A Brief History of the East End’s Timeless Holiday Traditions

The holiday season is a time of colorful lights, community and cheer, and the East End holds a cornucopia of local events that families flock to year after year. From tree lightings to festivals, celebrate Christmas, Chanukah and New Year’s with these timeless festivities—and some new ones, too.

1950s–1970s: Korean New Year’s in Montauk
Korean culture celebrates the solar new year by viewing the first sunrise from the easternmost point of land, which for New Yorkers would be Montauk Point. While impossible to pinpoint the inaugural Korean-American migration to Montauk, it’s surely one of the oldest East End holiday tradition, based on the mass Korean immigration to New York taking place between the 1950s through the ’70s.

1985: East Hampton House & Garden Tour
The annual house tour opens the doors of five Hamptons estates on Thanksgiving weekend while supporting the East Hampton Historical Society in its goals to educate and preserve local history. Festivities begin with a cocktail party at the Maidstone Club on Friday, November 29, with the tour on Saturday. easthamptonhistory.org

1988: The Big Duck Lighting
Not long after Kia and Pouran Eshghi donated The Big Duck to Suffolk County, the iconic fowl saw its first holiday lighting. Draped in festively lit garland, the duck continues to welcome local families to its grounds on the first Wednesday after Thanksgiving—December 4 this year—to sing duck carols, sip hot cocoa and await Santa’s arrival atop the Flanders Fire Department truck. bigduck.org

1993: East Hampton Holiday Tour, Santa Parade and More
East Hampton goes above and beyond every holiday season with several longstanding events that continue to delight local families and visitors alike. The annual Santa Parade reigns in Christmastime on Saturday, December 7 at 10 a.m., followed by the Lighting of the Windmill and the Holiday Night Market. The Holiday Party on takes place on Tuesday, December 10. And the 27th annual B&B, Inn & Attraction Holiday Tour will once again offer an up-close look at Hamptons living with a self-guided winter adventure on Saturday, December 14 from noon–4 p.m. easthamptonchamber.com

1996: Charles Dickens Festival
For more than two decades, Port Jefferson has magically transported visitors to the Dickensian era, as characters including Father Christmas, Scrooge and the classic chimney sweeps roam the streets. Once again taking place on the first weekend of the last month of the year, December 7–8, the festival includes a wide range of free attractions, including ice skating at the Village Center, Christmas caroling, Nutcracker performances and more hosted by various costumed characters. portjeff.com/dickens

1997: Southampton Parade of Lights
The Village of Southampton ushers in the holiday season with the 21st annual Parade of Lights on Saturday, November 30. The yearly procession sees decorated and lighted fire trucks and emergency service vehicles roll through the village at 5 p.m., leading to a Christmas tree lighting in Agawam Park, a visit from Santa at the Southampton Cultural Center and a spectacular fireworks display. If your child misses Old Saint Nick the first time—or thinks up some more gifts to ask for—they’ll get a second chance when he returns to Southampton on a horse-drawn buggy on Saturday, December 7 from 1 p.m. Horse-and-buggy rides will be available through 4 p.m. southamptonchamber.com

2002: Southampton History Museum’s Hearthside Cheer
Taking many forms over the years—from a classy cocktail party to an ugly sweater party—this year’s much-anticipated event features a designer tree auction with festive music and more. southamptonhistory.org

2008: Montauk Lighthouse Lighting
Just over a decade ago, the Lighthouse Committee had the bright idea to string thousands of LED lights around the Montauk Lighthouse and host an event for the first lighting of the season, and, sure enough, more than 3,000 people came to see the pride of The End aglow in holiday cheer. Head to Montauk on Saturday, November 30 at sunset, approximately 4 p.m., to take part in this beloved tradition, then plan to return on Sunday, December 1 from 11 a.m.–3 p.m. to meet Mr. Claus himself. montauklighthouse.com

2011: Sag Harbor Holiday Village
Though this event was not coined the Holiday Village at first, Santa has been making annual appearances in Sag Harbor for many years, travelling by fire truck to the Christmas tree lighting by the Long Wharf Windmill. Families can meet the man of the season from 3–5 p.m. on Saturday, December 7. sagharborchamber.com

2012: Greenport Shellabration
The first-ever Shellabration proved that Greenport doesn’t have an off-season—hundreds poured into 10 participating restaurants for scallops, clams oysters and more, while the local vineyards offered wonderful wine pairings. In 2019, the lineup has expanded to 15 eateries with shellfish, beer and wine options aplenty for anyone wearing an event wristband from noon–4 p.m. on December 7–8. Best of all, proceeds benefit the Southold Project in Aquaculture Training (SPAT) and Cornell Cooperative Extension’s Marine Program’s Back to the Bays Initiative. shellabration.li

2013: Chanukah MenorahCade & Chanukah Bowl
A parade of cars topped with menorahs drive through East Hampton from the Chabad of the Hamptons on Sunday, December 22 at 3:30 p.m. before arriving at Herrick Park for a public lighting of the giant menorah at 4 p.m. As always, East Hampton Mayor Paul Rickenbach will light the first light as the community engages in traditional Chanukah singing and blessings. Started in 2018, the Chabad of the Hamptons hosts a follow-up event, the Chanukah Bowl, at The Clubhouse in East Hampton, where families enjoy a fun day of bowling, latkes and the lighting of the bowling pin menorah. chabadofthehamptons.com

2013: Santa’s Workshop at the Shelter Island Historical Society
Shelter Island’s beloved children’s event returns on Sunday, December 8 from 1–4 p.m. for free photos with Santa, ornament and gift crafting and unwrapped toy drive for children in need. While Sunday is dedicated to the little ones, Saturday, December 7 is all about the grown-ups. Relax with friends while enjoying holiday refreshments, munching on hors d’oeuvres and grooving to live music. RSVP to the holiday part by December 4. shelterislandhistorical.org

2017: Southold Fire Department Fire Santa Parade
The young event has quickly become a staple in Southold, ringing in the holiday season with a Santa-led brigade of fire trucks, all decked out in colorful lights, wreaths and other decorations. See the parade light up the village after dark on December 21. southoldfd.com

2019: Dan’s Holidays in the Vines Hosted by RG|NY
Eat, drink and be merry! You’re invited to Dan’s Hamptons Media’s inaugural holiday wine-and-dine spectacular at the beautiful North Fork vineyard! The once-in-a-lifetime night on Saturday, November 30 brings together incredible local winemakers and chefs for wine tastings, a six-course pairing dinner and VIP experience with culinary legend Claudia Fleming of North Fork Table & Inn signing the new release of her classic The Last Course and VIP gift bag. HolidaysInTheVines.com