Wondrous Winter Activities in the Hamptons this December

Dana Trotter

The Hamptons is a great escape from the hustle and bustle with plenty of opportunities to delight in holiday cheer. Events range from ice skating with Santa Claus to a drive-through light show.

Buckskill Ice Rink

This winter, take time for the festive season and lace up your skates at The Buckskill Ice Rink. The Buckskill Ice Rink is the only refrigerated, NHL regulation-sized, ice rink in the Hamptons. Not only is their rink beautiful and spacious but their cozy clubhouse is available for anyone who needs a break with some hot cocoa next to the fire.

South Hampton Ice Rink

Offering ice skating no matter the weather conditions, South Hampton Ice Rink is the only covered rink in the Hamptons and is open for public skating this holiday season. This holiday season, you have the opportunity to skate with Santa himself on December 18th and 23rd. Grab your tickets to hit the ice with Santa Claus. Hang out after the ice in one of their new, rentable igloos. With plenty of space to enjoy the holidays covered under the stars, cozy up with board games and hot chocolate.

Sag Harbor Cinema

This Christmas day, bring the whole family for a special showing of the Christmas classic Polar Express at Sag Harbor Cinema. This heart warmer tells the story of a boy who boards a mysterious train waiting for him late on Christmas Eve.

Sag Harbor Historical Society

Sag Harbor Historical Society is hosting sing-along caroling with the Dickens Carolers on Sunday, December 19th at the Annie Cooper Boyd House. Refreshments will be available and awards will be given to the winners of the home decorating contest. Don’t miss this fun holiday event in Sag Harbor Village.

Hamptons Community Outreach

The holiday season reminds us how important it is to appreciate the family and friends we have and how lucky we all are. Each year, Hamptons Community Outreach works to better the lives of all families in the area, specifically children and teens. They offer multiple opportunities to get involved and make their Christmas dreams come true. Head to their website to Adopt a Santa Letter and surprise a local kid with the gift of their dreams. Donate to their Teens in Need program that focuses on underserved teens that are often overlooked during holiday toy drives and gift collections. If donating gifts directly is what you prefer, HCO has linked their Amazon wishlists with toys and gifts they hope to be able to give to the community this year.

John Jermain Memorial Library

This New Year’s Eve, John Jermain Memorial Library has put together a unique and family-friendly game event to kick off the new year. Bring the kids and drop by the library from 11-4 to enjoy Giant Jenga, Giant Connect 4, Cornhole, board games, and more!

West Hampton Beach Performing Center

Don’t miss the holiday favorite, The Nutcracker, live at the West Hampton Beach Performing Center. Join the Peconic Ballet as they run their production of the Nutcracker. Telling the well-known story of Clara and her beloved Nutcracker Doll as they journey to an enchanted wonderland forest and into the Land of The Sweets, the Peconic Ballet is sure to delight. Watch this year’s Peconic Ballet Theatre’s production of “The Nutcracker” with an all-new cast this Christmas season.

Riverhead Holiday Light Show

After spending the past three seasons at Long Island Sports Park in Calverton, Riverhead Holiday Light Show has moved to nearby Splish Splash Water Park. The annual drive-through attraction features dozens of elaborate light displays synchronized to music broadcast over your car’s FM radio. The popular 20-25 minute show runs through December 30. Car-load tickets are on sale now for $23 online and $25 at the door, check out the schedule and buy tickets at [http://Riverhead Holiday Light Show]holidaylightshow.com.

Topping Rose House

Each Friday night before Christmas, Topping Rose House celebrates the season outdoors around the fire and under the lights with holiday decorations, music, and refreshments. On the manicured grounds in Bridgehampton on Fridays at 4:30 pm, the friendly staff serves spiked apple cider for the parents and hot chocolate for the kids. The s'mores are for all to enjoy. Children are free and adults are $25.


Although days are shortening and temperatures are dropping, the East End's natural beauty is just as accessible in the tranquil wintertime. Bundle up and check out December events with the East Hampton Trail Preservation Society and find trails on the Suffolk Country Parks and Peconic Land Trust websites.

Shou Sugi Ban House

As magical and charming as the holiday season can be, it can also be quite draining. Those seeking relaxation and rejuvenation this holiday season need to look no further than the Shou Sugi Ban House. Book a wellness retreat for an overnight stay and immerse yourself in zen and healing. Unwind with their curated wellness menu and enjoy their peaceful and serene Guest Studios that include a cozy fireplace and Japanese soaking tub.

Their spa contains a wide offering of wellness options from Watsu therapy, bodywork, cupping, to their signature SSBH massage. Prioritize your wellbeing this holiday season and experience why Shou Sugi Ban House is a perfect escape from the craziness of the season.

Guild Hall

This season, Guild Hall has two unique exhibitions on display: The Uncanny Valley by Jeff Muhs and 90 Years, an exhibition showcasing 90 years of Guild Hall’s commitment to collecting artists of the Eastern End of Long Island.

Guild Hall is an art, entertainment, and education center for the community that collaborates with artists of Eastern Long Island. “90 Years features a selection of paintings, sculptures, photographs, and works on paper showcasing 90 years of Guild Hall’s commitment to collecting artists of the Eastern End of Long Island. The museum’s Director and Chief Curator, Christina Mossaides Strassfield, has chosen 90 works from all media to show the historical contribution of artists of the area.

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Dana's portfolio includes high-end residential sales and rentals as well as investment and land opportunities. She has successfully negotiated hundreds of property contracts and continues to work vigorously for buyers and sellers alike.

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