Past Events from September 17, 2023 – December 31, 2023 › Cities and Towns › Middlebury › – Happy Vermont

Vermont Events

The TAM Trek in Middlebury

Wright Park Seymour Street Extension, Middlebury, VT, United States

The TAM Trek is a trail race and fun run to help raise funds for the Trail Around Middlebury (TAM).  The event includes a 19-mile race, 10K and 5K races and fun runs for kids.  Register by Sept. 15. Most races start around 9 a.m....

Pop-Up Market and Free Concert in Middlebury

Triangle Park Main Street, Middlebury, VT, United States

Don't miss a pop-up artisan market at Triangle Park and the town green with vendors, prepared foods and crafts with a free concert by Mal Maiz at 11 a.m.

Middlebury Car Show & Fall Festival

Triangle Park Main Street, Middlebury, VT, United States

See more than 75 classic cars at the Middlebury Car Show & Fall Festival. The festival includes live music, more than 60 vendors, food, giveaways and more.

Spooktacular and Family Ghostly Gathering in Middlebury

Downtown Middlebury Main Street, Middlebury, VT, United States

Trick-or-Treat around downtown Middlebury from 3:30-5 p.m., then head over to the Town Hall Theater for crafts, a family dance and costume contest plus delicious food from Mexico in Vermont for sale from 5-7 p.m.

Holiday Bazaar in Middlebury

Congregational Church of Middlebury 30 North Pleasant Street, Middlebury, VT, United States

The annual Holiday Bazaar in Middlebury will feature a wide variety of gift and personal items, including crafts, fashion and fine jewelry, ties and scarfs, theme gift baskets books, toys, puzzles and games, household furnishings. There will also be a wide variety of indoor and...

Middlebury Maple Run: The Sweetest Half

Middlebury Maple Run South Street, Middlebury, VT, United States

The race includes a half-marathon, two-person relay, and three-mile fun run. One of New England's must-do road races, the Middlebury Maple Run: The Sweetest Half has earned a reputation as being well-organized and friendly. Enjoy a beautiful, scenic course that featuring vistas of the Green...

Middlebury Turkey Trot & Gobble Wobble

Middlebury Parks and Recreation 154 Creek Road, Middlebury, VT, United States

Middlebury Parks and Recreation hosts its 45th annual Turkey Trot & Gobble Wobble, featuring 5K and 10K races. Medals for winners and a raffle for all entrants will be offered. Bring two or more non-perishable food items to donate to the Addison County Food Shelf...

Santa Comes to Town in Middlebury

Town Hall Theater 68 S. Pleasant Street, Middlebury, VT, United States

Very Merry Middlebury 2023 kicks off with Santa’s arrival, horse and wagon rides, the hot cocoa hut and other festive activities in downtown Middlebury.

Astronomy Viewing Event in Otter Creek Gorge

Otter Creek Gorge Morgan Horse Farm Road, Weybridge, VT, United States

View the Geminids meteor shower—one of the largest meteor showers of the season with an average of 75 meteors per hour at their peak. Astronomers theorize that this shower will be particularly impactful due to its proximity to the new moon. Hosted by the Middlebury...

Winter Solstice celebration in Middlebury

Town Hall Theater 68 S. Pleasant Street, Middlebury, VT, United States

In the third annual solstice pageant, “A Winter’s Carol,” actors, dancers, puppets and revelers bearing lanterns will lead the audience in a ritual celebrating the shortest day of the year and the coming of the light. Free. For all ages. The event starts at Town...

Winter Solstice Party at Happy Valley Orchard in Middlebury

Happy Valley Orchard 217 Quarry Road, Middlebury, VT, United States

Celebrate the return of light at Happy Valley Orchard with Mountain Mac cider, pies, donuts, cookies and hot cider around the bonfire. Live music with the band Soulstice and a fiery performance with Cirque de Fuego. Free.

New Year’s Eve Fireworks and Ice Skating in Middlebury

Middlebury Rec Park 277 Mary Hogan Drive, Middlebury, VT, United States

Please join the Middlebury Parks and Recreation Department to bid farewell to 2023. Fireworks presented by the American Legion Post 27 will begin at 6:30 p.m. with free skating at the Memorial Sports Center immediately following at 7-8:30 p.m. Parking for the show will be...