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      Middlebury has one of the most unique small-town multi-use trail networks anywhere

      With the TAM (Trail Around Middlebury) encircling the whole town, it connects a number of multi-use trail areas together into one big trail network.

      In the network there is a good mix of trail styles - from smooth, easy trails suitable for a lazy Sunday afternoon stroll or suitably challenging trails for trail runners. For mountain bikers there is a good mix of fast and flowy, gnarly New England tech or great down-hill trails.

      Visit the websites and Facebook pages of the Middlebury Area Land Trust and the Addison Bike Club, linked below, to learn more about the unique partnerships that makes all of this possible.
      Disclaimer:
      Important: The trails of Middlebury are multi-use trails. Please show respect to all trail users. While mountain bikers are warmly welcomed on Middlebury trails, and have access to most of the trails, there are some trails that are limited to foot traffic only. Please respect these arrangements.
      Links

      Trail info last updated

      Activities Click to view
      Region Details
      • 5
      • 15
      • 26
      • 8

      Region Status
      Open as of Jun 25, 2026
      Local Trail Association

      Stats

      Avg Trail Rating
      Trails (view details)
      74
      Trails Mountain Bike
      54
      Trails Gravel Bike
      10
      Trails Adaptive Bike
      4
      Trails Winter Fat Bike
      17
      Trails Hike
      72
      Trails Trail Running
      72
      Trails Snowshoe
      14
      Total Distance
      31 miles
      Total Descent Distance
      14 miles
      Total Descent
      3,700 ft
      Total Vertical
      517 ft
      Highest Trailhead
      798 ft
      Reports
      353
      Photos
      17
      Completed Counter
      5,380

      Sub Regions

      Popular Middlebury Mountain Biking Trails

      • 95 ★ 0.0 • 659 ft • 13 ft • 166 •
      Popular blue difficulty singletrack. This multi-use trail can be used both directions and has a moderate overall physical rating with a 13 ft blue climb. Trail visibility is always easy to follow. On average it takes minutes to complete this trail.
      • 100 ★ 4.5 • 531 ft • 33 ft • 161 •
      Popular blue difficulty singletrack. This multi-use trail can be used both directions with a 33 ft blue climb. Trail visibility is always easy to follow. On average it takes minutes to complete this trail.
      • 85 ★ 0.0 • 3,619 ft • 28 ft • 154 •
      Popular green difficulty singletrack. This multi-use trail can be used both directions and has a easy overall physical rating with a 28 ft green climb. Trail visibility is always easy to follow. On average it takes 12 minutes to complete this trail.
      • 95 ★ 3.5 • 3,278 ft • 2 ft • 140 •
      Middlebury's Premiere "Must Ride" Trail
      • 100 ★ 2.5 • 4,400 ft • 254 ft • 133 •
      Though people ride this trail Downhill, we prefer to use it as a climber. Be aware as you ascend the trail. There are some blind high speed corners.
      • 75 ★ 5.0 • 4,928 ft • 0 ft • 132 •
      Sidewinder is part of the TAM trail system. It starts off the top of Chipman and is quite steep and high speed. Be on alert for hikers as this is a popular hiking trail. After you come off the hill the trail mellows out and has some fun...
      • 70 ★ 0.0 • 1 mile • 43 ft • 130 •
      Popular green difficulty family friendly gravel path. This multi-use trail can be used both directions and has a easy overall physical rating with a 43 ft green climb. Trail visibility is always easy to follow. On average it takes 6 minutes to complete this trail.
      BW2
      • 85 ★ 0.0 • 482 ft • 5 ft • 129 •
      Popular blue difficulty singletrack. This multi-use trail can be used both directions and has a moderate overall physical rating with a 5 ft blue climb. Trail visibility is always easy to follow. On average it takes minutes to complete this trail.

      Recent Ride Log Activity in Region

      Today

      • 0 rides

      Yesterday

      • 0 rides
      Past Week
      • 7 rides

      Photos of Middlebury Mountain Bike

      mtb
      56 |
      Jul 17, 2026 @ 4:41am
      Jul 17, 2026
      mtb
      92 |
      Feb 13, 2025 @ 3:07am
      Feb 13, 2025
      mtb
      111 |
      Feb 13, 2025 @ 3:04am
      Feb 13, 2025
      mtb
      144 |
      Oct 22, 2023 @ 12:13pm
      Oct 22, 2023
      mtb
      66 |
      Aug 6, 2023 @ 10:56am
      Aug 6, 2023
      mtb
      242 |
      Apr 3, 2022 @ 10:18am
      Apr 3, 2022
      mtb
      424 |
      Jul 29, 2006 @ 10:13am
      Jul 29, 2006
      mtb
      584 |
      Jul 29, 2006 @ 10:13am
      Jul 29, 2006
      mtb
      464 |
      Oct 28, 2013 @ 4:01pm
      Oct 28, 2013
      report
      mtb
      45 |
      Jun 25, 2026 @ 2:33pm
      Jun 25, 2026
      report
      mtb
      43 |
      Jun 25, 2026 @ 2:27pm
      Jun 25, 2026
      report
      mtb
      55 |
      Jun 19, 2026 @ 11:19am
      Jun 19, 2026

