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Our Favorite Winter Activities on the East End

By |Published On: January 23, 2020|

Although summer will always be the most popular time of year to visit the Hamptons, the East End has plenty to offer throughout the off-season months as well. Beat the wintertime blues with these fun activities to keep you entertained while we (not so) patiently wait for the warmer weather to return.

Bay Street

Bay Street Theater

Live Music

When it comes to live music, the East End has a little of everything to offer from live concerts to local band performances and karaoke. Suffolk Theater in Riverhead offers concerts throughout the year, often featuring music from your favorite artists such as the Beatles and Sinatra. Also, check out Bay Street Theater with many performances by local favorites including Nancy Atlas and Gene Casey and the Lone Sharks. In addition, there are many local breweries and wineries offering live music throughout the winter such as Greenport Harbor Brewery, Pindar Vineyards and Lieb Cellars or enjoy karaoke nights at local bars including North Sea Tavern and Publick House in Southampton. Whether you are looking for a relaxing afternoon at the winery or the full concert experience, you will be sure to find it on the East End.

Winter Wine Tasting

While some wineries close for the winter months, there are still many Long Island tasting rooms that continue to serve exceptional wine throughout the year and there is nothing quite like curling up on a cold day with a glass of red wine. A few of our favorite wineries to visit during the off-season include Bedell Cellars in Cutchogue and Sherwood House Vineyards in Jamesport, which both have working fireplaces to keep you warm in the winter. The tasting barn at Shinn Estate Vineyards in Mattituck is also a lovely spot for winter wine tasting offering a cozy wine library with couches and a beautiful view of the vineyards and wine cellar. Additionally, Clovis Point in Laurel encloses and heats their patio and continues to offer live music on the weekends throughout the winter months.

Southampton Ice Rink

Southampton Ice Rink

Ice Skating

As in most places, ice skating is another popular winter activity here on the East End. Southampton Ice Rink features a fully covered rink and offers many programs throughout the week for all skill levels from private lessons to hockey clinics. There are also concessions and indoor seating available at the ice rink in Southampton. Be sure to check out the outdoor ice rink in Greenport Village as well, located right next to the carousel in Mitchell Park. Both rinks offer plenty of free skating time throughout the week and on the weekends for you to enjoy.

Bowling in the Hamptons

Bowling in East Hampton


For indoor fun for the entire family, head to one of the East End’s popular bowling alleys. Both The All Star in Riverhead and The Clubhouse in East Hampton offer a wide array of fun activities from bowling to arcade games and pool tables, providing the perfect spot to spend a winter day. Keep an eye out for special deals including all-you-can-bowl for $20 on Thursday nights at The All Star. The Clubhouse also offers special events throughout the winter including Bingo Nights, Trivia Nights and Paint ‘N Sip events. Both facilities also feature a full bar and restaurant with drink and food specials.

Trivia Night

If you are looking for some weeknight fun, test your knowledge at a trivia night at a local bar or restaurant. With many East End spots offering trivia nights, you are sure to find a place for you. Locations include Townline BBQ in Sagaponack, Brewology295 in Eastport, Jamesport Farm Brewery in Riverhead, and The Mill Roadhouse in Westhampton Beach among many others. Make it a date night or team up with a group of friends for an evening full of trivia, fun and prizes with the drinks always flowing.

East End Art Museum

East End Art Museum

Visit an East End Art Museum

Spend a chilly winter day wandering through one of the East End’s many art museums or galleries. Some of the more popular locations include the Southampton Arts Center, Guild Hall in East Hampton and the Parrish Art Museum in Water Mill, all showing lovely exhibitions during the off-season. Not only do these galleries offer beautiful art to be viewed, but many run additional programs throughout the winter including films and live music for additional winter entertainment.