Best Fall & Halloween Events to Do in New York

Between my love of events and fall in New York, we’re back with another guide focused on the best fall and Halloween events in the state. From experience, here’s my top picks of thing you have to check out for the season.


Lyndhurst Mansion - Tarrytown, NY

Lyndhurst Mansion was designed in 1838 by architect Alexander Jackson Davis for William Paulding Jr. in a romantic Gothic Revival style.

During fall (about late September to late October), you can enjoy their Fall Classic Mansion Tour.

This one-hour tour covers two floors and treats visitors to a rare glimpse of the lavish decorative arts and furniture left to Lyndhurst by previous owners all while decorated with the splendor of the Fall Season.

The tour, which lasts an hour, visits approximately 16 rooms and involves climbing one staircase. You’ll visit the first floor of the Mansion; including the parlor, filled with furniture designed by architect A.J. Davis, and the sumptuous Civil War-era dining room. The second-floor centers around the opulent Grand Picture Gallery hung with an original collection of European paintings. Impressive Tiffany stained glass windows adorn the gallery and adjacent bedrooms.


The Great Jack O’Lantern Blaze

Part of Historic Hudson Valley at Van Cortlandt Manor in Croton-on-Hudson, NY. This spooky display of more than 7,000 illuminated jack o’ lanterns—all designed and hand-carved on site by their team of pumpkin craving artisans. Starting from mid September to about mid November every year you won’t want to miss Halloween inspired walk through all the unique pumpkin creations.

They also have a gift shop section and light bites like hot cider, beer, hot dogs/hamburgers.


Sleepy Hollow, NY

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Sleepy Hollow, NY is possibly most famous for The Headless Horseman.

"The Legend of Sleepy Hollow" is a gothic story by American author Washington Irving, contained in his collection of 34 essays and short stories titled The Sketch Book of Geoffrey Crayon, Gent. The character known as the Headless Horseman is believed to be a Hessian soldier who was decapitated by a cannonball in battle.


Not only that here’s few other activities that happen each year in this cute town next to Tarrytown (also a train ride via Grand Central Station from the city.)

Activities in Sleepy Hallow:

Headless Horseman Hayrides and Haunted Houses

Named “#1 Haunted Attraction in America”. New theme each season. The event includes a haunted walking trail, corn maze, 8 haunted attractions, gift shops and eateries. Operates September 25th and October weekends.

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Founded in 1849, this private cemetery is non-profit and non-sectarian. There are over 45,000 interments in its 90 acres.

Famous burials include Washington Irving, Andrew Carnegie, Walter Chrysler, Samuel Gompers, Elizabeth Arden, Leona Helmsley, Brooke Astor, and William Rockefeller. Walk or drive the grounds on your own or try an afternoon or evening guided tour here.


Apple Picking - Maskers Orchard, Warwick, NY

I’ve been to a fair amount of apple orchards and I still keep coming back to Masker’s Orchard. I love that they have a printed map of each apple type and section. Have a wide variety of apples. They have a farm store where you can get everything from pumpkins, to cider, to apple donuts, hayrides and corn mazes. It’s always a good time here.

Pro tip: Peak season in my experience is September to about first two weeks in October, late October not many apples are left and it gets to be pretty cold and wet.


Cider Tastings by the Fire - Angry Orchard - Walden, NY


At Angry Orchard’s in Walden, NY you can tour the orchard, do cider tasting flights, and they have a Treehouse Tour as well. It’s a really nice and relaxing spot to have a drink and sit by one of their fire pits on a chilly fall day.


New York City Wine & Food Festival

From brunches, burger bashes, to the Grand Tasting Hall. This food lovers event occurs every October in NYC with Food Network and the Cooking Channel. Not only that they help raise millions of dollars for the Food Bank For New York City.

More info on NYCWFF here.


Finger Lakes , NY

Wine Tasting, Hiking, WaterFalls and Watching the fall Foliage

Up for a drive? If you’re ready for some beautiful fall foliage, hiking, and wine tastings take a long weekend and drive up to the Finger Lakes.

Here’s my short list of favorites to check out:

Favorite Waterfalls:

Ithaca Falls

Taughannock Falls

Favorite Wineries:

Buttonwood Grove Winery

Thirsty Owl Winery

Other Top Picks:

Ithaca Farmers Market

It’s a Wonderful Life Museum /Seneca Falls

Women’s Right National Historic Park


Hope you get out there and explore the best of what New York has to offer this fall.

We’re always looking for more event inspiration. Tell us in the comments what your favorite events or things to are in New York!

Happy Fall Y’all!