Westchester County’s fall calendar is packed with standout experiences, from continued America 250 celebrations to iconic Halloween traditions and seasonal festivals. Just north of New York City, visitors can experience the best of the season with apple picking, scenic foliage, local dining and fall getaways across the County.
TOP THINGS TO KNOW
REV FEST 250 Comes to Life: Continuing with celebrations for America’s 250, REV FEST 250 will take place Oct. 24–25 at Ward Pound Ridge Reservation in Pound Ridge. The weekend brings the American Revolution to life with 500 living historians portraying soldiers and civilians, authentic Continental and British Army encampments, family friendly activities, live entertainment and a large-scale reenactment of the Battle of White Plains.
A Fall to Remember: Apple picking, pumpkin patches, cuddly farm animals, hayrides and more await at Westchester’s farms and orchards, while thousands of acres of parks and preserves offer colorful trails for hiking and leaf peeping.
Key Fall Events: Westchester’s fall lineup spans music, arts, agriculture, dining and outdoor recreation, with highlights including the new Autumn Glow Festival in New Rochelle, as well as the 100th anniversary of The Capitol Theatrem. Seasonal favorites include JazzFest White Plains, the Yorktown Grange Fair, Lyndhurst Fall Craft Show, Bicycle Sundays, Hudson Valley Restaurant Week and the Bedford Music Festival at Caramoor.
Halloween Happenings
The Great Jack O’Lantern Blaze returns to Van Cortlandt Manor, Sept. 18-Nov. 8, with a longer path and even more displays. Visitors can wander through an 18th-century landscape illuminated by more than 7,000 hand-carved jack o’lanterns, complete with synchronized lighting, an original soundtrack, movie monsters, storybook characters and a pumpkin dance party.
As Halloween approaches, Lyndhurst Mansion shifts into the spirit with seasonal tours, performances of The Masque of the Red Death, Gothic Market Weekend, and a special Dark Shadows Halloween celebration.
Washington Irving’s classic tale comes to life at Irving’s Legend, held Oct. 2-31 at the author’s Sunnyside home in Irvington. Master Storyteller Jonathan Kruk delivers a dramatic retelling of The Legend of Sleepy Hollow outdoors under the stars, accompanied by live music and sound effects. During the day, take one of the kid-friendly literary-themed Legendary Tours complete with lawn games, crafts and a shadow puppet show.
Witches take to the Hudson River at the annual SUP Witches Festival, held Oct. 10 in Sleepy Hollow. Hosted by Rivertowns SUP & Yoga, the fall tradition brings costumed witches and warlocks together for a paddle along the Hudson, while spectators join the fun onshore with live music, vendors, food and seasonal activities.
Ghost stories desend upon Armour-Stiner Octagon House in Irvington this fall. ’Tis the Wind and Nothing More, Oct. 2-11, features a dramatic reading of Edgar Allan Poe’s The Raven, while The Lady in White, taking place Oct. 16-Nov. 1, draws inspiration from a 1956 ghost story set at the house.
Expanded for 2026, Twilight Village at Sleepy Hollow returns to Philipsburg Manor Fridays through Sundays through October, with live storytellers, fire performers, an evening market, an appearance by the Headless Horseman and more.
Visitors can also investigate Ichabod Crane’s disappearance during the Headless Horseman Files, an interactive 18th-century whodunit, or experience the magical illusions of The Spirits of Sleepy Hollow Country.
Mystic Moon returns to Harvest Moon Farm & Orchard in North Salem, inviting visitors to follow the mischievous adventures of a playful witch through a whimsical lighted path in the woods.
Master Storyteller Jonathan Kruk leads Ghost Tours of the Tarrytown Music Hall, Oct. 3-18, sharing fascinating tales of the theater’s history, legends and mysterious happenings.
Leaf Peeping & Fall Fun
500 living historians bring the Revolutionary War to life at REV FEST 250, Oct. 24-25 at Ward Pound Ridge Reservation. The two-day event features authentic Continental and British Army encampments, military demonstrations, live entertainment, family-friendly activities, exhibitors and local food trucks.
