Find the top rated running trails in Dedham, whether you're looking for an easy short running trail or a long running trail, you'll find what you're looking for. Click on a running trail below to find trail descriptions, trail maps, photos, and reviews.
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I rode this trail in Sept 2024 before I knew it existed. I left a review on the HTT. SUPER connector trail between two great 5 star trails. I rode it on a weekday in late July 2025 and never saw a soul but I did see some wildlife.
I rate this 5 stars!
Traveling cyclist
Facebook
Wonderful trail. The bridge is amazing. Make sure you ride it at night when it's lit up!
Since I was traveling through the area on my way back to Ohio, I made a point of seeing the bridge with its fancy artwork. It was worth it. Weather didn't allow me to do much more than Madrid to Woodward and back. The cement trail was wide and clean. The bridge was great. There are informational signs before and on the bridge. After dark (and a rainstorm) I went from the trail parking lot in Madrid to across the bridge, to the viewing area and back. The 30 mph winds made it very breezy while on the bridge, but the lights made it so cool. I would encourage others to see it in daylight and again when the lights are on.
Ok section, kind of dull. Agriculture & cows. Found a bit of shade by a grain elevator for lunch. Several washouts filled with tumbleweeds as you get closer to Lind.
The Woodward-to-Perry Connector in the High Trestle Trail was long planned, requiring new bridges, land acquisition/donation and careful design. The result is spectacular. I rode this today on a cool Autumn day through harvested farm fields and along streams. The views are superb. The trail surface (paved concrete) is top notch. It crosses a few well-marked country roads but otherwise is a dedicated nature trail for hiking and biking. The entire route from Woodward to Perry is separated path except for two blocks of residential side street in Bouton. Although brand new, this trail is seeing use: groups of cyclists went by; numerous hikers and runners were out; and small kids on bikes near Perry were using it. It exits into residential streets in Perry that are well signposted to guide one to downtown or to the other trails beginning in Perry. Hats off to the County board of supervisors and the numerous volunteers and donors who made this happen.
We started in Akron and rode about 18 miles north. Loved it!!!
I rode from 1st street in Ankeny north to Slater then west to just outside of Perry. The map shows it is broken just west of Woodward but it in fact continues into Perry. I think it’s the HT Trail to Raccoon RV trail but there is not a map for that one. Definitely a 5 star trail! Traveling cyclist Facebook
I have ridden this trail on numerous occasions though I have not seen the bridge lit up at night. There is another reason to return to this fantastic trail! 5 stars from this rider. Traveling cyclist Facebook
A mile or so south of Lake View the trail is closed for another mile. Not to worry. You can take the highway south just short of the RR tracks, and take the gravel road to the end. The trail starts up again there.
A friend and I from Virginia stopped to do the High Trestle Trail in mid July on our way to South Dakota and enjoyed it very much. Very unique, beautiful area and the other bicyclists were very friendly. We stopped at the Flat Tire for a snack and my friend had a beer. Trail surface was clean. It was a great way to break up our long drive.
Seb
We ( recumbent trike & e-bike) headed West from the Kiwanis park. Turned around after 9km as the surface was really tough on the trike. There’s 2 good wheel tracks for bikes, but the trike had to ride partially in the coarse trail ballast. Scenic area with farm views and a huge windmill farm in the distance.
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