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22+ Long Island Adventures That Should Be On Everyone’s Summer 2022 Bucket List

May 13, 2022

There is nothing quite like a Long Island summer.  All year long locals and those who have been lucky enough to visit, dream of the season filled with spectacular boat days, the best lobster rolls in the world, outdoor concerts at the iconic Jones Beach, lawn parties where the rose is flowing and so much more.

From wine tasting among a sea of flower fields, to diving with sharks off the coast of Montauk, there is no shortage of epic outdoor experiences across the region.  That’s why our team gathered 22 of the most bucket-list worthy adventures for living your best #LongIslandLife this summer.  While some include iconic destinations and events proudly home to our region, our list offers many incredible off-beat experiences and hidden gems that will help make summer 2022 the best one yet.

Can’t Miss Summer 2022 Adventures on Long Island

1. Celebrate LGBT Pride in Epic Fashion with the “Invasion of the Pines” (Cherry Grove & Fire Island Pines)

Fire Island is a world-renowned destination for LGBTQ travel year-round, but the best time to visit is in the summer. During the warmer months, the communities transform into a hot beachfront destination rich with pool parties, daytime soirees, dancing, expertly crafted cocktails, and boutiques that stock items exuberant of island life in its prime.

Insider Scoop: Every year on July 4th, residents of Fire Island’s Cherry Grove and the surrounding mainland put on their best drag and catch a ferry over to Fire Island Pines where there’s a parade that spills out into a community-wide party at the Sip-N-Twirl and other waterfront clubs. As each drag queen leaves the ferry and marches onto the dock, she is announced by Panzi, the original 1976 invasion leader, now mistress of ceremonies. Insider’s tip: Those looking to attend the festivities must arrive at the Fire Island Pines dock no later than 11:00 a.m. as the ferry with the Drag Queens arrives at the Pines from Cherry Grove around noon.

2. Kickoff the Summer early with a Luxury Boat Show at the first-ever AQUAVERSE 2022 (Greenport)

Did someone say #YachtLife?! Kick off the summer early with a new one-of-a-kind event slated to take over the picture-perfect Greenport community. Anchored at the iconic 150-year-old restaurant Claudio’s Waterfront, the first ever  Aquaverse is free to attend and showcases luxury boats and yachts, flite board and water jet demonstrations, aquaculture events, speakers, fresh seafood, and a boatload of family fun! VIP Experience tickets are available for sale which include private yacht charter transportation to and from the event, restaurant reservations, a complimentary bottle of wine and entry into the hospitality lounge.

3. Take Memorial Day Weekend to New Heights & See the Fighter Jets at the Bethpage Air Show at Jones Beach (Wantagh)

bethpage airshow jones beach state park memorial day weekend

Soar into Memorial Day Weekend at Jones Beach State Park with the annual Bethpage Air Show – a spectacular and symbolic start to the summer season.  The annual aeronautic spectacle over the world-famous beach is arguably the most popular and largest airshows in the country, attracting upwards of 289,000 people in 2018. The show is welcoming back the US Navy Blue Angels as headliners and will feature stunts by dozens of vintage aircrafts.  Joining the Blue Angels will be a long list of both military flight teams and civilian performers, including the US Army Golden Knights Parachute Team, the U.S. Coast Guard, the U.S. Navy F-35C Tac Demonstration Team, and the world-famous Skytypers a widely known female aerobatic pilot, and more.

4. Get a Wakeboard Lesson & Pull up to Dinner by Boat with Over-The-Top Watersports Charter (Northport)

You’ve done paddle boarding and kayaking so kick it up a notch this year and try wakeboarding!  And you don’t have to head to Long Island’s crowded East End for an ‘Over the Top’ experience.  Over-The-Top Watersports charter and rental company is in the heart the historic, harbor front village of Northport, which still bears the trolley tracks laid in the early 1900’s as well as the vintage sweet shop operating since 1929.  The watersports company offers Wakeboarding,  Wakesurfing, and Waterskiing, lessons for all ages as well as tubing – just for fun! Not ready to hit the waves? Take a cruise during golden hour and capture unrivaled views (and photos) of the Northport’s harborside hills lined with sail boats and stunning Victorian style homes before pulling up to a local dockside restaurant for dinner by boat.

