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Long Island Fall Festival Guide For 2023

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Pumpkins stacked on straw bales, against the background of people strolling through an agricultural fair where the autumn harvest is sold. Shallow depth of field, blurry background.
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With the summer coming to an end, winter is slowly but inevitably creeping closer. But don’t you fret, because fall will swoop in to cool the heat and keep the frigid cold away for just a bit longer. 

Fall comes with the changing of the leaves, walks in the neighborhood, football games, the craving for apple cider, Halloween and so much more. What tops all these season-changing activities? Fall festivals!

Across Long Island spans a variety of fall festivals for all families to enjoy, whether you’re looking for hayrides, pumpkin carving, oyster eating, spooky frights, or face painting for the children. These festivals all along the Island begin right at the start of September and go all the way through October. 

Check out and experience the beauty of the fall colors, tasty foods, and festive activities from any of the locations listed below. 

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Long Island 2023 Fall Festivals

LONG ISLAND FAIR

Celebrating 181 years of Long Island Agriculture, take a trip to Old Bethpage’s Long Island Fair and enjoy a variety of traditional music, dancing, artisan demonstrations, contests, races, food, and more. 1303 Round Swamp Road, Old Bethpage. $10. 10 a.m.-5 p.m. Sept. 8-10.

EAST NORTHPORT FESTIVAL

Come on down and enjoy rides, games, craft vendors, the international food truck festival, sand city brewery craft beer garden, live music, and more. Great family fun. 185 Larkfield Rd, East Northport. Free. Friday 6 p.m.-11 p.m., Saturday 11 a.m.-11 p.m., Sunday 11 a.m.-6 p.m. Sept. 8-10.

WESTBURY STREET FAIR

Enjoy 100+ vendors, food trucks, live music, and a local-artists exhibit presented by Nassau County Art Craft Gift & Street Fairs, weather permitting. 200 Post Avenue, Westbury. Free. 10 a.m.-5 p.m. Sept. 9

DOCKSIDE FAMILY FESTIVAL

Have a free boat ride on the Bay at Captree State Park, along with live music, a magic show, food and merchandise vendors, pony rides, slot car racing, and more interactive displays. 3500 Ocean Pkwy, Bay Shore. 11 a.m.-5 p.m. Sept. 9

LI PICKLE FESTIVAL 

Gardiner’s Farm and the Greenlawn/Centerport Historical Society hold the Annual Pickle Festival. Experience pickles of every flavor and size, 30 craft vendors, delicious foods, a corn maze, a train ride, and family fun. 900 Park Ave, Huntington. $5. 10 a.m.-4 p.m. Sept. 16. 

DRAGON BOAT RACE FESTIVAL

The 9th Annual Dragon Boat Race Fest will feature competing teams along with a variety of Asian performances, food trucks, retail and cultural vendors. Hosted by The Greater Port Jefferson Chamber of Commerce. 101 East Broadway, Port Jefferson. Free. 8:30 a.m.-5 p.m. Sept. 16.

LONG ISLAND GARLIC FESTIVAL

The 21st Annual Garlic Long Island Garlic Festival celebrates 20 years with free admission for those born in 2003, giveaways every 20-minute mark, and more. Enjoy vendors with a wide variety of garlic-inspired foods, crafts, music, and just plain garlic to eat and plant. 4558 Sound Avenue, Riverhead. $5-11. 10 a.m.-6 p.m. Sept. 16-17.

26TH ANNUAL BAYVILLE WATERSIDE FESTIVAL

Enjoy vendors selling unique and handcrafted items, general merchandise for great prices, live music, a kids’ fun zone, a petting zoo, great food choices, and more. Fun for the whole family. Ransom Beach, Bayville. Free. 10 a.m.-5 p.m. Sept. 17.

BELLMORE FAMILY STREET FESTIVAL 

Experience an exciting street festival and carnival with crafters, vendors, live music, food, entertainment, and rides throughout the village. 2700 Pettit Avenue, Bellmore. Free. 10 a.m.-6 p.m. Sept. 21-24.

