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Best Harvest and Pumpkin Festivals in Westchester and the Hudson Valley this Fall

Enjoy bouncy houses, a petting zoo, and plenty of kid-friendly activities at the Town of Walden's annual Harvest Festival. Photo courtesy of the event
Enjoy bouncy houses, a petting zoo, and plenty of kid-friendly activities at the Town of Walden's annual Harvest Festival. Photo courtesy of the event
9/3/23 - By Katherine Dhurandhar

Fall festivals in Westchester and the Hudson Valley incorporate some of the season's spectacular offerings, including romping around local pumpkin patches and eating delicious apple cider doughnuts. Plus, many of these wow-worthy weekend events involve carnival rides, treats, and live music.

For even more ways to celebrate autumn, check out our guide to the best places for apple picking in the area, and be sure to peep our Best of September roundup for even more things to do.

Looking for even more family-friendly activities? Consult our Event Calendar and Fall Fun Guide, and sign up for our newsletters to get posts like this delivered to your inbox.

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Travel back in time at the New York Renaissance Faire, one of our favorite fall festivals. Photo by Deborah Grosmark
Travel back in time at the New York Renaissance Faire, one of our favorite fall festivals. Photo by Deborah Grosmark

Fall Festivals Near Westchester in September 2023

New York Renaissance Faire

Tuxedo
Saturdays and Sundays through October 8, 2023 plus Labor Day
Travel back in time for an amusing romp through 30 acres of Elizabethan England, with games, rides, food, fairies, performances, and roving actors jovially interacting with the crowd. Of course, wearing period attire adds to the fun and can be rented or purchased on-site. READ MORE

Harvest Festival

Bethel–FREE admission
Sundays from August 27 to October 1, 2023
Scheduled for six Sundays in 2023, the festival connects the community with local farms and artisans. Live music, a corn maze, horse-and-carriage rides, a tortoise sanctuary, and food trucks add to the attractions. Different performers are scheduled each week, including circus performers, balloon twisters, and magicians.  READ MORE

Germania Oktoberfest

Poughkeepsie
Friday, September 8-Sunday, September 10, 2023
Germania of Poughkeepsie presents this family-friendly event, featuring live German bands, Germania singers, German food, Bavarian dancers, vendors, and traditional beers for the adults. Children can enjoy games, contests, face painting, prizes, magic, and other activities. READ MORE

Nyack Septemberfest Street Fair

Nyack
Sunday, September 10, 2023
This family-friendly annual street festival held in scenic Nyack on the Hudson features 200+ vendors exhibiting jewelry, art, photography, collectibles, antiques, quality handmade crafts, unique gifts, and much more. The fair features live entertainment, plus great food and outdoor dining. READ MORE

Armonk Cider & Donut Festival, 5K Run, and BHPA Fall Carnival

Armonk –FREE admission
Sunday, September 10, 2023
Enjoy a variety of activities for families and, of course, donuts and cider. A pie-eating contest, donut fishing, live music, carnival rides, kids' races, a 5K, face painting, bouncy houses, and more are featured. READ MORE

Oktoberfest with Captain Lawrence Brewing Company

Yonkers–FREE
Saturday, September 16-Sunday, September 17
Cross County Center is hosting a Beer Garden for Oktoberfest, with live music, dancing, food, and fun. Come dressed in your best Lederhosen and Dirndl dresses for a true Oktoberfest experience! READ MORE

Town of Walden's Annual Harvest Fest

Walden–FREE
Saturday, September 30, 2023
Get ready for old-fashioned fun at this annual fall festival. Attractions include bouncy houses, a petting zoo, and a frog jumping contest. Live music and vendors add to the fun.  READ MORE
Enjoy live music and more entertainment during the day-long Pound Ridge Harvest Festival. Photo courtesy of the event
Enjoy live music and more entertainment during the day-long Pound Ridge Harvest Festival. Photo courtesy of the event

Fall Festivals Near Westchester in October 2023

Garlic Festival

Saugerties
Saturday, September 30 and Sunday, October 1, 2023
The annual 2-day garlic festival in Saugerties is hugely popular for a reason. More than a foodie's paradise-–with eats, demos, and more–the event also features kid-friendly attractions, such as a craft tent, live performances, and face painting. READ MORE

Soukup Farms Harvest Festival

Dover Plains
Weekends through October 21, 2023
Hit the pumpkin patch, hitch a hayride, and visit the exotic animals of the Two-by-Two traveling animal exhibit (on select dates) at the Soukup Farms Harvest Festival. There's also a climbable hay dragon, tractor exhibits, and a corn maze. Re-energize with a farm-to-table lunch. READ MORE

Fall Family Fun Days at the Farm

Kingston
Every weekend in October
Celebrate fall at the farm with family activities every weekend in October. Pick your own pumpkins and enjoy live music, hayrides, flower picking, meeting farm animals, a kids' crop maze, food & drinks, and more. READ MORE

Fall Harvest Celebration

Kerhonkson
Every weekend in October
Celebrate the fall harvest at Kelder's Farm, featuring scenic fall colors, apple and pumpkin picking, and all the usual 30+ farm attractions, including a giant jumping pillow, mini-golf, tube slides, farm animals, and tons of games. Food and drinks are also available, including a taproom for adults. READ MORE

