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15 FREE (oh yeah!) Fall Activities for Kids in Sleepy Hollow, NY and Nearby

By September 14, 2017 January 15th, 2020 No Comments

We know, we know, it’s a little sad that summer’s over. However, the good news is, we live in one the most fall-friendly places around (who does Halloween like Sleepy Hollow?). Nothing eases the back-to-school transition like taking advantage of all of the family fun the area has to offer. As a Sleepy Hollow orthodontist, Dr. Kothari gets the scoop from his patients on the local happenings and we’re more than happy to share. The best part? Everything on this list is free. Here’s the 914 Orthodontics guide to wallet-friendly Tarrytown and Sleepy Hollow activities for kids as well as some from the surrounding Rivertowns.

1. TaSH Farmers Market (Tarrytown and Sleepy Hollow Farmers Market) – Patriots Park, Border of Sleepy Hollow and Tarrytown

This vibrant farmers market was voted “Best of Westchester” for 2017 and we’re not surprised. It’s held every Saturday, Memorial Day through Thanksgiving, from 8:30am to 2pm in Patriots Park. This definitely makes the list of our top Sleepy Hollow and Tarrytown kids’ activities because of the host of children’s programs at the market, including the Macaroni Kids craft table, yoga classes, nature expeditions, storytimes and an experiential taste, see and discover booth. Plus, with music and over 30 vendors selling fresh fruits and vegetables, baked goods, cheeses, meats, poultry and more, it’s just as much a destination for grownups.

2. Harvest Hayride – Matthiessen Park, 1 Bridge Street, Irvington

There are a number of fall activities for kids in Irvington but the Harvest Hayride isn’t to be missed. On Saturday, October 21, from 6 to 8:30pm, spend the evening with family and friends at Matthiessen Park. Jake’s Rockin’ Country Band will play live tunes and the haunted hayride will run from 7 to 8:30pm. The event is sponsored by the FACE (Fundraising and Community Events) Committee.

3. Fall Family Flamenco Workshop Series – Warner Library, 121 North Broadway, Tarrytown

Thanks to an Arts Alive grant funded from ArtsWestchester, Sleepy Hollow and Tarrytown residents can enjoy free fun during Hispanic Heritage Month. Dive into Dance with Rebeca Tomás, an interactive flamenco workshop for the whole family will be held on Mondays, September 18, September 25 and October 2 at 6:30pm on the third floor of the library.

4. Self-Guided Sleepy Hollow Cemetery Tour – Sleepy Hollow Cemetery, 540 North Broadway, Sleepy Hollow

Get in the Halloween spirit with a visit to the Sleepy Hollow Cemetery. It’s on the National Register of Historic Places and it’s home to the grave of legendary Washington Irving as well as some other famous figures. While there are spookier nighttime tours for a fee, they’re probably better for teens and adults. A daytime visit works for all ages and there’s no admission during regular hours. Download a free map and head to the cemetery to explore and soak up the beautiful fall weather. You can also meander into the adjacent grounds and cemetery of the Old Dutch Church.

5. Play at the Riverfront Green Park Playground Riverfront Green Park, Peekskill

This Peekskill playground is sprawling with slides galore and climbing features. It’s one of the best around and you can’t beat the view. Make a day out of it by packing a picnic and taking a walk along the scenic walkway before catching a sunset.

6. Scarecrow Making – Patriots Park, Tarrytown

On Saturday, October 14 (rain date on Sunday, October 15) at 10:30am, bring old clothes and head to Patriots Park. The Tarrytown Recreation Department will be providing straw and frames for attendees to create their own scarecrows.

7. Moon Watch Over Hastings – Draper Park, Hastings-on-Hudson

This free family event in Hastings-on-Hudson is co-sponsored by the Hastings Historical Society and the village Arts Commission. On Saturday, October 28, from 6:30 to 9pm (weather permitting), people of all ages can marvel at the night sky during a moon- and star-gazing gathering.

8. Annual Sleepy Hollow Street Fair – Beekman Avenue, Sleepy Hollow

The 21st Annual Sleepy Hollow Street Fair will be held on Saturday, October 14 from 10am to 5pm, rain or shine. Let the kids loose in the kids’ carnival and then stroll through the fair checking out vendors and sampling food from local restaurants.

