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Formerly comprising two separate segments—one running northward from Keene to Walpole, and the other running southward from Keene to Fitzwilliam—the Cheshire Rail Trail now runs a continuous 32.9 miles through connections made in 2017 between the two sections and the former 1-mile Industrial Heritage Trail in Keene.
Initially settled in the 1730s, Keene developed a reputation as a manufacturing center in the mid-1800s when it served as a meeting point for three railroads: the Manchester & Keene Railroad, the Ashuelot Railroad, and the Cheshire Railroad. After the decline of the railroads in the 20th century, both the Ashuelot Railroad and Cheshire Railroad were transformed into rail-trails. Today, Keene is sustained by the tourism, insurance, and education industries.
The Cheshire Rail Trail now plays host to a variety of uses, including mountain biking and horseback riding, and in winter, cross-country skiing and snowshoeing are permitted. Note that the entire route may also be used by snowmobilers, who help maintain the trail.
The trail begins in the north at State Route 12 between Alyson’s Lane and Blackjack Crossing in Walpole. Most of the northern segment between Walpole and Keene is surfaced with hard-packed gravel. Cyclists should use a mountain bike; however, a small stretch between SR 9 and the center of Keene is paved and can accommodate wheelchairs.
Those who persevere along this part of the trail will be rewarded with abundant scenery, including wooded landscapes and natural rock walls; however, trail use is sparse until you reach Keene, and there is little to draw users off the trail. Note also the challenging terrain prior to Keene, including large rocks, flooding, and erosion; turns in the trail that can be challenging to spot; and several steep inclines. After crossing SR 9, a short paved segment takes you into Keene, host to Keene State College and Antioch University.
The town is also the meeting point for three other trails, including the 0.9-mile Jonathan Daniels Trail, located one block north along Island Street; the 1.3-mile Appel Way Trail, which meets up with the Jonathan Daniels Trail and begins just east of Keene High School; and the Ashuelot Recreational Rail Trail, which connects to the Cheshire Rail Trail at Emerald and Ralston Streets and stretches 21.5 miles southwest to Hinsdale.
Heading south, the Cheshire Trail’s second segment offers a much smoother and less-challenging experience for trail users than the northern segment as it travels just under 19 miles to Fitzwilliam. This segment feels more removed from town, and the mostly gravel surface is suitable for hybrid bikes.
Passing the Marlboro Street trailhead in Keene (there is a small parking area there), you’ll head up a short, steep dirt hill and cross a quaint stone arch bridge before crossing the Ashuelot River. In about 9 miles you’ll reach Troy, where you’ll find a few restaurants, some railroad relics, and an old train depot that has been refurbished into a museum.
Continuing southeast, you’ll pass through the town of Fitzwilliam, where an old railroad depot is undergoing renovation. The route then becomes relatively remote, officially ending in the outskirts of Fitzwilliam at the New Hampshire–-Massachusetts border. Note that the most convenient southern terminus for bikers and hikers is at the trailhead at State Line Circle and SR 12, as the section of trail east of SR 12 is prone to flooding in the rainy season.
To reach the northern endpoint in Walpole from I-91, take Exit 5 toward US 5/Walpole NH/Westminster. Head east on Westminster St., and go 0.8 mile. Turn right onto US 5 heading south, go 0.7 mile, and then turn left onto VT State Route 123 E (entering New Hampshire). Go 0.3 mile, and then continue onto SR 123 E. After 0.1 mile, turn right onto SR 12 S, go 4.2 miles, and turn left onto Blackjack Crossing. The parking area will be directly ahead in 0.1 mile. The trail endpoint is 0.3 mile north along the trail.
To reach the Troy trailhead from the intersection of SR 101 and US 202 in Peterborough, follow Grove St./US 202 W/Jaffrey Road, and go 6 miles. Turn right onto Main St./SR 124, and go 6.4 miles. Turn left onto Troy Road, which becomes Monadnock St. Go 2.6 miles, and turn right onto SR 12 N. Immediately turn left onto Water St. The parking lot will be to your left after about 450 feet. The southern endpoint is located about 10.9 miles south along the trail; note that there is no dedicated parking available for trail users.
Rode from the start near Keene ice north to Hwy 12. All paved until you cross Rt. 9 where it turns to hardpack. nice ride through golf course. Gets a bit rough north of Hurricane road. eventually started dropping to singletrack in places; just past huge former landfill just before Hwy 12 it got too wet to continue (early May). Gentle ~1% grade. This ride was good on my gravel bike. Mountain would be ideal but not necessary. Saw a few on fat bikes- overkill, but do not know whats north of 12. Moderate use on a Saturday afternoon closer to the city, including one horse.
Clear sunny day in May. Excellent conditions with sunshine and a gentle breeze to keep away the bugs. No ticks encountered. Walked 3.5 miles from the Blackjack Crossing trailhead.
