Whether you’re a dedicated Long Islander or a visitor craving a taste of the East Coast charm, there’s much to enjoy in the off-season between Montauk and Fire Island, New York. Long Island offers year-round excitement from scenic beachside trails and cozy vineyard tours to exclusive wintertime adventures. Let’s uncover some top off-season activities to explore from Montauk to Fire Island—and where to stay when you visit.
Why Visit Montauk and Fire Island in the Off-Season?
Long Island’s off-season is a hidden treasure. From the serene beauty of Fire Island’s Atlantic shores to Montauk’s historic lighthouses and trails, the cooler months allow for peaceful exploration without the bustling summer crowds. Here, you’ll find fresh perspectives on favorite locations and an invitation to explore winter-exclusive activities.
Winter and Fall Activities in Montauk, NY
1. Discover the Montauk Point Lighthouse
Winter in Montauk isn’t complete without visiting the Montauk Point Lighthouse, New York’s oldest lighthouse. Constructed in 1796, this historical site offers breathtaking panoramic views of the Atlantic Ocean and Long Island Sound. Open year-round, the Montauk Lighthouse is the perfect spot to begin your off-season exploration.
Pro Tip: Afterward, warm up with a cup of hot chocolate or coffee from one of the local cafes around Montauk village.
2. Hike Through Camp Hero State Park
For those who relish outdoor activities, Camp Hero State Park in Montauk provides some of the most beautiful trails on Long Island. Famous for its expansive views and military history, this park’s winding trails take you through coastal cliffs, dense forests, and meadows.
3. Surfing at Ditch Plains
Winter surfing is a must-try for thrill-seekers. The Ditch Plains Beach is a haven for seasoned surfers, with winter waves that provide an unforgettable experience. If you’re new to surfing, several local surf shops offer gear rentals and tips to help you get started.
4. Wine Tasting Along the North Fork
Long Island’s North Fork vineyards are open year-round, making them an ideal off-season escape. Sample locally produced wines like Chardonnay and Merlot as you tour some of the best wineries near Montauk. It’s a relaxing activity perfect for couples and wine enthusiasts.
5. Art and History at the Parrish Art Museum
Located in Water Mill, just a short drive from Montauk, the Parrish Art Museum showcases remarkable contemporary and classic art pieces. The museum hosts winter exhibitions and events, making it an excellent indoor activity on colder days.
Exploring Fire Island: Off-Season Delights
1. Fire Island Lighthouse and Museum
The Fire Island Lighthouse, a New York icon, offers stunning views of the Atlantic Ocean and surrounding dunes. During the off-season, take a peaceful, self-guided tour of the lighthouse. You can learn about the lighthouse’s significance in maritime history while soaking up the serene winter atmosphere.
2. Hike the Sunken Forest
The Sunken Forest on Fire Island National Seashore is a unique ecological treasure. This rare maritime forest, nestled behind dunes, is a perfect destination for nature lovers. Take a guided or solo walk through this mystical forest, where the quiet winter months provide an intimate experience with the surrounding flora and fauna.
Pro Tip: Download a map or guide before heading out, as some areas of the park may have limited cellular service.
3. Ocean Beach Village Stroll
The charming village of Ocean Beach offers quaint shops, art galleries, and quiet streets. In the off-season, the village takes on a peaceful ambiance, ideal for a slow day of shopping and dining. Many stores and restaurants stay open through fall and winter, providing unique gifts, local art, and delicious meals.
4. Explore Cherry Grove and Fire Island Pines
Known for their vibrant summer scenes, Cherry Grove and Fire Island Pines become peaceful winter getaways where you can enjoy quiet walks along empty beaches. The local communities in these areas welcome visitors year-round, and the laid-back atmosphere offers a refreshing break from city life.
5. Birdwatching Along the Fire Island Seashore
Fire Island’s beaches and marshlands make it a prime location for winter birdwatching. Explore coastal areas like Robert Moses State Park for a chance to see winter birds such as snow buntings and long-tailed ducks. The seashore’s diverse ecosystem attracts a variety of bird species throughout the year.
Day Trips and Adventures from Montauk to Fire Island
1. Wintertime in East Hampton
East Hampton shines in the winter months with quiet beaches and charming local shops. Visit the East Hampton Historical Society to learn about the area’s colonial past, or take a stroll down Main Beach. End your day with a cozy meal at one of the town’s year-round restaurants.
