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Halloween, Food Festivals, Apple-Picking, and More: Fall in Love With Westchester County

(Photo courtesy Westchester County Tourism)

Just 30 miles north of New York City and across the river from New Jersey, Westchester County is the perfect option for regional travelers looking for an easy daytrip or exciting weekend away.

Bordered by the Hudson River on the west and by Long Island Sound to the east, Westchester County spans across 500 square miles of New York state and is a perfect place for families, couples, and solo travelers eager to enjoy the crisp fall weather and celebrate the Autumn season.  

Fall Activities and Events:  

  • Halloween: Halloween enthusiasts know that Westchester is the place to be for spooky celebrations. From September 17 through November 21, The Great Jack O’Lantern Blaze will fill Van Cortland Manor’s historic grounds with a magnificent display of more than 7,000 illuminated jack o’ lanterns. Tickets are on sale now.  
  • History: More than 200 years ago, Washington Irving’s “The Legend of Sleepy Hollow” introduced the world to characters like the Headless Horseman and Ichabod Crane. These days, the village of Sleepy Hollow welcomes visitors to check out the Old Dutch Church from Irving’s tale and the Sleepy Hollow Cemetery, with famously historic graves, including Washington Irving, himself. Additionally, anyone who visits Irving’s historic home, Sunnyside, will have the chance to see “Irving’s Legend,” a dramatic outdoor performance by master storyteller, Jonathan Kruk. Complete with live music by Jim Keyes and an appearance from the Headless Horseman, this performance is sure to thrill audiences of all ages all October long.
  • Leaf Peeping: For next-level leaf peeping, Mianus River Gorge Preserve in Bedford, is a trail that looms 40 feet above the Mianus River. Despite the exhilarating view, the hike is easy and perfect for the whole family. And at Croton Gorge Park in Cortlandt, an easy two-mile hike includes gorgeous vistas of the New Croton Dam and its autumnal color palette. Additionally, the County offers a one-of-a-kind leaf peeping opportunity with Wings Air. Guests can score above the Hudson Valley for a bird’s-eye view of Westchester County’s colorful foliage.
  • Orchards and Farms: Farms of all kinds are located in Westchester County, offering fall activities like apple picking and wagon rides. Many of the farms in Westchester are family-owned and operated, some dating back 300 years. These farms include Harvest Moon Farm and Orchard (North Salem), Stuart’s Fruit Farm (Granite Springs), and Wilkens Fruit & Fir Farm (Yorktown Heights).
  • Eat: Westchester Magazine’s Wine and Food Festival is back this year, September 21-25, with plans for an epic week celebrating the region’s finest foods, spirits, and of course, wine. But Westchester is no novice to incredible culinary options. Since 2020, Westchester has been included in the New York City Michelin Guide, and in 2021, six newcomers to the Westchester restaurant scene made MICHELIN Guide’s Bib Gourmand list.
  • Drink: Hoppfest returns this year, September 25, with plans to be bigger, better, and beerier than ever before. Bedford Historical Society’s take on Oktoberfest will have a variety of brews, wine, food trucks, live music, games and more. For those looking for a beer alternative, Cortlandt’s the Pore the Core Cider Festival will also take place on September 25. For those who like to bike with their brew, Captain Lawrence Brewing Company (Elmsford), has partnered with Gotham Bike Tours to offer fall foliage bike tours with a final stop at the brewery for drinks and food.
  • Nature: Westchester is home to some of New York’s most beautiful gardens and nature preserves, including the picturesque Untermyer Gardens in Yonkers and Teatown Lake Reserve in Ossining. On October 23 and 24, Scarsdale’s Greenburgh Nature Center is hosting a Fall Festival, complete with activities like a pumpkin and scarecrow walk and apple-cider demonstrations, and is also introducing a new event, Run Wild, with a forest run and obstacle courses for kid’s 5-15.
  • Art: Westchester County has a variety of fascinating museums, galleries and historical sites, as well as unique cultural events on the docket, which include: In October, the Katonah Museum of Art will unveil its “Arrivals” exhibit, showing famous civilization origin stories with some 50 works spanning the 16th century to present; October 8-24, the White Plains Performing Arts Center is hosting “Masquerade!” a musical portrayal of Broadway composer, Andrew Lloyd Webber’s remarkable life and celebrated work; this fall, the Caramoor Center for Music and the Arts will have 10 indoor concerts, four afternoon tea parties, and on October 24, families are invited to attend a free Día de Muertos celebration with traditional Mexican dances and songs; on October 15, the Irvington Theater will screen another film under the stars at the Main Street School as part of their Sunset Cinema series.

Calling all music fans! Huge performers, like Billy Idol, Sheryl Crow, and The Beach Boys, will be performing at The Capital Theatre this fall.

Where to Stay:

  • Peekskill’s The Abbey Inn, named #3 on USA Today’s 10 Best New Hotels in the U.S. list, is offering a Leaf Peepers Package for travelers taking advantage of the fall season, and includes complimentary cider, caramel apples to enjoy while relaxing on a sunset porch or by the fire pits.
  • Formerly the Ritz-Carlton Westchester, The Opus Westchester is the region’s newest contemporary lifestyle hotel with reimagined luxury suites and superior dining.
  • For travelers planning to explore the historic villages of Sleepy Hollow and Tarrytown, the newly opened Sleepy Hollow Hotel and Conference Center is an ideal location and includes an on-site restaurant and café, Bistro Z, with locally sourced ingredients.

About Westchester County Tourism & Film Westchester County Tourism & Film is Westchester County’s official destination marketing organization. Its mission is to generate economic benefits by enhancing the image and promoting Westchester County as a premier business and leisure destination in the Hudson Valley region. Flanked by Long Island Sound and the Hudson River, Westchester is made up of big cities, small towns, villages, farms, and miles of natural beauty. The county is easily accessible by major interstate highways and parkways, its own regional airport, Amtrak and three commuter rail lines and is home to more than 40 hotels and conference centers. For information about visiting Westchester, visit or call 1-800-833-9282.

About the Author

New York Trend is a weekly news publication that focuses on issues and lifestyles of the African & Caribbean American communities throughout the New York metropolitan area and Nassau and Suffolk Counties of Long Island. It is a respected and well recognized news publication that has been in existence since 1989. Owner, Publisher and Executive Director, Dr. Teresa Taylor Williams has been at the helm of this award-winning publication since its inception. New York Trend continues to be the only black woman-owned, metropolitan newspaper in New York and Long island. New York Trend is the largest black-owned newspaper throughout Nassau and Suffolk counties.

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