Fairs, Festivals, and Year-Round Fun

Fine Wine & Food Festival | Nassau Coliseum
Sample gourmet fare from Long Island and NYC restaurants and food trucks, plus 150+ wines from the wine-growing regions of New York and New Jersey at this fun one-day fest.

NYC Scotch Walk | venues vary
What better way to spend a cold January day than slow-sipping six of Scotland’s favorite scotches at a half-dozen bars beloved by serious scotch connoisseurs?

Coney Island Polar Bear Club New Year’s Day Swim | Coney Island, Brooklyn
Kick off the new year with a memorably cold dip in the Atlantic Ocean, alongside fellow thrill-seeking swimmers on the boardwalk at Stillwell Avenue.

Maple Sugaring Day at Benner’s Farm | East Setauket, Long Island
Head to this 15-acre working family homestead on the last Saturday in February to experience the magic of organic maple sugaring.

Hops and Props Craft Beer Festival | Cradle of Aviation Museum, Garden City
Sample the handiwork of 25 craft breweries and take home a souvenir tasting glass at this fun fest celebrating local brews and bites.

New York City Restaurant Week | locations vary
From fine dining mainstays to trendy newcomers, more than 300 NYC restaurants across the city offer up the best for less. Here’s to taking a (bigger) bite out of the Big Apple.

The Chocolate Expo | Cradle of Aviation Museum, Garden City
Give into those chocolate-fueled fantasies at the Chocolate Expo, a one-day chance to taste and stock up on chocolate and other gourmet goodies from dozens of artisan vendors.

Macy’s Flower Show | Herald Square, New York City
A tradition for more than four decades, the Macy’s Flower Show runs two weeks in March, filling the flagship store at Herald Square with fragrant blooms and beautiful floral displays.

St. Patrick’s Day Parade | Fifth Avenue, New York City
Join green-garbed revelers along Fifth Avenue for the world’s oldest St. Patrick’s Day parade, which first rolled through the streets of New York in 1762.

Long Island Restaurant Week | locations vary
Long Island’s best restaurants pull out all the stops with eight days of deliciously imaginative dining and prices you won’t believe.

All Kids Fair | Melville
Nearly 100 vendors, tons of classes and workshops, free petting zoo, bounce houses, face painting, cotton candy. Prepare for a day of wide-eyed wonder and sugar-fueled sprints between exhibits.

Spring Winery Tours | Various Locations
Did you know Long Island is home to over 50 wineries? A favorite adult-themed day trip involves a rented limo, several dozen tasting rooms, and a great deal of laughing (pro tip: you can drink in the limo!). Ask your concierge for a recommended vendor.

St. John’s Lutheran Church Annual Spring Festival | Merrick
A family-friendly street fair. Old-fashioned bake sale will leave you lugging bags of bread and pastries through the craft vendors and garden sales to the bounce house to watch the kids squeal.

Huntington Tulip Festival | Heckscher Park, Huntington
Free, family-oriented, floral festival with over 20,000 tulips. Hands-on activities for children and family-friendly performances on stage. Art exhibitions and lectures may intrigue the adults.

International Migratory Bird Walk | Garvies Point Museum & Preserve, Glen Cove
Observe Long Island’s regional birds of field and forest as they return for the spring. Museum offers intriguing exhibits of the island’s geology and Native American lifeways through the seasons.

Antiques, Vintage, and Collectibles Show | Sagtikos Manor, Bay Shore
Dozens of vendors offering classic and vintage clothing, accessories, and home goods. For added fun, tour Sagtikos Manor while you’re there.

Peony Path Tour | Sagtikos Manor, Bay Shore
Who knew there was so much history, art, and science wrapped around the lovely peony? Learn while you relish the magnificent peacock fountain, enjoy live music, and a light snack.

Gay Pride NYC | multiple locations 
New York City celebrates Gay Pride with a month-long line-up of events, wrapping up with the NYC Pride March in late June.

July 4th Fireworks | multiple locations
From Jones Beach to Sag Harbor, 4th of July fireworks light up the night skies over Long Island.

