Spooky Season in the Hudson Valley 2026

Spooky season in the Hudson Valley is officially upon us, and there is no better place to celebrate Halloween on Saturday, October 31, 2026, than in and around Woodstock, NY. From quintessential small-town community parades to world-renowned haunted attractions and glowing pumpkin displays, the region comes alive with festive Halloween energy.

Top Halloween Events in & Around Woodstock 2026

• Woodstock Annual Halloween Parade (Woodstock, NY) The heart and soul of October 31 in Woodstock! Every year, locals and visitors gather along Rock City Road and the Village Green for the beloved Halloween Parade. Expect incredible handmade costumes, live music, local street performers, and trick-or-treating at local shops throughout the village. The parade typically kicks off in the late afternoon (~5:00 PM), making it perfect for families and costume enthusiasts of all ages.

  • Learn more and check updates at Woodstock Chamber of Commerce.

• Headless Horseman Hayrides & Haunted Attractions (Ulster Park, NY) Located just south of Kingston along Route 9W, Headless Horseman is consistently rated one of the top haunted attractions in the entire country. Featuring a terrifying theatrical hayride through cursed woods, a sprawling corn maze, multiple haunted houses, live stage shows, and food concessions, it is the ultimate destination for thrill-seekers. Advance online ticket reservations are strictly required.

  • Book tickets and view schedules at Headless Horseman Hayrides.

• Peace, Love & Pumpkins at Bethel Woods (Bethel, NY) For a magical, non-scary, lantern-lit experience, head over to the historic site of the 1969 Woodstock festival at Bethel Woods. Their annual walkthrough display features thousands of hand-carved, illuminated jack-o'-lanterns, themed glowing light displays, fall treats, and artisan crafts set against a stunning autumn backdrop.

  • Explore event times and tickets at Bethel Woods Center for the Arts.

• Trick-or-Treating & Historic Folklore in Uptown Kingston (Kingston, NY) Just 15 minutes down the road from Woodstock, historic Uptown Kingston (Stockade District) hosts vibrant Halloween festivities on October 31. 

  Old Dutch Church Haunted History Cemetery Tours (Uptown Kingston)

  • The Details: Located right in the heart of Uptown Kingston (272 Wall Street), the Old Dutch Church cemetery dates back to 1658. Every October leading up to Halloween, costume guides lead candlelit history and ghost walks through the graveyard, sharing local folklore, revolutionary-era legends, and tales of Kingston’s earliest residents.

  • Where to find it: Listed under regional Halloween itineraries and historic tours on Visit Ulster County's Halloween Guide and the Old Dutch Church Historic Site.

• • Halloween in the Historic Stockade District (Uptown Kingston)

    • The Details: On October 31, the Stockade Association hosts trick-or-treating, costume walks, and community gatherings among the 17th-century stone houses in Uptown Kingston, blending neighborhood Halloween fun with historic architecture.

    • Where to find it: Check community updates directly via The Stockade Association.

  • MyKingstonKids Annual Halloween Parade & Festival (Kingston)

    • The Details: The city's primary multi-block Halloween parade and festival features costume contests, live music, interactive games, and trick-or-treating along the main corridors of Kingston.

    • Where to find it: Event schedules and registration are available through MyKingstonKids.

• Trick-or-Treating on the Saugerties Village Green (Saugerties, NY) A short drive northeast of Woodstock, the village of Saugerties rolls out the red carpet for trick-or-treaters on Halloween afternoon. Main Street and Partition Street host a safe, family-friendly costume march with local merchants handing out candy.

  • Check local listings at Discover Saugerties.

Whether you’re a local costume fanatic or looking for the ultimate autumn escape in the Catskills, Halloween in and around Woodstock is pure Upstate magic. From family-friendly village parades and glowing jack-o'-lantern displays to candlelit cemetery tours and world-class haunted hayrides, there is no shortage of unforgettable ways to celebrate spooky season on October 31, 2026. Grab a warm cider, gather your favorite crew, and make the most of Halloween in the Hudson Valley!

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