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Best Harvest Festivals & Pumpkin Festivals in Westchester and the Hudson Valley for Fall Fun in 2025

The pie eating contest is just the start of the fun at the Armonk Cider and Donut Festival. Photo courtesy of the festival
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8/31/25 - By Katherine Dhurandhar

Fall is a magical time in Westchester and the Hudson Valley as the days become crisp and cool and the colorful autumn foliage paints the landscapes. And what better way to celebrate the season than at a local fall festival? 

We've picked out our favorite family-friendly fall festivals in the area, many of which offer fun seasonal activities for kids, from pumpkin painting to carnival rides. With the abundance of farms in the area, fall is the perfect time to sample the local harvest, from freshly picked apples to cider and doughnuts, and many of these festivals are held on the farms themselves.  So whether you want to pick apples, get lost in a corn maze, or enjoy live music while sipping local craft beverages, these festivals are sure to give you the fall vibes you're looking for. 

For even more ways to celebrate the season, bookmark our Guide to Fall Fun in Westchester and the Hudson Valley, our favorite fall day trips, and our Guide to Farms and You-Picks in Westchester and the Hudson Valley. 

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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.

Tips for Visiting Fall Festivals With Kids

  • Try to go early to avoid crowds.
  • Bring cash for food vendors and rides.
  • Check for online tickets or reservation requirements.
  • Check out the parking situation before heading out. Some festivals offer shuttles for your convenience.
  • Dress in layers and bring sunscreen and water.
  • Be ready for photo ops (pumpkin patches, hay bales, etc.).

Frequently Asked Questions for Fall Festival Fun in Westchester and the Hudson Valley

When do fall festivals in Westchester and the Hudson Valley typically happen?

Most fall festivals in the area are held in September and October, with a few extending into November. 

Are these festivals stroller-friendly?

Most fall festivals are stroller-friendly. However, some that are held at farms might require a jogger stroller or baby carrier.

Do we need to buy tickets in advance?

Most town/village and street festivals do not require advance tickets, but for those held on private farms, reservations are recommended. Tickets are often cheaper when purchased online in advance.

What age are these festivals best for?

These festivals are great for all ages as they offer entertainment for adults as well as activities for kids.

OUR LATEST VIDEOS

Best Fall and Pumpkin Festivals in Westchester and the Lower Hudson Valley

Fall Festival at Outhouse Orchards

North Salem
Daily through Sunday, November 2, 2025
Enjoy the beautiful scenery, explore the pumpkin patch, pick your own apples, and make lasting memories with a day full of exciting attractions, delicious treats, and fall fun at the Outhouse Orchards Fall Festival. Admission includes a hayride, access to the flower field, pumpkin patch, photo-ops, farm animals, bounce houses, and farm attractions! READ MORE

Fall Crafts at Lyndhurst

Tarrytown
Friday-Sunday, September 12-14, 2025
Fall Crafts at Lyndhurst features handmade and uncommon items from 200 makers you can't find anywhere else in the county. Plus, enjoy gourmet specialties, tastings from local distilleries (new for this year: a beer truck), craft demos like wheel-thrown pottery, and family activities such as interactive puppet theater, face painting, and storytelling. READ MORE

Armonk Cider & Donut Festival and 5K Run

Armonk – FREE
Sunday, September 14, 2025
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

Sleepy Hollow Street Fair

Sleepy Hollow – FREE
Sunday, September 21, 2025
Join the Village of Sleepy Hollow for the annual street fair on Beekman Avenue. The fair features nearly 200 vendors, arts & crafts, food, entertainment for the whole family, and a special appearance by the Headless Horseman. READ MORE

Croton Oktoberfest

Croton-on-Hudson– FREE
Saturday, September 27, 2025
Croton-on-Hudson's Oktoberfest will feature live music all day and over 60 amazing food, craft beer, and local retail vendors, plus a kinder-fest for the little ones, with music, food, and fun activities to keep them entertained! READ MORE

Armonk Outdoor Art Show

Armonk
Saturday & Sunday, September 27-28, 2025
The Armonk Outdoor Art Show has repeatedly been ranked among the country's top fine art and design art shows. Families can enjoy a wide range of activities beyond exploring the works of art, including kids' attractions and food trucks. READ MORE

Yorktown Fall Festival & Car Show

Yorktown – FREE
Sunday, October 12, 2025
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

Beacon Sloop Club Pumpkin Festival

Beacon
Sunday, October 19, 2025
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

Top Fall Harvest and Pumpkin Festivals in Rockland County

Nyack Septemberfest Street Fair

Nyack
Sunday, September 7, 2025
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

