Whether you refer to it as “out east” or “The Island,” there’s no shortage of things to do on Long Island, New York. Yes, you have your ritzy beaches and shops in the Hamptons and wild parties on Fire Island. But the 118-mile-long island is also home to top-notch wineries, fascinating museums, stellar dining and some of the best beaches near NYC. Better yet, it’s almost all accessible via public transportation on the LIE or LIRR.
Best things to do on Long Island, New York
Get your Instagram ready. At this unique Long Island attraction, you can spend hours running through lavender fields reminiscent of the French countryside and do an entire photoshoot of your picturesque experience. Once you’re done satisfying your social media needs, go ahead and pick your own bouquet or purchase one of the many lavender-scented products on sale. Blooms start in June! 7540 Main Road, East Marion (lavenderbythebay.com)
Wine plus cheese plus baby goats equals heaven. And that’s exactly what goes down here at this Peconic farm. Spend the afternoon sampling the artisanal cheese selection while you your kids play with the baby goats and other farm animals. It’s really the perfect spot to make any family member happy. 33705 North Road, Peconic (631-765-8042, catapanofarms.com)
You could spend an entire weekend wine tasting at the various vineyards. But if you’re limited on time, make a point to visit Lieb Cellar with tasting rooms in Cutchogue and Mattituck on the North Fork. No matter varietal preference— red, white, sparkling, or rosé—you’ll find a wine to suit your palette. Oh, and you can pair it with dinner and live music if you choose. 13050 Oregon Road, Cutchogue (631-734-1100, liebcellars.com)
While you have plenty of beaches to choose from up and down the coast of Long Island, one of the best is Cooper’s. Located in Southampton, it’s one of the best beaches in the U.S. and boasts over seven miles of white sand. Spend the day swimming, surfing and bodyboarding, or simply take a scenic stroll and set up a picnic in front of one of the many eye-popping mansions. 268 Meadow Ln, Southampton (experiencethebeach.com)
Sure, getting out to Long Island can feel like an adventure in itself. But here, there’s an actual adventure course to get your adrenaline pumping. You can climb, zip line, and walk across wobbly bridges connecting 140 platformed trees throughout the forest. To up the ante, they have glow-in-the-dark courses every other Friday with light up glow attire and laser light music. 75 Colonial Springs Rd, Wheatley Heights (631-983-3844, longislandadventurepark.org)
Unleash your inner book nerd and visit the spot that inspire F. Scott Fitzgerald to write The Great Gatsby. Filled with different hikes, yoga classes and meditation retreats, the grounds also have an event calendar full of cocktail parties and high teas. 127 Middle Neck Road, Sands Point (516-571-7901, sandspointpreserveconservancy.org)
If you’re more of a Walt Whitman fan than F. Scott Fitzgerald, you’ll love visiting the famous writer’s cottage. Browse his home, built in 1816, before checking out the permanent exhibition detailing Whitman’s life and rise to literary fame. If you’re looking for a more poetic experience, the estate hosts many poetry workshops as well as a poets-in-residence program. 246 Old Walt Whitman Road, Huntington Station (631-427-5240, waltwhitman.org)
You’ll feel transported back to the Gilded Age during your visit to the former estate of insurance magnate William Robertson Coe and Standard Oil heiress Mai Rogers Coe. Roam through the mansion and check out many of the original furnishings before venturing out to explore the 409 acres of manicured ground. The property is one of the remaining Gold Coast homes that retains its original plot of land, and it also acts as a venue for concerts and art exhibitions. 1395 Planting Fields Road, Oyster Bay (516-922-5926, plantingfields.org)
At this family-owned North Fork winery in Cutchogue, certified sustainable farming practices are applied in handcrafting wines from grapes grown at three vineyards. At its tasting room, a circa-1919 barn, certain current and limited-production reds and whites are available for tasting daily (reservations are required for groups of six to 10). Its Corey Creek property in Southold is open June to September. Another reason to toast this label: The 2009 Merlot was served at the 2013 Presidential Inaugural Luncheon. 36225 Main Rd, Cutchogue (631-734-7537, bedellcellars.com)
This microbrewery produces small-batch ales—annual, seasonal, and limited—available for tasting at its original location, a repurposed fire station in Greenport, and at a bottling plant/tasting room in Peconic. Noteworthy suds include Pith N' Peel; a citrusy IPA; and the full-bodied Black Duck Porter. In 2016, the brewery introduced its OG series, a line of batch beers handcrafted at its Greenport location. 42155 Rt 25, Peconic (631-477-1100, greenportharborbrewing.com)
This three-generation, family-run operation in Jamesport produces estate-grown wines on its 60 acres of vineyards and has a winery/tasting room housed in what was once a 19th-century barn. Known for its red, white and dessert wines, enjoy a five-tastings flight or book a reservation for parties of six or more. As for pairings, the vineyard’s food menu’s standouts are oven-baked flatbreads and bistro-style plates. 1216 Main Rd, Jamesport (631-722-5256, jamesportwines.com)
Adjacent to Montauk Point State Park, New York state’s oldest and still-active lighthouse continues to shine on Long Island’s easternmost tip. Purchase a ticket to climb up to the tower and take in 360-degree views of Block Island Sound and the Atlantic Ocean. Carefully explore the surrounding rocky coastline and visit the Montauk Lighthouse Museum, which features artifacts, photos and documents including ones signed by Thomas Jefferson and George Washington. 2000 Montauk Hwy, Montauk (631-668-2544, montauklighthouse.com)
This popular Smithtown eatery provides an all-day breakfast and lunch service that is worth the wait in line. With its cow-themed décor, the cash-only venue features well-sized portions with many ways to have pancakes, French toast and omelets. A specials board changes daily, but look for the Original Croissant French Toast or Egg McMoe, a bacon, egg and cheese sandwich on an English muffin. Make sure to bring extra bills and a hearty appetite. 108 Terry Rd, Smithtown (631-360-9227)
