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Best of October: 20 Things to Do in Westchester and the Hudson Valley

Celebrate the Mexican holiday of Dia de los Muertos with a FREE family concert at Caramoor. Photo courtesy of Caramoor
Celebrate the Mexican holiday of Dia de los Muertos with a FREE family concert at Caramoor. Photo courtesy of Caramoor
9/30/22 - By Katherine Dhurandhar

Halloween is the name of the game in October, which means Westchester and the Hudson Valley are alive with pumpkin patches, haunted houses, fall festivals, and of course trick-or-treating—so many opportunities to wear Halloween costumes!

In addition to tons of Halloween fun this month, there are several harvest celebrations, including the Soukup Farms Fall Festival, the Heritage of West Nyack Fall Festival, and the annual Columbus Day Pumpkinfest. For artsy fall fun, check out the premiere of the Serious Fun Arts Festival, featuring live mural painting and art making for the whole family, or the Magic of Storybook Animals art exhibit. 

Find more top October fun in our rundown of best ball festivals near Westchester, our Halloween Fun Guide for Westchester Families, and our Westchester Fall Fun Guide, 

We’re adding more events to our Family Activity Calendar every day, so don’t forget to check it frequently.  

Get our picks for every weekend in your inbox—sign up for our newsletters.

 

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There's a climbable hay dragon, tractor exhibits, a corn maze, and more at the Soukup Farms Fall Festival. Photo courtesy of the farm.
There's a climbable hay dragon, tractor exhibits, a corn maze, and more at the Soukup Farms Fall Festival. Photo courtesy of the farm.

Top Things to Do in Westchester with Kids this October

Peekskill Rotary Fall Festival

Peekskill–FREE
Saturday, October 1
The Rotary Club of Peekskill presents a new type of fall festival in 2022, featuring food, beer and cider trucks, craft and art vendors, a DJ, and musical acts. Children’s activities including a carved pumpkin contest, pumpkin painting, bike rodeo, obstacle courses, and mazes.  READ MORE

The Magic of Storybook Animals: Art Exhibit Opening

Rye–FREE
Sunday, October 2
Join the celebration of the opening of this fourth exhibition of original illustrations for children’s books focusing on animals in illustrated literature. Opening day festivities include live animals on the front lawn to greet visitors, art workshops, live music, and storytime with the illustrators themselves.  READ MORE

Eastchester Columbus Day Carnival and Parade

Eastchester–FREE
Friday, October 7-Monday, October 12
Eastchester goes all out Columbus Day weekend, with a four-day carnival, a holiday parade, and more. The carnival features lots of rides for all ages, games with prizes, vendors and exhibitors, and food. Time your visit around the schedule of live music, fireworks, and more.  READ MORE

Warwick Children's Book Festival

Warwick–FREE
Saturday, October 8
Join fellow readers to celebrate children’s literacy, share a love of the written word, discover new books, talk with those who create them, and have your book purchases autographed. The Book Festival welcomes back the beloved Uncle Brothers Band for a concert at 12pm. Visitors can also enjoy a kids craft pavilion, reading to certified therapy dogs, and several local food trucks. READ MORE

Headless Horseman Haunted Attractions Children's Day

Ulster Park
Saturdays, October 8 and 22
On Children's Day, the Headless Horseman Haunted Attractions tone down the scare level. Kids can enjoy a hayride and visit friendly characters along the way, in addition to the Magic Moon Maze, Haunted Gardens, Witch Hazel's Halloween House, and the Dinosaur Trail. Music and other surprises make this the perfect outing for families with young children. READ MORE

Pumpkinfest

Warwick
Monday, October 10
This annual Columbus Day tradition features a bouncy house, pumpkin painting, face painting, games, crafts, touch-a-tractor, refreshments, and more. Attendees can enjoy food, ice cream, and tasty treats from on-site vendors.  READ MORE

Serious Fun Arts Festival

White Plains–FREE
Wednesday, October 12-Sunday, October 16
The Serious Fun Arts Festival features arts activities ranging from concerts to live mural painting, a public art walking tour, and dancing in the streets. There will be sculpture, performance art, massive public art unveilings by renowned artists, fun family art-making and more throughout the downtown. READ MORE

