As the crisp air and vibrant colors take over the Hudson Valley this fall, Poughkeepsie is buzzing with plenty of exciting events. Whether you're a resident or just visiting, there's something for everyone to enjoy. From apple picking and corn mazes to music festivals and haunted houses, here’s a list of the top local happenings in Poughkeepsie and the surrounding areas this season.
1. Hudson Valley Hot Air Balloon Festival
Get ready to be amazed by a colorful sky filled with hot air balloons! The Hudson Valley Hot Air Balloon Festival is a must-attend event, offering a chance to watch beautiful balloons take flight over the picturesque landscape. The festival also features live music, food vendors, and family-friendly activities. This is one of the most visually stunning events in the region, so don’t forget your camera!
Location: Dutchess County Fairgrounds, Rhinebeck
When: September 6–8, 2025
2. Oktoberfest at Barton Orchards
What’s fall without a little Oktoberfest fun? Head over to Barton Orchards in Poughquag to enjoy authentic German food, live music, craft beer, and apple picking. This event is perfect for families or a day out with friends. Don’t miss the pumpkin patch, the corn maze, and the “fun park” where kids can play while you relax with a crisp cider.
Location: Barton Orchards, Poughquag
When: September 13–14, 2025
3. DuBois Farms Fall Festival
DuBois Farms is a local favorite during the fall season. With a beautiful farm setting, the Fall Festival features everything you love about autumn: pumpkin picking, hayrides, a corn maze, and live music. The farm also offers delicious homemade treats like apple cider donuts, which are a perfect treat to enjoy while walking around the farm.
Location: DuBois Farms, Highland
When: Every weekend in October
4. Kevin McCurdy’s Haunted Mansion
For those seeking some spooky fun, head to Kevin McCurdy’s Haunted Mansion for a frightful adventure! This haunted house attraction is a favorite in the region, drawing visitors from all over. The mansion’s eerie atmosphere and terrifying scares make it a top pick for Halloween lovers.
Location: 14 Krieger Ln, Wappingers Falls
When: October 3–31, 2025
5. Weed Orchards and Winery Harvest Festival
Combine wine tasting with the beauty of fall at Weed Orchards and Winery. During their harvest festival, you can sample wines, enjoy live music, and browse local artisan vendors. Whether you’re a wine connoisseur or just looking for a relaxing afternoon, this is a great spot to take in the fall vibes.
Location: Weed Orchards, Marlboro
When: September 20–21, 2025
6. Fall Arts Festival at Lyndhurst Mansion
Lyndhurst Mansion in Tarrytown hosts an annual fall arts festival that brings together 250+ artisans, crafters, and food vendors. Whether you're in the mood for unique jewelry, handmade pottery, or a delicious wood-fired pizza, this event has it all. Plus, the beautiful mansion grounds make for a perfect backdrop for your fall shopping.
Location: Lyndhurst Mansion, Tarrytown
When: October 18–20, 2025
7. Walktoberfest at Walkway Over The Hudson
One of the most scenic events in Poughkeepsie, Walktoberfest takes place on the Walkway Over The Hudson—a pedestrian bridge offering stunning views of the river and fall foliage. Enjoy local food, live music, and vendors while taking in breathtaking views. This event is perfect for a fall stroll with friends or family.
Location: Walkway Over The Hudson, Poughkeepsie
When: October 26–27, 2025
8. The 24th Annual Hudson Valley Wine & Food Festival
For those who love food, drink, and good company, the Hudson Valley Wine & Food Festival in Rhinebeck is a fantastic event to kick off the season. With over 300 wineries, breweries, and distilleries showcasing their best, plus gourmet food trucks, live chef demos, and mixology classes, this is an event you won’t want to miss.
Location: Dutchess County Fairgrounds, Rhinebeck
When: September 6–7, 2025
9. Boscobel Chamber Music Festival
If you’re a fan of classical music, the Boscobel Chamber Music Festival offers intimate performances at the Boscobel House & Gardens. Enjoy classical concerts against the stunning backdrop of the Hudson River. It's a perfect way to experience culture while soaking in the fall air.
Location: Boscobel House & Gardens, Garrison
When: October 4–12, 2025
10. Art Walk Kingston
For art enthusiasts, Art Walk Kingston is a great opportunity to explore the local art scene in one of the Hudson Valley's most vibrant communities. Over the weekend, visitors can tour galleries, attend art exhibitions, and meet local artists in their studios. If you’re in the area, it’s a fun way to experience the creative energy of the region.
Location: Kingston
When: October 18–19, 2025
FAQs About Poughkeepsie This Fall
What are the best outdoor activities in Poughkeepsie during the fall?
Poughkeepsie is perfect for outdoor enthusiasts in the fall! You can visit the Walkway Over The Hudson, go apple picking at local orchards, or explore the Dutchess Rail Trail. Hiking at Mount Beacon or Poet’s Walk is also a popular activity during this time of year.
When is the best time to visit Poughkeepsie for fall events?
The best time to visit Poughkeepsie for fall events is during September and October. Many of the region's top festivals, such as Oktoberfest, the Hudson Valley Wine & Food Festival, and Walktoberfest, take place during these months, offering the perfect way to experience the beauty and fun of fall.
Are there any family-friendly events in Poughkeepsie during the fall?
Absolutely! Many of the events in Poughkeepsie are family-friendly. From corn mazes at DuBois Farms to the harvest festivals at Barton Orchards, there’s plenty to keep kids entertained. Kevin McCurdy’s Haunted Mansion also offers less scary versions of its haunted attractions for younger visitors.
How do I get to Poughkeepsie from New York City?
Poughkeepsie is easily accessible from New York City by train. Take the Metro-North from Grand Central Station on the Hudson Line for a scenic and relaxing ride to Poughkeepsie, which takes about 1 hour and 40 minutes.
Conclusion
Poughkeepsie and the Hudson Valley offer an abundance of exciting events during the fall. Whether you’re into festivals, outdoor activities, or just soaking in the stunning views, this area has something to offer everyone. So, grab your cozy sweater, enjoy the crisp fall air, and get ready to make some unforgettable memories!
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