Fall Guide to Westchester County, New York

Posted by Tim Cotroneo
on August 11, 2025

WHITE PLAINS, N.Y. – August 11, 2025 –From nature preserves ablaze with foliage to lively harvest festivals and cultural events, fall in Westchester County offers something for everyone. Located in New York’s Hudson Valley, Westchester spans 500 scenic square miles between the Hudson River and Long Island Sound. Its proximity to New York City makes it an easily accessible and refreshing escape from the urban bustle. This seasonal guide, presented by Westchester County Tourism & Film, highlights the best ways to experience the beauty, flavors and festivities of fall 2025.

TOP THINGS TO KNOW:

REV FEST 250: Early kickoff to America’s 250^th anniversary with live reenactments at REV FEST 250 of Revolutionary events that happened in Westchester plus free family fun, held Sept. 27–28 (Croton Point Park).
Top Halloween Destination: Home of “The Legend of Sleepy Hollow,” Westchester also hosts The Great Jack O’Lantern Blaze, SUP Witches paddle and Headless Horseman-inspired events.
Hotel News: Kittle House Inn reopens after renovations. Fall packages are available at Windrose on Hudson and The Abbey Inn & Spa.
Family Fall Fun: 13 farms and orchards offer apple picking, hayrides, cider tastings and more.
Key Fall Events: JazzFest White Plains, Yorktown Grange Fair (an agricultural celebration), Lyndhurst Fall Craft Show, Gothic Harvest Market, Restaurant Week, Bicycle Sundays and Grateful Shred (a Grateful Dead tribute band hosting a Halloween evening showcase).
The Westchester Craft Beverage Trail offers a free mobile passport with perks to visit local breweries, distilleries, cideries and more across the County.

Boo & Beyond – Halloween-themed Events:

Now in its 21^st year, The Great Jack O’Lantern Blaze returns to Van Cortlandt Manor in Croton-on-Hudson for another season of gourd-geous displays. Held Sept. 12–Nov. 16, visitors can wander among more than 7,000 hand-carved, illuminated jack o’lanterns arranged in jaw-dropping displays. 2025 promises to be a magical year with several new installations, including a Pumpkin Promenade, Headless Horseman Hideaway for spooky sips and haunting visits from the Horseman himself, plus a new emerald-hued storybook pumpkin dreamscape – wickedly whimsical and perfect for photo ops.

Lyndhurst Mansion offers a full season of artful charm and eerie intrigue. From Sept. 12–14, explore the Fall Craft Show, where the mansion’s picturesque grounds set the stage for a curated showcase of handcrafted works by talented artisans. Then spooky season begins Sept. 25 with the Halloween Season Opening Party, featuring a festive mansion stroll, food, drinks and a preview of the popular Lyndhurst After Dark Running Oct. 16–26, this candlelit experience delves into the mansion’s shadowy past, rich with age-old superstitions and seasonal décor. From Oct. 25–26, The Gothic Harvest Market adds a spirited finale, with vendors offering oddities, antiques, gothic jewelry, witchy wares and autumnal treats.

Irving’s Legend returns reimagined this fall at Washington Irving’s historic Sunnyside in Tarrytown. Taking place under the stars, this immersive retelling of The Legend of Sleepy Hollow features live music, atmospheric sound effects and a haunting appearance by the Headless Horseman. A seasonal favorite, it continues to thrill audiences of all ages.

The Armour-Stiner Octagon House in Irvington offers three spine-tingling experiences this fall. Explore eerie lore on the Myths and Mysteries Tour, witness a ghost story come to life in The Lady in White and, near Halloween, join ‘Tis the Wind and Nothing More – a dramatic evening led by one of the home’s most mysterious residents, ending with a reading of Poe’s The Raven.

Rivertowns SUP & Yoga will host its annual “SUP Witches” paddleboard event on the Hudson River on Oct. 12. Paddleboarders of all levels are invited to dress in their best witchy attire and glide along the scenic shoreline in a spirited celebration of the season. With stunning views and a festive vibe, it’s a magical way to enjoy fall on the water.

On select dates from Oct. 3 to Nov. 1, Philipsburg Manor in Sleepy Hollow transforms into Twilight Village, an immersive evening filled with eerie encounters, live storytelling, curious market finds and a dramatic meeting with the Headless Horseman. Dive deeper into the legend with The Headless Horseman Files, a live-action 18th-century whodunit that investigates Ichabod Crane’s mysterious fate. For a mind-bending finale, The Spirits of Sleepy Hollow Country features two master illusionists conjuring a theatrical journey into the unknown.

