The South Shore of Long Island can provide any vacationer with the perfect off-season winter beach getaway. Whether you choose a Hamptons upscale retreat, the humble fishing village of Montauk, or a beachside bungalow on the Atlantic barrier of Fire Island, there is a perfect fit for every kind of winter adventurer. Better yet, due to low traffic many Long Island, winter vacation rentals offer great off-peak rates during this time of year!
The South Fork of Long Island is the summer getaway for the rich and famous. The South Fork starts in the Hamptons and ends at Montauk, the easternmost tip of Long Island and New York State itself. However, in the weeks after Labor Day, the locals flood the area to have the opportunity to enjoy the region. There are a variety of Hamptons vacation rentals and Fire Island vacation rentals.
Things to Do on Long Island in the Winter
1. Indoor and Outdoor Ice skating
As the winter season envelops Long Island, ice skating emerges as a quintessential winter fun activity, offering both indoor and outdoor options to enthusiasts. The Southampton Ice Rink, located just a mile past where Sunrise Highway enters Southampton, is a prominent feature with its large dome. It welcomes the public for ice skating sessions almost every afternoon during the colder months, making it a go-to spot for those looking to glide on the ice.
For those who prefer the charm of outdoor ice skating, heading east to the Buckskill Winter Club is a must. This venue boasts a full-sized outdoor ice rink, allowing visitors to skate under the stars and enjoy the crisp winter air. Whether you choose the enclosed environment of Southampton Ice Rink or the open, starlit experience at Buckskill Winter Club, ice skating on Long Island offers memorable moments of winter fun throughout the season.
2. Montauk Lighthouse – Winter Wonderland
For those looking for things to do in Long Island in the winter, heading to the Montauk Lighthouse is a great option. The trip to this easternmost point of New York is much quicker during the off-season without the summer crowds. It’s an ideal spot to experience the quiet of the holiday season and see a different kind of winter wonderland. You can climb the lighthouse for impressive views and take a peaceful walk on the beach afterward. It’s a unique way to enjoy the serenity of Long Island’s coast during winter.
Embrace the holiday spirit after a crisp walk on the beach by exploring the heart of Montauk, NY, where local microbrews await. A visit to the Montauk Brewery is a must-do winter activity, rounding out your experience with a taste of one of Long Island’s craft beer pioneers. Their relaxed tasting room embodies the “come as you are” ethos, making it a perfect spot to unwind and sample a variety of brews. The Driftwood Ale, a staple, is available year-round, but for those visiting in the winter months, the Arrowhead Red Ale offers a seasonal twist, available from December through April.
Continuing your journey westward, don’t miss a stop in Southampton, where the Southampton Publick House stands as a beacon for Long Island’s brewing scene. This establishment, known for its cozy atmosphere, becomes a hub for holiday events and gatherings. Sample the Double White, Altbier, or Keller Pils to experience some award-winning refreshment that captures the essence of winter on Long Island.
4. Wine Tasting
While the North Fork of Long Island is known for its wines, the vineyards along the South Fork are equally eclectic. Wӧlffer Estat and Channing Daughters Vineyards are Hampton’s staples Head up to Sag Harbor and enjoy Channing Daughters’ wide range of Reds, Whites, Pinks, and Oranges! Wӧlffer estate is further east, in the town of Sagaponack, and features old-world style wines, from a tight family of passionate vintners. You won’t want to miss this!
5. Harborfrost – Sag Harbor – Late February
Every year the Sag Harbor Chamber of Commerce holds this celebration of Fire and Ice to finish off the winter. Harborfrost happens on Long Wharf in Sag Harbor and treats them to a spectacle. Restaurants, usually shuttered until summer, open and treat guests to fine dining. Make sure to not miss the ice carving and fire throwers also on site! The night ends with a spectacular winter fireworks display – a rare sight in the cold months of February.
6. Cross Country Skiing
Long Island might be flat, but it still offers places for skiing if you know where to look. After a heavy snowfall, head to the Quogue Wildlife Preserve. Here, for a $5 rental fee, you can get snowshoes and skis to explore the trails. These trails are usually popular in summer but offer a unique experience in winter. Keep an eye out for local wildlife, including red foxes and bald eagles, as you ski. It’s a great way to discover Long Island in winter and provides fun activities for the whole family.
