Find the top rated mountain biking trails in Brookline, whether you're looking for an easy short mountain biking trail or a long mountain biking trail, you'll find what you're looking for. Click on a mountain biking trail below to find trail descriptions, trail maps, photos, and reviews.
















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As of June 1, 2026, the first half of this trail starting in Bedford, MA is nice, but due to construction, it stops about halfway - I believe somewhere in Lexington. You can choose to exit the trail and go onto Massachusetts Avenue to ride in the bike lane, but that involves riding right alongside traffic and can be very stressful and dangerous. My husband and I did this today and I don't think I will do this again. At any point, someone in a parked car adjacent to where you are riding can open up their door right into you. Also, the bike lane often shares a lane with cars and is pretty scary for people not used to this. I hope the rest of the Minuteman bike path opens up to bikers again soon!
There's another couple of miles of mostly paved trail that goes beyond the parking lot in Lebanon. That's an excellent section of the trail. It took us all the way to Glen Road in West Lebanon.
I parked at the Delta Dental stadium and proceeded south in this trail. I was alone. I saw some unhoused people’s tents by the water. At first I felt fine, I saw another woman walking her dog, but there wee very few people on the path. The a person passed me on a bike and then circled back to me, following me. I felt unsafe. I wanted to keep going, but it was clear to me this person would following me. I had to quickly retreat to my car. I don’t usually feel vulnerable, and I was terrified. Later I told a local friend about my experience and she told me that recently a person had abandoned their baby on this trail, aka it’s not a safe place to walk by yourself, especially as a wow man.
Lot's of stops along the way to enjoy the sites. It's a very well maintained small trail
I'd ridden this trail a couple years ago, doing it in small sections, and had found it to be a nice ride with a decent surface, quite reasonable for my older hybrid. I only did about 6 miles today, from Keene southward before turning back, and those couple of detours noted in another review are still in place - taking you out onto the road for short stretches likely to avoid power line work being done.
Lot's of stops along the way to enjoy the sites. It's a very well maintained small trail
I parked on 4th street and headed up stream. Met one dog walker along this stretch. The calm river views were peaceful and the trail mostly wide gravel. Crossing over Whittier St the trail becomes narrower with a challenging set of turns to go under RTE 16. The river becomes more lively and there is a nice view of rapids. The trail widens with more gravel when you reach the parking lot on Watson Road. I met several more dog walkers along this stretch
Other reviews are fair. Lots of starts and stops for a shorter trail, but also some nice lengths and well maintained. Being from the area, I knew what to expect. I had more fun dodging and beeping my horn at bunnies on my night ride, than I did going around children on my day ride. Nice either way.
It’s spring on the Rockingham and everything is in bloom! Lots is rocks blooming in the trail as well, so be careful. The horses have really chewed up the surface just past Chiver’s Pond towards Manchester - really lumpy and washboarded. It makes for some uncomfortable bicycling. All in all still a very pretty trail with lots to see along the way.
The trail is poorly maintained. Do not recommend.
Gorgeous walk. We made the mistake of bringing our bikes and missed the no bike sign. Woops. Lessons learned. Great walking path with kids and pups.
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