Downtown Rutland News & Events
Interested in sponsoring downtown events? Email us to learn about upcoming opportunities in 2025!
Halloween Parade in New Archie Comics Story!
Rutland City’s annual Halloween Parade is set to gain national attention as it becomes the focus of an upcoming Archie Comics story! Learn more >>
Rutland Winterfest
February 14-22, 2025
Saturday, June 21, 2025
Friday Night Live Concert Series
2026 dates coming soon
Downtown Rutland Street Party & Sidewalk Sales
2026 dates coming soon
October 2025
Saturday, October 25, 2025
Saturday, October 25, 2025
Tuesday, Nov. 18, 2025
Friday, November 28, 2025
Depot Park
Saturday, November 29, 2025
Thursday, December 11, 2025
November-December 2025
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.
Killington Wine Festival
Enjoy wine tastings at Killington Peak, in some of Killington's finest restaurants, and at Vermont's #1 Public Golf Course. Events for the weekend include live music, special deals, and the signature event of the summer.
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.
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.
Killington World Cup
A stop on the Audi FIS Ski Women's World Cup Tour you don't want to miss! Over 30,000 people converge to watch women race down the slopes of Killington Mountain, home to New England's largest vertical drop.