Insider Scoop: Discover Long Island readers can score 10% off when they book a reservation before June 1st –no coupon code necessary.

5. Live like Jay Gatsby – It’s the Roaring 20’s! (Various locations)

Long Island’s historic Gold Coast is home to stunning grand estates set against pristine gardens and shimmering coastlines. Tour the mansions of the Roaring Twenties where industry tycoons (including the Vanderbilts and Guggenheims) reigned supreme and served as the inspiration behind The Great Gatsby.  Stay overnight at the luxurious OHEKA Castle, often serving as a set for major Hollywood productions.  A few must-see mansions for the ultimate gilded age experience Old Westbury Gardens (Westbury), Sands Point Preserve (Sands Point), Coe Hall (Oyster Bay), Glen Cove Mansion (Glen Cove), Chelsea Mansion (Muttontown), and Marshall Field Estate (Lloyd Harbor).

6. Break Out the Fedoras & Feathered Hats and Head to the Belmont Stakes (Elmont)

Break out the fedoras and fascinators for the 154th Belmont Stakes at Belmont Park Racetrack. The iconic event, also known as “The Test of the Champion,” is the third leg of the Triple Crown—one of the most renowned horse-racing events in the world.  And did you know it takes place on Long Island? Whether you’re into betting on horses or not, attending the Belmont Stakes where history was made with Triple Crown winners including Secretariat and Justify, should be on everyone’s bucket list.  And it’s more affordable than you may expect with tickets as low as $40. The experience isn’t complete without sampling the Belmont Jewel—a bourbon, lemonade and pomegranate juice cocktail.  You can bet bartenders at the Garden Terrace will be mixing up plenty of this potent punch on race day.

7. Capture Photos of THE most Instagrammable, Euphoric Floral Oases in the Nation (Various locations)

Long Island boasts some of the most Instagrammable, euphoric floral oases in the nation.  And a few of these must-see flower fields will be in full bloom during the summer.  Lavender by the Bay features picture-perfect dreamy lavender farms with locations in East Marion and Calverton which also host farm stands that sell fresh lavender bunches, lavender honey, and other seasonal items. Waterdrinker Farm is known for its famed Tulip Festival in the spring and u-pick sunflower fields in the summer.  Visitors to the farm can spend the afternoon frolicking through the sea of yellow, checking out the collection of farm animals— and enjoying the sunflower fields at sunset – a summer vibe that cannot be matched!

8. Tee off where the pros golf at Long Island’s Championship, world-renowned courses (Bethpage)

Bethpage Black Golf Course on Long Island

Long Island has long been a golfer’s paradise for those “in the know.” As the host destination of 23 major golf championships, the region’s relationship with the professional sport dates back to the late 1800s. Most recently, Bethpage Black Course hosted The 2019 PGA Championship, the 2012 and 2016 Barclays PGA Tour events, and is set to be the site of the 2025 Ryder Cup—the biggest international golf event in the world. And the best part is, it’s a municipal course so it’s open to the public and even you can swing on the same course as some of THE best pro golfers to ever have lived.

Insider scoop: Bethpage State Park offers an abundance of beautiful hiking trails, paved biking and walking paths, open fields, and is a fabulous site for birdwatching or a picnic. 

9. Test Your Limits at WildPlay Jones Beach (Wantagh)

WildPlay Element Park at the iconic Jones Beach will put your endurance to the test with its many rope courses, 700-ft. long zipline, and 40-ft. bungee jump while overlooking the most visited beach in the state.  With three levels of obstacles to choose from, the park is the perfect place for kids and adults alike. Afterwards, hit the Jones Beach Boardwalk for even more family-friendly activities, food, and beach access.

