2022 Fall Guide

Get out your flannels and sweaters, fall is finally around the corner! Sherry Wiggs is your Local Guide for all things Fall 2022. Below you will find a list of festivals and events, apple orchards, pumpkin patches, food and farmer’s market suggestions, walking trails & more!

Festivals, Street Fairs & Events

  • Saturday September 10th at 2PM: JP Doyles Block Party Tarrytown, NY – Hang out and Enjoy the music for free, or join the VIP bash by purchasing tickets here.
  • September 10th & 11th: Hudson Valley Food & Wine Festival at the Dutchess County Fairgrounds; Rhinebeck, NY — Tickets required for this event. For schedule, event details and tickets, click here.
  • September 14th – 18th: White Plains Jazz Festival; White Plains, NY Some shows are free and some require the purchase of tickets. Full schedule and link to purchase tickets can be found here.
  • September 14th – 18th: San Gennaro Festival; Yorktown Heights, NY Hours, Event Schedule and details can be found here.
  • September 16th – 18th: Fall Crafts at Lyndhurst; Tarrytown, NY Tickets required. Fall Crafts at Lyndhurst is a massive market featuring local vendors, gourmet foods and craft shows. Details, hours and purchase of tickets available here.
  • Saturday September 17th from 11AM – 7PM: Sleepy Hollow Cultural Festival; Kingsland Point Park – Sleepy Hollow, NY – This is a free event featuring food, dances, crafts and a variety of children’s activities. Details can be found here.
  • Sunday September 18th from 9AM – 2PM: Armonk Cider & Donut Festival & Fall Carnival; Wampus Brook Park – Armonk, NY Click here for details.
  • September 23rd – October 2nd : Ardsley Fire Department Carnival; Pascone Park – Ardsley, NY —- Details here.
  • Saturday September 24th from 1PM – 5PM: Oktoberfest; Kingsland Point Park – Sleepy Hollow, NY Open to all ages. Details here.
  • Saturday September 24th from 11AM – 6PM: Hudson Valley Irish Festival on the Peekskill Riverfront; Peekskill, NY — A very popular event, multiple years running. Tickets and additional information can be found here
  • Saturday September 24th from 12PM – 11PM: Irvington’s Rocktoberfest: Mattheisen Park; Irvington, NY – Food trucks, music and fireworks. All ages welcome. Tickets available upon entry. For additional information, click here
  • Saturday October 1st from 10AM – 8PM: Ferry Festa at Dobbs Ferry Library; Dobbs Ferry, NY Storytelling begins at 1PM. Comedy Night 18 years+ starts at 5PM. See event schedule here.
  • Saturday October 1st from 12PM – 6PM: Croton Fall Festival; Vassallo Park – Croton-on-Hudson, NY Additional Details can be found here.
  • Saturday October 1st from 1PM – 9PM: Pleasantville Block Party; Pleasantville, NY Free admission. Car Show, Kids Fun Zone & More! Details and location here.
  • Saturday October 1st & Sunday October 2nd: Hudson Valley Garlic Festival; Saugerties, NY This massive festival hosts hundreds of local vendors. Tickets required. Event details, location, tickets and schedule can be found here.
  • Saturday October 8th from 10AM – 5PM: Sleepy Hollow Street Fair; Sleepy Hollow, NY For Updates and location, click here.
  • Saturday October 15th from 1PM – 4PM: Chappaqua Children’s Book Festival; Chappaqua NY — This is a free event and great for children of all ages. For details and location, click here.
  • Saturday October 22nd from 5PM – 11PM: Sleepy Hollow Block Party; Sleepy Hollow, NY — This is a free event. Additional event details and location can be found here.
  • Saturday October 29th from 5:30PM – 6:30PM: Tarrytown Halloween Parade; Tarrytown, NY For location and additional details, click here

Events for the kiddos…

There are Plenty of things to do with young children around the area during the fall months. Through October 30th, The Bronx Zoo is hosting a Dinosaur Safari featuring a new walk through experience where children can encounter over 52 life-sized dinosaurs (reservations required).

In addition, The Bronx Zoo’s Boo at the Zoo experience will be held Saturdays & Sundays from October 1 – 30 featuring costume parades, crafts and more. Special Dinosaurs in Darkness: The Hatching Nighttime walkthrough experience Fridays and Saturdays from October 7 – 29 from 7-11PM. These experiences are included with a General Admission ticket and the overlap makes it easy to plan a fun and eventful day for the kids. **Both Dinosaur exhibits Require Reservations**

Bear Mountain will be hosting its own Boo at the Zoo on Saturday October 29 from 10:30AM – 3PM at the Trailside Museum and Zoo location in Highland Falls.