Watch both armies assemble and march toward the weekend’s signature attraction—the Reenactment of the Battle of White Plains, a large-scale tactical demonstration.
Apple picking, hayrides, farm markets and seasonal treats draw visitors to Westchester’s farms and orchards. Local favorites include Muscoot Farm in Katonah, Harvest Moon Farm and Orchard in North Salem, Stuart’s Fruit Farm in Granite Springs, Wilkens Fruit & Fir Farm and Hilltop Hanover Farm in Yorktown Heights. At Faraway Farm Alpacas, visitors can reserve a tour to meet alpacas.
Walk into the depths of a dark forest and discover Fantastic Beasts™ and illuminated wizarding world moments at Harry Potter: A Forbidden Forest Experience, returning to Westchester Oct. 16, in the awe-inspiring woods of Franklin D. Roosevelt State Park in Yorktown Heights. This nighttime trail experience is designed for the whole family and books quickly, reserve your tickets today.
Autumn Glow Festival lights up Glen Island Park in New Rochelle, Sept. 11-Nov. 1. The immersive nighttime experience features hundreds of handcrafted Chinese lanterns illuminated with LED lights, transforming the park with towering sculptures inspired by folklore, culture and nature, along with food and entertainment.
Hands-on fall programs return to the Nature Center at Greenburgh this autumn. Apple cidering allows families operate an old-fashioned cider press, turning locally sourced apples into fresh cider to sample and take home. Creepy Crawlers offers another up-close nature experience, introducing visitors to snakes, tarantulas and other creatures while exploring how they survive in their habitats.
More than 4,300 acres of terrain and 35 miles of wooded trails make Ward Pound Ridge Reservation a standout for fall foliage. Other scenic spots 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 changing leaves from a different perspective with Bicycle Sundays, Sept. 13 through Oct. 4. A nearly 6.5-mile stretch of the Bronx River Parkway closes to cars, giving cyclists, skaters, joggers and walkers the chance to enjoy a traffic-free outing.
Westchester Soccer Club’s exciting season continues at Memorial Field in Mount Vernon with home matches running through Oct. 17.
Get a bird’s-eye view of the season with Wings Air Helicopters’ Fall Foliage Helicopter Tour. Departing from Westchester County Airport, flights offer aerial views of Kykuit, the Rockefeller Estate, the Sleepy Hollow Lighthouse and the Gov. Mario M. Cuomo Bridge.
Arts & Culture
One of Westchester County’s most signigicant revolutionary-era artifacts is on view at the Neuberger Museum of Art in Purchase through Dec. 20. The Declaration Distributed: Westchester County’s Holt Broadside of 1776 is a special exhibition centered around New York State’s historic adoption and distribution of the Declaration of Independence.
The exhibit offers visitors a rare opportunity to view this important document and highlights Westchester County’s critical role in the nation’s founding.
The Bedford Music Festival kicked off Caramoor’s fall season Sept. 6 with a full day of live music headlined by the Motet. The fall calendar continues with performances in the Rosen House Concert Series, tours, teas and other special events.
Sleepy Hollow Music Festival returns with a new date, Oct. 3, and features eleven bands across two stages at the river-front Kingsland Point Park. The dynamic 90’s nostalgia lineup includes headliners Everclear, The Smithereens with Marshall Crenshaw, Fastball, Sophie B Hawkins and more. Food trucks, beer gardens, thirty plus craft and specialty vendors, and children’s and Halloween-themed activities round out the event.
Step back almost 300 years into Yonkers history at the Sherwood House Museum, a pre-Revolutionary War farmhouse built around 1740. The museum is open Sundays from 1-4 p.m. beginning Sept. 13, with free admission.
Music, comedy and dance fill the fall calendar at Emelin Theatre in Mamaroneck, with jazz vocalist Jane Monheit on Sept. 26, comedian Rachel Feinstein on Oct. 1, Parsons Dance on Oct. 23 and GRAMMY-winning soul legend Booker T. Jones on Oct. 24.
