Winter brings snowflakes, light displays and a slew of holiday festivals that transform Long Island into a magical wonderland. Along with decorations, music and treats, embrace the excitement of the season at these festive gatherings.
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28th Annual Long Island Festival of Trees, Cradle of Aviation Museum
Renowned for its spectacular array of designer-decorated trees and gingerbread village, this event is the perfect place to find holiday home inspiration. Continuous live entertainment, Santa and a vendor marketplace are other fun components. Nov. 24, Nov. 25, 10am-6pm, Nov. 26, 10am-5pm. Click to go
Annual Holiday Boat Parade and Fireworks, View Restaurant
Dressed in lights and ornaments, boats will parade down the Connetquot River, followed by a firework display by Grucci. Back at View, there will be complimentary hot chocolate, cookies and a special appearance by Santa Claus. Nov. 25, 5:30pm. Click to go
Bay Shore’s 2017 Winter Festival & Small Business Saturday, Main Street
A holiday tradition on Main Street, this winter festival will have a tree and menorah lighting, music, treats and visits from Santa and Frosty the Snowman. Nov. 25, 3:30pm. Click to go
Sayville’s 11th Annual Miracle on Main Street, Sayville
The event will mark the beginning of the holiday season with a parade, tree lighting, ice skating rink, a gingerbread house competition, live reindeer and a visit from Santa. Nov. 25, 10am-9pm. Click to go
22nd Annual Charles Dickens Festival, Port Jefferson
A nod to the Dickensian era, the Village of Port Jefferson will have streets filled with wandering characters like Father Christmas, Dickens Mayor, Scrooge, the Town Crier and the beloved chimney sweeps. Dec. 2, Dec. 3, 10am-6pm. Click to go
Rocky Point Holiday Boutique, Rocky Point Middle School
Come for crafts, candles, home décor, jewelry, chocolates, crochet items, food, music and raffles. Dec. 2, 9am-3pm. Click to go
7th Annual Wooden Wonderland, Main Street Riverhead
Visitors will find something for everyone on their holiday list starting with local handmade wooden items, ornaments, home décor, rustic Santas and gnomes, unique handmade carvings, handmade soaps and candles. There will also be live woodworking and woodcarving demonstrations. Dec. 2, 10am-4:30pm. Click to go
Deck The Halls Gala at Planting Fields, Oyster Bay
Join in a holiday celebration filled with cocktails, hors d’oeuvres, dinner, dancing and a silent auction. Dec. 2, 7pm-11pm. Click to go
2017 Holiday Boutique at Deepwells Farm, Deepwells Farm Historic Park
Held in the 1845 Greek revival style farmhouse, the space will play host to original art, stained and painted glass, jewelry, handmade soaps, candles, marionettes, dolls, floral arrangements, Christmas ornaments and holiday cards. There will also be strolling musicians, raffle baskets and pictures with Santa. Dec. 2, Dec. 3, Dec. 9, Dec. 10, 10am-5pm. Click to go
38th Annual Holiday Festival, Stony Brook Village Center
Don’t miss a puppet parade, promenade of trees, live music, a model train exhibit and a visit from Santa. Dec. 3, 11am-8pm. Click to go
Historical Society of Islip Hamlet’s 24th Annual Holiday House Tour, Various Homes
The event will feature several historically and/or architecturally interesting homes decorated for the holidays as tour guides in Victorian garments greet visitors at each home. At the reception, there will be live entertainment, refreshments, a Chinese auction and a 50/50 raffle. Dec. 3, 12pm-5pm. Click to go
Hearthside Swing Time Party, Rogers Mansion
Partake in a holiday party from the 1940s with festive foods, cocktails and music from the Big Band Era. There will also be swing dancing lessons and performances by Anita Boyer & O.F.V.S. Dancers. Dec. 9, 5:30pm-7:30pm. Click to go
Annual Holiday Hike And Open House, Blydenburgh County Park
Calling all adventure seekers! Embrace the chilly weather with a hike from Blydenburgh County Park to Sweetbriar Farm and back. Then refuel with refreshments at the Holiday Open House. Dec. 10, 9am. Click to go
Kathleen King’s Cookie Exchange, Rogers Mansion
Take a break from the holiday hustle and bustle and bring friends to the museum’s annual Cookie Exchange. Sample and swap dozens of festively decorated homemade cookies. Pro tip: bring copies of your recipes, a tray to display your cookies and a container to take swapped cookies home. Dec. 14, 4pm-5pm. Click to go
4th Annual Ugly Christmas Sweater Party, The Stephen Talkhouse
Hello Brooklyn, a hip-hop and pop band from New York City, will perform at this festive event filled with food, prizes and a good time. Dec. 16, 10pm. Click to go