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Holidays on the East EndHolidays on the East End


Get ready for plenty of holiday cheer this season, festive events are back and in full swing! Below we highlight several East End holiday events on both the North and South Forks. Events are in order by date.

Friday, November 26th

Carriage House Holiday Shop, Southampton Historical Society, Southampton

The Southampton History Museum on Meeting House Lane in Southampton will host The Carriage House Holiday Shop and Designer Tree Auction. Martha Stewart and many well-known designers are creating tabletop holiday trees to benefit the museum’s free education programs. The silent auction begins Friday, November 26th at 11am and ends Saturday, December 4th at 4pm.

Mandala Yoga Holiday Bazaar, Amagansett

Mandala Yoga at 10 Amagansett Square on Main Street in Amagansett is hosting a Holiday Bazaar featuring some of the Hamptons’ finest local designers. Vendors include Hamptons Handpoured, Promised Land Jewelry, Sea Gyspy Botanicals, and Hidden Gem, among others. The Holiday Bazaar will take place from 1:30-5:30pm.

Saturday, November 27th

25th Annual Tree Lighting and Parade of Lights, Southampton

Southampton Village celebrates the 25th annual Firetruck Parade of Lights beginning at 4:45pm. There will be Christmas Carols by “VOSH” and “MOSH”, the annual Tree Lighting Ceremony, and a Spectacular Fireworks Display to round out the night. The event is sponsored by the Christmas Decorations Committee. Click here to learn more.

Lighting the Light, Montauk Lighthouse, Montauk

The most recognized landmark on Long Island, the Montauk Lighthouse, is celebrating their annual lighthouse lighting ceremony beginning at dusk or at approximately 4pm on Saturday, November 27th. On Sunday, Santa will make his traditional visit to Montauk Point. Sunday’s Christmas at the Light will take place from 11am until 3pm. This event is free for everyone.

Santa at The Homestead, 1760 Homestead Farm, Riverhead

Saturdays November 27th and December 11th, and Sundays November 28th and December 12th

For two separate weekends, from 11am-4pm each day, 1760 Homestead Farm on Sound Avenue in Riverhead is hosting time slots for family photos with Santa. Santa on the Farm requires advanced reservations (each 15 minute photo session is $45). Reservations for the photo sessions may be made by clicking here. The sessions also include a matted 5×7 photo. While you are visiting the farm, choose the perfect Christmas tree and or wreath at the farm shop. Also, pick up one of the handmade famous pies from the farmhouse.

Sunday, November 28th

Menorah Lighting in Sag Harbor

This annual Menorah Lighting tradition is sponsored by the Egosi family and the Sag Harbor Inn on the Long Wharf in the village of Sag Harbor. The Menorah Lighting begins at 6pm on the first night of Hanukkah.

Home for the Holidays, Mattituck Historical Society, Mattituck

Home for the Holidays takes place at the Mattituck-Laurel Historical Society on Main Road in Mattituck from 2-7pm. Refreshments will be served, along with a gift and bake sale for holiday shopping. Bring the children and enjoy kid’s crafts, tours of the museum (2-4:45pm), and visit Santa from 3:30-5pm. The caroling and tree lighting will take place from 5-5:30pm. The event is free for everyone. Call Lori for more information at 631-3841474.

Wednesday, December 1st

Holiday Lighting at The Big Duck, Flanders

This free event runs from 7-9pm and will feature a visit from Quackerjack, the Long Island Ducks baseball team mascot, duck carols led by students from the Riverhead Middle School Show Choir, refreshments and the ever-anticipated arrival of Santa Claus by fire truck.

Victorian Christmas, East Hampton Historical Society, East Hampton

Visit the East Hampton Historical Society on Main Street in East Hampton for a special holiday exhibition at the Thomas & Mary Nimmo Moran Studio. The exhibition runs through December 23rd, open from 11am-3pm, featuring festive décor, period clothing, antique postcards, and period period toys to recreate the atmosphere of a 19th century Christmas celebration. Pre-registration is requested. Tickets are $5 per person. Click here to register.