The Picture House Regional Film Center, also marks its 100th anniversary this September, celebrating with special screenings and events to commemorate the Centennial year. Fall programming also includes the six-week Fall Film Club in Pelham and Halloween weekend screenings of The Rocky Horror Picture Show.
Yorktown Stage celebrates the 50th anniversary of the musical, Annie, with lively performances of the beloved classic Nov. 14-29.
Two new exhibitions open on Sept. 18 at the Hudson River Museum in Yonkers: Exquisite Creatures and Borinquen Gallo: Jungle Bliss. More cultural stops include the Hudson Valley MOCA in Peekskill, the Katonah Museum of Art and ArtsWestchester in White Plains.
Where to Dine this Fall
Dine your way through the region during Hudson Valley Restaurant Week, returning Nov. 2-16. Participating restaurants throughout Westchester offer special prix-fixe menus, making it a great opportunity to try a new spot or revisit a local favorite.
New additions are bringing fresh flavors to Westchester’s dining scene. In Bronxville, Cafe Nelo from chef Giuseppe Fanelli blends Italian, American and European influences, while North River Oyster Bar in Sleepy Hollow serves seafood and cocktails on Beekman Avenue.
Cozy up at The Inn at Pound Ridge by Jean-Georges, where seasonal, farm-to-table fare is served in an 1833 inn. With reclaimed wood, rustic details and four working fireplaces, the longtime Westchester favorite offers an inviting setting for a memorable meal.
Surround yourself in history at Peter Pratt’s Inn, an American fine dining restaurant and bar located in a historic 260 year old farm house bordering a rustic pine forest in Yorktown Heights.
Sip your way through Westchester with the Westchester Craft Beverage Trail, connecting local breweries, cideries, distilleries and taprooms across the county. The free mobile passport lets visitors check in at participating stops, access special offers and earn points.
The Sailhouse Oysterfest brings oysters, seasonal food and drinks to the Hudson River waterfront for a lively dining experience. More information to come.
Autumn Escapes & Accommodations
Escape to the countryside at Bedford Post Inn, an intimate eight-room retreat surrounded by 20 wooded acres. Cozy guest rooms feature historic details and luxurious touches, while seasonal dining, daily yoga and outdoor experiences make it an inviting home base for a fall getaway.
Recently reopened following renovations, The Kittle House Inn in Chappaqua, pairs its 18th-century history with newly refreshed rooms and gathering spaces. Guests can also enjoy fine dining featuring seasonal Hudson Valley ingredients and selections from the property’s award-winning wine cellar.
Set on 26 acres overlooking the Hudson Valley, Tarrytown House Estate pairs charm with modern comforts and on-site dining at Chef Dale Talde’s acclaimed Goosefeather, a modern Cantonese restaurant. This fall, guests can book the Great Jack O’Lantern Blaze Experience Package, which includes two tickets to the seasonal attraction and daily breakfast for two.
Perched above the Hudson River in Peekskill, The Abbey Inn & Spa offers a peaceful fall escape in a beautifully restored former convent. Unwind at the full-service spa, explore the scenic grounds and enjoy seasonal, locally inspired dining at Apropos. For an extra dose of relaxation, the Stay, Sip and Spa Package includes overnight accommodations, welcome mimosas and a $200 spa credit.
One of Westchester’s more newly renovated hotel properties, the Westchester Marriott in Tarrytown offers updated guest rooms and suites alongside on-site dining, a fitness center, in-house golf simulator and convenient access to the area’s seasonal attractions.
Melanie Votaw is the Publisher and Executive Travel Writer of LuxuryWeb Magazine. She has visited more than 50 countries on 6 continents and written for such magazines as Executive Travel, Just Luxe, Business Insider, South China Morning Post, Travel Mindset, and more. She is a member of the International Food, Wine & Travel Writers Association, New York Travel Writers Association, and International Travel Writers Alliance. Melanie's photography has won awards, and she has also written 43 nonfiction books as either the author or ghostwriter.
0 Comments