MARITIME FESTIVAL

Hosted by East End Seaport Museum & Marine Foundation, the festival benefits the preservation of the Long Beach Bar (Bug) Light, educational programs, and museum offerings. Enjoy classic boat displays, kayak races, music, children’s activities, maritime demonstrations, sea shanties, and approximately 100 great vendors. 3rd Street, Greenport. Sept. 23-24.

COW HARBOR DAY

The weekend begins with the Cow Harbor 10K race, followed by festivities. Enjoy the annual Cow Harbor weekend concert, lighted boat displays with crews in costumes and accessories, a parade, sidewalk sales, arts and crafts vendors, and music venues. 158 Laurel Ave, Northport. Sept. 23-24.

WEST ISLIP COUNTRY FAIR

Travel over to the West Islip Country Fair, featuring over 100+ craft vendors, live music, a children’s area with bounce houses, slides, magicians, face painting, and more. Enjoy a wide variety of foods including Italian, Polish, Greek, hot dogs, funnel cakes, and more. West Islip Public Library, West Islip. 10 a.m.-4 p.m. Sept. 24. Rain date Oct. 1.

SEAFORD HARVEST FAIR 

At the Seaford Historical Museum, enjoy its 15th annual fair hosting a variety of live entertainment, vendors, raffles, food, and fun. 3890 Waverly Ave, Seaford. Free. 10 a.m.-4 p.m. Sept. 24.

HERITAGE COUNTRY FAIR

Hosting a longtime family fun event, the Smithtown Historical Society offers the community a chance to enjoy the Island Long Riders Cowboy Mounted Shooting displays, petting zoo, pony rides, vendors, and more. 239 Middle Country Road, Smithtown. $5. 12 p.m.- 4 p.m. Sept. 24, rain or shine. 

SAN GENNARO FEAST OF THE HAMPTONS 

Enjoy their 11th anniversary with fireworks, live entertainment,  food-eating contests, artisans, midway rides, and Italian delicacies. Good Ground Road, Hampton Bays. 10 a.m.-10 p.m. Sept. 23-24.

OKTOBERFEST

Enjoy live entertainment, contests, German-style food, beer from local craft breweries, costume, and  stein-holding contests, and more. 40 Peconic Ave, Riverhead. Free. 3 p.m.-9 p.m. Sept. 30. 

LONG ISLAND FALL FESTIVAL 

Come on down to Heckscher Park and enjoy a  world-class carnival, live entertainment, a beer and wine pavilion, and 300 vendors. 11 Prime Ave, Huntington. Free. Friday 5 p.m.-10 p.m., Saturday and Sunday 11 a.m.-10 p.m., and Monday 11 a.m.-5 p.m. Oct. 6-9.

“TASTE THE WORLD” LONG ISLAND 

“Taste the World” returns to Tanger Outlets for an experience of food inspirations from countries represented all around the world, including over 60 food vendors. They will offer live music, a beer and wine garden, virtual reality, rock climbing, and more. 152 The Arches Circle, Deer Park. $8 to attend each day (online) and $12 (at the door). Friday 1 p.m.-8 p.m. Saturday-Monday 11 a.m.-8 p.m. Oct. 6-9.

FRANKLIN SQUARE STREET FAIR

Enjoy 75+ vendors including food trucks, live entertainment, free parking, and free admission, presented by Nassau County Art Craft Gift & Street Fairs in association with Kiwanis International. Franklin Avenue at Hempstead Turnpike, Franklin Square. Free. 10 a.m.-5 p.m. Oct. 7. 

FALL COLONIAL FAIR

Experience potters, wool spinners, silversmiths, paper makers and beekeepers. The fair will host a real fire truck, beautiful jewelry, a petting zoo, pony rides, food, antique cars, a book sale and more. 336 Port Washington Blvd, Port Washington. Free. 10 a.m.-4 p.m. Oct. 7.

