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

Enjoy the fall on the beautiful grounds of Boscobel during the Heritage Apple Fest. Photo courtesy of Boscobel
Enjoy the fall on the beautiful grounds of Boscobel during the Heritage Apple Fest. Photo courtesy of Boscobel
9/4/22 - 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 community with local farms and artisans. Live music, a corn maze, and food trucks add to the attractions. 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

Cornwall Fall Festival

Cornwall–FREE
Sunday, September 24, 2023
The 48th annual fall festival returns to downtown Cornwall. Main Street is closed down and filled with vendors, food, and entertainment.  READ MORE

Walden 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

Port Jervis Fall Foliage Festival

Port Jervis–FREE
Sunday, September 24, 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
The Greeenburgh Nature Center hosts a Fall Festival on Saturday, October 22 and Sunday, October 23. Photo courtesy of the venue
The Greeenburgh Nature Center hosts a Fall Festival on Saturday, October 22 and Sunday, October 23. Photo courtesy of the venue

Fall Festivals Near Westchester in October 2023

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

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

Pumpkinfest

Pine Island
Monday, October 9, 2023
This annual Columbus Day tradition features a bouncy house, pumpkin painting, face painting, games, crafts, touch-a-tractor, refreshments, and more. Attendees can enjoy food, ice cream, and tasty treats from on-site vendors.  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

NY Sheep and Wool Festival

Rhinebeck
Saturday, October 21-Sunday, October 22, 2023
A mix of in-person and online activities are planned at the 2022 festival, with on-site attractions including sheep and goat shows, vendors, fiber artists and crafts, frisbee dogs, and a petting zoo. Workshops are held online. 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

Tompkins Corners Harvest Fest

Putnam Valley
Sunday, October 22, 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

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