Halloween Around Woodstock, NY

Halloween 2026 falls on Saturday, October 31. Listings below cover October 15 through November 2.

Everything Halloween around Woodstock, New York, from the village costume parade to the cover-band nights in Kingston. Every listing links to its own page with times and tickets.

The parade is the main event

Woodstock's Halloween belongs to the street rather than to any one room. The Woodstock Chamber of Commerce and Arts runs a costume parade through the hamlet on October 31, and in recent years it has stepped off around 5 p.m. with music from about 4:30, led by the Rock Academy Showband and Drum Line, and ended at the Village Green where Mill Hill Road, Tinker Street and Rock City Road meet. Costume judging happens on the Green once the parade arrives, in age categories, with prizes that favor homemade work. Pets have had their own category. Merchants through the business district hand out candy, and the roads close while it runs.

We are not the organizer. Those times are what the parade has done in recent years, not a confirmed schedule for this year, so check the Woodstock Chamber before you plan a drive around them.

Costumes here are not a joke

The chamber's own description of the town is that “Woodstock is known for our exceptional and creative costumes”, and that is not boilerplate. In past years the parade has been joined by the Rosendale Improvement Association Brass Band and a “Thriller” flash mob, a public workshop the day before has let anyone help build the parade itself, and 2025 brought a tribute to the fiftieth anniversary of The Rocky Horror Picture Show. Dress accordingly, or you will be the one who looks out of place.

Making a night or a weekend of it

The hamlet is walkable, which is the useful part: you can park once, catch the parade on the Green and still make a show. If you are coming up for the weekend rather than the evening, Woodstock Way and Hotel Dylan are the two closest beds to the middle of it, and there are more across the area on the lodging page. For food before a show, Silvia and Tinker Taco Lab are both a short walk from the Green, with the rest on the dining page. The Woodstock town guide has the whole picture, and things to do covers the daylight hours.

Halloween 2027

October 31 falls on a Sunday in 2027. The parade and the listings both land on this same page when they do, so there is nothing new to find.

Running something for Halloween around Woodstock that is not here? Send it over. Every submission is read by hand.