The towns and villages of the South Fork are beautiful in any season of the year, but the East End gets downright Hallmark-movie stunning come December. Light posts wrapped in evergreen, snowscape displays in shop windows and, of course, gorgeous, twinkling trees and menorahs to usher in the festive spirit (and sometimes lighthouses, boats and windmills, too—because, hey, it’s the Hamptons).
This year’s options are as plentiful as the presents in Santa’s bag, offering both kid-friendly and grown-up fun for the whole community. Mark the beginning of the twinkly season at one of these illuminating events.
Bonac Lights, East Hampton
When: Nov. 25th and 26th, 5:30 p.m. to 8:30 p.m.
Get in the holiday spirit for a good cause! For two nights only, walk through the fun, light-festooned grounds of East Hampton High School annual light and holiday decoration event lets you and your family kick-off the season in twinkly style (and your admission fee goes right to scholarships benefitting the East Hampton Student Association—now that’s the Christmas spirit!). A round of applause to Star of the East Lodge #843 who sponsored this year’s event. Huzzah!
Light the Lighthouse, Montauk
When: Friday, Nov. 26th, 4 p.m. to 7 p.m.
The iconic landmark gets all dressed up for the holiday season. Expect complimentary hot chocolate from Hamptons Coffee Company and holiday singalong at this only-in-Montauk event.
Ram’s Head Inn Winter Fest Featuring Annual Tree Lighting, Shelter Island
When: Saturday, Nov. 26th, 4 p.m. to 6 p.m.
Be part of a new tradition when the recently reopened storied Shelter Island spot hosts its first tree lighting. There will be hot chocolate and cider (with a twist for those of legal age), s’mores, fire pits, ornament making and holiday music.
Hampton Bays Christmas Tree Lighting and Santa, Hampton Bays
When: Sunday, Nov. 27th, 4:30 p.m. to 7:30 p.m.
Festivities include photos with Santa, caroling, gift bags and a tree lighting. There will also be a taco truck in case you’ve already had your fill of holiday grub.
First Annual Pridwin Tree Lighting, Shelter Island
When: Friday, Dec. 2nd, 6:30 p.m. to 9 p.m.
Santa will be on hand from 6:30 to 9 p.m. for photos. Ditto for live music, holiday cocktails, fire pits with marshmallow roasting (weather permitting), hot cocoa and cookies. The indoor tree gets lit at 5:30 p.m.
Lighting of the Windmill, Southampton
When: Friday, December 2nd, 5 p.m. to 7:30 p.m
Stony Brook Southampton’s annual event is a family-friendly affair that includes music, guided windmill tours, a photo booth and crafts. Take a break from all that and learn something new by attending the marine sciences lecture at 7 p.m. in Duke Lecture Hall. RSVP to [email protected]
Annual Barons Cove Tree Lighting Ceremony, Sag Harbor
When: Saturday, Dec. 3rd, 6:30 p.m. to 9 p.m.
The tree lighting itself takes place at 7:30 p.m., but kids from one to 92 will want to arrive early. Santa is coming to Baron’s Cove at 6:30 p.m., and yes, you can snap a pic with the jolliest old elf. Eggnog, frozen hot chocolate and gingerbread cookies are among the refreshments.
Light Up the Harbor, Sag Harbor
When: Friday, Dec. 3rd, 5 p.m.
The event begins with a candle-lit walk from the Windmill on Long Wharf to the annual tree. The tree and windmill lighting are at 5:30 p.m. Anyone who wants to join the carolers should meet at Annie Cooper Boyd House (174 Main St.) at 5 p.m. It’s BYOBOC (bring your own battery-operated candle).
Shelter Island Chamber of Commerce Tree Lighting, Shelter Island
When: Tuesday, Dec. 6th, 5 p.m.
This annual event begins with a tree lighting and caroling in front of the police headquarters and ends with hot cocoa, cookies and photos with Santa at the American Legion.
Winterfest Christmas Tree and Menorah Lighting, Westhampton
When: Saturday, Dec. 10th, 3 p.m.
The event begins at 3 p.m., and Santa will ditch his sleigh and hop on a fire truck for a 5:30 p.m. photo op. The tree lighting will take place on The Village Green. For more information, head to https://westhamptonchamber.org.
Lighting of the Long Wharf Menorah, Sag Harbor
When: Sunday, Dec. 18th, 6 p.m.
Temple Adal Israel will light the Long Wharf menorah, situated just below the windmill in front of Bay Street Theater, for the first time on Sunday, Dec. 18th.
East Hampton Menorahcade, East Hampton
When: Sunday, Dec. 18th, 3:30 p.m.
’Tis the season for menorah-topped cars rolling through the Hamptons. The East Hampton Menorahcade will feature a parade of such Hanukkah-happy vehicles traveling from the Chabad of the Hamptons (13 Woods Lane) to Hook Windmill, where the menorah will be lit for the first time.