Family-Friendly Activities in Westchester for Every Weekend This Fall

Never again say, “There’s nothing to do this weekend!” with this year-round guide to all things family fun in our area.

A continuation of our 52 Weekends of Family Fun feature.
For awesome summer activities, click here.


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  Gather the Family for Some Leaf Peeping

Westchester’s family-friendly trails truly shine during the autumn months, when the foliage is at its color-drenched peak. North and South County Trailways, The Rockefeller Park Preserve, Marshlands Conservancy, and Bronx River Parkway Reservation all offer both scenic sights and relatively flat, manageable day hikes.

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Photo by Tom Nycz for Historic Hudson VAlley

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  Scream for Halloween

Come October, the Headless Horseman acts as the Grand Marshall, summoning skeletons, spiders, and other spooky creatures for a march down Broadway at the annual Tarrytown Halloween Parade and street fair. The whole family will enjoy The Great Jack O’Lantern Blaze in Croton-on-Hudson (reserve well in advance), where dinosaurs, bats, and sea monsters — made from more than 7,000 carved pumpkins — are the main draw, while teens with serious scare tolerance can test their mettle at The Haunt at Rocky Ledge in White Plains.

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  Movie Night

Cozy up with your cuties to watch the latest family-friendly fall movie releases. The Alamo Drafthouse in Yonkers offers craft beers and handcrafted cocktails for the grownups, plus milkshakes and freshly baked chocolate chip cookies for the little ones — all brought directly to your seat for your viewing and eating pleasure. Up north, check out the recently renovated Bedford Playhouse, with an on-site café featuring everything from martinis and Manhattans to kid-approved favorites.

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  Go Apple Picking (Duh)

’Tis the season to don your buffalo plaid and head to an orchard. In North Salem, Harvest Moon Farm & Orchard goes all out with its Fall Fest, featuring food stalls (giant turkey legs, anyone?), music, apple cannons, pony rides, a pumpkin patch, hard cider for the 21-plus crowd, the county’s best cider doughnuts, and, of course, plenty of apples.

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Book ’Em

Get your young bibliophiles excited at the Chappaqua Children’s Book Festival, an annual Best of Westchester-winning family festival devoted to all things children’s books. The September event is a day of literacy, packed with book signings and readings, appearances by local authors, and book sales, plus bites from food trucks and other family-friendly activities.

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Photo courtesy of Bad Axe New Rochelle

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  Be a Bad Axe

Axe throwing is a surprisingly popular new trend — and it just landed in Westchester, with the January opening of Bad Axe New Rochelle. The Canadian backyard pastime is now a fun family excursion. Expect a two-hour event, where trained coaches teach the whole family to hit targets while ensuring proper safety. (Minors under 18 must be accompanied by a parent.)

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The Play’s the Thing

Mamaroneck’s Emelin Theatre has been putting on quality shows for the family for four decades. Expect to see kid- and parent-approved productions from ArtsPower and TheaterWorksUSA on their schedule, plus a new bilingual event by TeatroSEA, the premiere Bilingual Arts-in-Education Organization and Latino Children’s Theater in the U.S.

Photo courtesy of iFly

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  Skydive Without the Risk

Jumping out of an airplane probably isn’t on any parent’s “sure junior, that’s fine” list. But your young adrenaline junkies can experience the thrill, minus the risk, with an indoor skydive at iFly Westchester at Ridge Hill in Yonkers. Kids as young as 3 can take a dive, but this is also an excellent place to take broody teens who need something cool to do.

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Bronx Cheer

Boo at the Zoo is a guaranteed crowd-pleaser. This annual event, held during October weekends, just over the border at the Bronx Zoo, features Halloween-themed attractions, such as the extinct-animal graveyard, a costume parade, magic shows, and pumpkin-carving demonstrations. Don’t forget to stop along the candy trail for a sugar high before you head back home.

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Viva Italia!

No need to Metro-North it to Little Italy when the Yorktown Feast of San Gennaro is right in your backyard. The event was conceptualized by Hudson Valley transplant Michael DiCostanzo (his grandparents ran a sausage-and-peppers booth at the original stateside Festival of San Gennaro on Mulberry Street), who fill his version with live music, traditional Italian dancing, games, and a parade. Another fall Italian tradition is the Eastchester Columbus Day Carnival. For almost half a century, this celebration of all things Italian has been offering attendees delicious delicacies, plus a parade, rides, and games for the whole family.

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Go Full STEAM Ahead

Spend a day indulging your aspiring makers in one of the many fun-filled yet challenging STEAM activities offered at the Digital Arts Experience. Popular events have included a Minecraft Build-Off competition and the Dungeons & Dragons club. A big hit, held monthly, is Game Night, when kids can play Minecraft, Roblox, and Fortnite with each other — all in a supervised space, with a pizza party to top off the night.

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  A Dam Good Winter Event

You get a lot of bang for your buck when you take the whole family to Winter Wonderland at Kensico Dam. The roster includes circus performances, ice-skating on the outdoor ice rink, visits with Santa, and holiday-themed rides. Plus, check out the 40-foot Christmas tree and the large, beautifully lit menorah for a photo-worthy backdrop, as well as a great lineup of food trucks.

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  Chop Down a Christmas Tree

Starting the weekend after Thanksgiving, load the family into the minivan and wander through acres of evergreens at Wilkens Fruit & Fir Farm in Yorktown Heights or Stuart’s Fruit Farm in Granite Springs to find the perfect pine or fir to deck your holiday halls.

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  Fill Your Calendar With Holiday Cheer

The Greenwich Reindeer Festival starts in late November, bringing together St. Nick’s best sleigh-pullers, a Santa’s village, and holiday rides. Another beloved holiday character is the master of ceremonies at Armonk’s annual Frosty Day, featuring crafts, cookie decorating, rides, and its namesake parade. Celebrate the Festival of Lights at Chabad of the Rivertowns’ Chanukah Village, or find time for an evening out to the annual Yorktown Electric Lights Parade or to see a child-friendly production of The Nutcracker at the County Center.

Keep on reading for family-friendly activities for every season below…

Our Wine & Food Festival returns June 4-9!

Our Wunderkinds event takes place on May 23!

Our Best of Business Ballot is open through May 15!

Our Healthcare Heroes Awards event takes place on May 9!

Our Westchester Home Builders Awards take place on April 4!

Our Diversity, Equity & Inclusion Forum is March 14!

Unveiled: A Boutique Bridal Brunch is February 25!

Our Best of Westchester Elimination Ballot is open through March 6!

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