Fall Guide to Westchester County New York

As the crisp air of autumn rolls into New York’s Hudson Valley, Westchester County transforms into a landscape of vibrant foliage, bustling harvest festivals, and cultural events. Spanning 500 scenic square miles between the Hudson River and Long Island Sound, Westchester offers a rich blend of natural beauty, history, and seasonal charm. Just a short trip from New York City, it’s the perfect escape for those seeking to savor the sights, flavors, and festivities of fall. On behalf of HotelsEscape.com, here’s your guide to experiencing Westchester in all its autumn glory.

REV Fest 250 and Historic Celebrations

Fall 2025 kicks off with REV FEST 250 (Sept. 27–28, Croton Point Park), a lively tribute to Westchester’s role in the American Revolution. Visitors can enjoy live reenactments, family activities, and educational programming—all part of a lead-up to America’s 250th anniversary in 2026.

Halloween Highlights in Sleepy Hollow Country

Known worldwide as the home of The Legend of Sleepy Hollow, Westchester offers some of the most memorable Halloween experiences in the country.

• The Great Jack O’Lantern Blaze (Sept. 12–Nov. 16) transforms Van Cortlandt Manor into a dazzling display of 7,000+ hand-carved pumpkins. This year adds new features like a Pumpkin Promenade and Headless Horseman Hideaway.
• Irving’s Legend at Sunnyside offers an atmospheric, under-the-stars retelling of Washington Irving’s classic tale.
• Lyndhurst Mansion hosts its Fall Craft Show, Gothic Harvest Market, and the candlelit Lyndhurst After Dark tours.
• Philipsburg Manor’s Twilight Village and The Headless Horseman Files bring immersive storytelling to Sleepy Hollow.
• SUP Witches Paddle (Oct. 12) sees costumed paddleboarders take to the Hudson River for a whimsical on-the-water celebration.

Leaf Peeping and Outdoor Adventures

Westchester’s parks and nature preserves offer spectacular fall foliage. Favorites include Ward Pound Ridge Reservation, Teatown Lake Reservation, and Croton Gorge Park. For a truly unique view, book the Wings Air Fall Foliage Helicopter Tour to soar above the Hudson Valley’s colorful canopy.

Fall is also the season for apple picking and farm fun at spots like Harvest Moon Farm and Orchard and Stuart’s Fruit Farm, or even an alpaca meet-and-greet at Faraway Farm.

Seasonal Events & Festivals

The county’s calendar is packed with fall happenings:

• JazzFest White Plains (Sept. 10–14) brings GRAMMY-winning talent to the city’s venues.
• Yorktown Grange Fair (Sept. 5–7) celebrates over 100 years of agricultural tradition.
• Rocky’s 5K (Oct. 4) offers runners a scenic course through Rockefeller State Park Preserve.
• Bicycle Sundays give cyclists and skaters exclusive use of the Bronx River Parkway.

Arts, Culture & History

From world-class performances at the Emelin Theatre to contemporary exhibits at the Hudson River Museum and Katonah Museum of Art, Westchester’s cultural scene thrives in autumn. Historical treasures like the Sherwood House Museum provide a glimpse into the county’s colonial past.

Where to Dine This Fall

Food lovers can explore the Westchester Craft Beverage Trail, indulge in fall menus at Horsefeathers in Tarrytown, or plan their trip around Hudson Valley Restaurant Week (Oct. 27–Nov. 9). New culinary highlights include La Bastide in North Salem and Antique Garage in Rye.

Fall Stays and Getaways

Whether you’re looking for luxury or historic charm, Westchester’s accommodations shine in autumn:

• The Kittle House Inn – Historic elegance with refined hospitality.
• Windrose on Hudson – Scenic acreage and seasonal packages.
• Tarrytown House Estate – Gilded Age splendor with modern comforts.
• The Abbey Inn & Spa – Riverfront relaxation with farm-to-table dining and cruise packages.

Your Autumn Escape Awaits

From pumpkin-lit nights in Sleepy Hollow to sun-dappled trails in its nature preserves, Westchester County offers a fall season filled with color, flavor, and unforgettable moments. Whether you’re coming for a weekend or an extended getaway, there’s no shortage of ways to celebrate autumn here.

Book your fall escape to Westchester now and experience one of New York’s most vibrant seasonal destinations.