Downtown Rutland Events
The Downtown Rutland Partnership hosts and partners on several signature events throughout the year.
Interested in sponsoring downtown events? Email us to learn about upcoming opportunities in 2024!
February 16-25, 2024
April 2024
Green Up Day
Saturday, May 4th, 2024
Downtown Sip + Shop
Thursday, May 16, 2024
Saturday, June 2024
Fridays — July 26, August 16 + September 6
Saturday, October 26
Saturday, September 2024
Friday, November 29, in Depot Park
Saturday, November 30
November-December 2024
Thursday, December 12
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.