The pie eating contest is just the start of the fun at the Armonk Cider and Donut Festival. Photo courtesy of the festival
Best Harvest Festivals & Pumpkin Festivals in Westchester and the Hudson Valley for Fall Fun in 2025
Book your tickets now if you want to see the annual spectacle that is The Great Jack O'Lantern Blaze at Van Cortlandt Manor. Photo by the author
21 Best Things To Do in Westchester and the Hudson Valley with Kids September 2025, According to Mommy Poppins Editors
The Great Jack-o'-Lantern Blaze in Van Cortlandt Manor is a must-do Halloween event in the tri-state area. Photo courtesy of the Historic Hudson Valley
Best Halloween Events in Westchester and the Hudson Valley 2025 for Kids and Families
Outhouse Orchards Corn Maze. Photo by Matt Nighswander
GUIDE
Westchester & Hudson Valley Kids Fall Guide: Best Things to Do in 2025
Pick from a number of apple varieties at Hudson Valley orchards. Photo by Leslie Seaton via Flickr
Apple Picking in the Hudson Valley: Best Apple Farms and Apple Festivals
Apple picking is one of the family-friendly fall activities you can enjoy in the Hudson Valley with Kids. Photo courtesy of the author
Your 2-Day Itinerary for a Kid-Approved Fall Weekend in the Hudson Valley
Woodstock is the perfect fall getaway and just a two-hour drive away. Photo by Diana Kim
30 Fall Day Trips from NYC for Families
Get ready for back to school with all the right supplies, classes, and tips.
GUIDE
Back-to-School Guide 2025-2026
Enjoy glorious views on the Walkway Over the Hudson. Photo by Fred Schaeffer/courtesy of the Walkway.
50 Best Things To Do in the Hudson Valley with Kids
A visit to the United States Military Academy is a lesson in history and patriotism, but also tons of fun for families.
Visiting West Point with Kids: 37 Top Things To Do near the United States Military Academy
Kids can run, swing, slide, and even make music at Sally’s Dream Playground in Montgomery. Photo by Katherine Dhurandhar
Top Playgrounds in Westchester and the Hudson Valley Worth Driving To
The Saugerties Lighthouse is a stunning getaway no matter the season.
Sleep in a Lighthouse and More Hudson Valley Family Resorts and Hotels
Summer camps are a great way to make new friends and develop new skills
GUIDE
Summer Camps Guide for Westchester & Hudson Valley Kids
The Play Place in Elmsford is one of Westchester's top indoor play spaces.
Top Indoor Playgrounds and Play Spaces in Westchester
Roam the the cedar walk and gardens at Caramoor for a free, fun outing. Photo by Gabe Palacio
41 Free Things To Do in Westchester with Kids
Enjoy water sports at Westchester Summer Day in Mamaroneck. Photo courtesy of the camp
Best Summer Camps in Westchester for Kids
Palisade Center's Climbzone features themed rock walls as high as 40 feet. Photo courtesy of Climbzone.
20 Best Things To Do at the Palisades Center Mall with Kids
The Ausable Chasm has been described as the Grand Canyon of the Adirondacks and it's one of our top 100 things to do in New York State with kids. Photo by Anna Fader
Ultimate New York Bucket List: 100 Things To Do with Kids in NY State
Poughkeepsie's Gravity Vault is an indoor rock-climbing gym with classes for kids as young as 5. Photo by Kaylynn Ebner
Best Kids' Indoor Playgrounds and Play Spaces in the Hudson Valley
Mount Kisco's Grand Prix New York, a go-kart hot spot, offers birthday parties with racing, arcade play, and virtual reality.
17 Best Indoor Party Places for Kids in Westchester
GUIDE
Guide to Indoor Fun for Westchester & Hudson Valley Kids
