(Best) Things To Do In The Hamptons In The Winter (Off-Season)

November 29, 2017

The 10 Best Things To Do In The Hamptons In The Winter


Winter is coming soon! To celebrate, we’ve put together a list of our favorite things to do in the Hamptons in the Winter season. These are our top picks as a team at Plum Builders – things we love to do with our friends and family! Whether you’re just visiting for the season or have been here forever, have a look at our favorite things to do, and enjoy this winter!


Top Picks for Hamptons Winter Activities  Our Favorite Things to Do


Scheduled Trail Walks


Don’t stay inside all winter long. Take a scheduled trail walk alongside the bay and harbors, or plan your own self-paced walk with a friend or two. See the East Hampton Preservation Society website (http://www.ehtps.org/new-page/) for more information on scheduled activities.


Bike to the Beaches and Bays

The winter is a perfect time to take a bike ride to the beaches and bays. The roads are clearer, creating plenty of space for you to bike safely. While there, soak in the incredible views (perfect time to use your camera).


Go Ice Skating or Play Indoor Tennis


We recommend breaking out your ice skates and putting them to good use this winter. Head down to Town Pond when it’s cold enough to skate outside. When it’s not, check out the Southampton Ice Rink or the Buckskill Winter Club for ice skating.


Things To Do In The Hamptons In The Winter


You can also stay active in the winter in East Hamptons with indoor tennis. Winter is the perfect time to take lessons and be ready to compete when the weather warms up.


Visit Montauk Lighthouse and Cedar Point Park


This winter, be sure to make time to visit the historic Montauk Lighthouse. The lighthouse is among the oldest active lighthouses in the US (learn more). While you’re there, soak in the stunning sunsets at Cedar Park Point. Winter is such a perfect time to do this.


montauk lighthouse

“Go watch the sunset at Cedar point park by the light house. It’s gorgeous and no one really goes there in the winter so you get time to yourself… away from it all.” — Maritza G./Plum Builders


Celebrate Harborfrost in Sag Harbor


Spend a day celebrating winter with a festival on Main Street! Plans for the 2018 festivities haven’t been released just yet, but past years have been memorable – include the 2017 Fire & Ice celebration. Stay tuned to the website here for details: https://sagharborchamber.com/events/harborfrost/

Go to Gingerbread University (Riverhead)


gingerbread university


This one is a family favorite and truly one of the best things to do in The Hamptons in the Winter! Learn how to create your own incredible, edible gingerbread house in a one-hour decorating session. You’ll “graduate” from Gingerbread University with a creation to call your own and the confidence to build another. Reservations are strongly recommended. More info: http://www.gingerbreaduniversity.com/contact.


Visit the Guild Hall Museum


If you enjoy visual, creative, and performing arts, then this winter, schedule a trip to the Guild Hall Museum. This spectacular art museum features something for everyone in the community. Upcoming events include musical performances and art installations to benefit events and workshops. For more information, visit www.guildhall.org.


Enroll in a Workshop at the East Hampton Library

In the winter, many people take advantage of facilities that are normally very busy during the summer. The library is one of those places! The East Hampton library sponsors classes and activities year-round for local residents, from toddlers to adults. Special events include game nights for teens, 3D printing workshops, book clubs, author nights, and evening English as a Second Language classes for adults.


Dine Out at Our Favorite Restaurants


highway restaurant and bar


Get out of the cold and cozy up to good food and fun at one of our favorite restaurants and bars:


Dopo La Spiaggia – Italian eatery with a fireplace to keep you warm! 31 Race Lane

The Highway Restaurant and Bar – Fireplace, fantastic bar, and fun. 290 Montauk Hwy

Restaurant Week – Enjoy good eats at select restaurants during restaurant week at the end of March/early April every year.


Special: Donate to the East Hampton Food Pantry


This one is special to us at Plum Builders. Winter is traditionally a time of giving back to the community in various ways, and to each other, too. Every year, we at Plum Builders donate to the East Hampton Food Pantry and encourage you to do the same. Located at 159 Pantiago Road, the pantry accepts donations Monday through Thursday, from 9 AM to 2:30 PM. January, February, and March are the busiest months of the year for the pantry, so please consider donating as much as you can as early as possible.


Photo Credits: Facebook.com/Buckskill-Winter-Club, Facebook.com/MontaukLightHouse, Facebook.com/Gingerbread-University, Facebook.com/HighwayRestaurantandBar