Events Calendar

Events for any Bent

Presenting the Events of the Killington Valley

Tucked between Killington, Pico, Rutland, and Woodstock, the Red Clover Inn is the perfect home base from which to explore a wide range of events – from quirky to quintessential Vermont - all within a short drive. Food, fun, extreme sports, art, and everywhere in between; from inaugural events to annual classics, from intimate gatherings to all-out fests, in any season, the Red Clover staff will assist in finding an event that will become a memorable part of your stay. 

Pick your Vermont jaunt! For a comprehensive, searchable events database, please see Vermont’s statewide events calendar.

Here are just a few examples of the region’s premier annual events, listed chronologically. 

Killington Stage Race

Killington, Memorial Day Weekend

Fun for onlookers and racers alike! The Killington Stage Race is a series of three cycling races structured to cover a variety of terrain and distances, set against the lively Green Mountains.

Quechee Hot Air Balloon Festival

Quechee, Father’s Day weekend, Mid-June

Things are looking up… the skies over Quechee and the Upper Valley of Vermont and New Hampshire are filled with vibrant hot air balloons at the annual Quechee Hot Air Balloon, Craft & Music Festival, the longest running hot air balloon festival in New England.

Cooler in the Mountains Concert Series

Killington, Saturdays, Mid-July through Labor Day Weekend

Top names from the national music scene take the stage for seven free outdoor weekend shows. Grab a lawn chair and a beach blanket and head to the Snowshed Base Area for this family-friendly event produced by the Killington Pico Area Association and presented by Long Trail Brewing Company and Farrell Distributing.

Vermont JerkFest and Reggae Festival

Killington, late July/early August

Spice, music and food: catch the vibe at this Caribbean-style food festival held at Killington Resort. This family-friendly fest features Jamaican jerk hot food and the smooth sound of reggae music in the resort’s summer mountainside setting. The JerkFest will highlight spicy, locally and regionally-sourced specialty foods.

Art in the Park, Rutland

early August and early October

For more than 50 years, the Rutland area has come together to feature fine artists and crafters in this celebration of creativity, ingenuity, and design. Artists’ demonstrations, specialty food and beverages, children’s activities, live music, and performance art round out the events at Vermont’s longest-running outdoor art festival, held at the peak of the summer and autumn seasons.

Woodstock Winter Wassail Weekend

Woodstock, Mid-December

The traditional Wassail song begins, “Wassail! Wassail! All over town…” The picturesque town of Woodstock is the focus of Wassail Weekend, defined by twinkling lights and jingling sleigh bells, holiday stories, Yule logs, carols on The Green, lanterns, Santa’s Workshop, and house tours around the village green. Visit Woodstock during this magical weekend and enjoy a spicy, warming Wassail beverage while shopping; experience the holidays in 19th century Vermont at Billings Farm & Museum.