Grateful Shred brings a Halloween night full of jam-band magic to The Capitol Theatre in Port Chester on Oct. 31. This Grateful Dead tribute band captures the spirit of the originals with soaring guitar solos, rich harmonies and that unmistakable Dead vibe.

Leaf Peeping & Fall Fun:

Revolutionary Westchester 250 brings history to life this Sept. 27–28 with REV FEST 250 at Croton Point Park, commemorating Westchester County’s pivotal role in the American Revolution. Enjoy live reenactments, family-friendly activities and immersive educational programming – all part of a larger initiative leading up to the nation’s 250th anniversary in 2026. A second event will follow in Oct. 2026 at Ward Pound Ridge Reservation.

At the Nature Center at Greenburgh, families can experience the joys of traditional Apple Cidering. Use an old-fashioned press to make fresh cider from locally sourced apples, then enjoy a taste and take some home. Time permitting, guests may also visit the barnyard to feed the animals with leftover apple treats.

Taking place Sept. 10–14 in White Plains, JazzFest White Plains brings the city to life with free and affordable performances across downtown venues. From rising stars to world-renowned acts, including seven GRAMMY Award winners and nominees, the festival offers a dynamic mix of talent and styles for music lovers of all kinds.

From Sept. 5–7, the Yorktown Grange Fair, with the 2025 theme “Moo-ving Into the Next Century,” is celebrating over 100 years of agricultural tradition and community pride. This beloved fair showcases the best in local livestock, produce and flowers, along with arts and crafts, live music, exciting rides and family-friendly entertainment. This event has been a community staple since 1924.

Bicycle Sundays, a beloved Westchester tradition, rolls into fall through October. Enjoy the open road on the Bronx River Parkway – car-free and perfect for a scenic 13.1-mile loop by bike, skate or foot.

Catch the action at Memorial Field in Mount Vernon, where the Westchester Soccer Club brings high-energy excitement to the season. As the County’s first United Soccer League team, they’re lighting up this state-of-the-art venue with home games through Oct. 12.

On Oct. 4, Rocky’s 5K returns to Rockefeller State Park Preserve with a scenic course of wooded trails, rolling pastures and peak fall foliage. Perfect for both seasoned trail runners and first-timers, the event includes awards, t-shirts and refreshments in a spectator-friendly setting.

Westchester’s farmlands come alive in the fall with live music, BBQs, apple picking and more – making them must-visit social spots for the season. Popular destinations include Muscoot Farm in Katonah, Harvest Moon Farm and Orchard in North Salem, Stuart’s Fruit Farm in Granite Springs and Wilkens Fruit & Fir Farm and Hilltop Hanover Farm in Yorktown Heights. For a charming twist, make a reservation to stop by Faraway Farm Alpacas to meet their alpacas, Icelandic horses and donkeys.

With over 4,000 acres of diverse terrain and 35 miles of trails, Ward Pound Ridge Reservation is a top spot for soaking in autumn’s vibrant colors. It’s one of many parks across the County’s 24,000-acre system that come alive in fall. Other favorites include Teatown Lake Reservation in Ossining, Cranberry Lake Preserve in White Plains, Croton Gorge Park in Croton-on-Hudson, Graham Hills Park in Pleasantville and Edith G. Read Wildlife Sanctuary in Rye.

Take in the Hudson Valley’s fall splendor from above with Wings Air Helicopter’s Fall Foliage Helicopter Tour. Soar over iconic landmarks like the Kensico Dam in Valhalla and Kykuit, the Rockefeller Estate in Sleepy Hollow, while enjoying sweeping aerial views of the region’s brilliant autumn colors.
Family Fun Day returns to Untermyer Gardens Conservancy in Yonkers on Oct. 5 with magical performances, tours and plenty of engaging activities for the whole family.

Buffalo Maritime Center’s replica of the Erie Canal Boat Seneca Chief will make a stop at the Shattemuc Yacht Club in Ossining on Oct. 24 as part of its Bicentennial Voyage. This historic trip honors Governor DeWitt Clinton’s 1825 sojourn stretching from Buffalo to New York Harbor.

Westchester Comedy Club brings the laughs and a wealth of hilarious talent to Tre Angelique in White Plains and the Rye Grill & Bar.

