Want to get a taste of Vermont life during your next vacation? Whether you’re sipping freshly pressed cider on a small town green or joining the crowds at a state fair, local communities and inquisitive visitors unite at these special events in Rutland County.

11 Can’t-Miss Special Events in Rutland County, Vermont

Families sledding down Center St. in Rutland, VT during Winter Fest.

Spring and Summer Events: From Maple Season to July Fireworks

Poultney Maplefest (Poultney, VT)

Once the calendar flips to March, it’s full steam ahead for maple sugaring season in Vermont. Partake in a town-wide celebration of everyone’s favorite pancake companion at the annual Poultney Maplefest, complete with sugarhouse tours, a craft fair, and tree tapping competitions.  

Middletown Springs Strawberry Festival (Middletown Springs, VT)

Dig your fork into the tastiest strawberry shortcake in Rutland County at the Middletown Springs Strawberry Festival. For over 40 years, strawberry lovers have convened at the Historical Society on the Green for this free event, paired perfectly with live music and handmade goods from local artisans.

Basin Bluegrass Festival (Brandon, VT)

For one weekend every summer, the Basin Bluegrass Festival becomes the soundtrack to Vermont’s rolling green mountains. The three-day festival caters to classic country and bluegrass fans, with food and craft vendors on site. Stop by for a day or claim a camping spot and weekend pass for the full experience.

Killington Wine Festival (Killington, VT)

Combine premium wines, live music, mouthwatering food, and some of Rutland County’s most beautiful scenery, and you’ve got yourself the perfect summer setting. That’s just a day in the life during the Killington Wine Festival, where wining and dining is encouraged all weekend long. You’ll cross paths with a selection for every palate, whether you prefer sticking local with Vermont-made wines or exploring options from the likes of Spain, Japan, or Argentina.

Vermont State Fair (Rutland, VT)

You may be used to fried dough with cinnamon and sugar, but around here it’s all about the maple cream. Proudly held in Rutland every summer, you’ll find all the fair staples from farm animals and agricultural demonstrations to carnival rides and demolition derbies at the Vermont State Fair.

Brandon Independence Day Celebration (Brandon, VT)

Kick your typical Fourth of July weekend up a notch at the Brandon Independence Day Celebration. In addition to a much anticipated parade and fireworks display, the town hosts street dances, silent auctions, games, and live music.

Fall and Winter Events: Foliage, Costumes, and Holiday Spirit

Summer and Fall Art in the Park (Rutland, VT)

One of the most favored special events in Rutland County puts local artisans front and center. Happening twice a year at the Chaffee Art Center, Rutland’s Summer and Fall Art in the Park event is the place to pick up one-of-a-kind, Vermont-made goods.

Annual Rutland Halloween Parade (Rutland, VT)

Do you spend the year patiently awaiting the season of jack-o’-lanterns and creative costumes? Don’t miss the Annual Halloween Parade in Downtown Rutland, featuring over 100 floats and plenty of spooky spirit to go around.

Mount Holly Cider Days (Mount Holly, VT)

Whether you prefer your cider chilled or hot, get your fill straight from the source during the annual Mount Holly Cider Days. A century-old press is the star of the event, giving spectators a look at the cider making process from start to finish.

Two men demonstrating cider making at the Mount Holly CIder Days.

Vermont Holiday Festival (Killington, VT)

Around here, getting into the holiday spirit is all about sleigh rides, Santa’s Workshop, and the Festival of Trees. The Vermont Holiday Festival held at the Killington Grand Resort Hotel is a surefire way to add even more enchantment to the most wonderful time of the year.

Winter Fest (Rutland, VT)

While many flock to the ski slopes come snowfall, for one week of the season Downtown Rutland transforms into a winter recreation wonderland all its own. Snow sculpture contests, chilli cookoffs, art walks, and sledding down Center Street all headline the family-friendly Winter Fest.

These seasonal special events in Rutland County just skim the surface of fun things to do in the area. For more recommendations, connect with the community online at RealRutland.com or through #RealRutland on social media.