The most wonderful time of the year will bring several merry outings to the Hamptons.
As per usual, Montauk will be a buzz with merry holiday happenings over Thanksgiving weekend. The Montauk Community Church Rummage Fair (850 Montauk Highway, Montauk) will launch the fun on Saturday, November 30, from 9 a.m. to 2 p.m. There will be new and used toys, handmade items and other exciting finds. The Montauk Library (871 Montauk Highway, Montauk) will host its annual Holiday Book Sale from 10 a.m. to 3 p.m. It will feature gift books, art books, cookbooks, children’s books, decorations, jewelry and more. Finally, the pièce de résistance, the 11th Annual Lighting of The Lighthouse, will take place from 4 to 7 p.m. The festive gathering will include holiday music and caroling, and a special appearance from Santa. The Lighthouse will remain illuminated nightly until January 1, 2020. On Sunday, December 1, Christmas at the Lighthouse with Santa will take place from 11 a.m. to 4 p.m. The Lighthouse, which is beautifully decorated for the season, will welcome the man of the month, offer up some tasty hot cider and snacks, and feature some easy holiday shopping at the Gift Shop. There will also be pony rides available for younger children. Additionally, on Thursday, December 12, even more holiday cheer will engulf Montauk during the Montauk Chamber of Commerce’s “Starbrite” Storefront Lighting from 5 to 5:30 p.m. Montauk businesses will show-off their holiday decorations, with prizes at stake for best traditional, whimsical, and best display of Montauk and brightest displays. For more information, visit www.montaukchamber.com.
The beloved It’s A Wonderful Village, presented by Southampton Country Holiday, debuts on Saturday, November 30. From 12 to 3 p.m., you can take a quaint horse and buggy ride throughout the Village. Rides depart from Southampton Village Hall (23 Main Street, Southampton). The Parade of Lights will follow at 4:45 p.m. Then, it’s time for the tree lighting and a spectacular fireworks display. The evening will culminate with a special reception at Southampton Cultural Center (25 Pond Lane, Southampton) with Santa. It’s A Wonderful Village returns of Saturday, December 7 for more horse and buggy rides from 1 to 4 p.m. and a visit from Santa at the Chamber of Commerce (76 Main Street, Southampton) from 1:30 to 3:30 p.m. On Saturday, December 14, it’s another chance for horse and buggy rides – departing from Southampton Village Hall – from 12 to 3 p.m., and Santa will make an appearance at the Rogers Memorial Library (91 Coopers Farm Road, Southampton) from 2 to 4 p.m. It’s A Wonderful Village concludes on Saturday, December 21 with horse and buggy rides from 12 to 3 p.m. that depart from Southampton Village Hall. For more information, visit southamptonchamber.com.
The annual Lighting of the Big Duck (Route 24, Flanders) will take place on Wednesday, December 4 at 7 p.m. The evening will include a special appearance from Quackerjack, the Long Island Ducks baseball team mascot, carols sung by students from the Riverhead Middle School Show Choir, refreshments and the arrival of Santa Claus by fire truck. For more information, visit www.facebook.com.
Baron’s Cove Holiday Party & Tree Lighting (31 West Water Street, Sag Harbor, www.baronscove.com) will take place on Friday, December 6 from 3 to 9 p.m. The festive celebration will feature live music, a traditional tree lighting, and a cold weather accessories drive for Maureen’s Haven Homeless Outreach Program. Attendees are encouraged to bring a donation of a warm hat, gloves, scarves or socks.
The Holiday Season will Sparkle at Good Ground Park in Hampton Bays on Friday, December 6 from 3:30 to 5 p.m. The joyous affair will include some good old fashioned caroling with the Dickens Carolers, the chance to have your picture taken with The Grinch, hot cocoa from Hampton Coffee Co. and cookies donated by Krieg’s Bakery. Attendees are asked to bring a non-perishable item to help fill Santa’s Food Pantries for the Heart of the Hamptons. The annual St. Mary’s Episcopal Church Christmas Fair at St. Marys Episcopal Church (165 Ponquogue Aveue, Hampton Bays, www.stmaryshb.org) will take place on Saturday, December 7 from 9:30 a.m. to 2 p.m. Fair-goers will enjoy the famous cookie walk, handmade holiday items and gifts, and ornaments, fresh wreaths and greens, holiday décor, jams, pickles, soups, home-baked goods, jewelry, “American Girl Doll Clothes” and more, gift baskets and Chinese auction raffle baskets, and more. There will be a Christmas storytime at 10:30 a.m. in the Children’s Play Room., Santa Claus will arrive at 11 a.m. and a special Christmas fair raffle for an Apple iPad Pro (12.9 in) Wifi with Pencil ($1,250 Value).