Insider scoop: If you want a sneak peek of what to expect be sure to check out this episode of Long Island TV or our TikTok.

10. Swim Passed shipwrecks & Sharks for an Exhilarating spearfishing excursion (Montauk)

Believe it or not, you don’t have to take a trip to the Caribbean or Florida Keys to spearfish – or swim with sharks. Montauk-based Sea Turtle Dive Charters offers private inshore and offshore spearfishing excursions (for up to 6 passengers) from June through September. Spearfishing inshore will provide swimmers with views of shipwrecks and rocky beds home to striped bass, fluke, bluefish, sea bass, and more. Offshore cruises run July through September and are primarily for scoring mahi-mahi.

Insider scoop: Sea Turtle Dive Charters also offers full-day shark cage diving excursions off the coast of Montauk during the summer that allows divers to get up close and personal with an array of marine life—including mako and blue sharks, mahi-mahi tuna, sunfish, sea turtles, and porpoises.

11. Visit the Oldest Cattle Ranch in AMERICA and Ride Horses on the Beach (Montauk)

You probably wouldn’t expect the United States’ oldest ranch to be in beachfront Montauk, but that’s exactly where you’ll find Deep Hollow Ranch, established in 1658. The cattle ranch is older than the USA by more than a century – yes, we’re serious.

Insider scoop: Deep Hollow Ranch offers daily trail rides that wind through breathtaking scenery and pristine coastline – including white sand beaches. Check the Facebook page to book a ride or to learn more.

12. Ride the Fireball, Adventureland Theme Park’s NEW rollercoaster and the First in the Nation (Farmingdale)

Adventureland is a cherished family-owned business and a summertime stable for Long Island families.  And the iconic theme park is going all out for its 60th anniversary celebration this summer welcoming a new roller coaster, the FireBall; new game, the High Striker; and new claw machines inside its climate-controlled arcade. The FireBall is the fourth of its kind in the world and first and only in North America – and it’s right here in the heart of Long Island.  The vertical coaster is a must-see attraction with curves that make riders feel they are falling off the edge of a cliff. Don’t miss the park’s Tony’s Tavern which is introducing Wine Slushies, Cayman Jack Margaritas, and limited-edition A-Land Ale, which is only available at Adventureland.

13. Beat the heat at mind-blowing indoor attractions (Various locations)

Beat the heat this summer and check off another bucket list experience by visiting mind-blowing museums and awe-inspiring indoor attractions across Long Island.  Did you know Six lunar modules from the Apollo Program still sit on the surface of the moon, each with a plate that says: “Made in Bethpage, NY”.  Visit the Cradle of Aviation Museum in Garden City to explore over 100 years of Long Island’s aerospace heritage with replicas, real-life models, and interactive exhibits.  Or take a swing at the high-tech hotspot, Topgolf while enjoying live music, tasty food, and maybe even a drink underneath the temperature-controlled awnings. The Long Island Aquarium in Riverhead  offers sea lion shows, numerous touch tanks, kayak rentals, educational exploration tours sailing through the Peconic River, AND you can even dive with sharks.

Insider scoop: For exclusive savings at the Long Island Aquarium and other business throughout the region, download our FREE Downtown Deals Travel Pass. And for a behind-the-scenes look at TopGolf, watch our TikTok!

14. Experience vibrant art-deco décor that rivals South Beach at American Beech  (Greenport & Amagansett)

Long Island’s North Fork is known for its many historic bed-and-breakfasts among miles of farmland and some of the most acclaimed vineyards in the world.  But at the tip of the island, you’ll find a standout boutique with photo-ready vibrant art-deco décor that will transport you to South Beach.  American Beech is a destination all on its own with American Beech Restaurant, Black Llama Bar, events space, boutique, picture-perfect outdoor patio + vibrant nightlife not to be missed this summer.

