What to Do in Westchester This Fall

There are so many fun things to do this fall in Westchester. While many events have been cancelled due to COVID, there is still plenty to do in the area including the popular The Great Jack O’Lantern Blaze. Read on to check out some top picks to enjoy Westchster this fall.

Cool Things to Do in Westchester This Fall

The Great Jack O'Lantern Blaze
This is a view of the Great Jack O’Lantern Blaze at Van Cortlandt Manor in Croton-on-Hudson on October 12, 2015. (Photo by Tom Nycz)


  • Halloween enthusiasts know that Westchester is the place to be for spooky celebrations that run through November. Starting in September, The Great Jack O’Lantern Blaze fills Van Cortland Manor’s historic grounds with a magnificent display of more than 7,000 illuminated jack o’ lanterns. It’s the tri-state area’s biggest, most electrifying fall event.
  • Over 200 years ago, Washington Irving’s “The Legend of Sleepy Hollow” introduced the world to unforgettable characters like the Headless Horseman, Ichabod Crane and Katarina Van Tassel. These days, from October to November, the villages of Sleepy Hollow and Tarrytown brings the classic tale back to life with dramatic performances by master storytellers. Visitors can tour the 300-year-old Philipsburg Manor that transforms into a fearsome landscape, the Old Dutch Church from Irving’s tale and the Sleepy Hollow Cemetery, with famously historic graves, including Andrew Carnegie, William Rockefeller and Alexander Hamilton’s children, Eliza, Angelica and James.


  • Tune in to watch the pros during the 120th Annual U.S. Golf Open at Winged Foot Golf Club in Mamaroneck, now moved to September 17-20, 2020.
  • Farms of all kinds dot Westchester County, offering fall activities like apple picking, wagon rides and harvest fests. Many of the farms in Westchester are family-owned and operated, some dating back 300 years. Along the 17-mile trail that connects 13 farms and orchards, there’s no shortage of things to do.
  • And while there’s nothing like a brisk fall stroll, the County offers a next-level leaf peeping opportunity: a helicopter tour soaring over the Hudson Valley. This bird’s-eye view of Westchester County’s colorful foliage is made during a Wings Air helicopter ride.
  • In recent years, Westchester has emerged as a hub for craft beverage enthusiasts in New York state. Hot spots include River Outpost Brewing located in Peekskill, Wolf & Warrior in White Plains, Decadent Ales in Mamaroneck Sing Sing Kill in Ossining and Captain Lawrence Brewing Company in Elmsford.
  • Westchester County is also home to a cidery and a micro winery. South Salem Winery produces small batches of hand-crafted wine in the beautiful surroundings of the Gossett Bros. Nursery while Hardscrabble Cider on Half Moon Farm and Orchard epitomizes handcrafted, farm-to-bottle beverages with the dedication of a family-run business.


  • A former nun convent turned Westchester’s newest luxury hotel, The Abbey Inn & Spa is a boutique hotel featuring 42 distinctive guest rooms and suites, a full-service spa, and the Apropos farm-to-table restaurant delights with a Mediterranean-inspired menu that celebrates the bounty of the Hudson Valley. Located on historic Fort Hill, where Washington’s army set up a key lookout post in the Revolutionary War, the former 1902 convent of the Episcopal Sisters of Saint Mary’s has been beautifully repurposed as a secular retreat for today’s discerning travelers. Located just one hour from midtown Manhattan, The Abbey Inn feels a world away.

Check out more things to do in Westchester at Westchester County


Make the most out of your weekend!

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