Explore the best rated trails in Gloucester, MA, whether you're looking for an easy walking trail or a bike trail like the Heritage Trail (NH) and Swampscott Rail Trail . With more than 91 trails covering 478 miles you're bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.
Easy walk but the trail is not paved on the Medfield side; perfect if you want to minimize the impact on your knees
Rode the trail on Saturday 7/5/25. Liked that it was well shaded, rode by water, not many cross overs where you had to stop for cars and not crowded. I liked the trees on both sides. My only complaint would be you really need to make sure you have front end suspension when riding as there are alot of tree roots growing up under the asphalt- bumpy- outside of that it was a great ride!
Great trail. Bad culverts!!!
I bike rode Rockingham Rail Trail, Portsmouth branch for the first time today 6/29/25. Headed from Manchester east out 15 miles and back. Very nice trail, good base and I enjoyed the trail very much. HOWEVER, those underpass culverts 7-8 miles east of Manchester are DOWNRIGHT DANGEROUS!!!!! Very low clearance, terrible visibility, and a deteriorated and uneven riding platform all contribute to a recipe for a terrible accident and injury. I am a good rider, and I crashed today. I was barely creeping along and fortunately I was not seriously Injured. Something needs to be done to make these less dangerous. I do not know who is responsible for maintaining these underpass culverts, but please consider my concerns. I would volunteer to assist in improving these hazards. Reread the description and walking bikes in these culverts was recommended and I would agree. On site signage would be a good idea also. The trail gets 5 stars the culverts get 0 stars.
The Assabet River Rail Trail is varied and enjoyable. The tricky thing about it is that it exists as two disconnected sections, separated by 2 miles of fairly busy road that's only suitable for confident road warriors. And that's a shame because both sections are marvelous and have much to recommend them.
The northern section runs from South Acton, through Maynard, and barely into Stow. It passes right through downtown Maynard, where you can find some decent food options and a bike shop. Proceeding south, it turns into a wide, hard-packed dirt road, and then finally ends as a slightly rougher dirt path. You can also easily access the Assabet River Wildlife Refuge from here, which has miles of wonderful off-road bike paths.
The southern section starts in Hudson and passes through the eastern end of its downtown, where there are more services and some worthwhile shops, including a bike shop. As of 2025, this part also connects to a new 8-mile eastbound section of the Mass Central Rail Trail. But if you continue on the Assabet River Rail Trail, you'll climb up into Marlborough -- it's pretty consistently uphill as you head south, but it's good exercise and has at least one excellent view. The trail more or less ends in the center of Marlborough, near the library, and where there are a few more spots you can grab a bite or get a drink.
So although this one isn't a straight shot, it's easily the most pleasant way to tour these towns and see what they have to offer. I hope finish it some day, and make it a single continuous Acton-to-Marlborough trail it's meant to be.
The Nashua River Rail Trail is terrific. It's long, smooth, well-maintained, and beautiful. Since it lies in a relatively rural part of Massachusetts, I find it to be a lower-key ride than its eastern cousin, the Bruce Freeman Rail Trail, but still well-used. There's less to see and do along it, but that might be exactly what you're looking for. Wholeheartedly recommended.
Without question, this is one of the best rails trails in Massachusetts -- maybe even New England as a whole.
The northernmost section, closest to Lowell, are clearly older -- it's fairly narrow and the way through the center of Chelmsford isn't super well thought-out. As you head south, it quickly turns into a wide, well-maintained, gorgeous trail with beautiful scenery and a serene vibe. There are places to stop for food; a couple of swimming holes; NARA Park in Acton; the fabulous bridge over Route 2; the convenient access through West Concord, and more as you proceed -- including an intersection with the future crown jewel of Massachusetts rail trails (the Mass Central Rail Trail). The BFRT is now mostly complete as of 2025, and I think the only section still waiting to be built is the southernmost section in Framingham. I love the Bruce Freeman and I bet you will too.
I ride my bike & walk this trail & downtown Derry is a great bike ride to Salem, 14-miles round trip and always free parking ¿
Great local path. It is all paved except for a short area near the Norton line. It has gravel for about 50 feet. Flat with lots of trees. Some finishing touches needed at the crossing but they have lights set up for safety. It’s about 13 round trip. Used by walkers, runners, bikers. Great place to teach kids how to ride a bike. Not too crowded.
This was my first time on this trail, and I really enjoyed it. The views were amazing but there was one big take away I have for next time. If you can, bring a bike with suspension. I had my road bike and REALLY felt the poor condition of the path. It was still very bike-able though.
I parked at NARA park and biked to Chelmsford. Today parked in same place and biked to west concord. Path is in great shape. Lots of trees, waterways, bridges, towns. Got to “the end” to discover that it actually goes several more miles which I’ll save for another day. I liked the poetry booth in West Concord- very original. I highly recommend this for scenery, safety, convenience of restaurants and bathroom stops. My favorite find this year.
Yesterday we decided to see if the trail, south of West Concord, was finally open. Last year, there was a locked gate under an overpass, and the only way to get past was to drag the bike down a hill. But, to our delight, the gate is open, and we biked all the way to Sudbury, nearly to Route 20. The new leg of the trail is glorious, beautiful scenery, well-marked, great resting spots, with blinking lights at road crossings. At the end, it connects to the Mass Central Rail Trail, itself under construction, but people were biking on it anyway through a gap in the fence. The only thing missing: portapotties!
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