Thursday, December 2nd

First Annual Holiday Stroll, Westhampton Beach

Celebrate the season with the first annual Holiday Stroll on Main Street in Westhampton Beach from 6-9pm. Shop local and support the arts! This evening of shopping features many local Westhampton Beach businesses and restaurants. Each business is partnering to raise money for WHBPAC. Holiday strollers will pick up a punch card at the box office. Then, they will collect stamps from each participating retailer along Main Street. After shopping, guests could enter to win a deluxe holiday raffle while listening to the dueling piano show, @savagepianos.

Learn more and purchase tickets at whbpac.org or call 631-288-1500.

Saturday, December 4th

The Spirit of Christmas, Spirit’s Promise Equine Rescue, Baiting Hollow

The Spirit of Christmas encompasses holiday events all taking place at Spirit’s Promise Equine Rescue, located at 2746 Sound Avenue in Baiting Hollow, December 4th, 11th and 18th. These three Saturdays in December include holiday farm tours with Mrs. Claus and the elves, storytime, and a meet-and-greet with the Equine Reindeer. A nominal donation is requested for entry. Book online.

On Saturday, December 11th at 7pm, there is Line Dancing with Deanna. Tickets are $15 each with advanced sales only. No tickets will be sold at the door. Call 631-875-0433 for more information.

Fire & Ice Christmas Market, Spirit’s Promise Equine Rescue, Baiting Hollow

Saturdays, December 4th and December 18th, 4-9pm. Free admission.

The Fire & Ice Christmas Market will be held at Spirit’s Promise Equine Rescue in Baiting Hollow. This outdoor Christmas Market is inspired by the German Christmas Markets. Guests will enjoy magical lights, ice carvings, and fire dancing. Shop for unique gifts and taste baked goods, hot cocoa, and cider. An on-site gift wrapping service is available.

Holiday Tree Lighting, Shoppes at East Wind, Wading River

The annual holiday tree lighting will take place at the Shoppes at East Wind, located on NY-25A from 3-7pm. Guests will be able to write letters to Santa and place them in Santa’s mailbox. Holiday fun includes shopping at their Winter Fest, a live DJ and dancing, and much more. Santa will arrive and greet guests on a firetruck to light the tree and take photos with families. Free admission. Rain date is Sunday, December 5th.

Note: Santa will also be at the Shoppes Winter Fest on Saturdays, December 11th and 18th from 11am-5pm.

Railroad Museum of Long Island, Riverhead

Visit the Railroad Museum of Long Island, located at 416 Griffing Avenue in Riverhead, decorated for the holiday season on Saturday, December 4th and Sunday, December 5th from 11:30am-3pm each day. Santa arrives each day at noon. Refreshments will be served and the gift shop will be open. There is also a LIONEL Polar Express Trainset raffle. Free admission for everyone.

Pet Photos with Santa and The Grinch, Southampton Animal Shelter Foundation, Hampton Bays

Visit the Southampton Animal Shelter on Old Riverhead Road in Hampton Bays for pet photos with Santa and the Grinch from 10am-4pm. Schedule your photo sessions in advance! Email events@sasf.org to schedule. Photos are $20 and directly support the animal shelter. DIgital copies will be emailed to you, and physical photos will be sent to your mailing address. Call 631-728-PETS (7387) to learn more.

Light Up The Harbor, Sag Harbor

Light up Sag Harbor with the spirit of the season. The Sag Harbor Historical Society’s candle-lit walk leads to the Long Wharf for the annual Tree and Windmill Light-up tradition. The event begins at the Annie Cooper Boyd House on Main Street at 5pm. Guests are encouraged to bring their own battery-powered candle. Caroling and a countdown to the holiday light-up begins at 5:30pm. Holiday music will be played by WLNG radio station.

