Autumn events and activities in Westchester County
A day trip to leafy Westchester in autumn offers a variety of attractions: historic sites, scenic beauty, casual dining, and special events that will appeal to adults and kids of all ages.
Although Westchester is sometimes dubbed “upstate,” it is a misnomer. The vibrant river towns along the Hudson are only 30 minutes from New York City, making the destination an easy escape by car or Metro-North Railroad.
During autumn, the Hudson Valley comes alive with fall foliage. Here are some not-to-be-missed seasonal attractions:
The old Dutch Church in Sleepy Hollow, New York
If your brood is interested in stories of ghosts, goblins, and other tall tales, the place to start is in the village of Sleepy Hollow (once called North Tarrytown), immortalized in literature by Washington Irving. In this iconic ghost story, a Headless Horseman rides through the town at night, terrorizing the locals.
Here you can visit the 2.5-acre churchyard featured in Irving’s story. Not only the haunt of the Headless Horseman, he also is purported to be buried here. On-site, you can purchase a copy of Tales of the Old Dutch Burying Ground, a self-guided tour of the churchyard that includes a map.
Washington Irving grave in Sleepy Hollow Cemetery
Nearby is the beautiful Sleepy Hollow Cemetery, founded in 1849, where you can visit the actual grave of Washington Irving.
Some of the other many famous interments include John Dustin Archbold, a director of Rockefeller’s Standard Oil Company; philanthropists Brooke and Vince Astor; steel magnate and philanthropist Andrew Carnegie; real estate moguls Harry and Leona Helmsley; Walter Chrysler, found of the Chrysler automobile company, and journalist Francis Pharcellus Church, who penned “Yes, Virginia, there is a Santa Claus.”
Sleepy Hollow Cemetery is listed on the Register of National Historic Places and offers a serene setting with sculptures, mature trees, and plantings that change colors with the season.
During the fall, the cemetery offers walking tours by trained docents, some of which take place in the evening with kerosene lanterns.
Antique photograph of Sunnyside, the Dutch stone home of Washington Irving, Tarrytown, New York
Washington Irving’s home, now a house museum, is located just a few miles south close to the banks of the Hudson River.
On Thursdays through November 9th, visitors can take guide house tours and learn about Irving and his characters.. On Fridays through Sundays, the family-friendly “The Legend of Sleepy Hollow” includes the house tour (decorated for the season), a short shadow puppet film, and games on the lawn.
On select days in October, guests can attend Irving’s Legend, a dramatic performance outdoors under the stars with live music. Spoiler: The experience includes a visit from the Headless Horseman himself.
The 18th century Philipsburg Manor in Sleepy Hollow, New York”
Also in Sleepy Hollow, historic Philipsburg Manor is one of 14 sites that comprise the African American Heritage Trail of Westchester County. This non-profit museum includes a manor house with 17th- and 18th-century furnishings, a scenic water mill, a barn, a slave garden and a reconstructed tenant farmhouse.
The site was once home to 23 enslaved individuals who labored there for generations. Guided tours of the grounds with docents dressed in period garb bring history alive.
On select dates from late September through October, guests visiting Philipsburg Manor can witness the Spirits of Sleepy Hollow Country with performances and immersive experiences led by master illusionists.
Lyndhurst mansion in Tarrytown, New York
This impressive Gothic Mansion in Tarrytown, just south of the Mario Cuomo Bridge, sits on 67 expansive acres. Formerly the Jay Gould Estate, the property was designed in 1838, opened as a museum in 1965 and was recently featured in The Gilded Age TV series.
There is no better time to soak in Lyndhurst’s beauty and rich history than in the fall. The museum offers mansion tours, two-hour landscape tours, and daily passes just to explore the grounds.
During two weekends in October (10/19-10/22 and 10/26-10/29), the Lyndhurst After Dark tour explored the darker traditions and superstitions of the mansion with special seasonal house decorations.
The historic Tarrytown Music Hall
Located on Main Street filled with small shops and interesting dining venues, the Tarrytown Music Hall was erected in 1885 and added to the National Register of Historic Places in 1980. It is the oldest theater in the county and is considered an excellent example of Queen Anne Architecture.
Ticketed year-round music, dance, concerts, and comedy performances attract locals and visitors from the surrounding area. It is an experience just to sit in the theater and look around you.
An official site of the Haunted History Trail of New York, the music hall offers guided, immersive Ghost Tours during the month of October.
IF YOU GO
- Be sure to check opening hours and any closures for holidays or special events.
- Because of their popularity, most special events require advance ticketing.
- For additional information and many more options, see the Westchester County Tourism & Film and Historic Hudson Valley websites.
