MacKID Guide to Fall Fun in Westchester County

Apple picking, leaf peeping,Oktoberfest, festivals, and more!

By Kelly Fitzpatrick September 3, 2023

It's time for fall family fun in Armonk - Chappaqua - Mount Kisco - Pleasantville and we can hardly wait! We are lucky to have so many fall attractions and events in Westchester County and the Hudson Valley where families have been making fall memories for years. From picking apples to leaf-peeping to Oktoberfest fun ... Macaroni KID Armonk - Chappaqua - Mount Kisco - Pleasantville has all the details for you and your family to make the most of autumn in Westchester County and beyond.

Updated 10/20/23

Our new 2023 MacKID Guide to Fall Fun in Westchester County comes to you with thanks to The Armonk Outdoor Art Show!  Read more about this annual tradition here!


Farms, Orchards, and Markets in Westchester County and the Hudson Valley

Apple Picking in Westchester County and Beyond 

Leaf Peeping in Westchester County and Beyond

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Rockefeller State Park Preserve

125 Phelps Way, Pleasantville

Details: Crushed stone carriage roads serve as the wide and walkable trails through woods and pastures, past lakes, streams, and rock outcroppings.  Bring the carrier for smaller ones, as this is not a particularly stroller friendly walk, although it is ideal for toddlers to explore.

Westmoreland Sanctuary

260 Chestnut Ridge Road, Mount Kisco

Details: Well marked and well maintained trails great for hiking with families (although you will want the carrier again!).  Beautiful views and lots to explore from Betchel Lake to the playhouse to the Fern Garden.  There are many routes to choose from depending on the type of adventure you would like for the day.

Marsh Sanctuary

B Road, Mount Kisco

Details: The Marsh Sanctuary is a 156-acre nature preserve with trails, open space, a community garden, and a commitment to the protection of wildlife.  It is home to the largest freshwater marsh in Westchester County.  Lots of wildlife, a pond, wooded areas, and views.

Gedney Park

155 Millwood Road, Chappaqua

Details: Take a walk in the woods at Gedney Park and immerse yourself in spectacular fall foliage.  Family friendly with some opportunities for stroller walking if you still to the paved path which is still quite nice.  Bathroom facilities, a pond, and two playgrounds make it a perfect day out.

Willing to take a drive or looking for a weekend getaway?  You'll love our Leaf Peeping and Fall Foliage Guide to New York State!

Westchester County and Hudson Valley Fall Attractions:

Getty Images via Canva 

The Great Jack-o-Lantern Blaze

Van Cortlandt Manor
525 S Riverside, Croton-on-Hudson, NY 10520

From September 15th - November 19th the Van Cortlandt Mansion is illuminated with the magic of over 7,000 pumpkins.  This annual tradition is a long-time family favorite for Westchester County and Hudson Valley residents.  Tickets sell out quickly!

The Hudson Valley Shakespeare Festival


This summer favorite lasts through September 17th with the showing of Penelope. The new location is beautiful for a fall evening picnic prior to the show as the river views never disappoint. Better suited for families with tweens and teens.

New Exhibit at Greenburgh Nature Center: Dino Dig


September 7th - October 22nd

This Dino Dig Exhibit is open from Tuesday through Sunday at the Manor House and costs $5 per child. 10:30 a.m. - 4:00 p.m.

Renaissance Faire

Tuxedo Park

Step back in time on the themed weekends from the end of August through October 8th. Rides, food, entertainment, and gifts for the whole family.

Lyndhurst Mansion - Fall Classic Mansion Tour


October 14 - 28

Enjoy the grounds daily through December between 9:30 and 4:30 or take one of the guided tours.

Fall events in Westchester County

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Macaroni KID Armonk - Chappaqua - Mount Kisco - Pleasantville is adding fall events regularly as we find them, so check back often for updates!




  • November 4: 34th Annual Festival of Crafts, Whisconier Middle School, Brookfield, CT 9 a.m. - 
  • November 5: Mama and Child Wellness Expo: Due, New, and YOU! Mount Kisco
  • November 5: Yorktown Lantern Walk
  • November 11: Mount Pleasant Parks and Recreation Scarecrow Festival - Pre-registration required
  • November 18: Harvest Festival Sensory Art ant Play by Macaroni KID with Briarcliff Recreation Department - pre-registration required
  • November 18: Holiday Craft Fair, Yorktown