Kids explore the great outdoors Hudson Highlands Nature Center. Photo courtesy of the center
School Break Camps in Westchester and the Hudson Valley: Winter and Spring Break Camps
At Moe's Southwestern Grill, kids eat free on Tuesdays with the purchase of an adult entree. Photo courtesy of the restaurant
Restaurants Where Kids Eat Free in Westchester and the Hudson Valley
Kids under 1 are FREE hours at the Westchester Children’s Museum. Photo courtesy of the museum
GUIDE
Guide to Free Fun Things to Do with Westchester Kids
Kids can peek into the marine life in the aquariums at the Marine Education Center in Mamaroneck. Photo by Susan Miele
19 Free Things To Do Indoors in Westchester and the Hudson Valley: Indoor Places to Play
Castle Fun Center in Chester has a giant inflatable park, a rock wall, laser tag, and more. Photo by Katherine Dhurandhar
15 Family Fun Centers in Westchester and the Hudson Valley
Grab a colorful treat at Harley's Sweet Shop in Woodstock. Photo courtesy of the shop
25 Best Things To Do in Woodstock, NY, with Kids
Kids can climb the walls at the Cliffs in Valhalla. Photo courtesy of the Cliffs
32 Things To Do on a Rainy Day Indoors in Westchester and the Hudson Valley
Touch the soft rabbits at the Greenburgh Nature Center's petting zoo in Scarsdale. Photo courtesy of the center
Best Animal Petting Zoos near Westchester and the Hudson Valley Where Kids Can Meet Animals
Peekskill, NY, is a lovely riverfront community that acts an the unofficial gateway to the Hudson Valley.
25 Best Things To Do in Peekskill, NY, with Kids
Explore what makes things fly with the Westchester Children's Museum's Wind Tunnel Design Challenge. Photo courtesy of the museum
Visiting the Westchester Children's Museum in Rye: New and Ongoing Exhibits
Romp through the woods in the beautiful Catskills. Photo by Deborah Dadlani
40 Best Things To Do in the Catskills with Kids
GUIDE
Classes Guide for Westchester & Hudson Valley Kids
Tig & Peach offers drop-in, no reservations required, open play 7 days a week.
7 Indoor Playgrounds in Westchester and the Hudson Valley for a Wild Romp
Friends young and old enjoy the attractions and Legoland New York, the first major theme park in the Northeast in 40 years.
  VIDEO
Legoland New York: A Guide to Visiting the Hudson Valley Theme Park with Kids
Frost Valley YMCA offers a variety of day and overnight camps for kids ages 5-14. Photo courtesy Frost Valley YMCA
Affordable Summer Camps in Westchester and the Hudson Valley
These boredom-busting activities turn a stuck-at-home day into a lasting memory.
75 Indoor Activities for Kids on a Rainy Day
Kids love a birthday party filled with games and pizza at Chuck E. Cheese. Photo courtesy of Chuck E. Cheese
Best Fun Restaurants for Kids' Birthdays in Westchester
Head to the Mid-Hudson Discovery Museum from 5-8 pm on the third Saturday of the month to explore the museum for free, Photo by the author
Free Museums and Museum Days in Westchester and the Hudson Valley
Creating a baking soda volcano is a classic science experiment for kids. Photo by Sara Marentette Nighswander
67 Easy Science Experiments for Kids To Do at Home
Kids can while away hours of a day with a set of watercolors and a stack of new paper for painting. Photo by Sara Marentette
Crafts for Kids: 100 Awesome Art Projects
These kids' movies are classic hits!
75 Best Movies for Kids: Top Family Movie Night Ideas
GUIDE
Guide to Playgrounds & Parks in Westchester & the Hudson Valley
Suncatcher_Liz Baill @creativishmom
GUIDE
Crafts for Kids Guide: Thousands of Craft Ideas

