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 2025!
February 14-22, 2025
April 2025
Green Up Day
Saturday, May 3, 2025
Downtown Sip + Shop
2025 TBD
Saturday, June 21, 2025
Summer Fridays, 2025 Dates TBD
Saturday, October 25, 2025
Saturday, September 13, 2025
Friday, November 28, 2025
Depot Park
Saturday, November 29, 2025
November-December 2025
Thursday in December, 2025 TBD
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.