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Rutland Region Events 2019

Visit Rutland Vermont – the crossroads to all of Vermont’s most favorite group destinations! Groups love events. Add one of Rutland’s fun experiences to your tour itinerary and make even more memories for your guests!

February: Rutland Winter Fest

A week of fun in the snow! Enjoy ice skating, snow sculpting, street sledding, chili cook-off, and more.


March: Middletown Springs Maple Festival

Catch a glimpse into the art of early maple sugarmaking while sampling pure Vermont maple products.


March: Freezin For a Reason Polar Plunge

Visit Lake Bomoseen Lodge and take the plunge or enjoy activities like a breakfast buffet and live music while benefitting the Shriners Children’s Hospitals.


March: Vermont Brewers Festival at Killington

Enjoy over 100 exclusive beers created by Vermont brewers at this all outdoor winter themed festival at the base area of the K1 lodge at Killington.


May: Killington Stage Race

Watch cyclists race through Killington, VT.


June: Vermont Bike & Brew

Join MTBVT at Killington Bike Park for a weekend of organized mountain biking for all skill levels, Vermont’s largest downhill critical mass ride, on-site camping, vendors and demos, new and used bike sale, craft beer garden, whip-off competition, skinny bridge challenge, kids race and live music.


July: Vermont Symphony Orchestra at Mountain Top Inn

Experience musically-depicted majestic rivers, verdant fields, gardens in bloom, and the clear night sky in Chittenden.


July: Killington Wine Festival

Three days of wining and dining in the beautiful Green Mountains. Enjoy tastings, music, special deals and more.


July: Friday Night Live Free Concert Series

Enjoy music, outdoor dining, shopping, children’s activities and more on Center Street in Downtown Rutland.


August: Downtown Street Party & Sidewalk Sales

Enjoy a variety of family entertainment as well as local artists, crafts, food vendors and live music from area musicians.


August: 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 vendors.


August & October: Art in the Park

The Chaffee Art Center presents Art in the Park at Main Street Park in Rutland, featuring fine arts & crafts, demos, food, activities & music.


October: Dancing with the Rutland Stars

Watch professional dancers paired with local celebrities as they compete at The Paramount Theatre in Downtown Rutland.


For more information visit or call the Rutland Region Chamber of Commerce at (802)773-2747

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