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Logo for Robert Frost Mountain Cabins featuring stylized mountains and a cabin.
October 2026

Oct

11

Sunday, October 11 @ 8:00 AM to 1:00 PM

Ripton Ridge Run

Location: Former Ripton Elementary School, Ripton, VT
A mixture of trail, paved and dirt roads. ✨ Special Offer: Chris and Jaime provide complementary bibs to staying guests!
Three women wearing matching black t-shirts that say "RIPTON Vermont" pose together outdoors.

Oct

11

Sunday, October 11 @ 10:00 AM to 4:00 PM

Middlebury Car Show & Fall Festival

Location: Main Street, Middlebury, VT
75 classic cars and trucks on Main Street plus food trucks and live music.

Oct

18

Sunday, October 18 @ 9:00 AM to 2:00 PM

Middlebury Maple Run

Location: Middlebury, VT
USATF-certified event with scenic views of the Green Mountains and Adirondacks.
A lush green field with runners in the foreground, surrounded by mountains and rustic barns under a cloudy sky.

Oct

25

Sunday, October 25 @ 11:00 AM to 1:00 PM

SPOOKTACULAR

Location: Main Street, Middlebury, VT
The family friendly Trick-or-Treating Parade taking over Main Street Middlebury.
Logo featuring a green-faced witch with a black hat, surrounded by the words "Middlebury Spooktacular."
November 2026

Nov

6

11/6/2026, 5:00 PM to 11/6/2026, 9:00 PM

First Fridays

Location: Downtown Middlebury, VT
Middlebury businesses extend their normal hours for the first Friday of every month to provide visitors and locals alike a chance to experience more of our town later into the evening.
Aerial view of a snow-covered town at dusk, illuminated by streetlights and featuring a prominent church.

Nov

7

Saturday, November 7 @ 9:00 AM to 12:00 PM

Middlebury Farmer’s Market

Location: Middlebury VFW Post, 530 Exchange Street, Middlebury, VT
This year-round market is a weekly celebration of community, connection and the incredible bounty of Vermont’s farms and homesteads. Every Saturday from 9:00 to 12:00 at the Middlebury VFW Post at 530 Exchange Street, weather permitting MFM is outdoo… Read more
December 2026

Dec

4

12/4/2026, 5:00 PM to 12/4/2026, 9:00 PM

First Fridays

Location: Downtown Middlebury, VT
Middlebury businesses extend their normal hours for the first Friday of every month to provide visitors and locals alike a chance to experience more of our town later into the evening.
Aerial view of a snow-covered town at dusk, illuminated by streetlights and featuring a prominent church.

Dec

5

Saturday, December 5 @ 9:00 AM to 12:00 PM

Middlebury Farmer’s Market

Location: Middlebury VFW Post, 530 Exchange Street, Middlebury, VT
This year-round market is a weekly celebration of community, connection and the incredible bounty of Vermont’s farms and homesteads. Every Saturday from 9:00 to 12:00 at the Middlebury VFW Post at 530 Exchange Street, weather permitting MFM is outdoo… Read more

Dec

31

12/31/2026, 6:00 PM to 12/31/2026, 11:59 PM

NYE Fireworks & Public Skating

Location: Middlebury, VT
Celebrate New Year's Eve with fireworks and free skating in Middlebury.
Text reading "Happy New Year" written in snow.