The annual Lighting of the Windmill at Stony Brook Southampton (39 Tuckahoe Road, Southampton) will be held on Friday, December 6 from 6 to 7:30 p.m. The evening will include refreshments, music, an Alumni-Sponsored Photo Booth, crafts for little ones, guided windmill tours, and a special SoMAS Marine Science lecture at 7:30 p.m. at Duke Lecture Hall . For more information, visit www.stonybrook.edu.
The Festival of Lights Westhampton Beach and Winterfest will be held on Saturday, December 7. The event will begin with a Holiday Stroll on Main Street from 11 a.m. to 4 p.m., with in store specials. From 11 a.m. to 4 p.m., special children’s crafts can be created at Lynne’s, while cookie decorating will take place at Sydney’s from 12 to 4 p.m. A Holiday Spectacular can be seen at Westhampton Beach Performing Arts Center at 2 p.m. and there will be candy canes at Sugardaddy’s Toys and Cookies at Messina Jewelry. There will be events in Glovers Park from 2 to 5 p.m. Prosecco for adults and bubble water for the little ones can be found at Good Westhampton from 4 pm to 5:30 p.m. and hot chocolate cones at Impulse for Men. For more information, visit www.westhamptonchamber.org.
East Hampton Chamber of Commerce will host several holiday happenings on Saturday, December 7. The East Hampton Santa Parade will kick-off the merriment at 2:30 p.m. The parade starts on Main Street, in front of the First Presbyterian Church, and travels to the Hook Windmill. The East Hampton Lighting Of The Windmill is next up from 3:30 to 4:30 p.m. The gathering will encompass holiday caroling and music. The inaugural East Hampton Holiday Night Market will take over Newtown Lane from 4 to 8:30 p.m. The pop up will feature more than 50 artisan, craft and nonprofit vendors, 60 Newtown Lane and Main Street shops will remain open late, a Santa’s Village Experience, including “equine” reindeer, a holiday petting zoo, holiday caroling and live music, a best decorated storefront contest, Santa’s storefront scavenger hunt, gift-wrapping station, book fair, Long Island Winterfest experience preview, and more. The Santa’s Village Experience (from 4 to 8:30 p.m.) at Eileen Fisher will feature photos with Santa, a card for Santa station, Santa’s “Equine” Reindeer Exhibit, provided by Spirits Promise Rescue, shopping for adults with bites and sips. For more information, visit easthamptonchamber.com.
Sag Harbor Chamber of Commerce is hosting its annual Holiday Village on Saturday, December 7. The gathering will commence with the arrival of Santa Claus, who will arrive at the Windmill via Fire truck at 3 p.m. Then, he will listen to children’s Christmas wishes, and at 5 p.m., the Chamber will “Light Up” the giant Christmas tree at the foot of Long Wharf. For more information, visit sagharborchamber.com.
Light Up Amagansett, Amagansett’s second annual holiday extravaganza, will take place on Saturday, December 7 from 4 to 7 p.m. For more information, visit www.amagansettchamber.org.
Springs Improvement Society will host its 28th annual Lights of Love at Ashawagh Hall (780 Springs Fireplace Road, East Hampton) on Sunday, December 8 from 3 to 5:30 p.m. The Holiday Party will include caroling, music, cider, irresistible holiday sweets, special activities for kids, and the lighting of the Christmas tree on the Green. Attendees can purchase “Lights of Love” for $5 per light, with proceeds going towards the SIS Scholarship Fund. For more information, visit ashawagh-hall.org.