Annual Candlelight Tour, Southold Historical Society, Southold

The Southold Historical Museum’s Holiday Fair at Peconic Lane Community Center will take place from 9am-4pm. Find unique holiday gifts for everyone on your list. The event will feature a bake sale, crafts room and face painting for children. Santa will also be visiting to greet everyone! Lastly, there will be a holiday auction that features gift bakers for all ages. Admission and photos with Santa are free.

Village Green Tree Lighting, Cutchogue

The annual Village Green Tree Lighting will take place in Cutchogue on Route 25 beginning at 4:30pm. The event takes place at The Village Green, a collection of historic houses that tells the story of Cutchogue from 1640 to present day. Santa will visit, and delicious holiday cookies will be served. Call 631-734-7122 for more information.

Parade of Lights and Tree Lighting, Greenport

The annual Christmas parade in Greenport begins at 5pm from the corner of Main Street and Center Street. It will then continue through the village to Mitchell Park and will go until 7pm. The parade is presented by the Village of Greenport and the Greenport Fire Department. Rain Date is Sunday, December 5th.

Holiday Open House, LVIS, East Hampton

The Ladies Village Improvement Society (LVIS) will welcome everyone to the Gardiner Brown house at 95 Main Street in East Hampton from 2-4pm. Cider, cookies, and eggnog will be served. Mrs. Claus will make her appearance and will greet others and take photos with families.

Sunday, December 5th

Long Island Aquarium Santa Brunch, Riverhead

Celebrate the season with the annual Santa Brunch at the Long Island Aquarium in downtown Riverhead. Families enjoy a delicious buffet brunch in the Sea Star Ballroom. After the brunch, the family is welcome to take a tour of the aquarium. The visit to the aquarium is included in the brunch ticket price. Seating times are as follows: 10am, 12pm, and 2pm. Advanced reservations are required and can be made by calling 631-208-9200 ext 426. Hotel packages are also available.

Wednesday, December 8th

Holiday Musical Bingo, North Fork Brewing Co., Riverhead

Have fun playing bingo while listening to holiday tunes from 6:30-8:30pm at North Fork Brewing Co. on East 2nd Street in Riverhead. Guests can grab a bingo card with a beverage purchase. Event goers will also have a chance to win some free draft beer vouchers and other great prizes. Free to play. Seating is on a first come, first served basis.

Saturday, December 11th

Downtown Riverhead Holiday Parade & Riverfront Bonfire, Riverhead

Come see the Riverhead Lions Club 69th Annual Holiday Parade in downtown Riverhead beginning at 3pm. The parade begins on Main Street and loops south to the Peconic Riverfront where the Downtown Riverhead bonfire is taking place at 4pm. Visit Santa in the town’s Gingerbread House and take photos with him and your family. Be sure to bring your own thermos for complimentary hot cocoa and holiday treats. Santa’s House will be open from 5-7pm. Rain Date is Saturday, December 18th.

Holidays at the Hangar Artisanal Craft Fair, East Hampton Airport, East Hampton

Explore the holiday shopping event held at East Hampton Airport at 173 Daniels Hole Road from 12-4pm. Holidays at the Hangar will feature unique items for sale from local artists and artisans. These include jewelry, art, photography, glassware, holiday decor, woodworking, leather goods, and more. Crafts for kids, free coffee and hot chocolate, holiday treats, and visits from Santa will bring even more festive cheer. Contact Donna Fiumano for more information: 917-756-0184.

Sunday, December 19th

Holiday Concert with The Dickens Carolers, Sag Harbor

The Holiday Concert with The Dickens Carolers begins at 2pm, presented by the Sag Harbor Historical Society. There will be holiday treats and books for sale, along with a special outdoor holiday concert. The concert will be performed by The Dickens Carolers at the Annie Cooper Boyd House on Main Street.

Author: VGordon