Start the Holidays Off Right at These Premiere East End Events

Young couple walking in downtown for Christmas. Holding Christmas gifts and big Teddy bear. Wearing warm clothing.
Photo: iStock

Tis the season for festivals, parades and open houses leading up to Chanukah and Christmas! Deck your halls, stock your shelves and explore the East End this holiday season!

Ooh, and HOUSE TOURS are happening too…check out how you want your home to look at the annual East Hampton Historical Society House and Garden Tour November 23 and 24. The benefit event kicks off with a cocktail party on Friday, followed by a tour of five spectacular East End properties on Saturday. Starts at the Maidstone Club. 50 Old Beach Lane, East Hampton. 631-324-6850,

Next month is the Cutchogue Holiday House Tour, on December 8. Spread joy and cheer with friends and family this holiday season by wining and dining your way through four stunning homes and The Old House. Seasonal gifts will be available and a portion of ticket proceeds will go towards stocking the shelves of local food pantries. Cutchogue. 631-734-8282,

While on the North Fork, head to Jamesport—Shade Tree Nursery is now offering—in addition to Christmas trees, wreaths, roping, tabletop trees and kissing balls—custom and premade gift baskets featuring their own North Breeze Farm products. 1875 Main Road. 631-722-4041,

Southampton’s Parade of Lights & Annual Tree Lighting begins on November 24. Join the community for a parade of lights leading to the annual Christmas tree lighting. Enjoy caroling, horse and buggy rides, fireworks and a holiday reception with Santa. Southampton Village. 631-283-0402,

Also on November 24 is SoFo’s Annual Thanksgiving Open House. This year’s event includes a sacred blessing by the Shinnecock Nation, traditional dancing by the Shinnecock Youth Dancers, the unveiling of the new shark exhibit and the kick-off to SoFo’s Holiday Charity Drive, which will benefit the Animal Rescue Fund of the Hamptons and Southampton Animal Shelter Foundation. South Fork Natural History Museum (SoFo), 377 Bridgehampton-Sag Harbor Turnpike, Bridgehampton. 631-537-9735,

Santa Claus is busy this season!

Don’t miss the East Hampton Santa Parade on December 1. The parade begins on Main Street and turns onto Newtown Lane. Afterward, meet Santa and enjoy free cider and donuts by Rowdy Hall’s fireplace. For more info call 631-324-0362, or visit

The Greenport Parade of Lights and Tree Lighting also takes place on December 1. Wave to Santa and Mrs. Claus as they drive through the streets of the village aboard a decorated fire truck. Then, join local school children singing carols at the tree lighting in Mitchell Park and enjoy a cup of hot chocolate for extra holiday cheer. For more info, visit

Concurrently, for grownups, is Greenport Shellabration on December 1–2. This savory restaurant walk features the best in local shellfish, wine and beer. Wristband sales benefit Cornell Cooperative Extension Marine Program. Get info at

Plus there’s the Holiday Tree Lighting at the Shoppes at East Wind on December 2. Stop by to put a letter in Santa’s mailbox, meet the big man himself, dance to the tunes of a live DJ, and enjoy more holiday fun. Rain date: 11/8. The Shoppes at East Wind, 5768 NY-25A, Wading River. 631-929-3500,

And in Port Jefferson there’s the 23rd Annual Charles Dickens Festival December 1–2. See photos of amazing performances, an old-fashioned marketplace, carriage and trolley rides, a lantern-lit house tour and more at

What the–more Dickens? The annual Westhampton Beach Dickens Family Holiday Festival returns on December 8 with loads of family fun to be had as you explore the festively decorated village from 11 a.m.–3 p.m. Find all the deets at

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