Only a short ferry ride from Sag Harbor (or Greenport), Shelter Island offers a secluded weekend refuge, between Long Island’s North and South Fork. As a summer destination, this island comes alive between June through August as residents of Manhattan flock to the island to enjoy a peaceful reprieve from the everyday hustle and bustle of city life. Unlike its famous counterpart, the Hamptons, visitors can enjoy pristine beaches, serene hiking trails, and cozy cafés that are free from crowds and without a doubt, just as charming and picturesque. Whether you choose to spend your afternoon hiking around the island or prefer to mix and mingle with the A-list crowd at Sunset Beach, these are the 10 best things to do in Shelter Island for a weekend getaway this summer.
Hit the Beach
As an island, there's no shortage of swimming, sand, and sea. With plenty of Shelter Island beaches to choose from, some of the local favorites include Wade's Beach, which is excellent for families, and Crescent Beach, also known as Sunset Beach. On the south side of the island, you'll find Wades Beach, which has plenty of picnic tables, lifeguards, and a restroom. The adjacent Dickerson Creek, located behind Wade's Beach, is a paradise for clamming at low tide. However, if you want to dig for edible clams, you'll need a shellfish permit from the town hall. If you head back up to the northside, at only half a mile long, crescent beach is the most famous. Praised for its warm, calm waters, powdery sand, and 1950s' era striped umbrellas, thanks to The Sunset Beach Hotel, you'll find plenty of locals and visitors co-mingling on the shore.
Go Paddleboarding and Kayaking
Whether you're a veteran boarder or a SUP newbie, Venture Out on Crescent Beach has the best calm waters for taking out a board for an hour or two…or even three. Shelter Island Kayak, on the other hand, offers two-hour kayak tours from Coecles Harbor through nearby waterways if you'd prefer to avoid the crowds. Both companies can transport kayaks and paddleboards to the beach of your choice with a little advance notice, so there's plenty of options. At Shelter Island Kayaks, rentals are $30 for a two-hour minimum, while paddleboards are $30 an hour.
Rent a Bicycle
While most of the Shelter Island's beaches require a permit to park a car, if you're not a local and don't want to spring for the fee, you can rent a bike at Piccozzi's Bike Shop. Just a few blocks away from the North Ferry, visitors can walk over from Greenport and head to Piccozzi's Bike Shop, to rent a bike for $25 a day (or $20 for a half-day). Enjoy the sights around the beautiful town of Selter Island Heights before biking to Crescent Beach for a day of sand, sun, and fun. If you love it, then be sure to come on a Sunday to bike around Ram Island with plans to stopover for brunch at The Ram's Head Inn, who has a fantastic brunch on Sundays with entrees like brioche French toast and a duck confit hash with poached eggs and hollandaise. A stroll around the grounds is the perfect way to experience the easternmost part of the island that offers some of the best-uninhibited views.
Explore Shelter Island Heights
While we're on the topic of Shelter Island Heights, be sure to get lost amongst the cafés, locally-owned shops, and old-fashioned New England splendor. Grab a quick pastry for breakfast at Marie Eiffel Market, an adorable French bistro that will transport you to a side street in Paris, on the way in from the North Ferry. From there you can window-shop the island's collection of charming shops and enjoy the harbor views while you head up the hill to grab a coffee at Stars Café, or a Neapolitan-influenced pizza at Isola, and finally, (you can not leave the island without) a visit to the Shelter Island Pharmacy to try their legendary bacon, egg, and cheese on a roll.
Hike Mashomack Preserve
Protected by the Nature Conservancy, together with the residents of Shelter Island and Long Island, Mashomack Preserve covers a full one-third of the island. With 11 miles of coastline, woodlands, and acres of creeks and fantastic hiking trails, allow yourself a few hours of exploration as you hike through easy terrain in a beautiful serene setting. The mix of untouched coastlines, tidal creeks, and woodlands makes for a great place to spot ospreys, turtles, and other endangered wildlife. Be sure to head to their website to check out what's happening at the manor house, which, in addition to the best social events of the summer, offers a variety of environmental programs for adults and children.
Sip Some Craft Brews at the Shelter Island Brewery
If you want to mingle with the locals, visit the Shelter Island Craft Brewery. They brew their own small-batch beers using local ingredients and have fun, quirkily named beers like Nude Beach Ale. With plenty of well-shaded outdoor picnic tables, enjoying a nice fresh cold one away from the sun is the perfect way to sip the afternoon away. If you do get hungry, you can always pop into neighboring restaurant Maria's Kitchen where delicious chips and guacamole, pico de gallo, and chicken tacos are always on the menu.
Listen to Live Music at Shipwreck & Salt
An island favorite for visitors, locals, and boaters, The Shipwreck Bar at SALT Waterfront Bar & Grill is an old schooner transformed into an open-air bar that's been serving up drinks, food, and live music all summer long. While the posh elite call ahead to moor their boat directly to the boatyard, most patrons just enjoy a game of cornhole, a beanbag toss game, between cocktails, which always makes for a great way to make new friends. Just a few steps away, the main restaurant, SALT Waterfront Bar & Grill, also doesn't disappoint with a daily raw bar, a wide selection of locally caught seafood, as well as plenty of summery, easy-drinking cocktails.
Dine al Fresco
While there's plenty of restaurants on the island to choose from, like casual picnic tables at local diner The Islander or upscale fine dining at Vine Street Cafe, come summer, almost all of the restaurants offer outdoor seating. While it's well-known that Commander Cody's has the best seafood on the island, the locals will tell you their best-kept secret for dining out on a Wednesday is at the Pridwin Hotel. In summer, this classic hotel's front lawn is the scene of one of the best an all-you-can-eat cookouts. Not to mention, the upstairs balcony has one of the best dining views overlooking the ocean, crescent beach, and even Greenport (far off in the distance). For a more upscale-European vibe, you can walk a few steps down Shore Road to dine at The Sunset Beach Hotel for farm-fresh crudites and steak frites, followed by an apéritif.
Golf for the Day
If you'd rather avoid paddleboarding and sand, stay on land and try your hand at the local golf course. The Shelter Island Country Club is a public nine-hole course that covers 2,512 yards of widely varying terrain. Situated on one of the highest points on the island, you can't go wrong with spending a day playing golf with the best panoramic views of the Peconic Bay and Dering Harbor. We can't promise you'll set any course records, but we can guarantee they'll always be cold brews at The Flying Goat restaurant and bar waiting for you. As for aspiring golfers to be, you can take the kids to the Whale's Tale mini-golf course, where post-game victories are better celebrated by ice cream and games ar the Tuck Shop.
Grab a Drink at Sunset Beach
For many visitors, the two-story party scene at Sunset Beach, well known for it's iconic St. Tropez inspired yellow and white decor, outdoor fire pit, and ice-cold Frosé (a rosé wine slushie), is not to be missed. Many patrons arrive by boat—or more accurately, by yacht—to mingle with friends over delicious cocktails while dancing the night away with DJ Arman Naféei. While the hotel comes alive in the nighttime, during the day, hotel and restaurant guests can keep the party going by ordering drinks under colorful umbrellas on Crescent Beach or cure their hangover with a relaxing massage on the beach.