Find the top rated cross country skiing trails in Plymouth, 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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Once we figured out how to access the trail from the trailhead (hint.. it's tucked in right at the railroad tracks), we proceeded on to enjoy the beauty of this trail. As a first timer to the Cape, this trail showed me all I had hoped to see and experience. From woods, to murals, to water features, the rock beach and then finally the ferry, I was in awe the entire ride. You will find some tree root areas to be aware of and it's a busy path in many places but so worth it.
Although not as scenic as I had hoped it would be, it’s a nice enough trail. It can be busy with walker, runners and bicyclists of all ages. Many places that cross over roads but drivers seem to adhere to signs to watch for pedestrian and bike traffic. Trail is well marked as far as signage goes. There is one section that goes on a regular road for a short time but there is a bike lane and good signage to follow. Trail is largely shaded by tree canopies.
My 6 and 9 year old grandsons rode the 2.5 round trip with maybe 100 feet of walking their 20” mt bikes over rough spots and a couple of logs. The trail is 95% shaded. We parked on Breck Rd and crossed Thacher Rd to the trailhead. Lafayette Rd has a large circle at its end by Pope’s Pond that you clearly can park at.
This trail gets better and better as you get closer to downtown Boston. It also gets more crowded. Very scenic with lots of views of the river and such, but as always in Boston, there will be detours here and there due to construction. Probably gets better the more times you ride it and get to know its quirks. Not a trail if you are looking for speedy biking due to the number of pedestrians, runners, and other folks - it is certainly well-loved by Bostonians!
Western end beyond the Galen Bridge to Waltham gets squirrelly with odd and sometimes confusing routing and signage - not recommended unless you've got all day like I did.
Biked end to end today. Best described as two very different rail trails that are joined by a squirrelly connection.
Holliston (eastern) end is beautiful stone dust surface. It can be soft in places but is a terrific, well-maintained trail with excellent historical signage (think Casey at the Bat) and an unusually attractive short tunnel. Trail is long and straight and crosses several swampy water features chock full of flowers and wildlife. Sadly, the trail ends abruptly at the Holliston border with Sherborn with a short connector to a small parking lot.
The Holliston segment changes to pavement at the Milford town line and adds another mile or so to that segment. After that, there are a number of road crossings (some major) and sidewalks to make it to the main Milford rail trail.
The Milford segment is better described as a paved bike path that spends some time on a former railroad bed. The pavement is generally excellent, with only a few root heaves. It too is very attractive and an enjoyable ride as it winds through the woods and beside a lake. After an easier-than-expected crossing of the I-495 corridor, the trail continues north for another mile or so of rail trail until ending at the Hopkinton border.
All in all, each segment gets a 5 rating, each for very different reasons. The connection between the two is less interesting and makes the end-to-end experience less desirable. But credit where credit is due: Massachusetts drivers were invariably polite and respectful of the warning lights at all flashing road crossings. I'm not sure I could say the same about drivers in my home state.
We rode this August 6th 2026, started at 66 veterans memorial parkway instead of India point park ! SO much better. No porta potty’s anywhere to be seen, stopped at the stop and shop for Bathrooms ! Trails were great, although not used to having Bicycles stay Right and runners and walkers to the left… kind of Chaotic at times even mid week mornings Overall a great day !
Beautiful 1st ride on the Norwottuck Rail Trail. We parked at the Marshalls in Hadley (trail starts right behind the building) and road a little over 10 miles into EastHampton and back. It was a very easy ride (my 1st ride of this length) on asphalt.
I rode round trip from Mansfield to Norton which was 14 miles. It’s an absolutely beautiful trail, perfect for solo riders, couples, and families. Crossings are well marked and vehicles tend to stop immediately. Kids and adults might enjoy a detour to the airport in Mansfield. And ending in downtown Mansfield provides opportunity for a snack or beverage as there are several options readily available.
It was a warm summer day. We were one of two cars in the almost empty trailhead parking lot. The trail was cool and mostly in the late afternoon shade. There was enough space to ride bikes next to each other or walk 3 across. The gravel is not so deep as to slow you down. We saw two deer meander through a field. A great time was had by all.
Parked at Herring Cove Beach for free with our America the beautiful Senior lifetime pass. What an amazing trail! We got an early start so we did not encounter very many people at all. It was a brilliant cool summer morning on a beautiful trail. Up there as one of the best trails we’ve ever done and we ride all over the country. Of course we wouldn’t do it if we didn’t have an E bike being seniors, but it was a piece of cake. Beautiful scenery ranging from sand dunes to deep forest! 12.6 miles total for the day with a few side trips. We later took our chairs to the beach at the opposite end of the parking lot and watched seals playing and the tide go out for an amazing day. I would put pictures up, but it seems very difficult to get a picture on this site. Don’t miss this one!
From EBBP over mostly dedicated path or protected bike lanes:
Over Washington Bridge thru India Pt Park;
Under I-195 along S. Water St. crossing Wickendon St. onto bike path along Providence River;
Cross Michael S. Van Leesten Memorial (pedestrian) Bridge over river then head west uphill along Ship, Chestnut then Clifford Streets;
Clifford St over I-95 bridge, onto Friendship St downhill then left onto Broad;
Along Broad then right onto Peace St (next to St. Joseph's Med Ctr);
Peace turns into Waverly. Waverly left onto Cranston St.;
Cranston St. (unprotected) under Rte10 then left onto Depot St.;
Arrived!
Cranston St is very busy with moving and parked cars and peds. An alternative bypass: along Peace St as above, but at Dexter St crossing where it turns to Waverly, turn left onto Dexter. Then right onto Waldo St, down to the second side street left onto Brattle St; this tees into Potters Av (busy!), quick dogleg right/left onto Homestead Av, (which tees into) turn right onto Huntington Av. A few blocks later, you reach Cranston St. at the Rte 10 underpass; then continue as before. Note: the northbound Huntington Av here is a quiet side road after it splits from the main northbound side Huntington Av highway.
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