Housed inside an old bank, this refined steakhouse in Islip serves prime aged steaks and chops, seafood and contemporary American specialties (definitely try the Duck Fat Fries). Along with lunch and dinner, consider the two-course Sunday Price Fixed Menu (at $45 per person), or the three-course Wine Dinner Menu (at $40 per person, $50 paired with wines) held a few times a month. The building’s walk-in vault functions as a wine cellar, and the Gold Bar is for lounging with a prime cordial in hand. 605 Main St, Islip (631-277-7070, tellerschophouse.com)
Having moved to its current location in Water Mill in November 2012, this museum focuses on artists who have been drawn to Eastern Long Island’s landscape since the 19th century. Its collection of more than 2,600 pieces extends to American Impressionism paintings and pieces dating up through the 21st century. It holds collections by painters William Merritt Chase and Fairfield Porter, and it has put on exhibits displaying the talents of local schoolchildren as well as artists currently living on the island’s East End. 279 Montauk Hwy, Water Mill (631-283-2118, parrishart.org)
In Roslyn Harbor on a former Frick estate, this museum encompasses a sculpture park, a formal garden, walking trails and, of course, art. Rotating exhibitions run the full spectrum of artistic influences and mediums. Recent showings include Recent showings an exhibition about Art in the Jazz Age, and a new sculpture by Marko Remec. The museum’s permanent collection is impressive too, with over 500 works by 19th and 20thcentury European and American artists. It hosts educational and outreach programs for all ages as well. 1 Museum Dr, Roslyn Harbor, Greenvale (516-484-9338, nassaumuseum.com)
Want some history to go along with the stunning scenery? New York City native Theodore Roosevelt visited Oyster Bay on summer vacations as a teenager and fell hard for it. As a twentysomething wanting to settle down, Roosevelt purchased land in Cove Neck to build a family home. Here, he and his second wife, Edith, raised six children and hosted dignitaries, particularly during Teddy’s two presidential terms. In July 2015, this property reopened after a three-and-a-half yearlong, $10 million restoration project, and yeah, it’s a gorgeous place to visit. 20 Sagamore Hill Rd, Oyster Bay (516-922-4788, nps.gov)
Shelter Island, the 30-sq-mile getaway situated between Greenport and Sag Harbor, is a prime destination for low-key adventures and great home-cooking-style restaurants. One such joint has been serving residents and tourists alike for years. Nestled away in an ivy-covered hideaway off Smith Street is Commander Cody's Seafood, which serves the freshest local catches, including lobster, oysters, clams, calamari, and good old fish and chips, all at market prices. It is also BYOB, making a lobster dinner well within your vacation budget. Make sure to say hello to Cody when you're there! The 82-year-old man's the counter almost daily and ready to serve you up a hearty meal—and a smile! 41 Smith St, Shelter Island (631-749-1851).
The summer is the best time to visit this airy, 1960's inspired beach dream house as your stay includes access to any one of dozens of free concerts taking place every weekend between Memorial Day and Labor Day. In addition, the on-site restaurant was inspired by the culture and lifestyle of Byron Bay, one of Australia’s most authentic surf towns. It offers a simple, clean, fresh, local and organic market driven menu with a focus on daily caught seafood. So come for a dip on the beach, a delicious bite to eat, and an evening concert that will be well worth the three-hour trek out.
For the last 33 years, Oyster Bay has been hosting the East Coast’s largest waterfront festival that should please any seafood restaurant aficionado or oyster happy hour fan. Originally, it was conceived as a 125th birthday celebration of Teddy Roosevelt, whose family would vacation every year not far from the festival's current site. Today, it boasts over 200,000 attendees annually, and features live entertainment, pirate shows, midway tours, and lots of eating and shucking contests.
This massive waterfront amphitheater is where classic-rock buffs from the ’burbs meet their NYC counterparts. The booking alternates between iconic nostalgia acts like Joan Jett and contemporary sensations such as Kendrick Lamar. Whoever's playing, expect a rowdy, ballpark-style concert experience.
Dubbed a “perfect destination for summer dining” by The New York Times, Montauk’s favorite beachfront restaurant Navy Beach is a laid-back, family-friendly waterfront venue offering a memorable dining experience in a beach setting with casual coastal cuisine and breathtaking sunsets. Positioned on a 200-foot private beach, Newsday named it on of the top five water view dining spots on the East End. Boaters are welcome to anchor in the protected waters of Fort Pond Bay (41° 02′ 45.11″N, -71° 57′ 44.88″W), which was once occupied by the US Navy, and where two Navy piers are still part of the water landscape.
Completed in 1906, this historic mansion has 200 acres of gardens, landscaped grounds, woodlands, ponds and lakes. Their daily calendar includes a mix of educational tours, yoga and tai chi, and even a summer classical concert series, making this the perfect destination to feel like you've been transported into a Jane Austin novel, via the LIRR.
Explore more of Long Island
The Easternmost region makes for an ideal weekend getaway from NYC with stretches of farmland for pumpkin picking, restaurants helmed by NYC chefs and nearly 3,000 acres of vineyards sourcing the best Long Island wineries.
While some of the best bars in NYC are indeed running red and white these days—just look at these cool new spins on the wine bar—if you’re looking to get outta town, look no further than these North Fork wineries.
The Hamptons and Montauk have a reputation as the land reserved for the rich and pretentious. Well, forget what you heard!