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Holiday Special: The 2023 Datebook

Fri, 12/08/2023 - 13:21
A Hampton Ballet Theatre School tradition now in its 14th year, “The Nutcracker” returns
Kyle Froman

Sleigh bells ring: Are you listening? Here’s our carefully curated selection of the holly-est, jolliest events between Thanksgiving and New Year’s Day.

Thursday, November 23

Turkey Trot
The Village Green, Montauk

10 a.m. Admission: $20

Now in its 47th year, the Thanksgiving Day Run for Fun has become incredibly popular, with more than 1,000 people showing up in 2022. It’s an all-ages affair, with toddlers in strollers and elite runners on the three-mile or six-mile course.


Gingerbread House Contest
Project MOST Community Center, 44 Meadow Way, East Hampton

Through Dec. 13. Fee: $30 per kit

Project MOST brings back a tradition that many may remember from the days of Mary’s Marvelous: the gingerbread-house-decorating competition. Kits can be reserved online at, with dropoff beginning on Wednesday, Dec. 13 and a community viewing and awards on Saturday, Dec. 16 from 2 to 4 p.m.


Friday, November 24

Evergreen Open House
East Hampton Gardens, Gingerbread Lane

Through Sunday. Admission: Free

Hot chocolate, cider, and sweet treats will be handed out at an open house that begins on Black Friday and runs through the weekend. Ornaments, greenery, and Christmas trees will be for sale outside, and a chic cornucopia of décor and ornaments indoors. On Saturday, Santa will arrive at high noon; families have been invited to join him for a photo op. Dogs and cats are welcomed, too.


Marionette Show
East Hampton Library, 159 Main Street

2 p.m. Admission: Free

“Princess and the Pea” — in puppet show form. Kids follow along as a prince embarks on a journey to find himself a princess, learning along the way how sometimes the best things in life are those that are completely unexpected. Registration, at, is required.


Saturday, November 25

Holiday Makers Market
The Church, 48 Madison Street, Sag Harbor

11 a.m. to 5 p.m. Also Sunday. Admission:
$5, adults; under 12 free

The Church is transformed into a winter wonderland, with local makers – from jewelry designers and artists to food and skin-care producers — offering up an elite selection of handmade or homemade goods. There will also be a pop-up printmaking show and, at 1 p.m. both days, an outdoor community sing-along to spread good cheer.


Let There Be Lights
Ashawagh Hall, 780 Springs-Fireplace Road, Springs

Through Monday. Time T.B.A.
Admission: Free

A blind-auction fund-raiser, with 100 artists creating works – all in a format of 12-by-12 inches – in support of a new lighting system at the community house. You like an artwork? You bid, without knowing who the artist is. There will also be a silent auction.


House and Garden Tour
Clinton Academy, 151 Main Street, East Hampton

1 to 4:30 p.m. Admission: $85 in advance, $100 at door

The 38th annual East Hampton Historical Society house tour — a ritual snoop through some of East Hampton’s most interesting houses — is always a hugely popular event, and may be even more so this year, because the attractions include a stop-off at Grey Gardens, the former home of the Beales, near Georgica Beach. You may want to get your tickets early.


Lighting the Lighthouse
Montauk Point State Park

4 to 7 p.m. Admission: Free

Around dusk, free hot chocolate will flow courtesy of Hamptons Coffee and live, sing-along holiday tunes will be supplied by Sarah Conway and the Playful Souls, as the crowd awaits the main event: the festive illumination of the Montauk Lighthouse in thousands of string lights. This year’s honoree is a Montauk Harbor legend, “Admiral” Ed Michels.


Sunday, November 26

Afternoon Tea
The Baker House 1650, 181 Main Street, East Hampton

1:30 p.m. Also Sunday and Dec. 10.
Admission: $61 to $146

An afternoon of delicious dainties, with an assortment of teas from Southampton’s Plain T, flutes of bubbly, freshly baked sweets, and tea sandwiches. Reservations are a must. Children (who, we expect, will be dressed in their Eloise-ish best) have a special price, and adults can choose from a regular high tea or a “royal” spread with a extra Champagne or caviar.