Peace, Love & Pumpkins

Bethel
Friday, October 14-Sunday, October 30
View hand-carved jack-o'-lanterns and glowing pumpkin art as you walk the garden trails on the site of the Woodstock Festival. Exhibits include mermaids, dinosaurs, and Woodstock Festival icons. On Halloween weekend, shop the Night Fall Festival Market, featuring more than 50 craft and food vendors. READ MORE

Chappaqua Children's Book Festival

Chappaqua–FREE
Saturday, October 15
Meet children’s book authors and illustrators, and enjoy readings, signings, and assorted activities at the return of this annual festival. This year's festival is the largest yet, with 160 renowned children's book authors and illustrators participating. This year's theme is "A Walk Through the Woods." READ MORE

Beacon Sloop Club Pumpkin Festival

Beacon–FREE
Sunday, October 16
Dedicated to promoting environmental and social issues, the Beacon Sloop Club is hosting this festival offering kids' activities, a performance by the Rejuvenary River Circus, live music on two stages, and sails on the sloop Woody Guthrie. Pumpkin-themed cuisine is available for purchase. READ MORE

Celebrate Día de Muertos

Katonah–FREE
Sunday, October 16
Celebrate the Mexican holiday of Dia de Muertos with a FREE family concert at Caramoor, featuring mariachi music and traditional dance performed on three stages. Snacks and crafts are also included. Sellout alert! Reserve your spots ASAP. READ MORE

Heritage of West Nyack Fall Festival

West Nyack
Sunday, October 16
This annual event includes horse-drawn hayrides, a petting zoo, sheep shearing, pumpkin picking and decorating, storytelling, crafts, Colonial games, a pen-turning workshop, lace-making demos, musicians, raffles, and more. Revolutionary War military life is recreated through demos and exhibits. READ MORE

Arts Fest

Pelham and New Rochelle–some FREE
Thursday, October 20-Sunday, October 23
Celebrate the art and cultural community of New Rochelle and Pelham with live dance and music, studio tours, films, and exhibits. Scavenge for painted rocks (keep what you find!), join a class, decorate a cupcake. Hit the all-day music festival on Saturday in NewRo Park, including a car show. READ MORE

Addams Family Jr. Performance

Tarrytown
Thursdays, October 20 and 27
Check out a performance of "The Addams Family" presented by The Music Hall Academy and performed by 3rd to 12th graders.    READ MORE

Tompkins Corners Harvest Fest

Putnam Valley–FREE
Saturday, October 22
Packed into 4 hours, this fall festival features music, food, crafts, and vendors. Lou Del Bianco presents  "Monsters I Have Known," a fun show for kids, at 12:30pm. Browse the wares of assorted artisans, and pick up apples, pumpkins, and bounty from a local farm. READ MORE

Ragamuffin Halloween Parade

Chappaqua–FREE
Sunday, October 23
Enjoy inflatables, music, kids' activities, and a fun costume parade for Halloween.  READ MORE

Halloween Spooktacular at the Museum

Rye
Saturday, October 29
Swing by the Westchester Children's Museum for a fun-filled day of creepy-crawly crafts, science, stories, songs, and even a costume parade. Get dressed in your best costume, and join all the fun. READ MORE

Soukup Farms Harvest Festival

Dover Plains–FREE
Every weekend in October, plus Columbus Day
Hit the pumpkin patch, hitch a hayride, and visit the exotic animals of the Two-by-Two traveling animal exhibit (on select dates) at 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

Legoland's Brick-or-Treat Presents Monster Party

Goshen
Saturdays and Sundays throughout October
Legoland New York goes all-out for Halloween, with costume contests, dance parties, live entertainment, characters, and trick-or-treating. The event is included with the price of admission. READ MORE

The Great Jack-o'-Lantern Blaze

Croton-on-Hudson
Daily through October 31 plus additional dates in November
This renowned walk-through Halloween experience features more than 7,000 hand-carved, illuminated jack-o'-lanterns forming assorted impressive displays, with lighting and music enhancements. See the pumpkin carousel, windmill, and the New York City skyline. New for 2023, see an animated Ferris wheel and a jack-o'-lantern ode to circus sideshows. READ MORE

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