Fall Festivals on Long Island

Whether you're looking for family-friendly activities or refined experiences, there's a fall festival to cater to every preference. From pumpkin patches and corn mazes to live music, art exhibits, and delicious food, the options are plentiful. With the days becoming shorter and evenings cooler, now is the perfect time to embrace the spirit of the season and savor all that autumn has to offer.

Best Fall Fairs & Festivals on Long Island 2025

As the leaves change and crisp autumn air rolls in, Long Island comes alive with some of the most exciting family-friendly fairs and festivals of the year. From historic country fairs and maritime celebrations to pumpkin-packed weekends and Oktoberfest vibes, September and October 2025 are filled with must-visit events. Here’s your guide to the top fall fairs and festivals happening across the island this season.

🍂 September 2025 Fall Festivals

East Northport Festival

📍 East Northport

🗓 Friday, September 5 – Sunday, September 7, 2025

Kick off the season with a three-day celebration at John J. Walsh Memorial Park. Expect carnival rides, midway games, live music, and special guest character appearances—perfect for families looking for a weekend of nonstop fun.

Dockside Family Festival at Captree State Park (Free)

📍 Bay Shore

🗓 Saturday, September 6, 2025

This waterfront festival is a classic Long Island tradition. Highlights include boat rides, pirate-themed shows, RC car races, pony rides, magic acts, and even a Little Mermaid meet-and-greet. It’s a full day of fun by the bay.

The Long Island Fair at Old Bethpage Village

📍 Old Bethpage

🗓 Friday, September 12 – Sunday, September 14, 2025

Step back in time at one of Long Island’s oldest fairs. Explore livestock shows, homegrown produce, traditional craft competitions, artisan booths, and historic trade demonstrations. With entertainment for all ages, it’s like walking through history with a modern twist.

Water Lantern Festival

📍 Eisenhower Park, East Meadow

🗓 Saturday, September 13, 2025

Watch Eisenhower Park’s lake glow as hand-decorated lanterns drift into the water. The evening kicks off with live music and food trucks, followed by lantern decorating and a magical lakeside launch.

Port Jefferson Dragon Boat Race Festival

📍 Port Jefferson

🗓 Saturday, September 13, 2025

Cheer on colorfully decorated dragon boats racing across the harbor. With team spirit, cultural performances, and waterside festivities, this is one of the island’s most unique September events.

Draw Out Community Arts Festival (Free)

📍 The Heckscher Museum of Art, Huntington

🗓 Saturday, September 13, 2025

A day dedicated to creativity, the Heckscher Museum hosts interactive art projects for all ages. From watercolor painting to collage making, it’s a chance for families to explore their artistic side.

Harborfest

📍 Sag Harbor

🗓 Saturday, September 13 – Sunday, September 14, 2025

Celebrate Sag Harbor’s maritime roots with live music, food vendors, and kids’ games along Long Wharf. Expect classics like sack races and hula hoop contests alongside plenty of waterfront charm.

Garlic Festival at Waterdrinker Farm

📍 Riverhead

🗓 Saturday, September 13 – Sunday, September 14, 2025

Garlic lovers unite! Waterdrinker’s Riverhead location puts the spotlight on this flavorful veggie with garlic-themed eats, hayrides, barnyard fun, and live entertainment.

Syosset Street Fair

📍 Syosset

🗓 Sunday, September 14, 2025

Hosted by the Syosset-Woodbury Chamber of Commerce, this lively street fair features a kids’ zone with pony rides, bounce houses, and a petting zoo, plus plenty of local vendors.

Art in the Park (Free)

📍 Farmingdale Village Green

🗓 Sunday, September 14, 2025

Enjoy a day celebrating local artists as more than 20 creators showcase their work. It’s a relaxed outdoor festival perfect for strolling, shopping, and supporting the arts.

Bellmore Family Street Festival

📍 Bellmore

🗓 Thursday, September 18 – Sunday, September 21, 2025

Spanning four days, this community favorite brings carnival rides, craft expos, food vendors, and live entertainment to the heart of Bellmore. From sports zones to local business showcases, there’s something for everyone.

Pickle Festival at Gardiner’s Farm

📍 Huntington

🗓 Saturday, September 20, 2025

A quirky Long Island classic, the Pickle Festival serves up everything from pickle-on-a-stick to roasted corn. Kids can hop on the lollipop train or explore the corn maze for added fun.

Gallery North Outdoor Art Show & Music Festival (Free)

📍 Setauket

🗓 Saturday, September 20 – Sunday, September 21, 2025

This juried art show blends fine arts, crafts, food, and live music into one community-driven weekend in Setauket.

Greenport Maritime Festival (Free)

📍 Greenport

🗓 Saturday, September 20 – Sunday, September 21, 2025

Kick off with a festive parade, then enjoy wooden boat displays, water sports demos, and model ship building. With children’s activities and live entertainment, this nautical festival is a North Fork staple.

Brookhaven Country Fair

📍 Ridge

🗓 Saturday, September 20 – Sunday, September 21, 2025

Known for historic reenactments, agricultural displays, and even birds of prey, this fair combines local heritage with family fun. Don’t miss the craft vendors and live music.

Heritage Farm & Garden Fall Festival

📍 Muttontown

🗓 Saturday, September 20 – Sunday, November 2, 2025

Running through the entire season, this event offers pumpkins, autumn plants, décor, crafts, and kid-friendly activities. A perfect spot to stock up for fall decorating while keeping little ones entertained.

