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

Sep

3

Thursday, September 3 @ 3:00 PM to 7:00 PM

Midd Summer Market

Location: Triangle Park, Middlebury, VT
Every Thursday between May 23 and Sept 19 from 3:00 PM to 7:00 PM the Midd Summer Market will feature local artisans, food vendors and farms stands at Triangle Park in Middlebury. Live music and great vibes!
Aerial view of a small town with a church, green spaces, and a market area surrounded by hills.

Sep

4

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

Sep

5

Saturday, September 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

Sep

12

Saturday, September 12 @ 8:00 AM to 5:00 PM

Kelly Brush Ride

Location: Middlebury College, Middlebury, VT
Traverse the beautiful Champlain Valley by bike on one of six different routes ending at Middlebury College.
A person in a helmet stands beside a bicycle, overlooking a green field and distant mountains under a clear blue sky.

Sep

19

Saturday, September 19 @ 8:00 AM to 4:00 PM

Tour De Farms

Location: Addison County, VT
A fun way to visit local food producers by bike while enjoying panoramic views and iconic covered bridges.
A cartoon cow wearing sunglasses and a helmet is riding a bicycle energetically.
October 2026

Oct

2

10/2/2026, 5:00 PM to 10/2/2026, 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.

Oct

3

Saturday, October 3 @ 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

Oct

3

10/3/2026, 10:00 AM to 10/4/2026, 5:00 PM

Fall Open Studio Weekend

Location: Various Local Studios, VT
The unique opportunity to meet local artists in their studios during the beautiful Vermont fall.
A mailbox displaying an "Open Studio" sign stands in front of a unique, multi-level building surrounded by greenery.

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.