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Make the Most Out of the East End this Winter: Enjoy Museums, Beaches, Walk Around Towns & More During the Off Season!

If you love to travel and explore, heading out to the East End might be the destination for you this winter!

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The Montauk Lighthouse on a crisp Winter Day.

Photo by: Joe Galletta

Eastern Long Island is often thought of as a great Summer destination, but there are still plenty of fun things to do during the Winter. During the warmer seasons, the East End gets swamped with city dwellers, but this Winter could be your time to get the chance to take advantage of all that eastern Long Island has to offer with the luxury of peace and quiet.  
Right now is still a great time to go wine tasting, enjoy the great outdoors, plan for a close to home romantic getaway, or a weekend away with some friends. Think it’s not the best time to visit those sensational Long Island beaches out on the East End? Think again - beaches can be a part of your Winter fun too! The East End has a variety of winter time activities for all ages and all tastes. It’s no wonder it’s not hard to find the right activity for any group of people. 
Here are a few of our favorite things to do Out East during the Winter:
Visit the Vineyards
Long Island is vastly known for it’s infinite expansion of vineyards. From wine tasting, to wine tours, and live entertainment, it’s no wonder the Winter is still a great time to go to vineyards. Enjoy a day away from the hustle and bustle sipping a glass of rosé and immerse yourself in Long Island’s Wine Country. 
Wine Tours & Tastings
Interested in trying out a new local wine? Well the Winter makes for a pleasant season to do just that. You can beat the crowds and get a more intimate experience this season. Plan your own tour with a limo company to enhance your experience and  make your visit that much easier. 
Live Entertainment
The Winter still includes the free live music that comes with visiting an East End winery. Places that include this fun and free entertainment are: 
2015 Winterfest Live on the Vine
Go to Live on the Vine, this invigorating Winter Festival takes place in a variety of Long Island tasting rooms, hotels, and other venues on the East End over the course of 6 weeks. The festivities take place every Saturday and Sunday up until March 29th. 
Enjoy the East End’s Parks & Beaches Off Season
Do you miss going to the beach and feel as if there aren’t enough months in the year dedicated to beach weather? Well then go to the beach in the off season anyway. There is still plenty to do in the off season. Just because you can’t go in the water doesn’t mean the beach isn’t a great place to go on a crisp, refreshing walk or simply a place for you to  just take in the scenery.
Visit the Montauk Point Lighthouse
Take a tour of the many different parts of the New York's first built lighthouse. Located on the easternmost point of Long Island this sight to see is the fourth-oldest active lighthouse in the country. 
Go on a Seal Hike in Montauk
Enjoy a spectacular hike across Montauk’s shore in the search for seals with trained pros from the NYS Parks Department. You won't want to miss out on one of these great 3-mile hikes, they'll be happening on weekends now through March!
Join CRESLI for a Seal Walk at Cupsogue Beach
Join scientists on a 1.3 mile walk to learn about and observe seals this Winter! The CRESLI Seal walks take place from November up until May. This is a great walk to take with your children! Just be sure to dress warm: bring hats, gloves, warm waterproof shoes. 
Go for a Winter Stroll on the Beach
You may be surprised to find that during the off season, the beach is a popular spot for a walk outside. It’s a great way to get a nice peaceful scenery away from noise and distractions without having to deal with any of that heat. This is also a great time to get creative and take some of your own photos. A lot of people go out to the beach during the winter to get some beautiful, artistic photos of their own. 
Check Out a Walk Around Town
The East End has plenty of adorable walking towns to visit - Greenport, the village of Sag Harbor, and of course there are more than a few choices out in the Hamptons, to name just a few. There are plenty of sights to see and shopping to do. 
Greenport Village
Enjoy the abundance of shops and food markets or take a walking tour around the village’s countless restaurants and museums. Greenport is home to the famous 1920s carousel that is located right on the waterfront. There are historical places to visit and many small shops and boutiques. The village is also home to the Greenport Farmers’ Market. 
The Hamptons
Take advantage of all the entertainment the Hamptons has to offer. If you're looking to spend a night or two in the Hamptons be sure to make yourself aware of the enticing deals. In the Winter hotels in the Hamptons offer up rooms at a discounted price. If you're looking for a sweet shopping experience, most stores in the Hamptons are open in the off-season and are for the most part empty of shoppers. It makes it a lot easier to shop in Coach and Tiffany & Company when there are only a few people browsing. This is also the perfect time for you to score some great discounts. 
Sag Harbor
Sag Harbor, situated within East Hampton and Southampton, is the perfect town to spend the day walking around. Take a stroll around the village and soak in the old historic buildings. The village is best known for its whaling port and harbors a variety of things to do such as a golf course, whaling museum and many other nautical attractions. Treat yourself to a live show at Sag Harbor’s Bay Street Theatre, this non-for-profit theater offers year-round entertainment. 
Enjoy an Afternoon of Educational Fun at an East End Museum
A perfect opportunity to take the kids and expand their minds, or you could even just go with a significant other and make the trip  a sweet day-time date. The East End offers up a variety of different kinds of museums that are open year-round for you to enjoy. Here are just a few: 
Sag Harbor Whaling and Historical Museum, Sag Harbor
Sag Harbor Whaling and Historical Museum is a museum dedicated to the Sag Harbor's past as a prosperous whaling port. Nestled in the heart of Sag Harbor village, the Sag Harbor Whaling Museum houses the largest collection of whaling equipment in New York.
Atlantic Marine World, Riverhead 
Atlantic Marine World is an aquarium located in downtown Riverhead on over 3 acres of scenic land stretching along the Peconic River. Visit the aquarium and get an exclusive sight of the western hemisphere’s largest all-living Coral Reef display. 
The Parrish Art Museum, Southampton 
This museum is inspired by the life of Long Island’s East End. It offers art exhibitions, educational activities and publications. 
Railroad Museum of Long Island, Greenport
Located right on the Long Island Railroad main line, the Railroad Museum educates its visitors about the history of trains and the Long Island Railroad. Situated in the historic 1892 freight house of the LIRR, the museum displays permanent collections of railroad artifacts along with annually changing exhibits. 
This Winter, when you're looking for fun things to do, don't forget about the fun right here on Long Island! Grab your family & friends, and head out East for an afternoon getaway, or weekend full of fun!
What are some of your favorite parts about the East End during the Winter?
Leave your comments below! 


  • The Montauk Lighthouse on a crisp Winter Day. Photo by: Joe Galletta