hole golf course with reasonable rates. We love the hills throughout the club, which make for a proper golfing workout, but carts are available for rent, as are clubs. The Flying Goat Restaurant sits at the highest point of the island so you can enjoy dinner and drinks after the 18th hole and take in the beautiful view.

26 Sunnyside Ave, Shelter Island Heights, NY 11965
(631) 749-0416

  1. The Sylvester Manor: Once a Native American hunting, fishing and farming ground, this Shelter Island mainstay has been home to 11 generations of the same family since 1651. Over time it’s evolved into an organic educational farm supported by the island’s neighbors and friends and encourages community, a celebration of food, and the arts. Walk the grounds with your dog on leash and explore the stunning grounds and don’t forget to pick up some fresh fruits and vegetables at the market on site.

80 N Ferry Rd, Shelter Island, NY 11964
(631) 749-0626

  1. Bootleggers Alley: Known for the best fishing on the island (be certain to get a fishing license at Town Hall first), this small stretch of beach is the perfect spot for a long walk to Crab Creek.

Shelter Island Heights, NY 11965

C. Indoor Activities:

  1. Finlay’s Fiction: Book lovers, rejoice. Shelter Island has its own independent bookstore that specializes in the newest fiction and non-fiction works, from bestsellers to literary ingenues, new writers, memoirs and stunning books to show off on your coffee table. They also have a lovely children’s book section and YA offerings. It’s one of the most relaxing things to do on Shelter Island on a rainy day, or really any day.

8 Grand Ave, Shelter Island Heights, NY 11965
(203) 650-7616

  1. Black Cat Books: Since 1996 this vintage book shop has been buying and selling fine used books right in the heart of Shelter Island. You can browse over 20,000 fine and used titles in all subject matters in an inviting, relaxed atmosphere. Black Cat Books is the place to discover something new, or to chase down that first edition tome you never thought you’d find.

54 N Ferry Rd, Shelter Island, NY 11964
(631) 725-8654

Shelter Island Brewery
  1. Shelter Island Brewery: This craft brewery specializes in small batch brews made with local ingredients. Each brew is concocted and made by owner and brewer Jim Hull, so you know it’s as local and authentic as it gets. The brewery’s staple selection of beers are supplemented with an ever-changing selection of seasonal beers and it offers yummy snacks and board games to enjoy while you sip. Get there early to score one of the outdoor picnic tables and be prepared to chill.

55 N Ferry Rd, Shelter Island, NY 11964
(631) 749-5977

  1. White Oak Wine Garden: Made by Winemaker, Tom Spotteck of Lenz Winery in partnership with Kristian Clark, this lovely little wine garden featuring White Oak Wines specializes in a laid-back and elegant ambience in which to enjoy this classic Rosé wine. The property’s tasting room features some of the best boutique wine by Local Winemakers as well as an eclectic mix of indoor plants and outdoor gardens to explore while you imbibe.

2 Manwaring Rd, Shelter Island, NY 11964
(631) 749-5814

  1. Shelter Island Pilates & Barre: Founder Suzette Smith, is a former dancer who offers core-based workouts for people of all ages. Now with two locations, you can access a daily schedule of pilates-based and barre workouts using state-of-the-art technology or work one-on-one with a trainer.

8 Grand Ave, Shelter Island Heights, NY 11965
(631) 749-5042

D. Family- Friendly

  1. Whales Tale: This wonderful ice cream shop, arcade and mini golf emporium offers hours of fun and is one of the most exciting things to do in Shelter Island with the entire family. Whether it’s a cloudy day, after dinner or you’re just looking to switch it up from endless beach days, you can’t beat hearty scoops of Hershey’s ice cream and a fun romp through 18 holes of mind-bending mini golf. We also love its indoor fun offerings, featuring air table hockey, old school pinball games and more. Please note, Whales Tale is cash only.

3 Ram Island Rd, Shelter Island, NY 11964
(631) 749-1839

Peconic Water Sports
  1. Wade’s Beach: This family friendly beach offers tons of fun for tots and parents, alike. For kids, well what’s better than playing in the water, collecting seashells and building sand castles? Parents can hang back in their beach chairs knowing that the beach offers super calm, shallow waters without the Atlantic Ocean waves. There’s also super tidy restrooms, a covered gazebo for lunch and options to bring your own kayak and paddleboard for an added adventure.
  2. Peconic Water Sports: Looking to get out on the water with the family? The best water sports rental on the entire east end, Peconic Water Sports is the only company on Long Island that uses brand new boards, waterskis, kites, life jackets and boats each and every year. Its staff is professionally trained in not only safety but having a lot of fun. Whether you’re learning how to wakesurf or trying to progress to the next level in water skiing, its knowledgeable staff keeps it fun and educational out on the bay.

