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Top 20 Things to Do in Fall in Westchester County

Top 20 Things to Do in Fall in Westchester County

UPDATED JULY 2019: From picking apples to peeping at the changing leaves, there are plenty of family activities in Westchester County to keep you having fun all fall, including a Native American pow wow, the Hops and Harvest benefit, and making apple cider. Don't miss out on these opportunities to have the quintessential fall with your family!

1. It Couldn’t Be Cornier

Eat juicy corn on the cob, join a corn-shucking race, traverse a corn maze, and more at the CORNucopia Festival at Philipsburg Manor in Sleepy Hollow in late August through early September, and check out a host of other fall festivals nearby

2. An Apple a Day…

Take a wagon ride and pick your own apples from early September through late October at Wilkens Fruit & Fir Farm in Yorktown Heights, or find another apple picking orchard in the area with our full u-pick guide. 

3. Gone Country

Taste a slice of true country living at the Yorktown Grange Fair in Yorktown Heights—a tradition since 1923. Come early September, you can take a spin on the Ferris wheel, visit with farm animals, dance along to live music, and enter competitions to show off your homegrown veggies, flowers, and more.

4. Reflect & Respect

Courtesy Kensico Dam Plaza

Take a moment to reflect at the 9/11 Twilight Ceremony at Kensico Dam Plaza in Valhalla, home of Westchester’s Sept. 11 memorial, The Rising. The ceremony includes remembrance activities as well as volunteer opportunities. If you want to make the trip into the city, take in our tips for visiting the National September 11 Memorial & Museum in Manhattan.

5. For Equine Enthusiasts

Courtesy American Gold Cup

The American Gold Cup, one of the most prestigious equestrian sporting events in the world of international show jumping, takes place at historic Old Salem Farm in North Salem in mid-September. Find more local horse farms that offer riding lessons and more here. 

6. You’ve Got a Friend

Each September Sesame Street Live brings a new, interactive show for little ones to Mid-Hudson Civic Center in Poughkeepsie.

7. Handmade Gifts & Goodies

Shop for one-of-a-kind items during Fall Crafts at Lyndhurst in Tarrytown in mid-September. The weekend also includes gourmet foods, craft demonstrations, and kids’ activities.

8. When Pigs Swim

Don’t miss the swimming pig races at the Barn Dance at the John Jay Homestead in Katonah in mid-September. The annual fall fest also features a country barbecue, campfire, and live music by local bands.

9. Big Screen Under the Stars

Grab a blanket and cozy up with your little ones for a free, outdoor family film night in late September at Boscobel House and Gardens in Garrison. 

10. Bookworms & Baked Treats

Kids can meet and mingle with some of their favorite authors at the Chappaqua Children’s Book Festival in late September/early October. The fest is typically held at Robert Bell Middle School.

11. Fall on the Farm

In early October, head to Harvest Fest at the Stone Barns Center for Food and Agriculture in Pocantico Hills for a farmers’ market, hayrides, demonstrations and workshops on food and farming, and live music. This event sells out, so buy your tickets early!

12. A Toast for a Good Cause 

Greenburgh Nature Center

Raise funds for the Greenburgh Nature Center in Scarsdale at the Hops and Harvest Benefit. The gala features food from a local artisan chef, beverages from local wineries and breweries (for Mom and Dad), children’s activities, and more in October.

13. Gourds Galore

Pick your own pumpkins in October at Stuart’s Fruit Farm in Granite Springs or another pumpkin farm in the area.

14. A Legend Comes to Life

On select dates in October, head over to Sleepy Hollow for a live, dramatic performance of Irving’s Legend, Washington Irving’s classic tale featuring the Headless Horseman. With live spooky music and master storytellers, this is sure to get your family in the Halloween mindset. 

15. Lighting Up the Night

Bryan Haeffele

Don’t miss The Great Jack O’ Lantern Blaze, an outdoor walkthrough experience featuring thousands of hand-carved pumpkins, at Van Cortlandt Manor in Croton-on-Hudson. The Blaze opens in late September and runs through November. 

16. It’s Pressing Time!

In early October, the Heritage Apple Festival at Boscobel House and Gardens in Garrison features live entertainment, cider pressing, hard cider samples, apple treats for sale such as the apple cider doughnut, and interactive lectures about the history of apples in New York and colonial America.

17. A Real Treat

The Chocolate Expo, held at Museum Village in Monroe in late October, is the area’s biggest chocolate-themed event, with tons of local and regional sweets to be tasted and purchased as well as a host of activities for little ones.

18. Real Live Raptors

Get up close with birds of prey during Wings Over Wave Hill at Wave Hill  in nearby Bronx in early November. See red-tailed hawks and great horned owls, and participate in hands-on workshops, art making, and scenic nature walks. 

19. Time to Celebrate!

Planning a bar or bat mitzvah, Sweet 16, or other milestone party? Check out the Celebrate! Party Showcase at the Westchester Marriott in Tarrytown in late November. 

20. Turkey Day Parade

If you can’t make it into the city for the famous Macy’s parade, head to New Rochelle for the annual Valenti Thanksgiving Day Parade in mid- to late November. This is Westchester County’s largest parade with more than 1,000 participants.



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