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  • Distance: 37.8 km from Pittsfield
    Sun, Sep 20, 2026 at 7:30 AM

    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!

    See full details
    2 Miles5k10k19 MilesFun RunRunTrailWalk via RunSignup
  • Distance: 47.1 km from Pittsfield
    Sun, Sep 27, 2026 at 6:00 AM

    33 Years of Supporting Vermont Adaptive

    The Vermont 50 is an annual race held during the last weekend of September at Ascutney Outdoors in West Windsor, Vermont. All benefits go to Vermont Adaptive Ski and Sports. A wonderful place where youth and adults with disabilities gain a measure of self confidence and independence by participating in adaptive sports programs and activities year-round.

    Since 1993 the Vermont 50 has been a destination for mountain bikers and ultra runners to enjoy a challenging and scenic Vermont landscape course that is like no other. There is something for everyone. We offer the Vermont 50 mile Mountain Bike Race, Womens 2-person Bike Relay, Over 60 2-person Bike Relay, 50 mile Ultra Run, 50K Endurance Run, 2-3 Person 50 mile Run Team Relay and the Kids Fun Runs and Bike Rides.

    NOTE-This race does NOT allow E-Bikes.

    We are a family friendly event offering lots of kid centered activities such as the Hay Bale Treasure Hunt, The Fun Runs and Rides, clowns, face painting and more! Join us and find out why the Vermont 50 has become so popular. (Subject to change as COVID-19 rules and regulations apply.)

    Spots fill-up quickly so early registration is a must!

    See full details
    50k50 MilesFun RunRunUltra via RunSignup
  • Distance: 49.8 km from Pittsfield
    Sat, Oct 10, 2026 at 9:00 AM

    Downriver Rail Run

    10K Point to Point downhill run along the shores of Mascoma Lake and the Mascoma River on the Northern Rail Trail. Lovely and fast and no vehicles to mess with. Part of the Upper Valley Running Series

    10kRunTrail via RaceRoster
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