Downtown Rutland News & Events
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May 2027
Celebrate National Poetry Month
April 2027
July 10 to Aug. 14, 5 PM to 10 PM
Sat, October 3, 11 AM to 4 PM
Fri, Nov. 27, 5:30 to 6:30 PM
Sat, Nov. 28, 11 AM to 4 PM
Sat, Dec 12, 10 AM to 4 PM
February 2027
Regional Events
Rutland County is home to several amazing annual events to consider when you visit the area. To learn more, visit each individual website.
Art in the Park
A set of historically-occurring fine arts and crafts festival hosted by Chaffee Art Center in Main Street Park featuring pottery, paintings, photography, woodworking, fibers, jewelry and more from Vermont craftspeople. Two weekends a year—one in August and one in October! More details here.
Vermont State Fair
One of the oldest state fairs in the United States, the Vermont State Fair features amusement rides, performances, a demolition derby, races, fireworks, and more every August.
More details here.
Rutland Whoopie pie fest
Presented by the Chamber & Economic Development of the Rutland Region. Rutland’s annual Whoopie Pie Fest is a day filled with tasty fun! Don’t miss this event on Saturday, September 12th in Downtown Rutland! More details here.
Killington Uncorked
Get ready to uncork the excitement and dive into the heart of summer at Killington Uncorked (formerly Killington Wine Festival)! Hosted by the Killington Pico Area Association (KPAA), this beloved annual event isn’t just about wine. It is a full-on celebration of flavor, fun, and the stunning beauty of Killington.