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
Saturday — March 16, 2024
April 2024
Green Up Day
Saturday — May 4th, 2024
Thursday — May 16, 2024
Rutland County Pride Festival
Saturday — June 2024
Friday Night Live Concert Series
July + August 2024
Whoopie Pie Festival
Saturday — September 2024
Halloween Parade
Saturday — October 2024
Tree Lighting
Friday — November 25, 2024 in Depot Park
Window Contest
November — December 2024
Jingle Bell Shop
Thursday — December 2024
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
July 21-22 2023
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
August 15-19 2023
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
August 12-13 2023
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
Thanksgiving weekend 2023
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.