For those of you that might be looking for something a little bit closer to home, The Greenburgh Nature Center‘s Family Movie Night is on September 16 and will be showing A Bug’s Life at 7:30PM

Greenburgh Nature Center will also be hosting “Run Wild” forest runs and obstacle courses for children ages 5 – 15 years in September and October as a well as a Fall Festival on October 22 & 23 from 10AM – 3PM. A full calendar of events for The Greenburgh Nature Center as well as details can be found here. The Center has a lovely playground and activity center for children of all ages on the grounds. 

If you’re looking for places to go during down time, the Rivertowns boast a wide variety of parks and playgrounds. A few local favorites include: Mattheisen Park in Irvington, Pierson Park in Tarrytown and Barnhart Park in Sleepy Hollow.

There are also a variety of nature centers and preserves in the area:

Apple & Pumpkin Picking

Local favorites include:

Historic Sites, Spooky Activities & Halloween Happenings

Visit the Old Dutch Church & Burial Grounds: Sleepy Hollow, NY

  • Hulda: The Other Legend of Sleepy Hollow Saturdays & Sundays from October 15 – October 30. Must buy Tickets in Advance. Limited Availability. For tickets and showings, click here.

Visit The Sleepy Hollow Cemetery (adjacent) for the wooden bridge, described in Washinton Irving’s The Legend of Sleepy Hollow.

Visit Historic Hudson Valley‘s Unique Sites. View Events & Buy Tickets here.

  • HHV’s “Great Jack O’Lantern Blaze” at Van Cortlandtmanor in Croton-on-Hudson, NY. For tickets and schedule, click here.
  • HHV’s “Irving’s Legend” at Washington Irving’s Sunnyside in Irvington, NY. September 30 – October 31. For tickets and schedule, click here.

Visit Irvington’s Infamous Octagon House The only fully domed Octagonal residence known in existence. Tours available throughout September and October. For scheduling and tickets, click here.

Visit Lyndhurst Mansion: Tarrytown, NY View Events & Buy Tickets here.

  • Lyndhurst After Dark Candlelight Mansion Tours October 21 – 23 & October 27- 30
  • Lyndhurst Spirited Mansion Weekends “At Your Pace” Viewings available Saturday & Sunday October 22 – 23, Saturday & Sunday October 29 – 30

Visit Tarrytown Music Hall: Tarrytown, NY: View Events & Buy Tickets here.

  • Ghost Tours of the Tarrytown Music Hall – October dates To be Announced. For Updates and Tickets, click here.

Ride the Sleepy Hollow Haunted Hayride: Sleepy Hollow’s annual event. October 21 & 22 only. Tickets available online here

Attend “The Legend”: A gravity-defying cirque theatre performance narrated by the hologram of Washington Irving, commemorating the 200-year anniversary of The Legend of Sleepy Hollow. Created and Performed by Westchester Circus Arts. Performances in September and October. Tickets and show times available here.

Harry Potter: A Forbidden Forrest Experience brought to you by Warner Brothers at FDR State Park in Yorktown Heights, NY. Dates Available October – December. For tickets and Information, Click here.

Looking for a Day Trip? Go to The Renaissance Faire in Tuxedo, New York — Saturdays & Sundays through October 9. For Events & Tickets, Click here

Walks & Sightseeing…

Local Favorites include:

Farmer’s Markets…

The Hudson Valley Region is rich in fertile soil with an abundance of agriculture. The Rivertowns offer some of the best Farmer’s Markets (literally – The TASH has been ranked nationally) and boasts offerings from fresh produce, meats and dairy, to sangrias, honey, small gifts and more!

See Below for Local Favorites:

  • The TASH; Patriot’s Park – Tarrytown, NY; Saturdays from 8:30AM – 1:30PM through 11/19
  • Irvington Farmer’s Market; Main St. – Irvington, NY; Sundays from 9AM – 1:30PM through mid-November.
  • Pleasantville Farmer’s Market; Memorial Plaza – Pleasantville, NY; Saturdays from 8:30AM – 1PM through 11/19
  • Chappaqua Farmer’s Market; Chappaqua Train Station, South Lot – Chappaqua, NY; Saturdays from 8:30AM – 1PM through December
  • Muscoot Farm Farmer’s Market; Muscoot Farm – Katonah, NY* Great to bring the kids to and walk around the farm/visit 50+ animals after! Sundays from 9:30AM – 2:30PM through 11/21. 

For Foodies & Drink Enthusiasts..

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