Wednesday, November 29

Polar Bear Family Photos
John Jermain Memorial Library, 201 Main Street, Sag Harbor

3:30 to 5 p.m. Admission: Free

For those who didn’t manage to take a holiday card photo while on summer vacation this year, here’s a chance to snap one with a polar bear, a yeti, or a special loved one, complete with festive backgrounds and green-screen effects. Photos will be received within a week. Sign-up is at 631-725-0049, or ron the library website.


Thursday, November 30

Sag Harbor Girls’ Night Out
Sag Harbor Fire Department, 1357 Brick Kiln Road

5 to 8 p.m. Admission: $15

Just in case you haven’t started your holiday shopping yet, here’s where you can find a curated assortment of Long Island vendors offering up lovely wares as a benefit for South Fork charities. Light bites and wine are served, so it’s shop-’til-you-drop, drink-’til-you’re pink.


Friday, December 1

LongHouse Illuminated
LongHouse Reserve, 133 Hand’s Creek Road, East Hampton

4:30 to 7:30 p.m. Also: Dec. 2, 8, 9, 15, and 16. Admission: $45 ($35 for members)

For three weekends in December, LongHouse Illuminated returns after dark with garden paths lined with lights and glowing sculptures. The NeoPolitical Cowgirls youth performance troupe will perform “Zima,” bringing to life woodland creatures encountered as guests roam the grounds. A holiday market with festive music, food, drinks, art, and jewelry by East End artists will be held in the warmth of the pavilion. Visitors will also be allowed to touch and forage leaves, pine cones, and acorns to help create a “community meditation circle” of natural plant material. Baskets will be provided.


Hearthside Cheer and Tree Auction
Southampton History Museum, 17 Meeting House Lane

5 p.m. Admission: $35 for one, $60 for a pair

Christmas comes to the Rogers Mansion. Guests nibble and tipple while exploring 20 rooms furnished with Jazz Age decor, all decked out for the holidays. Christmas trees crafted by local artisans will be auctioned to benefit the museum.


Return of “The Nutcracker”
Southampton High School, 141 Narrow Lane

7 p.m. Also: Saturday, 1 and 7 p.m., and Sunday, 2 p.m. Admission: $25 in advance, $30 at door

It wouldn’t be Christmas without a trip to the Land of Sweets! A Hampton Ballet Theatre School tradition now in its 14th year, “The Nutcracker” returns with Tchaikovsky’s enchanting score, Sara Jo Strickland’s choreography, and dazzling costumes by Ms. Strickland, Yuka Silvera, and Kate McManus. Advanced students dance the roles of the Snow Queen, Sugar Plum Fairy, Dew Drop, and Arabian Princess, with professional guest artists as partners. V.I.P. seating at special ticket price; $15 entry for students on the day of.


Saturday, December 2

Gingerbread Holiday Market
East Hampton Village Hall, 86 Main Street

9 a.m. to 5 p.m. Admission: Free

Hugh King, the town crier, will open the East Hampton Village Market, a new event that benefits the East Hampton Food Pantry and promises to become annual. The East Hampton Middle School Bonnettes will sing on the lawn at 3:45 p.m. and three large gingerbread houses — depicting Village Hall, Mulford Farm, and a Candy House — will be raffled, with the prizes drawn at 4:15. More gingerbread houses, gingerbread trains, and gingerbread men will be available for purchase, alongside a plant-sale bevy of wreaths, amaryllis, poinsettia, and cyclamen.


Candy Cane Holiday Fair
Most Holy Trinity Catholic Church, 79 Buell Lane, East Hampton

10 a.m. to 3 p.m. Admission: Free

Gift-shopping in the Parrish Hall returns, with crafts (jewelry and other handmade items) wreaths and plants, as well as white-elephant wares and the added temptation of homemade holiday cookies and other refreshments. Those who knew and loved Most Holy Trinity’s annual Silver Tea from pre-pandemic days will appreciate this step back into the December action.


Santa Fly-In
Herrick Park, 67 Newtown Lane, East Hampton

10 a.m. Admission: Free

Father Christmas (a k a, the Big Man, St. Nick, Saint Nicholas, Santa, Chris Kringle) makes his appearance in the morning, arriving by helicopter as he did last year. Dressens Famous Donuts and hot chocolate will be passed out and, after greeting his young fans, Santa will be escorted in befitting style to the parade in his honor.


