Find the top rated cross country skiing trails in Holliston, whether you're looking for an easy short cross country skiing trail or a long cross country skiing trail, you'll find what you're looking for. Click on a cross country skiing trail below to find trail descriptions, trail maps, photos, and reviews.
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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!
I grew up in Fairhaven and moved away, but return every summer; the highlight of my trip being time spent on this bike trail and the Mattapoisett leg of it. Lots of “branches” if you want rack up some serious miles; Weeden Road, Gillette Rd, Mattapoisett Neck Road and continuing down Front (?) Street in Mattapoisett to Ned’s Point Lighthouse. Couple detours on the Fairhaven part and a stretch about a 10th mile that’s dirt and not conducive to a road bike. a 10th of a mile
I rode 20.5 miles of the southern section of the Air Line Trail from East Hampton to Willimantic on a very hot day in June. This section of the Air Line Trail offers gorgeous scenery, peaceful seclusion and a tightly packed gravel surface that is in very good condition throughout. Despite the heat the trail is very shaded which provided much needed relief from the sun. There are a fair amount of road crossings, most are very small, quiet roads and all of the busier roads have warning lights that can be activated to let motorists know you are crossing.
The only two small complaints I have is there is a lack of signage along the trail. There is one very short on road section that I almost missed getting back on the trail due to there being no signage, I just rightly assumed the small unmarked path on the road was the way to get back on the trail. The gates at the road crossings are on the narrow side which can make navigating through the road crossings difficult. I feel these two issues do not at all detract from what this section of the Air Line Trail has to offer.
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.
The Mattapoisett portion is open. It is a seamless continuation of the phoenix path and is very pretty, well maintained, and has a beautiful boardwalk near the end. It goes to a beach and you can then ride on a quiet road to Ned points lighthouse. Definitely worth the trip.
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.
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