2017 Long Island Holiday Festivals Not to Miss

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