East Hampton Village Santa Parade
Main Street and Newtown Lane, East Hampton

11 a.m. Admission: Free

The annual kickoff to the season brings the joyful noise to the business district. Expect costumes, candy canes, and possibly a few elves on the march. If the weather is looking uncongenial, a rain-date — or snow-date — decision will be announced on the village’s website.


Artisans’ Bazaar
Ashawagh Hall, 780 Springs-Fireplace Road, Springs

10 a.m. to 4 p.m. Admission: Free

The 13th annual Friends Bazaar, a popular and much-anticipated event, offers direct artisan-to-customer sales. Go for original, handmade items of quality: ceramics, photography, paintings, prints, woodware, jewelry, small sculpture, home decor, wearable art, scarves, knits, essential oils, soaps and skin products, leather goods, and more.


Gingerbread House Challenge
Rogers Memorial Library, 91 Cooper’s Farm Road, Southampton

11 a.m. Admission: $10 per team

Individuals and teams of up to five can enter a friendly, all-ages gingerbread house-decorating competition, in which prizes will be awarded for “Best Construction,” “Most Creative,” and “Best Decorated.” Festive refreshments will be served. Sign-up is required ahead of time via the library’s online calendar.


Homegrown for the Holidays
Hayground School, 151 Mitchell Lane, Bridgehampton

11 a.m. to 3 p.m. Admission: Free

This long-running annual craft sale brings together a bevy of small businesses including makers, bakers, and all sorts of vendors for a ginormous — as Buddy the Elf would say — family-friendly shopping event. Extra enticements include raffles, cookies and cocoa from the student-operated Hayground School Kitchen, crafty activities for kids, and gift-wrapping by donation to benefit the Hayground School.


Free Holiday Movies
Regal Cinema, 30-38 Main Street, East Hampton

1 p.m. Admission: Free

The traditional screening of free December-centric family movies at the cinema will provide a moment for children enjoying the East Hampton Village Holiday Celebration a chance to get off their feet. “The Grinch Who Stole Christmas” and “Fred Claus” are the featured attractions.


Mrs. Claus Meet-and-Greet
The L.V.I.S. Gardiner “Brown” House, 95 Main Street, East Hampton

2 to 4 p.m. Admission: Free

While her husband relaxes after his spectacular appearance next door in Herrick Park, Mrs. Claus will be cozily ensconced by the Christmas tree in the Ladies’ Village Improvement Society headquarters, greeting the children. Each child will be able to share their wish list with her and receive a special treat.


A Bird Happening
The Leiber Collection, 446 Old Stone Highway, Springs

3:30 p.m. Admission: Free

Monica Banks, an installation artist, will discuss her work with teacups and cakes with Sag Harbor’s April Gornik and Ann Stewart, the director and curator of the Leiber Collection. Videos of “bird shenanigans” are promised, as well as refreshments.


Baron’s Cove Tree Lighting
Baron’s Cove, 31 West Water Street, Sag Harbor

4 to 10 p.m. Admission: Free

There will be eggnog, hot chocolate, and warm gingerbread cookies for the kids, and candy cane martinis on offer for adults. Activities include a Christmas-stocking design event for kids in the Map Room at 4 p.m., the Tomas Hashhagan Band performing in the barroom from 5 to 7, classic carols from the Baron’s Cove Carolers, and the arrival of the big man himself, Santa, at 6:30. Brad Penuel takes over the live tunes from 7 to 10.


East Hampton Village Tree Lighting
The Sheep Pound, Gay Lane, East Hampton

5 p.m. Admission: Free

This year, there will be a ceremonial lighting on the big tree in the green triangle near the post office — between Egypt Lane, Gay Lane, and Pantigo Road — known as “the Sheep Pound” (a historic spot where sheep were corralled in the 17th through early 20th centuries, a fitting setting for a reminder of Biblical shepherds and the sheep of the manger).


Wolffer Estate’s Lighting of the Vines
Wolffer Estate Vineyard, 139 Sagg Road, Sagaponack

6 to 8 p.m. Admission: $175 general;
V.I.P. seating available

The twinkling lights won’t be just a festive display — they shine for a good cause. The Bridgehampton Child Care and Recreational Center is the beneficiary of this party, which will also include a silent auction of wreaths designed by East End artists and community members. There will be hors d’oeuvres, live music, and, of course, excellent wine.


