Fall Fun, Festivals, and Foliage: Your 2025 Guide to the Hudson Valley & Tri-State Region

millertonbusinessa
Sep 22
3 min read

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 - Every Saturday and Sunday 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 20 - October 26, 2025. Enjoy hayrides, a corn maze, pumpkin picking, farm animals, and seasonal treats at this family-friendly farm.

Millbrook Vineyards & Winery Harvest Party – Millbrook - October 25

Celebrate the season with wine, live music, and local food vendors.

Autumn in the Park - Copake Falls, NY - October 11

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 4 & 5

Handcrafted art, gourmet food, and beer gardens make this event a perfect fall day trip.

Little Apple Cidery Celebrations – Hillsdale - October 11 and 12

Celebrate the cidery’s 10th anniversary on October 11, then return on October 12 for Ciderfest XIII, 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 1–16

Photo: The Incredible Naumkeag Pumpkin Show

Spooky & Haunted Events

Haunted Fortress – Stanfordville - October 3rd for four weekends

A haunted walk-through experience that’s not for the faint of heart.

Forsaken Lands Haunted Attraction – Goshen - Sept 27 for 6 weekends

Immerse yourself in a high-intensity haunted trail.

The Haunted Mansion – Wappingers Falls - Sept 26 - 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.

Murder Mystery Dinner – Millbrook Vineyards & Winery - Sept 26

A night of intrigue, great wine, and delicious food—costumes encouraged.

Outdoor Adventures & Leaf Peeping

Fall Foliage Half Marathon & 5K – Rhinebeck - October 13

Lace up for a scenic run through peak foliage.

Poughkeepsie Regatta – Poughkeepsie - October 4

A full day of rowing competitions along the Hudson River, perfect for a crisp autumn afternoon.

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.