Signature events in the Rutland Region

Each year the Chamber & Economic Development of the Rutland Region (CEDRR) hosts events that bring neighbors, businesses and visitors together in downtown Rutland and across the county. Here is what to know, with dates, places and what to expect. For what’s happening this month, see the events calendar.

Whoopie Pie Festival

Downtown Rutland’s Whoopie Pie Festival began on August 27, 2022 as the Parade of Heroes & Whoopie Pie Festival, with Center Street turned into a grass-covered “green street.” The fifth annual festival, on September 12, 2026, drew more than 8,000 attendees, 13 whoopie pie vendors from across the Northeast, and food, craft and entertainment vendors. Judges awarded “Overall Best” to Sweet Birch Coffee Roasters and Bakery of Wallingford, and attendees voted The Gettin’ Place of Whitehall, New York, “People’s Choice.” Local nonprofits and service organizations hosted informational booths, and the day began with the Whoopie Pie Mile fun run. Casella Waste Systems was the 2026 Premier Sponsor.

Workforce in Motion Summit

The Workforce in Motion Summit is a hands-on day for students in grades 7 to 12, their chaperones and parents, and adults looking to change careers. The inaugural summit and Equipment Rodeo took place on Thursday, May 21, 2026 at Vermont State University Castleton, running from 9:00 a.m. to 2:00 p.m. and free with pre-registration. Attendees met dozens of local and regional employers, tried skills such as welding, masonry, CPR, robotics and landscaping, learned about paid internships and scholarships, and heard from Governor Phil Scott. More than 1,000 students, employers, educators and industry partners took part. CEDRR organized the summit with the Rutland Regional Planning Commission, the Rutland Region Workforce Investment Board and Workforce in Motion, Inc. Casella Waste Systems was the title sponsor.

Annual Meeting and awards

Every fall CEDRR gathers members and neighbors to review the year and honor the people and businesses shaping the region. The 2025 Annual Meeting was held on October 28, 2025 at the K-1 Base Lodge at Killington Resort, where CEDRR recognized Bernie Carr (Volunteer of the Year/Decades), Russ Marsan (Community Leader of the Year), Casella Waste Systems (Innovator of the Year) and Mike Solimano of Killington Resort (Business Leader of the Year). Read about the 2025 award recipients. The 2026 Annual Celebration was held on October 8 at the Casella Theater at Vermont State University Castleton, with awards for Community Leader, Entrepreneur, Young Professional, Volunteer and Member of the Year.

Monthly mixers

CEDRR mixers are generally held on the second Tuesday of the month from 5:00 to 7:00 p.m., each hosted by a different business or nonprofit, with food from a local caterer, door prizes and a 50/50 drawing. They are open to everyone. See the mixers page to find the next one.

More events across the region

Each year, the Rutland Region hosts award-winning, nationally recognized events welcoming thousands of visitors to our towns. These events include the Rutland Halloween Parade, the Vermont State Fair, Relay for Life, Killington Music Festival, the Basin Bluegrass Festival, Gift of Life Marathon Blood Drive, and more.

Questions about an event, or interested in sponsoring or hosting? Call CEDRR at (802) 773-2747.