White Post Farms Fall Festival

📍 Melville

🗓 Weekends, Saturday, September 20 – Sunday, October 26, 2025

One of Long Island’s most beloved family attractions, White Post Farms fills weekends with pumpkin picking, hayrides, animal encounters, and seasonal shows.

Hallockville Museum Farm Country Fair

📍 Riverhead

🗓 Saturday, September 27 – Sunday, September 28, 2025

Celebrate North Fork’s farming history with traditional craft displays, folk art, and agricultural exhibits at this old-fashioned country fair.

Glen Cove Family Fall Festival

📍 Glen Cove

🗓 Sunday, September 28, 2025

A family-oriented day of food, fun, and entertainment in the heart of Glen Cove.

Fall Fun Fest at Sands Point Preserve

📍 Sands Point

🗓 Sunday, September 28, 2025

Set on the Preserve’s beautiful great lawn, this event features arts, crafts, animals, and music to welcome the new season in style.

🎃 October 2025 Fall Festivals

Spooky Fest at CSTL

📍 Rockville Centre

🗓 Select Dates, Friday, October 3 – Sunday, November 2, 2025

Spooky Fest offers both spooky and not-so-scary fun. From haunted trails and costumed characters to a zombie dinosaur attraction, it’s a must for Halloween lovers.

SouthamptonFest (Free)

📍 Southampton

🗓 Saturday, October 4, 2025

Celebrate the arts, history, and culture of Southampton Village with a day packed with performances, family activities, and local food.

The Great Pumpkin Palooza at Lenny Bruno Farms

📍 Manorville

🗓 Weekends: October 4-5, 11-12, 18-19, 2025

Pumpkin and sunflower picking, giant lawn games, pedal cars, live music, and a corn maze make this one of the most festive fall stops for families.

Massapequa Park Street Fair

📍 Massapequa Park

🗓 Sunday, October 5, 2025

Park Boulevard turns into a bustling street market with 150+ vendors, food stands, live music, kids’ rides, and fun extras like mechanical bull rides and oyster shucking.

Montauk Fall Festival

📍 Montauk

🗓 Saturday, October 11 – Sunday, October 12, 2025

Head out east for live music, Oktoberfest foods, and local brews at the Montauk Chamber of Commerce’s signature fall event.

Mill Neck Manor Apple Festival

📍 Mill Neck

🗓 Saturday, October 11 – Sunday, October 12, 2025

Apple pies, fresh cider, children’s games, and live music come together at this fall favorite, complete with a pie-eating contest.

Long Beach Fall Festival

📍 Long Beach

🗓 Saturday, October 11 – Sunday, October 12, 2025

Celebrate autumn by the shore at Kennedy Plaza with vendors, entertainment, and family activities.

Riverhead Country Fair

📍 Riverhead

🗓 Sunday, October 12, 2025

A massive event that blends carnival fun with agricultural and craft competitions. Shop, eat, and explore one of Long Island’s largest country fairs.

Mourning at the Sagtikos Manor

📍 Bay Shore

🗓 Sunday, October 12, 2025

Step back into Victorian times and learn about unusual mourning customs. This unique event also features live music, crafts, and historical demonstrations.

Town of Babylon Fall Festival (Free)

📍 Copiague

🗓 Saturday, October 18, 2025

Held at Tanner Park, this free event includes hayrides, inflatables, crafts, food trucks, and live music—all with a view of the water.

Long Island Oyster Festival

📍 Oyster Bay

🗓 Saturday, October 18 – Sunday, October 19, 2025

One of the biggest waterfront celebrations on the East Coast, the Oyster Festival features fresh seafood, entertainment, and plenty of family activities.

Rock Hall Country Fair (Free)

📍 Lawrence

🗓 Saturday, October 18 – Sunday, October 19, 2025

This historic site hosts a weekend of family fun, with magic shows, crafts, and music in a country-style setting.

Port Jefferson Oktober Harvest Fest (Free)

📍 Port Jefferson

🗓 Saturday, October 18 – Sunday, October 19, 2025

Celebrate Oktoberfest season with a harborfront twist. Expect live music, seasonal food, and plenty of fall cheer throughout the village.

Merrick Fall Fest & Street Fair

📍 Merrick

🗓 Friday, October 24 – Sunday, October 26, 2025

Three days of fair fun with carnival rides, midway games, and family-friendly entertainment.

Town of Islip Apple Festival (Free)

📍 Sayville🗓 Saturday, October 25, 2025

Enjoy apple-themed treats, live music, and local vendors. A kids’ zone with pony rides, petting zoo, and inflatables makes this festival especially family-friendly.

Fall Festival at Hicks Nurseries

📍 Westbury

🗓 Through Sunday, October 26, 2025

This month-long celebration features fall décor shopping, kid-friendly activities, and the return of Otto the Ghost in his beloved animated Halloween story.

🍁 Wrapping Up

From street fairs to lantern festivals, Long Island’s fall season is brimming with things to do for families, couples, and anyone who loves the magic of autumn. Whether you’re craving local food, historic traditions, or just a festive day outdoors, there’s no shortage of bucket list experiences this September and October.

With so many exciting events lined up, make sure to enjoy the best of Long Island’s autumn festivals and create lasting memories this season!