Trail is in great shape although the first .25 mile (going north to the very end from the parking area at the end of Blackjack Crossing) is overgrown and a bit muddy. The first .25 mile stretch going south is the same, but then the surface is very good with crushed rock. There are muddy spots as you pass through the deep cut areas, but other wise, excellent. We walked but mountain bikes would fare very well. Road bikes NOT recommended.
Went from the southern end of the trail on the MA border to Troy. The trail seems to be in better shape than some of the other reviewers experienced. There are some roots, loose gravel, rocks, but nothing that any decent mountain bike can't handle. I wouldn't take a hybrid on this trail and forget about a street bike. The view of Monadnock from the Rockwood Pond was stunning and like a postcard with the changing color of the leaves. As far as finding the trail head, that one is easy. Set your GPS to McCallister Road, Fitzwilliam and you can't miss it. You can see the gate and a sign that directs you to the start of the trail. I will continue on the trail from Troy and write a second review.
Biked Cheshire and Ashuelot late Sept 2017. Parts were in good, not great condition, some mud, rocks, narrow grassy trail. huge mud puddle about 9 miles into Cheshire trail. Its Access point at NH-MA line impossible to find. Had to go to Keene to find trails.
This portion of the trail is well maintained and is a pleasure to ride. The slightly (2% grade) uphill run north was of benefit for the obviously downhill ride back to State Line - a ride of just over 20 miles.
This portion of the Cheshire is of interest historically, because it is over this railroad that Henry David Thoreau and companions (as well as R.W. Emerson and many other Concord, Ma residents) used to reach their beloved Mt. Monadnock. Thoreau traveled the rails in 1952, 1858, and in 1860. And the Troy Depot, now a historical museum, is a delight. Call ahead for an appointment.
We were unable to ride on the Ashuelot Trail so we picked up the trail from Keene And headed north ... we were able to do a 10 mile round trip shaded and scenic
I took a touring bike, and I was glad for my 48cm tires. The section near Keene was smooth, but a few sectionS were sandy, muddy or rocky, high curb cuts at road crossings, aND eroded road, in one section. I didn't encounteranyone for miles. As a solo woman, im always wary, but pepole were friendly, but respectful, and I felt safe.
Picked up the trail from Troy to Keene which was mostly downhill and ended in a neighborhood. If you have google on your phone, you can bike to the center of town where all the shops and eateries are. From where the trail ended, it was a few miles to town. The entire route was unpaved and very rough. I highly recommend a mountain bike but it is doable on a hybrid. It's all uphill on the return to troy. Great work out! :)
We rode from Fitzwilliam to Troy, NH. I used a hybrid bike and it was a bit challenging on this trail. I'd highly recommend a mountain bike because the trail is rough with large rocks, soft sand and muddy in spots. This section is not paved. It's wooded, passes a pond and marshes and if you like to a little challenge, this path is for you.
I do not recommend this for small children or beginners.
I didn't do the entire rail trail. We started at Fitzwilliam and end at Troy. I would recommend a mountain bike but a hybrid would get by because it is not paved. There were sections that had loose gravel, soft sand and large rocks on the path but worth the views the woods, ponds and old decommissioned train stations. Inside Troy Depot had some antique furniture and equipment that you look through the window. It was like time had stop at the old depot.
I would highly recommend older children or adults to ride this trail. It would be too rough for little kids under 13 years old.
From the Rte 12 state line south end to Troy is about 12.5 miles. Roadbed conditions vary wildly, from relatively hard pack dirt to rocky fire road to muddy, narrow path (with some soft here and there). Still, an enjoyable ride (saw a porcupine and two deer today).
I also came across a caravan of ATV riders, to whom I gave a wide berth and a respectful nod. They aren't supposed to be there (I think), but I wasn't about to tell them.
I'm looking forward to the Troy-to-Keene leg of this, which I have not done yet.
We love riding the sleds from Rindge / Pearly Pond to Troy for chinese food at Dragon Palace!
Actually I found this trail connects all the way down to Gardner, MA. by the Pearly Brook Reservoir (gate on Green Street entrance). The trail goes by Pearly and then crosses route 140. The trail is then paved along route 140 and then turns into unpaved rail bed. At the 140/12 junction you can re-enter the trail behind the liquor store and make you way the 202/12 junction where the trail is now paved. You follow the paved trail to the end then take a right onto a residential road (Elm Street) and then take the first left (Pond Street) which brings you across the street from a RiteAid. Ride through the RiteAid parking lot and past a bunch of old factories and across Jackson Ave and onto Lincoln St. You will find an entrance back onto the rail bed on the left. This rail bed will get you onto the Cheshire trail and you can get up to Keene. This is a really nice ride.