3253 Noyack Rd, Sag Harbor, NY 11963
(631) 680-0111

  1. Camp Quinipet: This nature-focused summer camp offers all the trappings of a traditional camping experience with the options of overnight camp, day camp and a sailing camp for kids. It’s the perfect opportunity for kids to learn new skills while parents can enjoy a quiet day at the beach.

99 Shore Rd, Shelter Island Heights, NY 11965
(631) 749-0430

  1. HiBerry Beach Lane: This small, quiet beach on an inlet is a bit hidden among tourist crowds, and all the better. It’s amazing for a summer stroll, where you can walk around the point towards Hay Beach Point. It’s also dog friendly and has zero crowds, even in the peak of summer.

E. 21+/Adult Activities

  1. Shipwreck Bar: This is the go-to spot on the island for live music and a frothy drink or a good old bottle of beer. Outfitted out of a real boat, this boatyard favorite is a great pre-dinner drink spot, especially if you’re dining at Salt next door, or a great destination for happy hour if you’re biking around the island.

63 S Menantic Rd, Shelter Island, NY 11964
(631) 749-5535

  1. Sunset Beach: This European-inspired swanky chic spot has everything you’ll need to enjoy a perfectly made adult beverage at one of their two bars while enjoying the sunset. You’ll want to break out your most stylish looks for this spot. The scene-and-be-seen crowd won’t disappoint.

35 Shore Rd, Shelter Island Heights, NY 11965
(631) 749-2001

The Perlman Music Program
  1. The Perlman Music Program: Get a dose of culture on the island and enjoy an evening concert over at this hidden outpost on Crescent Beach, where gifted young musicians and faculty from around the world perform under the tent each summer season.

73 Shore Rd, Shelter Island Heights, NY 11965
(212) 877-5045

  1. 18 Bay: One of the top rated restaurants on the island and throughout the Hamptons, this husband and wife team offers a special menu each night of ala carte items sourced from the finest farms and local purveyors on the East End. They also make a great cocktail.

23 N Ferry Rd, Shelter Island, NY 11964
(631) 749-0053

  1. Salt Restaurant Bar & Grill: Watch your favorite team on the large screen TV with a basket of fries and a beer on tap or take in the beauty of the boats coming in at this marina favorite. Pro-tip: it’s got one of the best lobster rolls on the island. Stop by Shipwreck Bar down the road before dinner for a pre-sunset cocktail.

63 S Menantic Rd, Shelter Island, NY 11964
(631) 749-5535

As you can tell, there’s plenty of things to do in Shelter Island. The joy lies in discovering what you want to do when. Our recommendation? Try and do it all, and then come back for more.

Shelter Island Beaches – Your Complete Guide to Fun in the Sun

Shelter Island beaches are some of the best beaches in the Northeast, and certainly in the Hamptons.

While they may not have the gigantic Atlantic Ocean waves (and freezing temps!) and miles of sand to traverse before you even hit the water, what can we say? We’re partial to our beloved bay beaches. They’re calm, peaceful and intimate. You can literally get out of your car or bike over and set up your beach spot in five minutes flat. You also get prime boat and even yacht watching depending on the time of day you’re there. But whenever you decide to hit up the beaches in Shelter Island, you can be promised fun in the sun and prime relaxation. Think no crowds, no noise and only good vibes.

Amidst its 8,000 acres and 29 miles of East End beauty, we’ve counted about five well-known Shelter Island beaches outside of private swaths of sand and little coves that grace the island. These five beaches offer everything from a fun people watching scene to unique wildlife to family-friendly bonding time. Whichever beach you choose, you can’t go wrong. We’re breaking down our favorite Shelter Island beaches and what makes each one of them so special.

What makes Shelter Island beaches so special? For one they’re all incredibly clean. No matter where you head, you can be promised pristine surroundings and a respect of the water and environment. Another facet we love about beaches on Shelter Island is that they’re rarely crowded. Even Crescent (aka “Sunset) Beach, which is home to the Sunset Beach Hotel and adjoining restaurant, rarely gets too packed during the day. Reason being is that you need a beach pass to access any of our beaches, which isn’t that easy to obtain if you’re not a local resident. That leaves endless space for you and your crew to lounge without feeling like you’re on top of people. Beyond that, it’s the simple beauty of Shelter Island you gain at every beach vantage point that always has us wishing for one more beach day.

