There might be plenty of states around the U.S. that claim to do justice in the name of Halloween and October, in general, but no such state is as versatile in its celebrations as New York is. With the state being broken up into four main sections - New York City, Downstate, Upstate, and Long Island - there's seemingly no end to the haunted festivities.

Additionally, this entire state is absolutely dripping with a history dating back to the colonial period, riding in on the horsetails of Washington Irving's Headless Horseman. From the best Halloween parade one has ever seen to the haunted trails that slither through northern New York, this state knows how to crank up its creepy festivities.

Related: These Are The Best Weekend Road Trips New Yorkers Can Take In The Fall

Halloween On Long Island

Although it's the least-known part of New York with the exception of the Hamptons, Long Island is home to vineyards, pumpkin patches, cornfields, and, of course, haunted houses. With a unique suburban atmosphere, it's a miniature version of all that Upstate New York and the city have to offer a visitor.

Pumpkin Picking, Haunted Houses, And More

Anyone heading east on Long Island is bound to encounter some of the best pumpkin farms there are. While the South Fork is home to the Hamptons, the North Fork is home to vineyards and farmland. Both offer great options for apple picking from early September through early October and pumpkin picking throughout October. Those stopping by a farmstand will undoubtedly be lored in with the tantalizing scent of roasted corn, and perhaps a hot apple cider or two. At night, the North Fork is home to several corn mazes that permit nighttime mazing, as well as haunted houses in both Nassau and Suffolk Counties.

These are some of the best stops on the East End:

  • Harbes Family Farm: One of the largest on the island, home to a vineyard, corn maze (daytime and nighttime), and plenty of activities for kids including pumpkin and apple picking.
  • Schitt's Family Farm: Pony rides, inflatables, pumpkin picking, and free hayrides, as well as a haunted house.
  • Wickham's Fruit Farm: One of the oldest farms on Long Island, home to apple picking, pumpkin picking, and berry picking during the summer season.
  • Windy Acre Farm: Pumpkins, apples, fresh apple cider, and cider donuts can be found on this farm.
  • Woodside Orchards: For the adults, Woodside Orchards is home to hard craft cider, apple cider donuts, and various baked goods during the fall season.

Halloween In New York City

Some people might not immediately think of New York City when it comes to October festivities, the biggest draw of the month is the Halloween Parade. One might not find pumpkin picking within its city limits, but they'll certainly find things like ghost tours and themed bar or pub nights.

The Halloween Parade

Every year, New York City throws what's known as one of the biggest, and most well-known, Halloween parades in the country. Held annually on October 31st, each year has had a different theme as floats and parade attendees march through the Village from Sixth Street to Canal Street. While the parade is free to watch from the sidelines (costumes according to the parade's theme are encouraged), tickets to participate in the parade are $35 - $500 to march in the very front.

There are two themes for 2021: LET'S PLAY!!! and All Together NOW! The first theme encourages parade-goers to dress in anything game or gameshow-related, while the second is in celebration of 'the most epic story of all – the story of us, the story of “everyday people” resilient in our joy, determined to dance through dark times, and heroically devoted to one another.'

Downstate & Upstate New York

Two of the most popular locations in New York State for Halloween are Downstate and Upstate. The Hudson Valley is in a full-color array during the fall season, and the scenery alone is enough to convince one to take a drive through its scenic mountains. Further north in the Catskills and Adirondacks, things are a bit more remote but no less beautiful - many would claim even more so. See here for a full list of apple-themed stops in the Hudson Valley.

Sleepy Hollow

The Hudson Valley also happens to be home to Sleepy Hollow, where the legend of the Headless Horseman allegedly took place. While the story might be a mere legend, the atmosphere in this town around Halloween certainly is not. The entire town transforms, with shop windows featuring spooky scenes, restaurants that plan creative menus accompanied by local pumpkin beer, and plenty of haunted happenings to choose from, including:

  • Sleepy Hollow Haunted Scream Park
  • Sleepy Hollow Hayride
  • Headless Horseman Hayrides (nearby in Ulster, New York)

The Great Jack O'Lantern Blaze

One event that visitors begin booking tickets for well in advance is the Great Jack O'Lantern Blaze. Located in the Historic Hudson Valley, visitors will have the chance to walk through an 18th-century setting while observing some of the most creative pumpkin art in the country. More than 7,000 pumpkins are on display each year, all of which are hand-carved by local artists.

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