Insider scoop: The Black Llama Bar and Alex Vinash Boutique were featured on an episode of The Real Housewives of New York City!

15. Escape the Crowds & Vacation Like a Real Hamptonite (Shelter Island & Sag Harbor)

Sunset Beach on Long Island

Just a five-minute ferry ride away from the bustling beach crowds of the Hamptons lies a secluded, 8,000-acre (confirm) island that’s been called the “un-Hamptons” for its tranquility.  This picturesque retreat is filled with historic hotels, bed & breakfasts, and over 2,000 acres of nature preserves – providing a low-key hideaway with a perfect combination of casual charm and exclusive seclusion – ideal for celebrities. Bicycle the island’s rolling hills, kayak its calm waters, relax on Sunset Beach, or browse the many shops and exquisite eateries in Shelter Island Heights. Stay at the Ram’s Head Inn, House on Chase Creek, or the recently renovated historic Chequit Hotel or The Pridwin Hotel & Cottages.

Originally, a whaling port, Sag Harbor is another off-beat Hamptons Village and must-see destination. This historic, Instagrammable downtown is filled with small restaurants, boutiques, and antique shops – many of which are located in restored whaling cottages from the 19th century. Watch the rich and famous dock their yachts or grab a photo of the iconic Sag Harbor Cinema, built in 1890 to host vaudeville and burlesque shows.

16. Climb to the Top of the Oldest Lighthouse in the State (Montauk + various locations)

Fire Island Lighthouse on long Island

Lighthouses have been guiding ships at sea to, from, and around the East Coast for centuries with the oldest being Montauk Point Lighthouse built in 1796. Montauk Point Lighthouse is well-known for being the first lighthouse in the state with George Washington himself authorizing construction. But did you know the Horton Point Lighthouse in Southold was also commissioned by the nation’s first president as well? Built a bit later in 1826, the Fire Island Lighthouse and it’s 182-step climb to the top is a must see and don’t miss the scenic, six miles of hiking trails surrounding the historic structure. A much smaller and unique lighthouse is the “Bug Light” in Greenport, which you visit via boat with Peconic Cruise Line. Don’t miss the opportunity climb to the top to take in magnificent vistas this summer.

17. Party like a Long Islander & Experience Live Entertainment on Main Streets Throughout the Summer

Credit: Benny Migs

The heart and soul of Long Island Life can be found in the many historic, waterfront, restaurant-laden bustling downtown villages across the region’s suburban landscape. Main Streets on Long Island come “alive” with festivals and entertainment throughout the summer – like “Alive After 5” Patchogue, a local favorite hosted by the Great Patchogue Chamber of Commerce. For those who have yet to attend an “AA5”, the festival enhances the already lively downtown with expanded outdoor dining experiences, rotating lineup of live music, artisan vendors, and craft beverages from all over the region. Similar summer festivals include:

18. Experience the Unparalleled Scene on the Nautical Mile in Freeport

The combination of restaurants and workboats, open-air bars and fish markets, live music and foghorns on the Nautical Mile provides a unique blend of nautical charm and street fair revelry that you won’t find anywhere else. Seafood lovers can enjoy a slate of open-air eateries right outside or on one of the busiest docks on the South Shore offering mussels, clams, blue crabs, and lobsters. A few staples include Hudson’s on the Mile, Jeremy’s Ale House, Rachel’s Waterside Grill, and Elliot’s on the Mile. On summer nights, hundreds of locals flock to the strip flanked by water where antique lighting shines over the bustling sidewalks and where party boats line up along Woodcleft Canal.  The Nautical Mile is not just a must-see destination for partiers and seafood lovers.  It is one of Long Island’s best family friendly attractions featuring mini golf, a four-acre waterfront park, dinner cruises, fishing charters, and more.

