• Taleen Krug

Best Fairs and Festivals on Long Island

Updated: Nov 1



It's a great time to go out and visit some of the best outdoor fairs, outdoor festivals, and other events on Long Island.


Long Island is an island that extends from the Atlantic Ocean to the Great South Bay. It has a population of 4 million people and is known for family fun, its vineyards, golf courses, and beautiful beaches.


And in the fall, it's festival time on Long Island September through October featuring a wide variety of outdoor dining, musical entertainment, food vendors, craft beverages, craft vendors, fair foods, and many family-oriented events.


Changing Seasons

Fall is coming up fast, Sept. 22 officially and that equates to enjoying outdoor activities, great food from food vendors and outdoor musical performances, and a wide variety of annual events on Long Island for families.


Aside from these usual tourist places, Long Island also has a rich cultural history with numerous festivals and events which include the autumnal equinox celebration.


There are lots of great things to do if you're into food trucks, craft beverages, music, art, or all of the above. So be sure to add the food festivals for kids, the music festival, art gallery fairs, car shows, and more to your calendar.


If you want to experience some of the most popular events in Long Island, NY, here's where you need to go.


Garlic Lovers

If you love garlic make sure you go to Long Island’s only garlic festival and enjoy a wide variety of live music, hayrides, farm animals, and tons of garlic. At 4558 Sound Ave., Riverhead. $5-11. 10 a.m.-6 p.m., rain or shine. Sept. 10-11, 17-18.


Long Island Fair

The Long Island Fair is one of the country's longest-running agricultural festivals. See vendors, activities, and competitions. Old Bethpage Village Restoration, 1303 Round Swamp Rd., Old Bethpage. $20 adults; $15 seniors and kids 5-12; under 5 free. 10 a.m.-5 p.m. Sept. 16, 17, 18.


Dragon Boat Race Festival

The 8th annual boat race festival invites local and regional teams to compete and will highlight music and dance performances, children’s activities, and vendors for attendees. Port Jefferson Harbor. portjeffdragonboatracefest.com Free. 8:30 a.m.-5:30 p.m. Sept. 17.


Fall Festival

Your all-day ticket gets you to access to the hay maze, all sorts of delicious food options, a meet and greets with a ghost, and more. Hicks Nurseries, 100 Jericho Tpke., Westbury. $20. 10 a.m.-5 p.m. Sept. 17-18, then every weekend until Halloween.


Hallockville Museum Farm Country Fair

Celebrate Hallockville’s biggest fundraiser of the year with food trucks, live music, endless vendors, a petting zoo, exhibits, and more. Hallockville Farm, 6038 Sound Ave., Riverhead. Free. 10 a.m.-5 p.m. Sept. 17, 18.


Irish Feis and Festival

Celebrate Irish culture and history with plenty of dance and competitions at the 50th annual Feis and Festival. Enjoy an Irish marketplace and kids’ activities all at Nickerson Beach Park, 880 Lido Blvd., Lido Beach. $10, free for under 12. 9 a.m.-6 p.m. Sept. 18.


West Islip Country Fair

Enjoy a variety of foods from all around the world as well as more than 100 craft vendors, kids’ activities, live music, and more. West Islip Public Library, West Islip. Free. 10 a.m.-4 p.m. Sept. 18.


Syosset Street Fair

Plenty of vendors and live music to partake all of at 59 Jackson Ave., corner of Jackson & Underhill Aves., Syosset. Free. 10 a.m.-5 p.m. Sept. 18.


Smithtown Heritage Fair

Listen to live music, historic home tours, a petting zoo, blacksmithing, and more at Smithtown Historical Society’s at Smithtown Historical Society, 239 E. Main St., Smithtown. 10 a.m.-5 p.m. Sept. 18.


Cow Harbor Day

The Cow Harbor Day festivities are the perfect place for family and friends to spend time. See a parade and then go shopping, have delicious food, hear live music, and hop on some amusement rides. At Northport Village Park, Main St., Northport. Free. 12 p.m.-5 p.m. Sept. 18.


Bellmore Street Fair and Carnival

The 36th Annual Bellmore Family Street Festival is the place for excellent live music, food, arts &and crafts, carnival rides, and more. Sunrise Highway and Bedford Avenue, Bellmore. Free. Sept. 22-25.


San Gennaro Feast of the Hamptons

This feast is where you will find music, crafts, rides, and of plenty of food. There will be new activities this year as well as a Hampton Bays train station, Good Ground Road, and Hampton Bays. $5, under 12 free. 10 a.m.-10 p.m. Sept. 24, 10 a.m.-8 p.m. Sept. 25.