Eastchester Columbus Day Carnival and Parade

Eastchester
Friday, October 6-Monday, October 9, 2023
Eastchester goes all out Columbus Day weekend, with a four-day carnival, a holiday parade, and more. The carnival features lots of rides for all ages, games with prizes, vendors and exhibitors, and food. Time your visit around the schedule of live music, fireworks, and more.  READ MORE

Pound Ridge Harvest Festival

Pound Ridge
Saturday, October 7, 2023
Expect fun for all ages at this annual festival, including live music, a beer garden, and food trucks. Fun for kids includes a root beer garden, face painting, a haunted house, laser tag, pumpkin decorating, games, rides, and contests. READ MORE

Pumpkin Picking Autumn Celebration

Katonah–FREE
Saturday, October 7-Monday, October 9, 2023
Join Muscoot Farm for Columbus Day weekend. The farm celebrates the fall season with a pumpkin picking and hayride fundraiser. You can also source the perfect pumpkin from its garden. READ MORE

Yorktown Fall Festival

Yorktown–FREE
Sunday, October 8, 2023
Jefferson Valley Mall & the Yorktown Chamber of Commerce proudly presents the 16th annual Yorktown Fall Festival, with 150+ vendors, children's rides & crafts, live musical performances & dance Performances, food trucks & beer garden, a senior lunch, a 200+ car classic car show (with awards) presented by the Road Knights, plus a Nathan's hot dog eating contest. READ MORE

Cornwall Fall Festival

Cornwall–FREE
Sunday, October 8, 2023
The 51st annual fall festival returns to downtown Cornwall. Main Street is closed down and filled with vendors, food, and entertainment.  READ MORE

Pumpkinfest

Pine Island
Monday, October 9, 2023
Celebrate the local harvest of pumpkins and spend the day outdoors enjoying the warm sunshine and crisp fall air. This annual tradition features pumpkin painting, face and henna painting, a children’s bouncy house, yummy food, and touch-a-tractor.  READ MORE

Pearl River Day Festival

Pearl River
Saturday, October 14, 2023
This annual festival features food, live music, kids' activities, arts and crafts, and more. The street fair runs through 6pm, with entertainment continuing till 8pm.  READ MORE

Tompkins Corners Harvest Fest

Putnam Valley
Saturday, October 14, 2023
Packed into 4 hours, this fall festival features music, food, crafts, and vendors. Lou Del Bianco presents  "Monsters I Have Known," a fun show for kids, at 12:30pm. Browse the wares of assorted artisans, and pick up apples, pumpkins, and bounty from a local farm. READ MORE

Pelham Pumpkin Festival, Book Sale and 5K Fun Run

Pelham
Saturday, October 14, 2023
Anticipate a great day in the crisp autumn air for all ages at Pelham Children's Center annual fundraiser Pumpkin Festival, including live music, a massive book sale, a 5K race, and a Kid's (U12) 1/2 mile Fun Run. Fun for kids includes pie eating contests, jumbo inflatable slides, Fun Run, bounce house, ornate face painting, talented balloon twisters, a trackless train, cotton candy, apple cider donuts, a pony ride, and a petting zoo. Adults can enjoy a 5K race, gift raffle, food trucks, pumpkin patches, and FIVE hours of your children being thoroughly... READ MORE

Fall Family Fun Fest

Olivebridge
Sunday, October 15, 2023
The fall festival at the Ashokan Center features apple cider demos, pumpkin painting, hayrides, nature hikes, crafts, food, live music, and more. READ MORE

Beacon Sloop Club Pumpkin Festival

Beacon
Sunday, October 15, 2023
Dedicated to promoting environmental and social issues, the Beacon Sloop Club is hosting this festival offering kids' activities, a performance by the Rejuvenary River Circus, live music on two stages, and sails on the sloop Woody Guthrie. Pumpkin-themed cuisine is available for purchase. READ MORE

Rocktober Festival

West Nyack
Sunday, October 15, 2023
Join JCC of Rockland in celebration of their 36 years in Rockland County. There will be inflatables, a touch-a-truck, a ninja ropes course, face painting, a petting zoo, a children's concert, food trucks, and more. READ MORE

Port Jervis Fall Foliage Festival

Port Jervis–FREE
Sunday, October 15, 2023
Get ready for family fun at this annual street fair, with more than 100 vendors, live entertainment, a petting zoo, and more. READ MORE

NY Sheep and Wool Festival

Rhinebeck
Saturday, October 21-Sunday, October 22, 2023
Attractions at the New York Sheep and Wool Festival include llama, sheep, and goat shows plus vendors, fiber artists and crafts, frisbee dogs, and a petting zoo.  READ MORE

Walktoberfest

Poughkeepsie
Saturday, October 21-Sunday, October 22, 2023
More than 100 vendors await offering shopping, dining, and children's activities at this two-day event. Expect pumpkin painting, art projects, sand art, karate demos, princess character appearances, a dance performance, Home Depot construction kits, and more. Enjoy the view! READ MORE

Places featured in this article:

Bethel Woods Center for the Arts
Beacon Sloop Club and Riverfront Park
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