Rode this trail from Gardner SF to Troy, NH. It's a little hard finding the trail in downtown Winchendon, but once I found the trail again it was pretty consistent. The Winchendon trail is paved from the route 202/12 junction and runs into downtown,take a right then a left into the RiteAid parking lot. From there you go through the parking lot and stay straight. You then take a left then another right. After that you will see a trail entrance and will be on your wy again
I live in Fitzwilliam, so I thought I would provide a current status on this trail.
It is too bad that this rail trail is in such sad shape as this would be one of the premier trails in the state. Much of the section in Fitzwilliam is very remote and passes bogs, marsh and ponds. Very scenic, but the trail surface leaves much to be desired.
There is a place to leave a car at the beginning of the trail at the state line. There used to be a station located here, called State Line, of course. Look for a side road off Rt 12 on the west side just after entering NH. The trail heads off across the marsh.
The first section of this trail is fair, at best. It is very sandy in sections and not suitable for bikes with road tires. Also, the trail gets chewed up a bit from the snowmobiles and ATVs (which are not allowed, but that doesn't deter them).
After the first long section along the marsh and through the woods the rail trail crosses Templeton Turnpike (dirt road) and follows that road up along a brook. If the trail is in sad shape, take the road as it goes in the same general direction until the intersection with Number 4 Road at Stone pond. Templeton Turnpike becomes pavement here (well, sort of, it is also in sad shape).
The section along the marsh here is sometimes under water due to beaver activity.
The rail trail eventually crosses a paved road (Collins Pond Road) and passes Collins Pond. There used to be a nice rock cut and bridge here, but it was filled in long ago (sad). The section of trail along the pond and into Fitzwilliam Depot can be wet. There are also large rocks in the trail here and some left over ballast from the rail days just before the depot.
The train depot in Fitzwilliam has recently be renovated, but there is not much inside at the current time. The depot store is now closed. They also did not allow parking at the store and there is little parking at the depot due to the fire station next door.
After the depot the trail heads towards Troy. It crosses Rt 119 at another nice rock cut that was filled in (sad again). The trail is generally uphill to Rhododendron Road where it begins to descend into Troy. There are a couple of muddy sections but in general the trail is hard packed dirt with little sand. There is another rock cut where the trail passes under some power lines. There is also a large mud puddle which never seems to dry out just before Rhododendron Road.
As you enter the Troy depot, watch for glass, especially through the cut under Rt 12. The Troy Depot would be an interesting visit, but I have never passed there when it was open. You can look in the windows and see some of the historical railroad artifacts.
Also, for some reason, the town of Troy has "No Parking" signs in the area. I never understood why as there is nothing in the area and there is a large area where parking would not be a problem. There is a nice sandwich shop off the square. I am sure the businesses in the area would enjoy customers.
Troy and Fitzwilliam are constantly complaining about no business and taxes, yet they seem to go out of their way to discourage visitors. The Cheshire Line continues into Massachusetts where there are long sections of paved trail. There are always cars parked at the trail heads in that area. The NH section could be just as busy by improving the surface and providing some parking facilities. Sad that this resource is underused.
Swanzey and Keene are making a real effort to improve their trails. Maybe someday the towns on the south end will get there act together. Until then, this section of trail is probably best for mountain or cross bikes.
I rode this trail on Tuesday, Sept. 11. I had difficulty finding the trail head at the state line. When I finally did. a neighbor said it was in rough shape and was mainly used by snowmobilers. In Fitzwilliam, I got some information at the police station. The chief said it was rideable and it was about 18 miles to Keene. My wife when on to Keene to wait for me. After a few miles of very rough riding, I wished I had my mountain bike rather than the hybrid. To make things worse, there were several bad slopes at the road crossings. The surface was soft soil or sand and steep. (There must have been trestles at these locations when the rail road was in place. It was also difficult to find the trail on the north side of town. It was getting late when I finally found my wife and I decided that if the northern section was anything like the southern section, I would skip it and head for another trail. I have done over 100 trails in 43 states and this was one of the roughest rail trails I've ridden. Thank goodness it was only a little over 16 miles rather than the 18 estimated by the police chief.