19. Soak up the NYC skyline with a private yacht courtesy of Long Island Boat Rentals (Port Washington)

Long Island Boat Rentals (LIBR) offers captained and bare yacht and party boat rentals out of the Manhasset Bay. From romantic sunset cruises around Manhattan or sightseeing off Long Island’s Gold Coast, LIBR will make your dreams a reality the envy of Instagram followers. Long Island Boat Rentals also offers private training classes and adventure tours complete with floats, wakeboards, and other water-sporting accessories for endless fun on the water!

Insider scoop: For a preview of the exclusive experience, check out this episode of Long Island TV or our TikTok. And for an exclusive discount on your private bareboat rental, present our FREE Downtown Deals Travel Pass.

20. See a Legendary Performance Under the Stars at the Iconic Northwell Health at Jones Beach Theater (Wantagh)

Rocking out to a legendary band under the sky on a hot summer night at the oceanfront Northwell Health at Jones Beach amphitheater has been a perennial favorite of Long Islanders for decades. Jimmy Buffett has been among the most frequent acts at Jones Beach, performing his annual summer show and tailgate party here for many years. Highlights of the A-listers performing at the iconic Jones Beach venue this summer include the Backstreet Boys, Third Eye Blind, Chris Rock + Kevin Hart, Train + Jewel & Blues Traveler, Lynyrd Skynyrd, Tim McGraw, Dave Matthews Band, Steely Dan, The (formerly Dixie) Chicks, Josh Groban, Rod Stewart & Cheap Trick, Chicago and so many more!

21. Taste award-winning wine with a car-free tour of Long Island Wine Country

Rated by Wine Enthusiast as one of the ‘Top 10 Wine Regions’ in the world, Long Island Wine Country is home to over 60 vineyards and world-class tasting rooms. From rich Cab Francs to versatile roses and legendary bubbly, regional-inspired brews, and top-shelf liquor, Long Island has grown award-winning, high-quality ingredients for wines and spirits in unmatched settings where winding farmlands and waterfront vineyards serve as picturesque backdrops.

Insider scoop: Many of the accommodations in the area offer complimentary shuttle services or packages that include an escorted tour of local vineyards. Click here for information on how to see our award-winning Wine Country by train. And for even more car-free adventures, click here.

22. Bar Hop by Boat in the Hamptons And Fire Island Hampton Bays & Ocean Bay Park)

Flynn’s is a summer time staple with live music, lobster rolls, and waterfront views. But did you know that Flynn’s teamed up with The Moon Chaser to offer a truly unique experience–a cruise that provides the opportunity to see the iconic Fire Island Lighthouse. Kick back and enjoy the summer breeze and magnificent sunsets as you set sail from Captree State Park in Babylon to this famous Fire Island landmark. Dine on the water at Flynn’s, a community gem with a buffet of steamed lobsters, the day’s catch, Flynn’s Famous Baked Clams, prime rib, and other delicious eats. Sway to the music and enjoy the party atmosphere of iconic Fire Island summers before heading back to the mainland.

Just slightly east, in Hampton Bays, two restaurants are taking “bar hop” to a whole new (sea)level. Cowfish and RUMBA, two highly praised restaurants, offer more than just fantastic fare and tiki vibes but a “RUMBarge” that will take guests from one property to the other for dinner, drinks, dancing, whatever fits your vibe. The complimentary water taxi welcomes guests aboard for its season opener this Memorial Day Weekend.

23. Lobster Rolls with a View

Lobster rolls are synonymous with a Long Island summer, and it goes without saying no bucket list is complete without one (or a dozen). There are several famed spots on Long Island’s East End like Shinnecock Lobster Factory in Southampton or The Lobster Roll (LUNCH) in Amagansett where everyone from Bill Clinton to Jerry Seinfeld has pulled over and dined at the roadside retro shack. But some say they taste even better when consumed with a water view like at Peter’s Clam Bar. This hidden gem is far off the east end and the oldest clam bar on Long Island. And while a lobster roll with a view of the channel is a must.

Insider scoop: The restaurant’s Annual Clam Eating Contest should be a site on everyone’s 2022 bucket list.

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