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Running trails in Middlebury, CT
Middlebury has 1 trail in the directory. They're ranked here by rating weighted by review volume, across 25 Google reviews. Filter by surface, loop, distance, shade or lighting to get to the run you're actually planning — no made-up difficulty score, just the facts you'd check before driving out.
No trails match those filters.
How to pick a trail in Middlebury
- Match the surface to your legs. Asphalt and concrete are fast, predictable and runnable year-round but the least forgiving; crushed limestone and dirt take the sting out of high mileage; boardwalk is flat and scenic but slick in the wet. If your shins or knees are complaining, the fix that actually works is varying the surface you run on rather than chasing one "best" one.
- Loop or out-and-back? A loop finishes back at the car with no backtracking; on an out-and-back you simply turn round at half your distance.
- Check the hours before a 6am run. Plenty of trails sit inside parks that gate at dusk and don't unlock until well after sunrise, so a trail that's perfect at lunchtime can be locked at 6am.
More on all of this in the trail-running guides.
Browse Middlebury trails by type
Running trails near Middlebury
Worth the short drive — the closest towns with trails in the directory.