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Addison County Annual Events 2020

For the true Vermont experience add an event to your itinerary! Find more details at

February 15-17 : Winterfest, Middlebury – a weekend of winter events for the whole family.

May 25 : Memorial Day Parade, Vergennes – remember our military and enjoy the parade.

June 28 : Foodaroo 5, Middlebury – featuring 30+ Vermont food and beverage all-stars, internationally acclaimed street performers, live music, King Arthur Flour baking contests, and surprises for all ages!

June 20 : Pocock Rocks Music Festival & Street Fair, Bristol – Bristol’s own block party featuring live music from well-known regional bands, microbrews, wine, hard ciders, and spirits, plus specialty foods, gifts and crafts.

July 4th : July 4th Celebration, Bristol – outhouse races, huge parade, vendors, crafts and great food.

July 12-19 : Festival on the Green, Middlebury – week-long family-friendly music festival supported by community donations and volunteers.

August 1 : Vermont Day at UVM Morgan Horse Farm, Weybridge – open house at Morgan Horse Farm

August 4-8 : Addison County Fair & Field Days, New Haven – rides, music, animals and great food.

August 22 : Vergennes Day, Vergennes – Pancake breakfast, 65+ crafters/vendors, horse drawn wagon rides, bandstand music, chicken BBQ, children’s venue, Rubber Duckie race.

September 19 : Eat on the Green – a sampling of foods from top area restaurants, live music, games for kids.

September 26 : Bristol Harvest Festival, Bristol – A full day of live music on the bandstand, activities for kids, pony rides, live demonstrations, crafters, vendors, and area non-profit organizations.

September 27 : Better L8 Than Never Car Show, Bristol – Cars, vendors, great food, live DJ, raffle drawings, piston toss, kids’ activities, bake sale and more. Fun for the whole family!

December 5 : Holiday Stroll, Vergennes – A full day of family-friendly holiday festivities throughout Vergennes.

December : Cool Yule, Bristol – Holiday celebration throughout December, including The Chocolate Walk and Lumen Celebration of Fire & Light, bazaars, concerts, activities and shopping.

December : Very Merry Middlebury, Middlebury – a whole month of holiday events.

Contact: For more details about these events and experiencing Middlebury and the region visit

Please confirm all dates with the organizer.


Rutland Region Events 2020

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 22 – Snow Sculpture Contest during Winter Fest
Main Street Park, corner of West Street and Route 7, Rutland, VT

February 18 – Rutland WinterFest Art Walk
Downtown Rutland, Center Street and Merchants Row, Rutland, VT 

February 18 – Center St. Night Sledding during Winter Fest
Center Street , Rutland, VT  

March – Middletown Springs 31st Annual Maple Festival
On the Green, Middletown Springs, VT  

March – Vermont Brewers Festival at Killington
 Killington Resort, 4763 Killington Road, Killington, VT 

May 23-25 – Killington Stage Race 2020
Town of Killington, Route 4 East, Killington, VT 

June 12-14 – Vermont Bike & Brew
Killington Bike Park, Killington Ski Area, Killington Road, Killington, VT

June 44th – Annual Middletown Springs Strawberry Festival
 Middletown Springs Historical Society, Park Ave.
Middletown Springs, VT 

July – Vermont Symphony Orchestra performs at Mountain Top Inn
The Mountain Top Inn, 195 Mountain Top Road, Chittenden, VT 

July 17-19 – 18th Annual Killington Wine Festival
Killington Resort, 4763 Killington Road, Killington, VT 

August 1Downtown Street Party
Downtown Rutland, Center Street and Merchants Row, Rutland, VT 

August – Vermont State Fair
 Vermont State Fairgrounds, 175 Main Street, Rutland, VT 

October 3-5 – 58th Annual Art in the Park
Main Street Park, corner of West Street and Route 7, Rutland, VT

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

Please confirm all dates with the organizer.