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Fall Fun, Festivals, and Foliage: Your 2026 Guide to the Hudson Valley & Tri-State Region
Updated: Sep 13
Crisp air, vibrant leaves, and the scent of apple cider—it’s one of the most beautiful times of year in the Hudson Valley and Tri-State region. Whether you’re seeking festive harvest celebrations, spine-tingling haunted attractions, or the perfect weekend for leaf peeping, there’s something for everyone this fall.
Fall Festivals & Harvest Celebrations
Soukup Farms Harvest Festival – Dover Plains - Most Weekends in October
Take a scenic hayride to the pumpkin patch, explore the corn maze, and enjoy family activities. Don’t leave without a bottle of their famous maple syrup.
Kesicke Farm Fall Festival – Rhinebeck - Every Saturday and Sunday 10am - 5pm
from September 26 - November 1, 2026. Enjoy hayrides, a corn maze, pumpkin picking, farm animals, and seasonal treats at this family-friendly farm.
Autumn in the Park - Copake Falls, NY - October 10
Pumpkin Painting, Cornhole, Face Painting, Apples, Kid's Crafts, Photo Opportunities, Booths, Live Animal Show, Hiking, BEAR BUS, Food Truck, and More!
Oktoberfest at Rhinebeck – Fairgrounds - October 10 & 11
Handcrafted art, gourmet food, and beer gardens make this event a perfect fall day trip.
Ciderfest at Little Apple Cidery – Hillsdale - October 10 & 11
Celebrate Ciderfest featuring live music, tastings, and seasonal fare.
The Incredible Naumkeag Pumpkin Show- Stockbridge, MA - Every Wednesday through Sunday from October 1 - 31
All Children (13 and under) are FREE on Wednesdays and Thursdays from October 1–15
Spooky & Haunted Events
Haunted Fortress – Stanfordville - October 2rd for four weekends
A haunted walk-through experience that’s not for the faint of heart.
The Haunted Mansion – Wappingers Falls - Oct 2 - Nov 1
Classic haunted house thrills in a historic setting.
Local Trunk-or-Treats
Check your town’s Parks & Recreation page for safe, family-friendly trick-or-treat events throughout late October.
Outdoor Adventures & Leaf Peeping
Fall Foliage Half Marathon & 5K – Rhinebeck - September 26
Lace up for a scenic run through peak foliage.
Apple Picking - Check their websites for picking dates
Spend the day at Rose Hill Farm or Greig Farm in Red Hook for fresh apples, cider donuts, and farm views.
Corn Mazes - Late August through the end of October
Navigate your way through the corn maze at The Farm Store in Millerton, Soukup Farms in Dover Plains, or Kesicke Farm in Rhinebeck.
Best Time for Leaf Peeping
Peak foliage in the Hudson Valley typically runs from late September through mid-October, depending on weather conditions.
For the best views:
Drive along Route 22 near Millerton for rolling hills and open farmland.
Hike the Harlem Valley Rail Trail for a car-free leaf-peeping experience.
Visit nearby Bash Bish Falls State Park for a mix of waterfalls and autumn color.
