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Best Things To Do in Westchester and the Hudson Valley this Weekend with Kids

Nearly 200 authors will be in attendance at the Chappaqua Children’s Book Festival! Photo courtesy of the event
Nearly 200 authors will be in attendance at the Chappaqua Children’s Book Festival! Photo courtesy of the event
9/27/23 - By Katherine Dhurandhar

Looking for the best things to do in Westchester and the Hudson Valley this weekend? Here are some family-friendly events and activities to add to your list.

Standout events this weekend include the Chappaqua Children's Book Festival, the Monarch Butterfly Festival, and the annual 2-day Garlic Festival. Parents can rock out by the river while the kids have fun at the family-friendly Rocktoberfest in Irvington or join in other fall celebrations, including Walden's annual Harvest Fest and the Peekskill Rotary Fall Festival. 

For more fun fall activities in Westchester and the Hudson Valley, check out our picks for the best pumpkin patches, best corn mazes, and amazing places to view fall foliage. 

More Things To Do in Westchester and the Hudson Valley this Week with Kids:

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Take a hayride through the foliage at the Soukup Farms Harvest Festival. Photo courtesy of the festival
Take a hayride through the foliage at the Soukup Farms Harvest Festival. Photo courtesy of the festival

Things To Do this Weekend in Westchester and the Hudson Valley with Kids

Pumpkin World

Pomona
Opens Friday, September 29
Pumpkin World is an interactive family-friendly fall extravaganza featuring a 45-minute jack-o'-lantern trail illuminated with intricately hand-carved pumpkin art sculptures. The festival also includes a whimsical Pumpkin Village offering more fall fun for the whole family to enjoy with music, games, merchandise, and thrilling pumpkin-carving competitions by master artists. READ MORE

The 10th Annual Chappaqua Children's Book Festival

Chappaqua–FREE
Saturday, September 30
The 10th Anniversary of the Chappaqua Children’s Book Festival (CCBF) is the largest one yet, with 180 authors in attendance and celebrity authors Mary Pope Osborne and Alan Gratz leading the charge. There will be author readings and special presentations, illustrator demos, book signings, a bubble bus, and books for sale. Food will be available from gourmet food trucks and from the Chappaqua Farmers Market.  READ MORE

Mamaroneck Monarch Butterfly Festival

Mamaroneck–FREE
Saturday, September 30
Join the flutter of activity at Harbor Island Park with the Village of Mamaroneck Committee for the Environment's 2nd Annual Mamaroneck Monarch Butterfly Festival! Local families can enjoy a free event filled with food, arts, crafts, and activities to learn how to help the Monarch butterfly. READ MORE

Rocktoberfest

Irvington
Saturday, September 30
Come enjoy live music, food trucks, and fun at Matthiessen Park. There will be a kid zone and other family-friendly activities.  READ MORE

Town of Walden's Annual Harvest Fest

Walden–FREE
Saturday, September 30
Get ready for old-fashioned fun at this annual fall festival. Attractions include bouncy houses, a petting zoo, and a frog jumping contest. Live music and vendors add to the fun.  READ MORE

Soukup Farms Harvest Festival

Dover Plains–FREE admission
starts Saturday, September 30
Hit the pumpkin patch, hitch a hayride, and visit the exotic animals of the Two-by-Two traveling animal exhibit (on select dates) at the Soukup Farms Harvest Festival. There's also a climbable hay dragon, tractor exhibits, and a corn maze. Re-energize with a farm-to-table lunch. READ MORE

Garlic Festival

Saugerties
Saturday, September 30-Sunday, October 1
The annual 2-day garlic festival in Saugerties is hugely popular for a reason. More than a foodie's paradise-–with eats, demos, and more–the event also features kid-friendly attractions, such as a craft tent, live performances, and face painting. READ MORE

Peekskill Rotary Fall Festival

Peekskill–FREE
Saturday, September 30
The Rotary Club of Peekskill's annual fall festival features food, beer & cider trucks, craft and art vendors, a DJ, and musical acts. Children’s activities include a carved pumpkin contest, pumpkin painting, bike rodeo, obstacle courses, and mazes.  READ MORE

Scarecrow-Building Festival

Chappaqua
Sunday, October 1
Families are invited to build their own scarecrow with all materials provided. READ MORE

Jay Day

Rye
Sunday, October 1
Celebrate American culture with live music, book signings, face painting, hands-on art and planting activities, pony rides, historical house tours, balloon twisting, and geocaching with prizes. Purchase items from craft vendors, including old-fashioned silhouette portraits and vintage maps.  READ MORE

Dashing For Dylan Kids Fun Run & Family Fun Day

Rye Brook
Sunday, October 1
Join the Dashing for Dylan Kids Fun Run & Family Fun Day and help reach the goal of fundraising $50,000! This goal will assist in providing help to families in need. Family fun activities include tie-dying with Marla Beth Designs, Wacky Inflatables, face painting, My Balloon Guy, and the tumble bus.  READ MORE

Devitt's Anniversary Car Show & Fall Fest

New Windsor–FREE
Sunday, October 1
Celebrate fall with a classic car show plus fall festivities including live music, food trucks, pumpkin painting, face painting, a ride-on train, and games. Follow Suit will be jamming along with Newburgh Brewing in the beer garden, and multiple craft vendors will be selling handmade goods.  READ MORE

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