Find the top rated horseback riding trails in Massachusetts, whether you're looking for an easy short horseback riding trail or a long horseback riding trail, you'll find what you're looking for. Click on a horseback riding trail below to find trail descriptions, trail maps, photos, and reviews.
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.
As of 6/3/25 this trail is still closed south of 11th street.
There is a detour indicated, which we tried to follow, but quickly lost track of.
Found another way to access the trail further south, only to realize that we'd gotten onto the part of the trail that was officially closed.
I'm sure this will warrant a higher rating once it has re-opened, but we were more than a bit disappointed today.
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!
...we rode the western part... (is there a tool to edit a review?)
We rode the eastern part of the trail today, starting at the CT/MA border towards Douglas. The first 6-8 mls are well maintained and a good ride even with a street bike. Nice scenery, too. But then things get worse around Douglas. Rough surface with crushed stone, sand and deep puddles after a rainfall (like today). Looks like the track has not been maintained in a while and detoriates. A mountain bike is a big plus and highly recommended in some parts of the trail. Was a good ride though but do not expect a smooth one.
This is described as a 3.5 mile section but we only went about half way to the dam from the Stanley Mill. It is passable on bikes but has roots and larger stones along the stone path. It's really more a walking trail. The farm mentioned in the description was an interesting side visit and had very nice bath & water facilities. However, for a great biking experience the 10 mile section starting at Woonsocket is paved and a far more pleasant ride.
Just rode the trail south to the Sudbury line. The east west trail is finished to the west for another 8 miles. It connects to the Hudson Trail at the end.
I rode the entirety of the Southwick Rail Trail coming from the Farmington Canal in CT. The Farmington is in very good condition, the Southwick is in even better condition! There are mile markers every mile, the scenery is very peaceful and the trail is very flat making it an easy ride. I stopped as soon as I hit the Columbia Greenway but it is also a seamless transition to that trail as well.
I didn't notice any places to pull off for food but its a short trail so I don't consider that a negative. The trails that join this one really give you so many options for ride length or to visit the trail towns along the way.
Overview The Old Colony Rail Trail is named after the railroad line that operated in Massachusetts and Rhode Island. At 8 miles, the trail offers a serene journey through quiet Cape Cod beach towns. The trail is suitable for a short ride out and back, or a longer journey when combined with the Cape Cod Rail Trail. About the Route The eastern point of the trail starts at Depot Road, in the center of Chatham, across from the fire station and adjacent to Veterans Field, home of the Chatham Anglers baseball team of the Cape Cod Baseball League. Here you will find ample parking in the elementary school lot across the street, a large playground, and rest rooms just a short walk down the hill at the Chatham Community Center. The route, in general, is flat, family-friendly, and easily managed. The first 1.5 miles of the trail is mostly on quiet quaint streets with slight vehicular activity. The reminder of the trail is on an off-road dedicated child-safe bike path. Inexperienced cyclists should face few difficulties. Should you wish to bi-pass the first 1.2 miles share-the-road portion of the trail, you can park at the Chatham Airport on George Ryder Road or the parking lot at the corner of Meetinghouse Road (Route 137) and Main Street (Route 28). If you start at Depot Road, begin by proceeding down Hitching Post Road for 0.2 mile, then turn left onto Tip Cart Drive. At the bottom of the hill, cross over Crowell Road to join the first segment of the off-road trail. The trail passes tennis and pickle ball courts, basketball court and parking lot through a short wooded area emerging to cross Stepping Stones Road. At the bottom of Stepping Stones Road continue straight across the intersection and onto Wilfred Road. This on -street portion of the trail is only 0.6 mile and Wildred Road is a quiet neighborhood street with scarcely any vehicle traffic. The off-street trail continues at the end of Wilfred Road. Here the trail begins its loop around the Chatham Airport before pausing at George Ryder Road where signage directs you to turn right to continue on the Old Colony Rail Trail or left for the short ride to West Chatham. This section of the Old Colony Rail Trail offers a unique view of this small airport used primarily for personal small aircraft. Lunch can be obtained at the airport restaurant or a short ride to West Chatham and rest rooms and water bottle fill are available at the police station located across from the airport hanger on George Ryder Road. After crossing George Ryder Road, and passing a rest area with picnic table, the remaining 5.4 miles of the trail remain off-road. While there are several cross streets along the way, the trail, in general, is peaceful, enjoyable and extremely well maintained. Here you can enjoy the solitude of nature, for the next few miles, interrupted only by other trail users. You will pass a granite post border marker announcing your entry into the town of Harwich from Chatham. Approximately three (3) miles from George Ryder Road is a half-round-about and then crossing over Route 39. While this can be a busy crossing, warning signs alert drivers to slow down and visibility for both trail users and drivers is good. Once crossed, the trail continues past Brooks Park in Harwich Center where there are restrooms and water bottle fill available (in season). Approximately 1.2 miles from this point, the trail reaches its western end at the next roundabout where it connects with the Cape Cod Rail Trail from the north and west.
Ran on this trail in the winter and was great! Very comfortable for running :)
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