2. Sands Point Preserve
The Sands Point Preserve on Long Island’s North Shore is a magnificent estate with grand mansions, scenic trails, and ocean views. Explore the castle-like Hempstead House, take a guided tour, or wander the gardens and trails for an enchanting winter day trip.
3. Cold Spring Harbor
This charming village on the North Shore of Long Island features cozy coffee shops, boutiques, and a historic whaling museum. Take a scenic drive up to Cold Spring Harbor to enjoy the winter wonderland atmosphere and explore the beautiful coastal views.
4. Coney Island Amusement Park
A New York classic, Coney Island is a destination that draws visitors even in winter. While some rides close, the boardwalk remains open, and attractions like the New York Aquarium and local food stands serve visitors year-round.
Pro Tip: Visit the amusement park during the holidays to see seasonal light displays and winter festivities.
5. Wine and Beer Tastings
From amber ales to hazy IPAs, Long Island’s breweries and distilleries offer diverse tasting experiences. Stop by one of the North Fork breweries to sample locally crafted beverages or join a tasting tour for an immersive experience.
Seasonal Dining and Cozy Retreats on Long Island
Long Island’s culinary scene thrives even in the colder months. From Montauk to Fire Island, off-season dining highlights include farm-to-table restaurants, waterfront seafood spots, and quaint cafes. Here are some must-visit dining experiences.
1. Farm-to-Table Dining on the North Fork
Experience local flavors at one of the North Fork’s farm-to-table restaurants. The off-season allows for intimate dining experiences where you can savor freshly prepared dishes from Long Island farms.
2. Seafood Delights in Fire Island
Winter is a perfect time to enjoy seafood on Fire Island. Local spots offer fresh catches from the Atlantic, including lobster, clams, and oysters. Relax by the shore and savor the taste of the East Coast.
3. Cozy Cafes and Bistros in Montauk
Montauk offers several cozy cafes and bistros, perfect for warming up after a day of winter activities. Try a hot bowl of clam chowder, locally brewed coffee, or a delicious pastry while taking in the winter scenery.
4. Boutique Wineries and Vineyards
Winter in Long Island’s wine country is an experience not to be missed. Many North Fork vineyards offer private tastings and vineyard tours, letting you sip on local wines like Chardonnay and Pinot Noir by a roaring fireplace.
Planning Your Stay on Long Island: Where to Book
Looking for the best place to stay during your off-season adventure on Long Island? Book with New York Rental By Owner to find comfortable and unique vacation rentals from Montauk to Fire Island. Enjoy options that range from cozy beach cottages to luxurious vineyard retreats, all hosted by local owners who know the best places to visit.
Why Choose New York Rental By Owner?
Booking with New York Rental By Owner ensures a unique, personal experience with each stay. Avoid the crowded hotels and enjoy accommodations that give you a home-like feel with local insights into the best spots to visit on Long Island.
New York Rental By Owner provides exclusive properties perfect for families, couples, and solo travelers looking to enjoy the quiet beauty of Long Island’s off-season.
Getting Around: Transportation Tips
1. Long Island Railroad
The Long Island Railroad is a convenient and scenic way to travel between Long Island destinations. It connects New York City to Montauk and Fire Island, offering affordable and efficient transportation for your off-season adventure.
2. Fire Island Ferries
Ferries operate year-round to Fire Island, with routes departing from Bay Shore and other Long Island ports. Enjoy a scenic ride across the Great South Bay and begin your Fire Island exploration.
3. Local Jitneys and Buses
Local jitneys and buses make it easy to travel around Long Island and explore each town. This is especially helpful for hopping between Montauk, Fire Island, and other nearby attractions during the winter.
Plan Your Next Long Island Getaway
Long Island is filled with hidden gems, especially during the quieter off-season. From Montauk’s beaches and wineries to Fire Island’s serene landscapes, each destination offers something unique. Explore these unforgettable experiences this winter and fall, and book your stay with New York Rental By Owner for an authentic and memorable Long Island adventure. Whether you’re seeking beach walks, lighthouse tours, or cozy meals, the best of Montauk to Fire Island New York awaits you.
