It has a ton of stereotypes, yes, but there are also a whole lot of awesome things to do on Long Island, New York. You may be familiar from the city’s eastern appendage from your friends envy-inducing gram’s raging at parties on Fire Island, lounging beach-side in the Hamptons or surfing in Montauk. Well, envy no more! Make your own exciting memories at NYC’s most popular weekend getaway spot. After all, some of the best beaches near NYC call Long Island home, as do world-renowned wineries, inventive breweries and spectacular art museums. So hop on the LIE or LIRR and discover these out east gems.
RECOMMENDED: Full guide to Long Island, New York
Best things to do on Long Island, New York
Bedell Cellars, Cutchogue
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 May 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)
Greenport Harbor Brewing Co., Peconic
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 Leaf Pale Ale, an autumnal beer; 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)
Jamesport Vineyard, Jamesport
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)
Montauk Point Lighthouse, Montauk
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)
Maureen’s Kitchen, Smithtown
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)
Tellers Chophouse, Islip
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 three-course Wednesday Night Wine Dinner Menu (at $40 per person, $50 paired with wines). 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)
Parrish Art Museum, Water Mill
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)
Nassau County Museum of Art
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 original drawings by Peter Max and photographs by Ansel Adams. The museum’s permanent collection is impressive too, with over 500 works by 19th and 20th century 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)
Sagamore Hill National Historic Site, Oyster Bay
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)
Photograph: Courtesy CC/Flickr/Mark Goebel
Commander Cody’s Seafood, Shelter Island
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).
Photograph: Courtesy Yelp/Rick B.
Looking to try out a North Fork winery?
Ashoka Indian Restaurant
Craving Indian food? Look no further than Ashoka Indian Restaurant on the Upper West Side. Order some battered and fried onion bhaji ($8), vegetable samosas ($8) or coconut curried shrimp ($12) to nibble on while you decide on your entrees. Assemble a veritable feast by ordering a variety of Indian favorites to share. Rich chicken tikka masala ($16), spicy Mangalorean fish curry ($18), braised lamb shank with garlic and onions ($18) and verdant saag paneer ($14) ought to get you started. Don’t forget to order some lamb biryani ($16) and a side of garlic naan ($5) to soak up all the excess sauce. Still have some room for dessert? Good, because you’ll want to end the meal with a mango or rose lassi ($5), fig-saffron ice cream ($8) or gulab jamun malai, a traditional Indian sweet flavored with cardamom ($8). The restaurant also provides live music every Friday, Saturday and Sunday.
Venue says: “Lunch only, eat unlimited appetizers & main courses for $12.95 or $13.95. Mention Time Out to receive 10% off on your meal only at Dinner”