SOUND & SKATE FESTIVAL

Gather with the community as they celebrate the intersection of art, music and sport. Enjoy over 50 vendors including food trucks, skate demonstrations, a mural/graffiti contest, live music, live painting and more. 170 Moores Lane, Greenport. Free. 11 a.m.-6 p.m. Oct. 7.

MILL NECK MANOR APPLE FESTIVAL

Located on Mill Neck Manor’s 86-acre campus, showcasing many apple varieties, specialty meats, cheeses, baked goods, jellies, fudge and more. The festival also features Deaf technology, healthcare checkups, children’s face painting, crafts and more. 40 Frost Mill Rd., Mill Neck. $20 suggested donation for parking per vehicle. 9 a.m.-4 p.m. Oct. 7-8.

MOURNING AT THE MANOR

Mourning at the Manor features Revolutionary era crafts demonstrators and 3rd N.Y. Revolutionary Regiment encampment. Children can enjoy crafts, puppet shows, story time and games. Experience strange customs and traditions as well. 677 West Montauk Hwy, West Bay Shore. $10 for adults, $5 children (6-14), under 5 free. $2 discount per adult with a non-perishable item for donation. 10 a.m.-4 p.m. Oct. 8.

OYSTER FESTIVAL

Organized by the Oyster Bay Rotary Club and partnered with Catholic Health, this largest waterfront festival on the East Coast is an annual tradition. It offers live entertainment, shows, and an oyster eating contest, along with various seafood dishes and traditional festival food. 25 West End Ave, Oyster Bay. Free. Oct. 14-15. 

HALLOWEEN FEST AND PARADE

Downtown Riverhead is transformed into a Halloween hometown this October. Families are invited to dress up in costume and join the festivities, streets filled with goblins, ghouls, tricks and treats. Festivities include coffin races, a parade, trick or treating and more. 133 E. Main St., Riverhead. Free. Oct. 20 (rain date Oct. 27).

HEMPSTEAD LAKE FALL FAMILY FRESHWATER FISHING FESTIVAL

Enjoy a range of activities at the fishing festival, including fall favorites such as pumpkin decorating and a casting for pumpkins contest. This event also showcases fly fishing instruction, demonstrations and outdoor exhibits by local fishing clubs. Children can enjoy inflatables and there will be food available for purchase. Eagle Ave, West Hempstead. Free. 11 a.m.-4 p.m. Oct. 21.

MERRICK STREET FAIR

Presented by the Nassau County Art, Craft, Gift and Street Fairs and the Merrick Chamber of Commerce, join in on some fair fun including food trucks, carnival rides, games and more, weather permitting. 1 Broadcast Plaza, Merrick. Free. 10 a.m.-5 p.m. Oct. 21-22. 

GREAT JACK-O-LANTERN SAIL

Watch your carved pumpkin sail along the lake at this Great Jack-o-Lantern Sail. The first 50 carved pumpkins received will be placed on flotation devices with lights and sailed around the lake behind kayaks. Children can enjoy games, inflatables, trick-or-treating and funny photos. Families can also walk through the “Spooky Den” and enjoy the staff-curated displays. 625 Belmont Ave, West Babylon. Free. 3 p.m.-6 p.m. Oct. 28.

PUMPKIN FEST

Participate in the pumpkin fun just before Halloween and enjoy hayrides, light refreshments, raffles, pumpkin picking and more. There will also be a DJ and an apple pie eating contest. 1100 Old Nichols Rd., Islandia. Free. 12 p.m.-3 p.m. Oct. 28.

SPOOKY FEST

Catch a fright, or non-spooky attraction, at this year’s Spooky Fest. Enjoy non-spooky activities such as a walk through the enchanted forest with friendly displays and characters, arts and crafts, a Halloween DJ, face painting and fortune telling. Experience The Spooky Woods if you dare, with zombie robotic dinosaurs and more zombie scenes, recommended for children 7 to 12 years old. 1450 Tanglewood Road, Rockville Centre. $20 for non-spooky attractions and $25 for all attractions. 6:30 p.m.-9:30 p.m. Oct. 6-Oct. 29 (every Friday. Saturday and Sunday).

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