      Videos of Middlebury Mountain Bike

      chipman
      mtb
      0:09 | 112 | Nov 6, 2013
      chipman
      mtb
      0:15 | 142 | Nov 6, 2013
      committed back yard
      mtb
      3:58 | 261 | Oct 11, 2010

      Recent Trail Reports

      statustraildateconditioninfouser
      Super Seven
      Jun 25, 2026 @ 5:24pm (America/New_York)
      Jun 25, 2026
      Ideal Big ash tree down across trail, blocking...htfmybackyard
      Chipman Road
      Jun 8, 2026 @ 1:58pm (America/New_York)
      Jun 8, 2026
      DryRoad/Trail conditions nominal.PETER7c4Enp
      East Coast
      May 19, 2026 @ 7:37am (America/Denver)
      May 19, 2026
      IdealVTtrailbuilder Sugarbush
      TAM Trail- Chipman Access
      May 12, 2025 @ 9:18am
      May 12, 2025
      Wettao-of-clen
      Sidewinder
      May 12, 2025 @ 9:18am
      May 12, 2025
      Variabletao-of-clen
      Sidewinder
      May 12, 2025 @ 9:18am
      May 12, 2025
      Variabletao-of-clen
      Old Pine
      May 12, 2025 @ 9:18am
      May 12, 2025
      Idealtao-of-clen
      Lower Bittersweet
      May 12, 2025 @ 9:18am
      May 12, 2025
      VariableCouple of muddy spots. Tree limb down...tao-of-clen
      The Wall
      May 12, 2025 @ 9:18am
      May 12, 2025
      VariableCouple muddy spots and water running downtao-of-clen
      Rabbit Hole
      May 12, 2025 @ 9:18am
      May 12, 2025
      Variabletao-of-clen

      Activity Feed

      usernameactiontypetitledate
      pauldwGJI1Awishlistregionactivity #101271399
      Aug 11, 2026 @ 4:06pm
      Aug 11, 2026
      stevefromBurlyaddphotoactivity #99364304
      Jul 17, 2026 @ 4:41am
      Jul 17, 2026
      wymaniiwishlistregionactivity #98319888
      Jul 3, 2026 @ 2:10am
      Jul 3, 2026
      htfmybackyardaddreportactivity #97793451
      Jun 25, 2026 @ 2:27pm
      Jun 25, 2026
      esbeebuhlwishlistregionactivity #97642282
      Jun 23, 2026 @ 11:44am
      Jun 23, 2026

      Recent Comments

      usernametypetitlecommentdate
      ricracktrailSafety BreakBlocked
      Jul 19, 2024 @ 3:38pm
      Jul 19, 2024
      Tintin918trailSuper SevenRiding pretty well. Tree diwn across trail...
      Jul 16, 2024 @ 6:26am
      Jul 16, 2024
      DryanptatrailMegaWattI think maybe it's supposed to be XC
      Jun 22, 2023 @ 4:10am
      Jun 22, 2023
      jbehounektrailWright Park - TAMRode this on my gravel bike and it was in good...
      Sep 7, 2020 @ 6:41pm
      Sep 7, 2020
      stevefromBurlytrailMegaWattwhat is "technical XS"?
      Aug 5, 2020 @ 1:15am
      Aug 5, 2020

      Local Badges


      Activity Type Stats

      activitytypetrailsdistancedescentdescent distancetotal verticalratingglobal rankstate rankphotosreportsroutesactivity logs
      Mountain Bike5421 miles2,995 ft10 miles512 ft
      #4,357#33173534,066
      Gravel Bike109 miles571 ft4 miles509 ft
      #2,629#1429125
      Adaptive Bike42 miles144 ft3,468 ft85 ft
      #5,270#3226
      Winter Fat Bike1710 miles1,867 ft5 miles492 ft
      #2,188#17301
      Hike7230 miles3,432 ft13 miles518 ft
      #5,594#27349130
      Trail Running7230 miles3,432 ft13 miles518 ft
      #4,869#24349309
      Snowshoe146 miles663 ft2 miles187 ft
      #1,087#321409

