Where To Find The Most Holiday Cheer In The Hamptons: A Parade Of Lights, Santa Parades, Tree Lightings And More

Love a good seasonal extravaganza?

Montauk’s holiday festivities will commence on Saturday, November 24 with the Montauk Community Church Christmas Fair (850 Montauk Highway, Montauk), taking place from 9 a.m. to 2 p.m. The seasonal extravaganza will include baked goods, handmade items, Christmas decorations, new and used toys, and other gifts, and the Rummage Sale rooms will also be open. Another holiday shopping destination, the Montauk Library Holiday Book Sale (871 Montauk Highway, Montauk), will take place from 10 a.m. to 3 p.m. and there will be gift books, art books, cookbooks, children’s books, decorations, jewelry and much. much more available. Then, it’s time for one of the most anticipated moments of the year, the Lighting the Lighthouse (2000 Montauk Highway, Montauk), which will take place from 4 to 7 p.m. A special guest will have the honor of launching this year’s spectacular sight. On Sunday, November 25, Santa will be making an appearance at the Lighthouse from 11 a.m. to 4 p.m. – where attendees will also enjoy caroling, pony rides and refreshments. For more information, visit www.montaukchamber.com.

It’s A Wonderful Village, presented by Southampton Country Holiday, debuts on Saturday, November 24. From 12:30 to 3:30 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 5 p.m. Then, it’s time for the tree lighting and a spectacular fireworks display. The evening will culminate with a reception at Southampton Cultural Center (25 Pond Lane, Southampton). It’s A Wonderful Village returns of Saturday, December 1 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 8, it’s another chance for horse and buggy rides – departing from Southampton Village Hall – from 12:30 to 3:30 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 continues on Saturday, December 15 and Saturday, December 22 with horse and buggy rides from 12:30 to 3:30 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, November 28 at 7 p.m. 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, November 30 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.

East Hampton will host an all-day holiday affair on Saturday, December 1. The merriment commences with the East Hampton Santa Parade that will take place at 10 a.m. Once Santa makes his way down Main Street and Newtwon Lane, he will stop by Rowdy Hall (10 Main Street, East Hampton) to meet with little ones. There will also be free cider and donuts by the fire. The LVIS Holiday Open House (95 Main Street, East Hampton) will take place from 2 to 4 p.m. Attendees will enjoy refreshments, have the chance to meet Mrs. Claus, and can fit in some holiday shopping. Finally, it’s time for the East Hampton Village Christmas Tree Lighting Ceremony at c/o The Maidstone (207 Main Street, East Hampton). Taking place from 4 to 6 p.m., the cheerful event will include live music, hot cocoa and more refreshments, carolers, children’s activities, and the Grand Lighting of the Christmas Tree, of course. For more information, visit easthamptonchamber.com.

The Hampton Library’s 25th Annual Holiday Open House (2478 Main Street, Bridgehampton) will take place on Saturday, December 1 from 2 to 4 p.m. As they wait for the Lions Club to escort Santa from the North Pole, guests will be treated to cookies courtesy of South Fork Bakery, hot cocoa from Starbucks and cider, cozy winter tales, and delicious soup from the Bridgehampton School. Once the special guest has arrived, it’s time to light the holiday tree, which will be followed by caroling and music from the Bridgehampton School Band. For more information, visit www.hamptonlibrary.org.

Sag Harbor is hosting its annual Holiday Village on Saturday, December 1 from 3 to 5 p.m. The afternoon will include Christmas music curated by WELJ, a visit from Santa Claus who will arrive at the Windmill on a Fire Truck at 3p.m. and the giant Christmas tree at the foot of Long Wharf will brim with holiday pizazz for the first time of the year at 5 p.m. For more information, visit sagharborchamber.com.

Light Up Amagansett, Amagansett’s holiday extravaganza, will take place on Saturday, December 1, from 4 to 8 p.m. You can meet Santa at the Amagansett Fire Department at 4 p.m., and then join in on some caroling, followed by the tree lighting near the train station courtesy of the Amagansett Village Improvement Society. After the lighting, there will be a historical walk down Main Street with Hugh King. For more information, visit www.amagansettchamber.org.

Westhampton Beach’s Christmas Tree and Menorah Lighting at the Village Green will be held on Saturday, December 1 from 5:30 to 7:30 p.m. The evening will include holiday music, food, cookies from Beach Bakery, hot chocolate from Hampton Coffee Company and a visit from Santa. The following weekend, the Greater Westhampton Chamber of Commerce will host a Westhampton Family Fun Holiday Festival on Saturday, December 8 from 11 a.m. to 3 p.m. The seasonal extravaganza will include a variety of children’s activities, including tea time at Tweed with Wicked Sisters Tea, a holiday book reading at Tweed Toys, a candy cane toss at Beach Bakery, hot chocolate cones at Impulse, build a candy cane ornament at Chic, a Mickey and Minnie meet and greet at Messina, a holiday paint session at Pawcasso, and craft a holiday ornament at Good Westhampton. For those looking to add a new family member this holiday season, the Bideawee adoption van will be onsite with pups and kittens that are available for adoption. Shoppers that find something special at a Chamber or Commerce Member store, you can wrap the holiday gift in the free wrapping center. Emily’s Apple Puff Food truck will also be making an appearance. For more information, visit www.westhamptonchamber.org.

Springs Improvement Society will host its 27th annual Lights of Love at Ashawagh Hall (780 Springs Fireplace Road, East Hampton) on Sunday, December 2 from 3 to 5 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.

The annual Lighting of the Windmill at Stony Brook Southampton (39 Tuckahoe Road, Southampton) will be held on Friday, December 7 from 5:30 to 7:30 p.m. The evening will feature refreshments, music, guided windmill tours, crafts, a photo-booth sponsored by Alumni, and a festive display by Stony Brook Southampton Hospital in the Stony Brook Southampton Center Cafeteria. There will also be a lecture by Janet Nye, Associate Professor at the School of Marine and Atmospheric Sciences, in the Duke Lecture Hall at 7:30 p.m. that will cover “The Future is Now: Climate Change and New York Fisheries.” For more information, visit www.stonybrook.edu.

Prior to the Hampton Bays’ Annual Tree Lighting on the Village Green on Saturday, December 8 at 4:20 p.m., Boots on the Ground Theater’s Dickens Carolers will spread a little holiday cheer. They will be performing at the Lyzon Hat Shop (16 Main Street, Hampton Bays) at 3 p.m. and then head down Main Street to the Cannuscio Trail. At 3:45 p.m., they will make their way to Good Ground Park and at 4 p.m. there will be carols by the Westhampton Beach Performing Arts Center Teen Repertory Theater. For more information, visit www.hamptonbayschamber.com.