Past Events from September 24, 2022 – May 16, 2025 › Rutland County › – Happy Vermont

Vermont Events

Recurring

Rutland Winterfest

Downtown Rutland Center Street & Merchants Row, Rutland, VT, United States

Rutland Winterfest is back and bigger than ever! From February 14 to 22, Rutland will transform into a winter wonderland filled with fun, adventure and community spirit. Celebrate the start of Winterfest on Feb. 14 with dazzling downtown ice sculptures and festive activities at local...

Winter Group Hike in Poultney

East Poultney Church Parking Lot 1500 East Main Street, Poultney, VT, United States

Ready to explore the beauty of winter?  Slate Valley Trail volunteers are leading a series of fun, guided hikes to showcase different trails this winter. It’s the perfect chance to discover the trails, make friends and enjoy the comfort of hiking in a group. This...

Rutland Cold Rolled Fatbike Festival

Giorgetti Athletic Complex Oak St Ext, Rutland, VT, United States

The Rutland Cold Rolled Fatbike Festival is back for 2025. Fatbikers from around New England and New York gather in Rutland for  group rides, demos, and hearty brews around warm fires. Check mtbvt.com for tickets and updates. Presented by Fiddlehead Brewing, and hosted by Mountain Bike Vermont and Pine...

Middletown Springs Maple Festival

Middletown Springs Historical Society 4 Park Avenue, Middletown Springs, VT, United States

Don't miss the Middletown Springs Maple Festival! The 2025 Middletown Springs Maple Festival will feature a maple sugaring demonstration, maple vendors, exhibits and talks on the history of maple sugaring, music and homemade lunch selections and maple desserts. All proceeds from the Maple Festival and...

Poultney MapleFest

Poultney MapleFest 188 Main Street, Poultney, VT, United States

The Poultney MapleFest is an annual celebration of Vermont's maple heritage, bringing together the community to indulge in the sweet flavors of the region. This event showcases the best of Vermont—sugarhouses, a tree tapping, food, the Fifth Season Ride, family activities, and more. Find a...

Analog Cycles’ Fifth Season Ride and Race

Poultney Poultney, VT, United States

Analog Cycles' Fifth Season Ride and Race in Poultney is a feast of mud, slush and maple syrup. What better way to spend a day than trudging up snow covered dirt roads and hanging out in steaming sugar shacks?  The Fifth Season Ride and Race...

Winter Group Hike in Poultney

Fairgrounds Trailhead 131 Town Farm Road, Poultney, VT, United States

Ready to explore the beauty of winter?  Slate Valley Trail volunteers are leading a series of fun, guided hikes to showcase different trails this winter. It’s the perfect chance to discover the trails, make friends and enjoy the comfort of hiking in a group. This...

Recurring

Maple Open House Weekend at Baird Farm

Baird Farm 65 West Road, North Chittenden, VT, United States

Baird Farm in Chittenden invites you to enjoy sugarhouse tours, tastings, boiling (weather permitting), rosemary waffles, giveaways, outdoor maple activities and more. Tree tapping at 1 p.m. on both days. -Courtesy photo / Vermont Tourism 

Jukebox: Heavy Metal Strings in Rutland

The Paramount Theatre 30 Centre Street, Rutland, VT, United States

The Paramount Theatre and the Vermont Symphony Orchestra turn it up to 11 as the Jukebox quartet plugs in and goes electric for a rock and roll inspired show. Rock out to classics by Van Halen, Led Zeppelin, Tool and others, and also dig into...

$35

Pond Skimming at Killington

Killington Killington Road, Killington, VT, United States

Killington's annual Pond Skimming Competition returns! Watch this annual rite of spring featuring 100 skiers and snowboarders who will attempt to make their way across a pond. The Killington Pond Skimming awards ceremony will take place outside on the K-1 Lodge patio at 2 p.m. Registration...

Witches Walk – Creepy Crawl in Brandon

Downtown Brandon Park Street, Brandon, VT, United States

Join the Witches Walk and Creepy Crawl in Brandon, an evening of spookiness, music, food and more. Witches Walk is a celebration of witches, costumes and fun for everyone. Come dressed as a witch, warlock, a ghost, creepy ghoul or clown, or a superhero!...be creative...

$10.00

Spring Fling at Pittsford Village Farm

Pittsford Village Farm 42 Elm Street, Pittsford, VT, United States

Celebrate the season with games and activities at Spring Fling at Pittsford Village Farm. Enjoy treats and drinks, music and nature crafts. This event is co-hosted by Maclure Library and Pittsford Village Farm and is free and open to everyone. Pittsford Village Farm sits on...