Long Island Harvest Festival

The Long Island Harvest Festival is the place to purchase fall favorites such as apples and pumpkins and other autumn items. Enjoy family-friendly activities and live music as you shop and enjoy the items from food trucks. Tanger Outlets, Riverhead. $6. 10 a.m.-5 p.m. Sept. 25.


Grand Baldwin Fall Festival

The Baldwin Festival is back with more than 100 vendors and live music, as well as activities for the young and old. Municipal lot at Baldwin Public Library, 2385 Grand Ave., Baldwin. Free. 12 p.m.-4:30 p.m. Oct. 1.


Bethpage Street Fair

Food trucks, live music, and a bounce house await you and your family at the Bethpage Street Fair. 356 Broadway, Bethpage. Free. 10 a.m.-5 p.m. Oct. 2.


Fall Harvest Festival

There’s always something to do at the Fall Harvest Festival. Enjoy a large assortment of fall favorite food items along with hayrides, a corn maze, and kids' activities. 485 Edgewood Ave., Saint James. $12. 11 a.m.-5 p.m. Oct. 4-5, then every weekend until Halloween.


Fall Colonial Fair

The Fall Colonial Fair has live music, food, and a petting zoo, take a tour of the Sands-Willets House or see Revolutionary War reenactors take you back in time. Sands-Willets House, 336 Port Washington Blvd., Port Washington. Free. 10 a.m.-5 p.m. Oct. 8.


Montauk Fall Festival

The 41st Annual Montauk Fall Family Festival kicks off with a great clam chowder event followed by rides, street paintings, food, live music, and shopping. There will be no shortage of fun at this festival. Village green, Montauk Highway, Montauk. Most events are free. 11 a.m.-5 p.m. Oct. 8-9.


Huntington Long Island Fall Festival

The Long Island Fall Festival is returning for some fun with an array of food, vendors, crafts, and other activities. Heckscher Park, 164 Main St., Huntington. Free. Oct. 7-10.


West Hempstead Street Fair

Enjoy live music, food, and more than 50 arts, crafts, and farmstand vendors offering up their specialties. At 671 Nassau Blvd., West Hempstead. Free. 10 a.m.-5 p.m. Oct. 9.


Riverhead Country Fair

The 46th annual Riverhead County Fair will be the place to be if you require fun on a cool autumn day. Enjoy all sorts of crafts, food, music, and rides. Main Street, Riverhead. Free. 10 a.m.-5 p.m. Oct. 9.


Mill Neck Manor Apple Festival

This year’s festival will be a drive-thru where you can “Grab & Go” and fill up on apples and other festival picks. Mill Neck Manor, 40 Frost Mill Rd., Mill Neck. 11 a.m.-4 p.m. Oct. 9-10.


Oyster Festival

If you love oysters, then this festival is the one for you. It’s known as the East Coast’s largest waterfront festival and comes back after 2 years. At Theodore Roosevelt Memorial Park, 63 Larrabee Ave., Oyster Bay. Free. 11 a.m.-6 p.m. Oct. 15-16.


Valley Stream Community Fest

This annual event is back with plenty of live music, good food, a petting zoo, a car show, and kids’ activities. A great fest for everybody. At Rockaway Avenue between Sunrise Highway and Merrick Road, Valley Stream. Free. 10 a.m.-5 p.m. Oct. 22.


Pumpkin Fest

Celebrate Halloween early with pumpkins galore at the 17th annual Pumpkin Fest. Enjoy all things pumpkin and fun and games for all. At 1100 Old Nichols Rd, Islandia. Free. 11 a.m.-1 p.m. Oct. 22.


Halloween Fest and Parade

Celebrate Halloween with a coffin race, trick or treating, on-stage performances, and a goblin parade all on Main Street, Riverhead. Free. 3 p.m.-7 p.m. Oct. 22.


Get Busy

Instead of sitting at home watching TV this autumn why not get outside and enjoy one of these fun fall festivals and fairs with friends and family?


Take time to enjoy some sweet homemade apple juice, and a chewy doughnut, and go pick a Halloween pumpkin to welcome autumn in Long Island, New York.


It will soon be Halloween followed by Thanksgiving and Christmas, and New Year's when you’ll be saddled down with all the chaos and festivities! Take time out now to enjoy this wonderful time of the year.

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