Where to Celebrate Your Hamptons Holiday Season in 2014

Montauk Lighthouse comes to life at Christmastime
Montauk Lighthouse comes to life at Christmastime, Photo: Thinkstock

As the holiday season alights, the East End becomes awash in a blend of magic, wonder and cheer. Our villages and hamlets put on their holiday best, showing off before settling into their winter slumbers. Unique celebrations abound, providing ample opportunity for residents and visitors to create fantastical memories and yearly traditions.

Some holiday traditions endure in the Hamptons, while others fall away with the passage of time and the shifting cultural and economic landscape. Who remembers all the years when East Hampton stood out among the local hamlets and villages at Christmastime, as every tree along Main Street was wrapped in blue lights? They were charming and distinctive—they cast the village in a different light than those with white or multicolored bulbs. Today, Town Pond holds the last lonely bastion of that bygone time—one little tree holding its blue vigil for days past in the center.

Perhaps as a tribute, each year on Three Mile Harbor Road one group of homeowners recreates the rows of blue-lit trees along their street. Hopefully that tradition will continue, and new ones are born each year.

Southampton is a winter wonderland starting on November 29, when the annual Parade of Lights goes down Windmill Lane and drives around Southampton village to Agawam Park for the Christmas tree lighting. Local vocal choirs VOSH and MOSH will perform, with a holiday reception to follow. The Southampton festivities continue on December 6, with a holiday village stroll complete with carolers, horse and buggy rides, refreshments and more. And on December 13, kids will be able to meet Santa. Hayrides will be available each weekend by Scorpion Farms.

On December 6, head to the First Presbyterian Church on Main Street, Southampton for the annual Christmas bazaar, then see the Live Nativity on December 13, where the church’s youth groups tell the Christmas story.

East Enders can also head to Montauk on November 29 for the annual Lighting the Lighthouse event. Santa has promised to make an appearance at this joyous event, which will include holiday music and caroling. And as a bonus treat, Dan’s Papers founder Dan Rattiner is set to do the honors of “flipping the switch.” The lights will remain on every night until January 1. The lighting rain date is scheduled for December 6.

The next day, on November 30, head to Christmas at the Lighthouse for hot cider, snacks, pony rides for the kids and photos with Santa. Admission is free. The rain date is scheduled for December 7. Other Montauk events include the Jingle Bell Hop on December 5; the Annual Senior Citizens’ Dinner at the Montauk Fire Department on December 7; and the Star Bright Lighting Contest, where businesses compete for the title of Best Decorated Montauk Business, on December 10. Closing out the holiday 2014 season for Montauk is a visit from Santa at the firehouse on December 14.

Montauk Point on January 1 sees another tradition—the annual pilgrimage of Koreans and Korean-Americans to watch the first sunrise of the New Year. Korean culture calls for the first sunrise to be seen from the easternmost accessible point of land, and Koreans from Long Island and the New York metro area traditionally make the pre-dawn trip to Montauk Point to greet the sun and anticipate all that the New Year holds, as the lighthouse becomes awash in golden sunlight.

East Hampton is also awash in lights for the holidays. On November 29, take a tour of the area’s beautiful houses and gardens with the East Hampton Historical Society. On December 6, head to the village for the Santa Parade, which begins on Main Street and travels onto Newtown Lane, where kids will be able to meet Santa. The festivities continue on December 13, with the free “Dickensian Christmas” readings at Clinton Academy. On December 14, take a candlelit tour of decorated historical houses, with costumed guides, musicians and other period-style entertainment. Revelers can also enjoy a lantern tour of Main Street on December 19. Also on December 19, celebrate Chanukah with Chabad Lubavitch with a public menorah lighting in Herrick Park.

On December 6, Westhampton Beach holds its annual Holiday WinterFest, where participants can ride the Westhampton Beach Holiday Trolley to events around the village. Among the many activities and attractions, local stores host kids’ craft stations and holiday treat stations, carolers wander the streets and Santa and Mrs. Claus entertain with stories and fun. Later that evening, Jews and Christians celebrate the holidays together at the annual Christmas tree and menorah lighting ceremony on the Village Green. Caroling by the Westhampton Beach High School chorus and the Hampton Synagogue’s Youth Choir will fill the evening with the festive sounds of the season. Enjoy free hot cocoa and cookies. To top off the evening, Santa Claus himself arrives by fire truck.

Wolffer Estate Vineyards lit for the Holiday Season
Wolffer Estate Vineyards lit for the Holiday Season, Photo: Kelly Laffey

Wölffer Estate Vineyard has its own celebration on December 6, with the Festival of Lights. The South Fork vineyard will host a silent auction of holiday wreaths and other décor designed by local artists and designers, and a lighting of the vines with 15,000 LED lights illuminating the fields. Enjoy holiday jazz by Vanessa Trouble while enjoying Wölffer’s various wines and hard ciders. Tickets sell out quickly, so head to wolffer.com while you can!

The annual Holiday Lighting of the Big Duck in Flanders is held the first Wednesday after Thanksgiving each year, coincidently the same day the of the nationally televised Rockefeller Center Christmas tree lighting. Not that we’re biased or anything, but attending a duck lighting in person is a bit more quack-tastic and oh-so-Long Island!

The North Fork is also busy with holiday events. On November 29, the annual Greenport Christmas Tree Lighting will take place in Mitchell Park. Then, on December 6 and December 7, Greenport will host its annual Shellabration, giving visitors the opportunity to enjoy the fresh shellfish of Peconic Bay paired with local wine at restaurants throughout the village. There are some great deals, including $5 tapas-sized portions of local shellfish and $3 wine tastings.

With so many holiday events, you can’t see them all. Find a few favorites and enjoy them year after year. It’s how family traditions are born.

Visit our Events Calendar for more great holiday activities and ideas!

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