Classic and Custom Car Show | Great South Bay Shopping Center, West Babylon
Hundreds of hot rods, lowriders, custom and stock classic cars on display. Live music competes with the roar of V8 engines. Dozens of food stands. Show benefits the Stony Brook University Children’s Hospital.

Great South Bay Music Festival | Shorefront Park, Patchogue
A craft village, food court, and Kidzone frame a lively music festival with 60 performers on four stages. Styles from classic rock to zydeco will delight even the most jaded music enthusiast.

Oyster Festival | Roosevelt Park, Oyster Bay
The East Coast’s largest waterfront festival. Live music, midway rides, and the iconic oyster eating and shucking contest. Ships on display and pirate shows delight the young and young at heart.

Annual Fine Arts and Crafts Show | The Village, Ocean Beach
A juried show of the region’s top artists and artisans. Huge variety of handmade wares on sale at every price point, and when you’re tired of shopping, sit and enjoy the beautiful South Oyster Bay view.

Alive After Five | Main Street, Patchogue
Consistently voted Best Outdoor Festival on Long Island (Best of Long Island contest) - see why for yourself. Live music, artisans, dozens of cuisines to choose from, and lots of children’s activities.

Labor Day Weekend Craft & Gift Show | Seaford
Local small businesses offer handmade crafts and gifts you won’t find anywhere else. Rides, games, and live entertainment for the children. Food and drink selections keep you fuelled all weekend long.

Bayville Waterside Festival | Bayville
The best place to enjoy live music from the area’s best bands. Inflatable rides, face painting, and a petting zoo will have the children squealing with delight. A variety of food and drinks for the grown-ups.

Plainview Annual Fall Festival | Old Bethpage Public Library, Plainview
Held just outside Plainview’s Old Bethpage Library, this event features live music along with fair foods and loads of activities for children. Prepare for a day of fun!

Fall Festival and Classic Car Show | Malverne
Mom loves the wealth of craft and gift vendors offer their wares. Classic cars on display for Dad to admire. Children enjoy the pet parade, costume contest, and of course the pumpkin patch.

Montauk Fall Family Festival | Montauk Green, Montauk
The clam chowder contest is definitely the star of the show. Enjoy Oktoberfest-style food and drink, a farmer’s market, live music, and free carousel rides.

Mill Neck Family Fall Harvest Festival | Mill Neck Manor House
A Long Island tradition for over 50 years. Sample baked goods, seasonal produce, and local cheeses while the kids have their faces painted and explore the pumpkin patch.

Autumn Art & Craft Festival | Stony Brook University
Over 100 artisans display hand-crafted jewelry, blown glass, fine art, leatherwork, woodwork, and textile crafts. Original art and unique gifts abound, and artists are happy to talk shop.

St. Thomas Holiday Craft Fair | St. Thomas the Apostle School, West Hempstead
A beloved regional craft fair where you’ll find the perfect Christmas gifts for everyone on your list. Be sure to stop by the country kitchen for mouth-watering homemade treats.

Holiday Tree Lighting | Vanderbilt Museum & Planetarium, Centerport
Bundle up and celebrate the season with the traditional lighting of the museum’s holiday tree. Come early and explore 43-acre Eagle’s Nest estate, the intriguing wild animal dioramas, and a planetarium show.

Hallockville Christmas | Hallockville Museum Farm, Riverhead NY
Celebrate local agricultural traditions and folk arts with the whole family! Features children’s games and activities, farm animals, craft demonstrations, and of course Santa Claus.

The Dickens Festival | Port Jefferson Village
The town transforms into the Dickensian era. Characters including Father Christmas, Scrooge, the Town Crier, and chimney sweeps roam the streets. Ice skating, performances, and family fun.

Holiday Festival | Stony Brook Village Center
You simply must see the Legends & Spies parade. Towering 14-foot legends including Ward and Dorothy Melville, Captain Jonas Smith, and spies like Caleb Brewster march through the village. Live music, carolers, and Santa himself might stop by.