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Best Harvest Fairs and Pumpkin Festivals in Westchester and the Hudson Valley for Fall 2024

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
9/1/24 - By Katherine Dhurandhar

Harvest festivals in Westchester and the Hudson Valley celebrate the region's spectacular seasonal 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 the season, bookmark our Guide to Fall Fun in Westchester and the Hudson Valley, which includes our picks for the best places to go apple picking, leaf peeping, and more.

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As always, if an event piques your interest, click through to our listing for all the details, including addresses, times, and recommended ages. And keep in mind: Really cool things to do with kids often book up quickly, so register or buy your tickets ASAP.

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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

September Harvest Festivals in Westchester and the Hudson Valley

Harvest Festival at Bethel Woods Center for the Arts

Bethel – FREE
Sunday, September 1, 2024
Highlighting local farms, artisans, and flavors, this annual farmers market features live music, food trucks, crafts, special offerings, and more. Special attractions for this day include hayrides, a corn maze, henna tattoo artist, pet adoptions, and visitors from Rosehaven Alpacas.  READ MORE

Germania Oktoberfest

Poughkeepsie
Friday, September 6-Sunday, September 8, 2024
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 8, 2024
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

Fall Harvest Celebration at Kelder's Farm

Kerhonkson
Opens Saturday, September 21, 2024
Celebrate the fall harvest at Kelder's Farm and enjoy scenic fall colors, apple and pumpkin picking, a corn maze, and all the farm attractions, including a giant jumping pillow, mini-golf, tube slides, farm animals, and games. Food and drinks are also available, including a taproom for adults. READ MORE

Hudson Valley Apple Festival at Barton Orchards

Poughquag
Saturday, September 21-Sunday, September 22, 2024
Celebrate the season with apple picking plus a full day of fun for the whole family. Pay-one-price admission includes a full day of fun for the whole family, including entertainment by Magician Zach Alexander (Saturday), Two by Two Zoo (Sunday), pig races, the fun park featuring the new Mega Slide, newly refurbished haunted house, corn maze, hayrides, live music, petting zoo, wooden ship playground, and dog park too!  READ MORE

Armonk Cider & Donut Festival and 5K Run

Armonk – FREE
Sunday, September 22, 2024
Enjoy a variety of activities for families and, of course, doughnuts and cider. A pie-eating contest, doughnut 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 22, 2024
The 51st annual fall festival returns to downtown Cornwall. Main Street is closed down and filled with vendors, food, and entertainment.  READ MORE

Port Jervis Fall Foliage Festival

Port Jervis – FREE
Sunday, September 22, 2024
Get ready for family fun at this annual street fair in downtown Port Jervis, with more than 100 vendors, live entertainment, a petting zoo, and more. READ MORE

Town of Walden's Annual Harvest Fest

Walden – FREE
Saturday, September 28, 2024
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, food trucks, and vendors add to the fun.  READ MORE

Hudson Valley Garlic Festival in Saugerties

Saugerties
Saturday, September 28-Sunday, September 29, 2024
The annual two-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

Apples & Wine Festival at Weed Orchards & Winery

Marlboro
Weekends from Saturday, September 28-Sunday, October 6, 2024
Celebrate the harvest season at Weed Orchards. Enjoy the beautiful Hudson Valley views as you pick your own produce. Multiple varieties of apples are available. Family-friendly activities include face painting, hay rides, and live music. The farm serves special apple-themed food and drinks, plus cider and delicious Jane's ice cream.  READ MORE

New York Renaissance Faire in Tuxedo

Tuxedo
Weekends through Sunday, October 6, 2024, 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

October Harvest Festivals in Westchester and the Hudson Valley

Eastchester Columbus Day Carnival and Parade

Eastchester
Friday, October 11-Monday, October 14, 2024
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

Pumpkin Picking Autumn Celebration at Muscoot Farm

Katonah – FREE
Saturday, October 12-Monday, October 14, 2024
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

Fall Fest at Weed Orchards & Winery

Marlboro
Saturday, October 12-Sunday, October 13, 2024
Celebrate everything fall at Weed Orchards. Enjoy the panoramic views and autumn colors as you pick your own produce. Enjoy family-friendly activities, incuding pumpkin picking, pumpkin painting, face painting, a playground, hayrides, and live music. Fall-themed food and drinks, seasonal beers and sangria, and delicious Jane's ice cream will be available as well as apple cider doughnuts and caramel apples.  READ MORE

Yorktown Fall Festival & Car Show

Yorktown – FREE
Sunday, October 13, 2024
The Yorktown Chamber of Commerce invites visitors to this day-long festival featuring more than 150 vendors, plus children's rides and crafts, live musical and dance performances, food trucks, a beer garden, a senior lunch, 200+ car classic cars, and a Nathan's hot dog eating contest. READ MORE

Pearl River Street Festival

Pearl River
Saturday, October 19, 2024
This annual festival features food, live music, kids' activities, arts and crafts, and more. The street fair runs through 6pm, with entertainment continuing until 8pm.  READ MORE

NY Sheep and Wool Festival

Rhinebeck
Saturday, October 19-Sunday, October 20, 2024
Attractions at the New York Sheep and Wool Festival include sheep shows, vendors, crafts, frisbee dogs, and a petting zoo.  READ MORE

Fall Family Fun Fest at the Ashokan Center

Olivebridge
Sunday, October 20, 2024
The fall festival at the Ashokan Center features fresh apple cider pressing, pumpkin painting, broommaking, hayrides, live music, seasonal food, guided hikes, and fun for all ages. READ MORE

Beacon Sloop Club Pumpkin Festival

Beacon
Sunday, October 20, 2024
Dedicated to promoting environmental and social issues, the Beacon Sloop Club hosts 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

Walktoberfest at Walkway over the Hudson

Poughkeepsie
Saturday, October 26-Sunday, October 27, 2024
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

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About the Author

Katherine Dhurandhar
Katherine Dhurandhar is a Community Publisher for Mommy Poppins, representing the Westchester and Hudson Valley region of New York, and a freelance copyeditor for Westchester Publishing Company. In her free time, she enjoys hiking, camping, and traveling with her husband and son.
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