Arts & Culture:

Caramoor offers a rich lineup of arts and cultural experiences this fall with its Rosen House Concert Series, featuring a diverse range of acclaimed artists across genres. Enjoy Afternoon Teas on select dates in September, the Bedford Music Festival on Sept. 13 headlined by Big Head Todd and the Monsters and the annual Herb Fair & Market on Sept. 20.

Step back in time at the Sherwood House Museum in Yonkers, open Sundays from Sept. 7 – Dec. 7. Built in 1740, it’s the oldest pre-Revolutionary tenant farmhouse in the area and admission is free.

This fall, Emelin Theatre in Mamaroneck offers a dynamic lineup of live performances from comedy and dance to magic and more. Highlights include two-time Emmy Award–winner Judy Gold on Sept. 18, the high-energy contemporary dance of Ailey II on Oct. 12 and mind-bending magic and mentalism by Devonte Magic on Nov. 8. There’s something for every kind of theatergoer.
From contemporary installations to iconic American masterpieces, Westchester’s museums offer a rich mix of creativity and culture. Hudson River Museum in Yonkers is a must – and has been selected as an inaugural winner of the Bridgemaker Prize from Art Bridges, founded by philanthropist Alice Waters. More spots to visit: Explore mid-century works at the Neuberger Museum of Art in Purchase, cutting-edge exhibitions at Hudson Valley MOCA in Peekskill, ever-evolving displays at the Katonah Museum of Art and dynamic programming at ArtsWestchester in White Plains.

Where to Dine this Fall:

A Tarrytown favorite since 1981, Horsefeathers is a local legend serving up classic and New American fare with a side of Sleepy Hollow lore. Named one of USA TODAY’s Bars of the Year, Horsefeathers is beloved for its welcoming vibe, lively Halloween celebrations and enduring charm that keeps locals and visitors coming back year after year.

Hudson Valley Restaurant Week returns Oct. 27 through Nov. 9, making for an easy way to explore the best of Westchester dining, including its many Michelin-reviewed restaurants.

Westchester’s dining scene continues to impress with a wave of standout newcomers. From authentic French fare at La Bastide by Andrea Calstier in North Salem to La Casa Purchase, a sister spot to the Michelin-recognized Bronxville original, fresh flavors abound. Vida Restaurant in Thornwood builds on the success of Augustine’s in Mamaroneck, recently named one of the nation’s top restaurants by USA Today. Also new is Rye’s Antique Garage, blending Turkish and Greek influences in a stylish setting.

The Westchester Craft Beverage Trail offers a flavorful journey through the County’s local breweries, distilleries, cideries and taprooms. With a free mobile passport, participants can check in at each stop, earning points and unlocking rewards along the way. It’s a fun and easy way to explore Westchester’s vibrant craft beverage scene, guided by the makers behind the region’s finest pours.

Autmn Escapes & Accommodations:

A Chappaqua landmark since 1790, The Kittle House Inn – formerly Crabtree’s Kittle House – has recently reopened after a renovation. Guests will still find historic charm with refined hospitality. Once a post-Revolutionary farm, the inn now features 14 thoughtfully designed rooms, acclaimed dining, an award-winning wine collection and elegant event spaces.

Formerly the Crotonville Conference Center, Windrose on Hudson is now a reimagined destination for leisure getaways, special celebrations and corporate retreats. Set on 62 scenic acres in the heart of the Hudson Valley, it invites guests to gather, connect and experience the beauty of the region. Check out their Great Jack O’Lantern Blaze package to take advantage of seasonal savings.

Tarrytown House Estate blends 19th-century grandeur with modern comfort on a 26-acre hilltop property. This historic retreat offers guests an immersive Gilded Age experience alongside contemporary amenities, including seasonal Cantonese cuisine at Goosefeather, helmed by acclaimed chef Dale Talde. Travelers can also enjoy up to 35% off with the Advance Purchase

Nestled along the Hudson River, The Abbey Inn & Spa offers a serene fall retreat with sweeping views and seasonal charm. Set in a beautifully restored former convent, guests can relax at the luxurious spa and enjoy farm-to-table dining at Apropos, For an extra touch of indulgence, the Sunset, Sips & Cruise Package includes a riverfront cruise aboard the Emerald Princess, a restored 100-foot yacht, complete with indoor comfort and an open-air deck for panoramic Hudson Valley views.