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

Enjoy author meet-and-greets plus a family-fun zone and hand-on activities at the Chappaqua Children's Book Festival this Saturday. Photo courtesy of the event
Enjoy author meet-and-greets plus a family-fun zone and hand-on activities at the Chappaqua Children's Book Festival this Saturday. Photo courtesy of the event
9/19/25 - By Katherine Dhurandhar

Looking for the best things to do in Westchester and the Hudson Valley this weekend? Here are our editors' picks for the best family-friendly events and activities!

Kids can get up close with dozens of dalmatians at the FASNY Museum of Firefighting's free Dalmatian Day in Hudson, which also includes games, prizes, and access to the museum. Alternatively, they can meet the authors and illustrators of their favorite books and enjoy the family fun zone at the annual Chappaqua Children's Book Festival.

Or, head to the Catskills for the opening weekend of Hunter Mountain Oktoberfest, which also includes kids' activities and scenic skyrides.

Those are just a few of our top picks for this weekend; read on for all the best things to do this weekend with kids in Westchester and the Hudson Valley. 

More Things To Do in Westchester and the Hudson Valley:

OUR LATEST VIDEOS

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

Watershed Literary Festival

Rye
Friday, September 26 - Sunday, September 28
The Watershed Literary Festival, held at the Rye Meeting House, brings together readers and writers to explore ideas, spark imagination, and celebrate the creative accomplishments of writers from Rye, the Hudson River Valley, and the Greater New York region. READ MORE

Myths & Mysteries of The Octagon House: Halloween Season Tour

Irvington
Opens Friday, September 26
Journey back through the history of Irvington's Octagon House to unravel the myths that have developed around the mysterious and unexplained events of the past. Visitors will learn about the unusual lives of the residents who walked the house's halls, its architectural connections to 19th-century spiritualism, and the uncanny experiences people have had inside its walls.  READ MORE

REV FEST 250 at Croton Point Park

Croton-on-Hudson – FREE
Saturday, September 27
Get ready for REV FEST 250—a high-energy, two-day commemoration where history meets modern-day fun! Taking place in scenic Croton Point Park, this immersive festival brings the past to life with live music, nonstop entertainment, craft beverages, and mouthwatering bites from local food vendors. READ MORE

Chappaqua Children's Book Festival

Chappaqua – FREE
Saturday, September 27
The annual Chappaqua Children's Book Festival is always a spectacular day in Westchester. There is real magic in meeting the people behind the stories your family loves and learns from. Meet authors and illustrators, enjoy live storytimes with authors, learn from author talks, and have a ton of fun at the Family Fun Zone! READ MORE

Dalmatian Day at FASNY Museum of Firefighting

Hudson – FREE
Saturday, September 27
Dalmatian Day is a family-friendly extravaganza that includes a meet-and-greet with live dalmatians, games and prizes for kids, dalmatian-themed crafts, an exciting hose racing team demo by Owego Hose Teams, and a special appearance by Smokey Bear. READ MORE

Sleepy Hollow Oktoberfest

Sleepy Hollow – FREE
Saturday, September 27
Feast on German food and beer from local eateries and dance to live Bavarian music at Sleepy Hollow’s annual Oktoberfest in beautiful Kingsland Point Park. There will be children’s activities at the Kathryn Davis River Walk Center.  READ MORE

Croton Oktoberfest

Croton-on-Hudson – FREE
Saturday, September 27
Croton-on-Hudson's Oktoberfest will feature live music all day and over 60 amazing food, craft beer, and local retail vendors, plus a kinder-fest for the little ones, with music, food, and fun activities to keep them entertained! READ MORE

Rock n' Roll Playhouse Presents Music of Chappell Roan for Kids at Garcia's

Portchester
Saturday, September 27
The Rock and Roll Playhouse presents a Pink Pony Party celebrating the music of Chappell Roan and more at the Capitol Theatre in Port Chester. The band offers games, movement, stories, and an opportunity to rock out. READ MORE

Armonk Outdoor Art Show

Armonk
Saturday & Sunday, September 27-28
The Armonk Outdoor Art Show has repeatedly been ranked among the country's top fine art and design art shows. Families can enjoy a wide range of activities beyond exploring the works of art, including kids' attractions and food trucks. READ MORE

Hudson Valley Garlic Festival in Saugerties

Saugerties
Saturday & Sunday, September 27-28
The annual two-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

Hunter Mountain Oktoberfest

Hunter
Opening weekend Saturday & Sunday, September 27-28
Grab your lederhosen and head to the Catskills for this Oktoberfest at Hunter Mountain. Enjoy Scenic SkyRides with sweeping autumn views, shop crafts and delicious food from local vendors, dance to live music, and take part in family-friendly fun for three beautiful weekends. READ MORE

Congers Fall Festival

Congers
Sunday, September 28
The annual Congers Fall Festival features local craft vendors, live music, food vendors, and tons of kids' activities, including pumpkin painting, birdhouse painting, face painting, henna tattoos, and an interactive display by Bach to Rock Music. READ MORE

Port Jervis Fall Foliage Festival

Port Jervis
Sunday, September 28
Get ready for family fun at this annual street fair in downtown Port Jervis, with more than 100 vendors, live entertainment, a petting zoo, and more. READ MORE

Fairy Houses and Gnome Homes

Teatown
Sunday, September 28
Flutter into an enchanted world full of wonder and fun at Teatown Lake Reservation. Learn what living things need to survive – even mythical creatures! Hear a story about fairies, then create a fairy or gnome home in the woods from natural materials. READ MORE

Places featured in this article:

About the Author

Katherine Dhurandhar
Katherine Dhurandhar is a Community Publisher for Mommy Poppins, representing the Westchester and Hudson Valley region of New York, and a freelance copyeditor for Westchester Publishing Company. In her free time, she enjoys hiking, camping, and traveling with her husband and son.
Recent Articles By Katherine Dhurandhar:
Read more articles by Katherine Dhurandhar.