9. Admire the Fall Foliage – Various Places

If you’re looking for free activities for kids in Dobbs Ferry, Tarrytown, Sleepy Hollow, Ossining or anywhere in the Hudson Valley, then look no further than your local park because the shores of the Hudson River are prime leaf peeping territory. The brilliant but fleeting fall colors tend to reach their peak somewhere between early October and early November, though it varies every year. You can stay on top of the timeline with the New York Fall Foliage Report. Some of the best spots for this natural spectacle include Old Croton Aqueduct State Historic Park (15 Walnut Street, Dobbs Ferry), Kingsland Point Park (Palmer Avenue, Sleepy Hollow) and the Teatown Lake Reservation (1600 Spring Valley Road, Ossining).

10. Tarrytown Halloween Parade and Block Party – Starts in Patriots Park, Tarrytown

On Saturday, October 28, put on your best Halloween costume and watch the floats and bands as they travel from Patriots Park starting at 5:30pm, head down Broadway and finish up on Main Street.. The Halloween extravaganza was voted “Best of Westchester” three years running. After the parade, stay for the block party on Main Street for food, a DJ and live performances. A rain date is scheduled for Sunday, October 29.

11. Storytime at the Library – Warner Library, 121 North Broadway, Tarrytown

Storytimes at the Warner Library are always one of our favorite free activities for kids in Tarrytown and Sleepy Hollow because they encourage a love of reading and learning. The fall storytime session will run through December 15. Here’s what’s on the schedule:

  • Stories & More (ages four through 7) – Mondays at 4pm
  • Bouncing Babies (babies who aren’t walking yet) – Tuesdays at 11:15am
  • Tales for Tots (all ages) – Tuesdays at 3:30pm
  • It’s Toddlerific! (walkers ages one through three) – Wednesdays at 10:15 and 11:15am
  • Cuentos y Canciones (all ages) – Fridays at 10:30am
  • Teddy Bear Storytime (all ages) – One Thursday a month at 7pm
  • Saturday Stories (all ages) – Two Saturdays a month at 11:30am

12. Take a Hike

Hiking is another excellent Westchester activity for kids and teens. They’ll get fresh air and exercise while trekking through the beautiful scenery of the Hudson Valley. For the older crowd, the three-hour, six-mile loop to the top of Anthony’s Nose in Peekskill has a view that makes it totally worth it. For young kids, Mommy Poppins has some great ideas for easier hikes in the area.

13. Enjoy a History Lesson – The Hastings Historical Society, 407 Broadway, Hastings-on-Hudson

On the first Saturday of the month, September through June, from 2 to 4pm, the Hastings Historical Society holds an open house at its location in the former Draper Observatory in Draper Park. The public is invited to stop in to see their current exhibit and learn about the history of Hastings-on-Hudson. It’s perfect for future historians!

14. Dobbs Ferry Festa – Cedar and Main Streets, Dobbs Ferry

On Saturday, October 14, from 1 to 8pm, attend the largest Dobbs Ferry family event of the year. The annual street fair, to be held rain or shine, will feature vendors, food, music, entertainment, music and crafts.

15. Friends of the Old Croton Aqueduct ‘s Walks & Tours & More – Various Locations in Ossining, Sleepy Hollow and Tarrytown

The Friends of the Old Croton Aqueduct hold guided walking tours throughout the fall that are free and open to the public. The tours are educational and make for fun fall activities for kids in Ossining, Tarrytown and Sleepy Hollow as long as they’re old enough for a longer walk. On Saturday, October 7 at 10am, attendees will meet at the Joseph Caputo Community Center (95 Broadway, Ossining) for the “Weir Tour.” You’ll watch a short film about the Aqueduct before walking to the Double Arch Bridge and into the original 1842 brick water tunnel to learn about its history. On Sunday, October 29 at 10am, the program will meet at the Riverwalk in Tarrytown (western-most end of Van Wart Avenue) for “Ramble Along the Riverwalk and Aqueduct Trails Past the Estates of Gilded Age Millionaires.” This five-mile loop is more appropriate for families with older kids and teenagers. The series finishes on Saturday, November 4 with “Retracing the Capture of Revolutionary War British Spy Major Andre.” Attendees will meet at the northeast-most parking lot at Sleepy Hollow High School (210 North Broadway) at 10am to retrace the steps of the capture of Major John Andre, a Revolutionary War spy. The four-mile, two-hour walk will include a short visit to the Historical Society of Sleepy Hollow and Tarrytown’s museum to look at artifacts related to the event.

Dr. Kothari

Author Dr. Kothari

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