Congers Fall Festival

Congers – FREE
Sunday, September 28, 2025
The annual Congers Fall Festival features local craft vendors, live music, food vendors, and tons of kids' activities, including pumpkin painting, birdhouse painting, face painting, henna tattoos, and an interactive display by Bach to Rock Music. READ MORE

Port Jervis Fall Foliage Festival

Port Jervis – FREE
Sunday, September 28, 2025
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

Pearl River Street Festival

Pearl River
Saturday, October 18, 2025
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

Rockland Historical Society Fall Festival

West Nyack – FREE
Sunday, October 19, 2025
Celebrate Rockland's history at this fall festival with an encampment of 18th-century tents, open-fire pit cooking, militia drills, musket firing, and other living history demonstrations! Kids' activities include mini golf, old-time crafts, balloon animals, face painting, glitter tattoos, horse-drawn wagon rides, and pumpkin picking, decorating, and painting.  READ MORE

Awesome Fall Harvest and Pumpkin Festivals in Dutchess County

Germania Oktoberfest

Poughkeepsie
Friday, September 5-Sunday, September 7, 2025
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

Family Fun Weekend at Barton Orchards

Poughquag
Saturday & Sunday, September 6-7, 2025
Join the annual family fun celebration at Barton Orchards! READ MORE

Carni "Fall" Festival in Wappingers Falls

Wappingers Falls – FREE
Thursday, September 18-Sunday, September 21, 2025
Wappinger's Carni"fall" is a four-day celebration with carnival rides, live music, fireworks, food trucks, games, and activities, including donut-eating and pumpkin decorating contests. READ MORE

NY Sheep and Wool Festival

Rhinebeck
Saturday, October 18-Sunday, October 19, 2025
Attractions at the New York Sheep and Wool Festival include sheep shows, vendors, crafts, frisbee dogs, and a petting zoo.  READ MORE
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

Best Fall Family Festivals in Orange County

New York Renaissance Faire in Tuxedo

Tuxedo
Weekends through Sunday, October 5, 2025, 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

Cornwall Fall Festival

Cornwall – FREE
Sunday, September 21, 2025
The 51st annual fall festival returns to downtown Cornwall. Main Street is closed down and attendees can enjoy a variety of local vendors offering unique crafts, goods, and delicious food, along with live music and entertainment for all ages. The festival also features activities for children, including games and crafts. READ MORE

Good Vibes & Tractor Rides Fall Festival at Wagon Wheel Farm

Goshen
Saturday & Sunday, October 4-5 and 11-12. Also on Monday, October 13, 2025
Enjoy the best that fall has to offer at Wagon Wheel Farm, with pumpkin and sunflower picking, a bounce house park, pony rides, live bands, adult beverages, food trucks, fresh cider donuts, and more.   READ MORE

Warwick Applefest

Warwick – FREE
Sunday, October 5, 2025
This festival features more than 150 craft vendors, more than 75 food vendors, four stages of live music, and an apple pie baking and eating contest. There's also a children's carnival, and Warwick stores are within easy reach for additional browsing. READ MORE

Sugar Loaf Fall Festival

Warwick – FREE
Saturday & Sunday, October 11-12, 2025
Art, crafts, food, and music are all on tap at the annual Sugar Loaf Spring Festival, plus family-friendly activities including face painting, petting zoo, bouncy houses, a kids zone, and a witches parade for a magical touch. READ MORE

Top Fall Harvest Festivals in Ulster County and the Catskills

Harvest Festival at Bethel Woods Center for the Arts

Bethel – FREE
Sundays, August 31-October 5, 2025
Held every Sunday this fall, Bethel Woods' annual Harvest Festival features 100+ local farm, artisan, and craft vendors. Plus, enjoy family art-making, a corn maze, hay wagon rides, live music, food trucks, and more!   READ MORE

Fall Harvest Celebration at Kelder's Farm

Kerhonkson
Opens Saturday, September 6, 2025
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

Apples & Wine Festival at Weed Orchards & Winery

Marlboro
Weekends from Saturday, September 20-Sunday, October 5, 2025
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

Hudson Valley Garlic Festival in Saugerties

Saugerties
Saturday, September 27-Sunday, September 28, 2025
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

Fall Family Fun Fest at the Ashokan Center

Olivebridge
Sunday, October 19, 2025
The fall festival at the Ashokan Center has something for all ages, including hayrides, cider-making, blacksmith demos, pumpkin decorating, live music, guided hikes, and tasty food! READ MORE

Places featured in this article:

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

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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