Sunday, December 3

Wreath Workshops
Marders,120 Snake Hollow Road, Bridgehampton

10 a.m. Also Dec. 10. Admission: $125 adults, $85 children 12 and up

Heads-up: These workshops sell out fast, with a strict limit of 12 guests per session. If you can score a coveted spots, you’re in for a real treat. And with its winter-wonderland backdrop, a trip to Marders this time of year is always a lively holiday excursion.


“A Christmas Garland” Choral Concert
Bridgehampton Presbyterian Church, 2429 Montauk Highway

3 and 5:30 p.m. Admission: $10 students,
$35 adults, $75 preferred

Walter Klauss conducts the South Fork Chamber Orchestra as the Choral Society of the Hamptons performs its annual holiday concert. The program includes Bach’s “Christmas Oratorio” and  “What Sweeter Music” by John Rutter.  The performance ends with a round of carols, with audience participation.


Tuesday, December 5

Prep Your Pup for the Holidays
Animal Rescue Fund of the Hamptons,124 Daniels Hole Road, Wainscott

5:30 p.m. Admission: $35

A unique class offering insight into Fido’s state of mind during the hectic weeks of December, when he has to cope with guests and a groaning board of food temptations. With tips and techniques for keeping your pet calm and off the kitchen counter. Pre-registration is required at


Thursday, December 7

Bridgehampton Community Menorah Lighting
Hampton Library, 2478 Main Street, Bridgehampton

4:30 p.m. Admission: Free

At dusk on the first night of Hanukkah, organizations including the Hampton Library, Friends of the Library, Bridgehampton Village Improvement Society, and the Bridgehampton Association will gather to light the first “candle” on the menorah together.


Long Wharf Menorah Lighting
Long Wharf, Sag Harbor

6 p.m. Admission: Free

Sag Harbor’s Temple Adas Israel hosts an annual menorah lighting on Long Wharf, complete with prayers, songs, hot chocolate, and jelly doughnuts. Clergy and members of other Jewish congregations are welcomed to attend, and families will be offered a box of candles for their home menorahs.


Saturday, December 9

Polar Bear Plunge
Cooper’s Beach, 268 Meadow Lane, Southampton

9 a.m. registration, 10 a.m. plunge. Admission: $25 for participants

“Get freezin’ for a reason,” says Heart of the Hamptons, a Southampton-based nonprofit, which needs to raise $350,000 to continue supporting more than 2,100 families in need of food, home-heating help, and other types of assistance. Cold-water plungers can register as individuals or teams; the registration fee includes a baseball cap.


Merry Madoo Market
The Madoo Conservancy, 618 Sagg Main Street, Sagaponack

10 a.m. to 3 p.m. Admission: Free

Chestnuts will — literally — be roasting over an open fire and hot cider and vin chaud (after 12 noon) will be mulled during the annual artisanal shopping event at the Madoo gardens. Unusual goodies on offer will include: paperwhites grown at Madoo, lady-apple pomanders tied with vintage velvet ribbon, fresh-cut boughs, bespoke pottery from Mae Mougin, gardening tools from Sneeboer, and other unique stocking stuffers.


By Hand Artisans’ Gifts
Ashawagh Hall, 780 Springs-Fireplace Road, Springs

10 a.m. to 4 p.m. Also Sunday. Admission: Free

The By Hand Artisans’ Holiday Gift Show, in its 24th year, features artworks in fused glass, knits and felted wool creations, wood crafts, beach glass items, handmade soaps and toiletries, ceramics, jewelry, honey, and more. Motto: Happiness Is Handmade.


Old-Fashioned Holiday Tea
First Presbyterian Church, 120 Main Street, East Hampton

1 to 3 p.m. Admission: $20 adults,
$10 children

The Tea’s the Season Holiday Tea, with hot cuppas and assorted sweet and savory treats, will be held upstairs in the church’s Session House, behind the main edifice. Tickets are available on the church’s website.


