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7 Exciting Free Family Events in September: An Ultimate Westchester Festival & Events Roundup

  • Writer: Jennifer Medley
    Jennifer Medley
  • Sep 11, 2024
  • 4 min read

As the summer days begin to dwindle and the crisp autumn air approaches, Westchester is gearing up for an array of captivating events to celebrate the vibrant month of September. This roundup highlights seven free family events you won't want to miss this September in Westchester, ranging from cultural festivals to environmental adventures, promising unforgettable experiences for both kids and adults alike.

Two women looking at an outdoor booth.
 

A large crowd of people along a street lined with vendor tents.
A view from Yonkers Riverfest. Photo from Yonkers Downtown BID.

Kicking off this list is the beloved Yonkers Riverfest, a celebration that takes over downtown Yonkers every year. With live music, delectable food vendors, and engaging activities for kids, this event is the largest one-day festival in Westchester and is a perfect way to soak up the last days of summer. The festival is on September 14th from 12:00-7:00pm, and encompasses a large swath of downtown Yonkers, including Getty Square, Larkin Plaza, Chicken Island and the Downtown/Waterfront areas. With a large list of vendors, performers, and activities, you and your kids will have a blast exploring all this festival has to offer!



A street at nighttime lined with vendors and people, with a sign hanging above that says "Sleepy Hollow Haunted Hayride and Block Party"
A view of a past Halloween block party. Photo from Historic Hudson River Towns.

Next up is the Sleepy Hollow Block Party, a festive gathering that pays homage to the history of this picturesque village, held on September 14th. Celebrating the Sleepy Hollow's 150th anniversary, families can enjoy lively entertainment, spooky surprises, and a variety of delicious treats while surrounded by the enchanting atmosphere that the village is famous for. The fun kicks off at 2:00pm in Patriot's Park for a parade featuring marching bands, fire trucks, and even special guests such as the Headless Horseman! The event then continues with vendors, live music, food eating contests, and children's activities until 10:00pm on Beekman Avenue. Items for a time capsule will also be collected at the party, and there will even be a fireworks display at 8:00pm. This festival isn't held annually, it's a very special event to celebrate the village's anniversary, so you do not want to miss this!



A line of children with a guide at the edge of a pond, facing away from the camera.
Children's programming at the Sheldrake Environmental Center. Photo from Sheldrake Environmental Center.

Embark on a nature-filled adventure at the End-of-Summer Family Fun Walk at Sheldrake Environmental Center, located in Larchmont. Led by knowledgeable experts, families will enjoy a leisurely stroll, learn about the changing seasons, and foster a deeper appreciation for the environment in a fun and engaging way. The walk runs from 10:00am-11:00am on September 14th, and the environmental center also features a playground and trails leading around Sheldrake Lake, which visitors are welcome to explore. Whether you want to sit back and observe the beautiful surroundings, or take a more active approach to sight seeing, this spot is a great choice for families looking to enjoy nature. Be sure to check out the center's other free programs too!



A carnival crowded with people, with red, white, and green decorations hanging above the crowd, and a red saint statue facing away from the camera.
The Yorktown San Gennaro Festival. Photo from TAPinto.net.

The Yorktown San Gennaro Feast brings a taste of Italian culture to Westchester, offering a delightful fusion of authentic cuisine, vibrant music, and traditional festivities. Parents and children can revel in the cheerful ambiance, indulge in mouthwatering dishes, and immerse themselves in the rich heritage of the San Gennaro celebration. The festival lasts five days, from Wednesday, September 18th through Sunday, September 22nd, and kicks off with a ceremonial procession of San Gennaro on September 18th at 6:00pm. The festival hours are 5:00-11:00pm Wednesday-Friday, 12:00-11:00pm on Saturday, and 12:00-10:00pm on Sunday. Activities include food vendors, carnival games, and amusement rides, all taking place at 1826 Commerce Street.




Three children facing away from the camera wearing pink butterfly wings and huddled around an activity booth.
Children attending the Mamaroneck Monarch Butterfly Festival. Photo from Eventbrite.

Witness the magic of nature at the Third Annual Mamaroneck Monarch Butterfly Festival, where families can marvel at the graceful fluttering of these beautiful insects. Engage in educational activities from a variety of vendors, explore butterfly habitats, and learn about the importance of conservation in a fun and interactive setting that will captivate children of all ages. The festival will be held on September 21st from 10:00am-1:00pm at Harbor Island Park, with a rain date scheduled for the next day. Each child will receive a passport to track their ‘migration’ at the festival on a mini obstacle course, making for both an educational and entertaining afternoon! Costumes are also encouraged of your child's favorite pollinator (butterflies, bees, beetles, wasps, bats, hummingbirds), with a contest being held for the best costume.



A small white barn in a flower garden.
The grounds of Muscoot Farm. Photo from The Friends of Muscoot Farm.

Add a touch of whimsy to your day with Muscoot Farm's Fairy Walk in Katonah, a magical event that's sure to enchant your family. Children will delight in this fun experience where they'll take a walk around the trails of Muscoot Farm, discovering tiny fairy dwellings along the way. Costumes are encouraged and there's even a fun fairy-themed craft! This whimsical annual event takes place on September 24th, and visitors can come any time between 12:00pm and 3:00pm. The grounds also feature a barnyard with a variety of animals and a farm museum on property too, making this a great event for families with both fairy and farm lovers.



Children sitting in a circle around an adult reading a story to them.
Children attending a storytime at the Chappaqua Children's Book Festival. Photo from the New York Times.

For book-loving families, the Chappaqua Children's Book Festival is a literary haven that brings together authors, illustrators, and young readers in a joyous celebration of storytelling. Dive into a world of imagination, attend interactive workshops, and discover new literary treasures that will ignite a lifelong love for reading in children. The festival is on September 28th from 10:00am-4:00pm at the Chappaqua train station and will feature storytimes, author talks, illustration demos, and a family fun zone! 160 authors will be in attendance, including Laura Numeroff (the “If You Give a Mouse a Cookie” series), 2024 Caldecott Medal winner Vashti Harrison, Victoria Kann (Pinkalicious), and Dan Gutman (the My Weird School series). Be sure to check their website for a full list of authors and their works to see if your child's favorite author will be there!


Don't miss out on these captivating events that promise to create lasting memories for your family this September in Westchester. From cultural celebrations to nature-inspired adventures, there's something for everyone to enjoy this month, and the best part is that they're all free! If you've got the time, I definitely recommend checking out each and every one of these events.



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