      Frequently Asked Questions

      ▼ What are the best places to ride in Middlebury?
      Middlebury has 6 areas to explore for mountain biking. The top rated areas are:
      ▼ What are the highest rated mountain biking trails in Middlebury?
      The highest rated mountain biking trails in Middlebury are: View all mountain biking trails sorted by rating.
      ▼ What is the best time of the year to ride in Middlebury?
      Based on activity log data, the most popular months to ride in Middlebury are:
      • September (84 activities)
      • August (69 activities)
      • October (59 activities)
      Check the Middlebury reports page for current trail conditions, recent trail reports, and seasonal information from the local community.
      ▼ Where can I park to ride in Middlebury?
      There are 9 parking locations listed in Middlebury. The most popular parking spots are: View all parking and trailhead locations on the map to plan your visit.
      ▼ What is the longest trail in Middlebury?
      The longest trail in Middlebury is Wright Park - TAM at 1.6 miles. View all trails sorted by distance.
      ▼ What are the best & highest rated hiking trails in Middlebury?
      ▼ What are the best & highest rated trail running trails in Middlebury?
      ▼ How many trails are in Middlebury?
      Middlebury has a total of 74 trails. Of those, 54 are designated for mountain biking. Browse top mountain biking trails in Middlebury to find detailed information including difficulty ratings, distances, and trail conditions.
      ▼ Which trail has the most elevation gain in Middlebury?
      The trail with the most elevation gain in Middlebury is Super Seven with 254 ft of elevation gain. View all trails sorted by elevation gain.
      ▼ Which trail has the most elevation descent in Middlebury?
      The trail with the most elevation descent in Middlebury is Sidewinder with 320 ft of elevation descent. View all trails sorted by elevation descent.
      ▼ What activities are most popular in Middlebury?
      Middlebury supports the following activities: Mountain Biking, Gravel Biking, Adaptive Biking, Winter Fat Biking, Hiking, Trail Running, Snowshoeing.
      ▼ What bike services are there in Middlebury?
      The following bike services are available in Middlebury:
      • Bike Shop (2)
      • Trail Association (1)
      • Land Managers (1)
      Browse the full Middlebury directory for details.
      ▼ What are the steepest mountain biking trails in Middlebury?
      The steepest mountain biking trail in Middlebury is Sidewinder with an average grade of 6.2%. View all trails sorted by grade.
      ▼ Are the trails open in Middlebury?
      The overall region status for Middlebury is Clear / Green. Out of 53 trails:
      • Clear / Green: 43
      • Minor Issue / Yellow: 7
      • Significant Issue / Amber: 2
      • Closed: 1
      View the full trail status page for the latest updates.
      ▼ What type of bike is most common in Middlebury?
      Based on activity log data, the most common bike types used in Middlebury are:
      • XC (6 activities)
      • AM (5 activities)
      Check the Middlebury activity logs for more details.
      ▼ What are the most popular Strava Segments in Middlebury?
      The most popular Strava segments in Middlebury are:
      • Rehab (Before Exit) (510 athletes)
      • Sidewinder DH (464 athletes)
      • Early exit, eh? (454 athletes)
      View all Strava segments in Middlebury.
      ▼ What are some popular technical trail features in Middlebury?
      There are 5 technical trail features (TTFs) in Middlebury. Some popular features include: View all technical trail features in Middlebury.
      ▼ What trails are closed in Middlebury?
      There are currently 1 closed trails in Middlebury. The breakdown of all trail statuses is:
      • Clear / Green: 43
      • Minor Issue / Yellow: 7
      • Significant Issue / Amber: 2
      • Closed: 1
      View all closed trails for the latest updates.
      ▼ Are there accessible or adaptive trails in Middlebury?
      Yes, there are 4 accessible/adaptive trails in Middlebury. View all adaptive trails in Middlebury for specific accessibility information.
      ▼ Are there local clubs or events in Middlebury?
      There are 1 local clubs or associations listed in the Middlebury directory. Browse the local directory for details.
      ▼ What are the most popular mountain biking trails in Middlebury?
      ▼ What are the best beginner ride trails in Middlebury?
      The best beginner mountain biking trails in Middlebury are: View all beginner mountain biking trails in Middlebury.
      • By WillieJacobszTF Pro Trailforks SBP SWW & contributors
      • Admins: VMBA, Velomont, Jwduston, ACBC
      • #13074 - 12,823 views

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