Fall Bucket List for Kids: 20 Top Things To Do in Westchester and the Hudson Valley

Run wild in the forest obstacle course at Greenburgh Nature Center this fall. Photo courtesy of the center
Run wild in the forest obstacle course at Greenburgh Nature Center this fall. Photo courtesy of the center
9/8/23 - By Marisa Iallonardo

It's hard to pull together a fall bucket list because we love all fall activities: the leaf-peeping, the pumpkin picking, and the fun to be had around Halloween. Sleepy Hollow is the center of the Halloween universe, after all, and Westchester and the Hudson Valley abound with fall activities. 

Here, we’ve rounded up 20 of our favorite fall activities near Westchester that are sure to please everyone from little ones to teens. Many of them are even FREE.

If this fall bucket list isn't enough entertainment for your family, be sure to bookmark our list of family-friendly fall festivals near Westchester and the Hudson Valley and our seasonal Guide to Fall Fun for more great things to do.


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Our Fall Bucket List for Kids in Westchester and the Hudson Valley this Fall

1. Go Apple Picking

Pick some perfect apples at one of the many farms in Westchester and the Hudson Valley. (Don’t forget to sample the apple cider donuts!)

2. Hit a Fall Festival

Speaking of donuts, don’t miss the Cider & Donut Festival at Wampus Park in Armonk on Sunday, September 10, 2023.

RELATEDApple Picking Destinations in Westchester and the Hudson Valley

Fall bucket list New York Renaissance Faire
Jousting knights are just one of the attractions at the New York Renaissance Faire in Tuxedo Park. Photo courtesy of the event

3. Visit the Renaissance Faire

Head to the New York Renaissance Faire on weekends from now until Sunday, October 8, 2023. (Bonus: Kids under 4 are FREE!)

4. Run at Greenburgh Nature Center

Let kids try a forest run and obstacle course at Run Wild at the Greenburgh Nature Center. The runs are held on Saturday, September 30, 2023 and Sunday, October 1, 2023.

5. Celebrate Books 

Make reading even more fun with a stop at the Rye Children's Book Festival, which features author signings, storytimes, and more on Saturday, September 23, 2023. The following week, on September 30, 2023, check out the Chappaqua Children's Book Festival, too. 

6. Explore the Hudson Valley

Go on a Hudson Valley day trip: Beacon, Saugerties, and Cold Spring are all great picks.

7. Take in the Arts 

Head to Nyack for the multi-weekend Phoenix Festival, which includes a whole variety of live entertainment, including kid-friendly shows and starts on September 28. 

RELATED: Hayrides and Farm Fun for Kids Near Westchester

Fall bucket list The Great Jack O'Lantern Blaze
Watch as pumpkins come alive at the Great Jack O'Lantern Blaze. Photo by Susan Miele

8. See The Blaze

Take part in a Westchester tradition: The Great Jack O’Lantern Blaze runs from Friday, September 15, 2023 through Sunday, November 19, 2023.

9. Hit the Garlic Festival

Saugerties toasts the potent veggie with its festival on Saturday, September 30-Sunday, October 1, 2023.

10. See Some Sheep

Animal-loving kids will want in on the NY Sheep and Wool Festival, which kicks off on Saturday, October 21, 2023. 

11. Visit a National Treasure—for FREE

Enjoy free admission to a national park on Saturday, September 23, 2023, and Tuesday, November 11, 2023. Local options include the Eleanor Roosevelt National Historic Site, the Home of Franklin D. Roosevelt National Historic Site, and Saratoga National Historical Park.

12. Shop the Farmers Market

Visit a local farmers market before the outdoor venues close for the season, which usually happens at the end of October or in November.

RELATED: Fall Festivals in Westchester and the Hudson Valley

Fall bucket list bicycle Sundays
Take a family bike ride on Bicycle Sundays. Photo courtesy of the Westchester Police Department

13. Ride a Bike

Clock in your last rides of the year as part of Bicycle Sundays on the Bronx River, which wraps up on Sunday, September 24, 2023.

14. Hunt for Fall Foliage

Go leaf-peeping at one of these gorgeous lookout points in the area.

15. Go Pumpkin Picking

Bring home a pumpkin for carving from one of these local farms.

16. Get Lost in a Maze

Find your way out of one of these area corn mazes.

17. Hit the Trails

Choose one of these kid-friendly local hikes—and then start exploring!

18. Learn the Legend of Sleepy Hollow

Ring in the Halloween season with a visit to Washington Irving’s historic home in Irvington to learn more about The Legend of Sleepy Hollow. The all-ages event kicks off on Friday, September 15, 2023.

19. Snuggle an Alpaca

19. Get up close and personal with an alpaca at one of these Westchester farms. And don't miss them dressed in their Halloween finest

20. See Stars 

Walking over a bridge is cool in the daytime—but even cooler at night, especially when it's at Walkway Over the Hudson. Families can even don their Halloween costumes for the Friday, October 27, 2023 session.  

This post was originally published in September 2021 and has since been updated.