*All photography in this article is by Doug Young.

wades beach landscape
Wades Beach

Shelter Island Beaches You Must Visit:

Best Family Beach:
Wades Beach

Best Romantic Beach:
Shell Beach

Best Beach for Swimming:
Hay Beach

Best Beach to Explore Wildlife:
Reel Point

Best Beach for Adventures (Kayaking/Paddleboarding):
Crescent Beach

Best Shelter Island Beach For The Family – Wades Beach

Wades Beach is one of our favorite Shelter Island beaches for a number of reasons. One is that it has a roped off swimming portion of the beach that is often watched over by a lifeguard. It also features a clean changing room and bathroom facilities right there. We love the soft, gentle waves and wide open space, where even your most active brood has an area all to themselves on which to play. Picnic tables make for easy, no-fuss lunches, and the perfect setting for beach snacks. Visit anytime of day for fun in the sun.

114 S Midway Rd, Shelter Island, NY 11964

best shelter island beaches for family is wades beach
Wades Beach

Best Romantic Beach – Shell Beach

Shell Beach is considered the romantic one of the Shelter Island beaches as it’s just a remote sliver of expanse roughly three quarters in length that protrudes into the Shelter Island Sound. You would never just happen upon Shell Beach, but once you make the trip, you’ll be so grateful you did. Shell Beach lacks amenities and offerings but makes up for it in the form of clean warm waters, beautiful wildflowers and views of West Neck Harbor and South Fork. Parts of Shell Beach play host to wildlife like piping plovers as well as other nesting birds. But perhaps the reason it got its name is for the millions of beautiful tiny shells lining the beach that turn the sand an iridescent color when the sun casts itself in a certain light. This is the perfect spot for a romantic picnic, a deux, and maybe even an “I do.” Visit at dusk or sunset for a meditative beach moment.

Oak Tree Lane past West Neck Point, Shelter Island, NY 11964

best shelter island beaches for romance include shell beach
Shell Beach

Best Beach for Swimming – Hay Beach

This beach located on the northern tip of Shelter Island has magnificent views toward Greenport, East Marion, Orient and Gardiners Island with five points to access its sandy expanse. Historians tell us it got its name during the Revolutionary War, when trees were cut and picked up by ships to deliver to George Washington’s troops during winter months. After the war, tenant farmers paid their rent in hay, dropping it off on Hiberry Lane where ships picked the bales up to deliver to landlords. Anyway, regardless of nomenclature, we love swimming at Hay beach due to its vast size and total intimacy. It’s unfussy, super quiet and yet seems to just go on for miles. It offers plenty of privacy so you’ll never ram into a fellow swimmer. It’s dog friendly, too! Go in the morning for sunrise with the Northeastern views onto the nearby North Fork.

Point Lane, Shelter Island, NY 11964

Best Shelter Island Beach to Explore Wildlife – Reel Point Preserve

Grab your binoculars and birding sheets, this fragile sand peninsula of Reel Point Preserve is a picture perfect paradise for animal lovers. It was donated to the Peconic Land Trust in 1995 by Marsha and Herb Stern and is a beautiful wildlife habitat at the tip of Ram Island. With a topographic mixture of American beach grass, seaside goldenrod, and bayberry, the peninsula is a haven for migratory birds and butterflies, including osprey, piping plovers and Monarchs. Go early mornings for peak birding.

The End of Club Drive on Ram Island, Shelter Island, NY 11964

Best Beach for Adventures (Kayaking/Paddleboarding) – Crescent Beach

Home of the famous Sunset Beach Hotel and restaurant, Crescent Beach is one of the most popular Shelter Island beaches, featuring fun-the-sun crowds popping rosé all day and looking for a good time. But did you know it’s also one of the best beaches for adventures like kayaking and paddleboarding? Venture Out paddleboarding and kayak rentals is a vendor lining Crescent Beach during the summer, making it easier than ever to have an on-water adventure straight from the beach. All you have to do is head over and get sized for your next outing and you’ll be on the water in no time. Once you’re back you can check out the epic sunset, for which the beach is nicknamed before turning it in for the night, or head over to Sunset Beach and hang with the party crowd. Head out in the morning for a smooth experience before the boats come in and make waves.

Shore Road, Shelter Island, NY 11964

best shelter island beaches for adventure is crescent beach
Crescent Beach

When it comes to Shelter Island beaches, you simply can’t go wrong. Depending upon your mood, who you’re with and what you’re game for, the island offers an array of beaches that are perfect for any situation. The best part is that you can visit all of them!

(Please note for all Shelter Island Beaches, beach permits are free for residents; however, visitors can obtain a weekly vehicle permit at Seven B&B for access to all beaches on the Island. Also, camping, nude bathing, and motor vehicles are prohibited on all Town Public Beaches. Animals are prohibited on all Town Public Beaches from Memorial Day through Labor Day.)