Magic of Montauk Fair
Montauk Town Green, 743 Montauk Highway

2 to 7 p.m. Admission: Free

Actual, real-live reindeer will be among the extremely jolly attractions at this year’s holiday fair, as well as a “local hot cocoa contest,” decorated holiday path (sponsored by Lighting the Christmas Joy decorating services), gift booths, kids’ activities, food trucks, a holiday bar with beer, mulled wine, and Montaukila tastings. Rain date: Dec. 10.


Rockabilly Ruckus
East Hampton Library, 159 Main Street

3 p.m. Admission: Free

A Long Island–based rockabilly band called the New York Vendettas (with the Holiday Horns) will convene in the library’s Baldwin Room for an afternoon of old-fashioned rock-and-roll, with kissing-under-the-mistletoe hits from artists like Elvis, Chuck Berry, and Darlene Love.


Thursday, December 14

Winter Concert
East Hampton High School, 2 Long Lane

6:30 p.m. Free admission

The talented choral and instrumental students of the East Hampton High School music department will present a concert of seasonal music open to all. 

Friday, December 15

“Wonderful Christmastime” Handbells
First Presbyterian Church, 120 Main Street, East Hampton

1 p.m. Admission: $20 adults, $10 children

Attendees have been asked to bring a nonperishable food donation for the South Fork food pantries or an adult-size hoodie for donation to Maureen’s Haven homeless-outreach program.


Saturday, December 16

Scrooge & Co. Reading
East Hampton Library, 159 Main Street

Noon. Admission: Free

Be transported to the London of 1843 as Laura Jasper, a theater director and workshop leader, reads “A Christmas Carol.” The timeless Dickens tale of Tiny Tim and the Ghosts of Christmases Past, Present, and Future is suitable  for adults and children of school age. Registration can be done by calling the library at 631-324-0222, extension three, stopping by the adult reference desk, or visiting

Playful Souls and Ugly Sweater Party
The Stephen Talkhouse, 161 Main Street, Amagansett

8 and 10 p.m. Admission: $25 and $15.

Sarah Conway and the Playful Souls put on their annual Christmas concert at 8 p.m., with a playlist of lesser-known holiday gems — rock, country, blues, and gospel. Ages 21 and over. That’s followed at 10 by an Ugly Sweater Party with tunes by Hot Date.


Sunday, December 17

Ringing the Harbor Bells
St. Andrew Catholic Church, 122 Division Street, Sag Harbor

4 p.m. Admission: Free

The uplifting sounds of the Harbor Bells, a handbell choir, will ring out once again at St. Andrew Church, featuring traditional carols and other seasonal favorites. Guests should bring a nonperishable food item to donate, supporting the Sag Harbor Food Pantry.

Boat Parade Viewing Party
Inlet Seafood Dock and Restaurant, 541 East Lake Drive, Montauk

5 to 8 p.m. Admission: $100 adults, $50 children

Dancing to a live band, drinks, food, and an unobstructed view of the fishing fleet, decking out in twinkling lights, are the draw at this second annual event, which benefits the Montauk Food Pantry. It sold out in 2022 and likely will again. Tickets are available at

Sunday, December 31

“Noon” Year’s Eve Dance Party
John Jermain Memorial Library, 201 Main Street, Sag Harbor

10:30 a.m. Admission: Free

Kids are invited for a New Year’s Eve dance party and countdown (to noon) with popcorn and games. No registration is required.


New Year’s Eve at the Talkhouse 
The Stephen Talkhouse, 161 Main Street, Amagansett

10 p.m. Admission: $50

Dancing, high spirits, and live music are on tap at the Talkhouse. For ages 21 and up. Tickets are available at


New Year’s Party at Baron’s Cove
Baron’s Cove, 31 West Water Street, Sag Harbor

6 and 9 p.m. Admission: $125 first seating, $175 second

Highlights of the night include festive party favors (noisemakers, anyone?), live music, and a spectacular view of the annual Sag Harbor fireworks, weather permitting. Reservations can be made at


New Years Prix Fixe at Gurney’s
Gurney’s Montauk, 290 Old Stone Highway

5:30 and 8 p.m.
Admission: $120 first seating, $170 second

A lavish, four or five-course prix-fixe supper is served in the Scarpetta Beach dining room, overlooking the wintery ocean waves. Reservations, a must, are at


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