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 their opportunity to enjoy the region. There are a variety of Hamptons vacation rentals and Fire Island vacation rentals.
The Best Long Island Off-Season Activities: Montauk to Fire Island.
1. Ice skating
Only about a mile after Sunrise Highway snakes into Southampton, the Southampton Ice Rink dominates the small stretch of road. The large dome is unmistakable, and has public ice skating available almost every afternoon once cold weather rolls around. If skating outside is more your thing, head east. The Buckskill Winter Club features a full sized outdoor ice rink so you can skate under the stars.
2. Montauk Lighthouse
Avoid the crowds and head to the Montauk Lighthouse in the off season! You’ll find that the long ride to the end of the south fork is quick without the summer traffic. Travel to the easternmost tip of New York and enjoy the serenity of a wintery beach scene. Climb the lighthouse, and then enjoy a walk on the beach. You can even act the famous scene from Eternal Sunshine of the Spotless Mind, and whisper to your partner “meet me in Montauk.”
After enjoying a wintery stroll on the beach, head to the center of Montauk, NY and enjoy a brew. Visit the Montauk Brewery to top off your list of things to do in Montauk. The laid back tasting room invites you to “come as you are” and enjoy their range of brews. The Driftwood ale is available year round. For a seasonal theme, try the Arrowhead Red Ale, available December through April. As you make your way West, don’t forget to stop in Southampton! Southampton Publick House is a Hamptons for Long Island drinks. The restaurant and bar has a warm, welcoming feeling. Try the Double White, Altbier or Keller Pils to enjoy award winning refreshment.
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 Hamptons 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 vinters. 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 is relatively flat, so there’s not a lot of skiing to be done., that is, Unless you know where to look. If there’s been a good snowfall, head south, to the Quogue Wildlife Preserve! For only $5, you can rent snowshoes and skis and take to the trails that most people only brave in the summer months. Wind through the trails and keep an eye out for the resident wildlife. You may see a bright red fox, or even a rare bald eagle.
7. East Hampton Windmills
Driving east on Route 39, it’s impossible to miss the large windmills that dominate the centers of East Hampton and WaterMill. There are 11 windmills on South Fork, which may be the most in the entire United States. The first windmill was built in the mid 1600’s- before our Country was founded. Head to the Hamptons in the off season to avoid traffic, and enjoy a slow drive to see all 11!
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 Jacskson 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, 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. 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 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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