3 running, cycling, and fun run events in Middlebury, Vermont

From big races to Saturday morning group runs—find running, cycling, and fun run events and connect with the local endurance sports community.

• ACORN's Tour de Farms [acornvt.org] [Register at runsignup.com]
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  Sat, Sep 19, 2026 at 8:30 AM

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  Join us for our second Tour de Farms in and around Middlebury, this year with a family-friendly route! Enjoy panoramic views and beautiful back roads as you visit local farms in Middlebury,...

  Join us for our second Tour de Farms in and around Middlebury, this year with a family-friendly route! Enjoy panoramic views and beautiful back roads as you visit local farms in Middlebury, Weybridge, Cornwall, and Salisbury, Vermont. This scenic ride features several relaxed farm stops with multiple food producers who will offer you a taste of all the Champlain Valley has to offer! All samples are included in the ride, but cash is handy in case you'd like to purchase products along the way. Don't worry about carrying all of your goodies on the bike; we'll have a farm van to pick up your purchases and deliver them to the finish for you!

  Much of the course is along dirt and/or gravel roads, so grab your gravel grinder or your mountain bike. If you've got a road bike, consider putting wider tires on it for this ride. It'll be worth it! E-bikes are welcome and encouraged as a comfortable option. Many Vermont libraries offer free E-bike rentals, and our local bike shop and tour sponsor, Frog Hollow Bikes, has a great rental fleet.

  Commemorative t-shirts and bike jerseys are available for pre-sale!

  There will be a rolling start time for all ride distances. 37 Mile riders will begin between 9:00 and 9:30 am, plan to check in between 8:30 am and 9:30 am. 8 Mile riders will begin between 10:00 and 10:30 am, and plan to check in between 8:30 am and 9:30 am. Inexperienced and slower riders should plan to leave as close to 9 am as possible to ensure they complete the route, which is a little longer than in previous years. We will send off several different waves of riders, so don't feel like you have to be first in line. Waves prevent farm stops from becoming overwhelmed and ensure proper road safety.

  100% of the proceeds from the Tour fund our work at ACORN and directly support our local foodshed. Given the importance of this ride to our work with farmers and food producers in the Champlain Valley, we invite riders to fundraise or make an additional donation. This is in an effort to lean on our committed local network of supporters during this time of uncertain funding.

  No One Turned Away for Lack of Funds. Please get in touch with us if you’d like a scholarship or to purchase a ticket on a sliding scale: info@acornvt.org.

  8 Miles 40 Miles Cycling Gravel

  616 Exchange St, Middlebury, Vermont, 05753, United States
  OpenStreetMap Google Maps
• TAM Trek [maltvt.org] [Register at runsignup.com]
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  Sun, Sep 20, 2026 at 7:30 AM

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  The TAM Trek is a trail race and fun run to raise money for the Trail Around Middlebury (TAM) in Middlebury, VT. This trail is a19-mile long footpath, encircling the village of Middlebury and linking...

  The TAM Trek is a trail race and fun run to raise money for the Trail Around Middlebury (TAM) in Middlebury, VT. This trail is a19-mile long footpath, encircling the village of Middlebury and linking several hundred acres of town land, conserved properties, schools, and other local landmarks. All distances start and finish at Wright Park in Middlebury, Vermont.

  The 19 mile race course travels the entire TAM through the towns of Middlebury, Cornwall, New Haven, and Weybridge, VT. The trail is scenic, rolling, and includes incredible views of the Green Mountains to the east and the Adirondacks to the west. 19-mile race departs at 7:30 AM.

  The 10K course is entirely on single-track trail through Wright Park and the Otter Creek Gorge Loop (trail maps available at www.maltvt.org), with around 400 feet of elevation gain and several fairly technical sections. 10k race departs at 9 AM.

  The 5K course is a challenging combination of wide and single track trail. It takes place entirely in Wright Park, looping from the southern entrance to Belden Falls and back. 5k race departs at 9:15 AM.

  The 2 mile fun run is family-friendly and includes walkers and runners alike. The course follows Otter Creek and is entirely on trail. It highlights the best parts of Wright Park and is popular for families with young children and those who enjoy walking. We welcome dogs on leash! YOUTH AGES 12 AND UNDER ARE FREE. Fun run departs at 9:30 AM.

  GPS link to race start/finish.

  Course map

  Day of registration is available beginning 45 minutes before each race start. Please bring a check or exact change for the quickest experience!

  Day of pricing is $70 for 19-mile, $55 for 10k, $40 for 5k and $25 for fun run. Free for kids 12 and under!

  2 Miles 5k 10k 19 Miles Fun Run Run Trail Walk

  Seymour St Ext, Middlebury, Vermont, 05753, United States
  OpenStreetMap Google Maps

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