Heading north from Whitcomb's Mill Rd., the surface is fairly smooth crushed stone/gravel and slightly uphill. At about 1.1 mi., the trail takes a detour off the former rail bed onto a very rough, rocky path in order to cross Hurricane Rd. (Apparently, the railroad used to pass under Hurricane Rd., but there is no longer a tunnel or underpass.) Continuing upgrade, the surface is smoother once again, but there are some sandy spots that can catch one by surprise. At 3.5 mi. there's a wooden bridge that crosses a stream bed which was dry on this crisp early September day. Unfortunately, the view to the left from the bridge is dominated by the grassy slopes of a covered landfill. A few tenths further along there is a small pond off to the right with a beaver lodge, but the presence of the landfill's maintenance building and the noise from a nearby road spoil the idyllic setting. Leaving the landfill behind, the trail passes through a deep cut in the rock along a path that becomes somewhat rough and rocky. At 4.6 mi., there's an information tree with a smallish map provided by the Westmoreland Sno-Belters along with some postings by area businesses. Just across Route 12 is the Summit Steak House if you're looking to take a break. The next mile or so is smoother and slightly downhill. At 5.6 mi., the rail trail intersects another trail in close proximity to a dirt road and an open area with some dirt piles. My wife and I decided this was a good place for a lunch break and a turn-back point, so a description of the rest of the trail will have to wait for another time. But this section was rather disappointing. The roughness was not to our liking, plus we never were far away from a road with its attendant noise. The lack of any scenic spots along this section (save for the pond at the landfill) made for a rather boring ride. Hopefully, the section further north will prove more interesting and pleasant.
I biked the Cheshire North Branch trail the past week. It was a pleasant ride I must say.
This was my first biking on a non-asphalted surface. I enjoyed it. The experience was very different from biking on the road.The views were nice. I particulary remember the one where I had to pass amidst big rocks. It reminded me of the days when we took a train in a mountain region as a kid.
I stopped for a while and looked around .The rocks, the trees, the greenary, the blue sky,the silence gave a peaceful feeling. I had a hard time finding the trail from Keene but luckily I had a map and with the help of a local was able to get through the streets and find the trail.
I did not see many bikers or hikers on the trail , not sure if it was because I was biking on a weekday.
I plan to bike the south branch very soon. (Winchendon -- Keene)
Another clear but cold day to explore more of this old B&M trail. Started from funky, Christian church
off Rt.12 at Lawrence Road in Troy, ended at Collins Pond Rd. crossing east of Fitzwilliam Depot; one-way
distance roughly 8 miles. Trail is slightly uphill from Troy to the high point one half mile east of Rockwood
Pond, then a slight downhill grade past Fitzwilliam Depot. The trail surface is a mix of packed dirt, some sandy
spots, and frozen mud that has been torn up from ATVs and motorcycles. Also, there is evidence of recent
work on clearing the trail with a bulldozer at various spots, which means it is maintained, but the riding
is somewhat challenging and riding through frozen mud is hard work, especially on the inclined portions.
Yet, this is a very scenic ride through evergreen woods, past ponds, swamps, and wetland areas, with some spectacular views of Mt. Monadnock along the way.
Highlights: Troy depot is completely restored and a visitor's center (see photos); Rockwood pond has the
best views of Mt. Monadnock (see photos); Fitzwilliam Depot general store for a snack.
From the google satellite views, I can trace this trail all the way to South Ashburnham, MA, where it looks
like it meets an existing railway. I look forward to exploring this trail more in the spring.
This trail is advertised in a Keene area recreation guide. Rode this section yesterday,
a crisp, clear November day. Parked on the side of road at Lawerence Road in Troy, NH.
The trail roughly parallels route 12 but moves off into the wilderness and stays fairly
level with a slight downhill grade into Keene. The first half is quite scenic and often
remote, passing rock walls and wooded hillsides, and through several cuts that were
blasted through 30-40 feet of rock, which were adorned with icicles. A mountain bike
is a must for the varied terrain, but the ride is pretty smooth and moderately easy.
There is a steep, short, sandy downhill slide at the route 101 crossing, riders should
be cautious. From here it is easier to ride on Marlboro St., bear slight right on Eastern Ave.,
and then you can pick up a paved rail trail into downtown Keene, NH.
"We heard about this old B&M branch while riding on the Ashuelot Trail last year. We rode from Keene north west toward Walpole and returned for the first section. It is about 10 miles one way and has a real scenic cut at the height of land. The trail is packed gravel and a little challenging in places. It does not now go all the way to Walpole. We then found the end that heads toward Winchendon off Rt.101 south east of Keene and rode toward Troy and Fitzwilliams. It is sandy at the start but crossed a very high viaduct and quickly lost the back yard riding and became very scenic all the way to Troy. It passes thru Troy in a cut of land and does get rather wide south of Troy for a mile or so, but returns to a great dirt ride all the way to Fitzwilliams. We had lunch there and returned. We rode north out of Winchendon, Mass. looking for the southern end and found parts, but in Mass. it is not improved and until the NH line was not very nice or easy to follow. We used several roads to go around bad sections. After crossing into NH it really got scenic and passed thru swamps and wood with some great rock bridges. Approaching Fitzwilliams it passed a quarry that is now a lake, but we had to climb up and down to roads that have been filled in rather than repairing bridges or putting culverts in. If you like exploring you should go to Keene and explore this rail trail and the Ashuelot and this trail. More use by bikers will hopefully lead the State to make more improvements. Keene is linking these sections in town and the LBS should be able to give you directions. "
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