One of Long Island’s iconic features, the windmills of East Hampton and WaterMill, stand as a testament to the area’s rich history, predating even the founding of the country. With 11 windmills scattered across the South Fork—potentially the most in any single region in the United States—these structures offer a unique glimpse into the past. Visiting during the off-season lets you take a leisurely drive along Route 39 without the summer traffic, allowing for an unobstructed view of these historic landmarks. This journey not only serves as an antidote to the winter blues but also ranks among the most intriguing winter activities in the area. It’s a perfect way to spend a day in the quieter months, exploring the garden city’s heritage and architectural marvels.
8. Parrish Art Museum
The South Fork has countless museums and art galleries – one of the largest being the Parrish Art Museum, right along Route 39 in WaterMill. You can see the sprawling building from the main road and makes a great place to stop and marvel at the art of the region. The Museum’s purpose is to highlight the art made in the several artists’ colonies on the South Fork. The Hamptons is home to well-known artists like Jackson Pollock, Lee Krasner and Willem De Kooning, the next South Fork protege may be on the walls at Parrish!
9. Award Winning Dining
While much of the South Fork of Long Island shutters after Labor Day, there still are several world-class restaurants to enjoy in the off-season. The best part is, that you may not need to even make a reservation! Many restaurants offer off-season discounts to tempt adventurous pallets. Grab a steak at Bobby Van’s in Bridgehampton, or Lulu Kitchen and Bar in Sag Harbor. The Bell and Anchor, also in Sag Harbor has a chic nightly prix fixe for your enjoyment. If you’re worried about finding a great bite to eat – don’t hesitate to ask a local. They can help you find the places you don’t want to miss.
10. Aviation Museum and Outdoor Adventures in Garden City
Discover Long Island’s rich history in aviation with a visit to the aviation museum located in Garden City, a testament to the area’s pivotal role in early flight history. This museum, nestled near the heart of Long Island, offers an educational and engaging experience for all ages, making it a perfect destination for winter activities. After exploring the museum’s extensive collection of aircraft and artifacts, consider extending your adventure to the nearby Hempstead Lake State Park. This park, easily accessible from Deer Park and other Long Island communities, provides a serene backdrop for a winter stroll or a brisk hike through nature. With its expansive landscapes and quiet trails, it’s an ideal spot for those looking to enjoy the outdoors and perhaps even spot some local wildlife. Combining a visit to the aviation museum with the natural beauty of Hempstead Lake State Park offers a diverse day out, embodying the spirit of discovery and the variety of experiences available on Long Island.
11. Fire Island
After October, the amount of people who live on Fire Island dwindles to under 500 for the entire island! Venture out on one of the Fire Island ferries, or take the Robert Moses Parkway to enjoy the intimate landscape of this quiet, Long Island gem.
1. Nature/Seal walks
During the winter, seals flock to Fire Island where they can sun themselves on beaches and take a rest from swimming. Many conservation organizations host seal walks up and down the empty white sand beaches to see the plump marine creatures. Stony Brook University gets together for long walks in January along Jone’s Beach on the western part of the island, where you’re guided by a researcher happy to help you enjoy the wintery scene.
2. Sunken Forest Preserve
Take the Sailors’ Haven ferry across the Great South Bay to the Sunken Forest Preserve. Part of the Fire Island National Seashore, the Sunken Forest is a part of the National Parks Department. The forest, which is dominated by trees, gets its name because it lies between the dunes of Fire Island, appearing “sunken” in sand. The trails are peaceful in the winter and have the added benefit of being tick-free in the low temperatures.
3. CJ’s in Ocean Beach – one of the only restaurants open
Because of the dwindling off-season population on Fire Island, there aren’t many places to get a bite to eat. Head to Ocean Beach and check out CJ’s, one of the oldest establishments on the island. CJ’s is the only restaurant in Ocean Beach that opened after October and is the creator of the famous Fire Island cocktail, Rocket Fuel. While winter might not be the best time to try this frozen drink, CJ’s is happy to be a winter warmer with great food and good company.
It’s clear that just because summer ends, doesn’t mean that you have to plan your Long Island getaway for next May. The Hamptons are a Long Island beach getaway a short distance from NYC to escape the city crowds and perfect for any season. With some creative planning and an adventurous spirit, you might find that there are plenty of things to do on Long Island from Southampton to Montauk!
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