Upper Charles Trail


38 Reviews

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Upper Charles Trail Facts

States: Massachusetts
Counties: Middlesex, Worcester
Length: 13.9 miles
Trail end points: Whitney St & Mill Stone Dr (Sherborn) and 480 Cedar St. (SR 85) (Milford)
Trail surfaces: Asphalt, Crushed Stone
Trail category: Rail-Trail
ID: 6218353

Upper Charles Trail Description


Shaped like a checkmark, the Upper Charles Trail links Milford, Holliston and Sherborn—towns in Massachusetts’s bucolic MetroWest suburbs. Ornamented by an eight-arch stone bridge and a historic tunnel, the trail’s well-maintained asphalt and crushed stone surfaces provide a great place for a relaxing stroll or a journey of several miles through New England nature.    

About the Route 

The Upper Charles Trail makes the shape of a checkmark. From the western endpoint outside Milford near Hopkinton, the trail proceeds south to the center of Milford, then northeast to the eastern endpoint in Sherborn. Refer to the TrailLink Map for details. 

From the western endpoint, the asphalt trail heads south, largely following SR-85, skirting the western side of the NEMBA Trails at Milford, a hiking trail network. (The trail is entirely paved in Milford; the unpaved sections are in the eastern part of the trail in Holliston.)  The trail finds the Charles River, following alongside it, before crossing I-495. Continuing south into Milford, the trail passes Louisa Lake and Milford Pond, with opportunities for fishing or a picnic. 

At Milford’s Fino Park, a short spur takes the trail further into the town of Milford about 0.5 miles south, letting off at Spring St and N Bow St (Milford). In Milford, south of Fino Park, the main trail turns east. A short on-road segment takes the trail east on Main Street, south on Beach St before quickly bearing left at Mt Pleasant St, where the trail picks ups about 200 feet ahead. Signs for a bike route mark the way. 

Leaving Milford, the trail heads northeast, passing through a commercial shopping area before crossing back under I-495. Crossing the town line into Holliston, the trail surface becomes crushed stone. Just south of Holliston’s town center, the trail uses the Phipps Tunnel to cross Highland St. Designed for steam trains, the tunnel’s curved stones make it a historic marvel. 


In Holliston, trail passes a historic depot that now houses local shops. Northeast of the town is the trail’s crown jewel, the Bogastow Brook Viaduct, a beautiful stone bridge with eight arches. As the trail nears its eastern trailend, it traverses the nature-filled Dopping Brook Conservation Area. The Upper Charles Trail’s eastern trailend is just over the town line between Holliston and Sherborn, at Whitney St & Mill Stone Dr (Sherborn).    

Trail History 

The Upper Charles Trail is a rail-trail on two historic rail lines: the Milford Branch and the Milford Secondary. The segment between Milford and Sherborn was formerly the Milford Branch of the Boston and Albany Railroad. The line opened in 1847. After declining in the early 20th century, passenger service on the Milford Branch ended in 1959, and freight in the late 70s.

The Milford Secondary, north of Milford, was opened in 1872, and originally leased by the Providence & Worcester Railroad (P&W). Over the mid-20th century, the line’s rail companies petitioned abandon the line, which was allowed between Hopkinton and Milford in 1959. The present-day trail spur from Fino Park into the town of Milford was abandoned in 1987.

Plans for a rail-trail began in the 1980s, but decades of negotiations between local government and line’s owners stalled development. The first segment of the trail opened in 2012. 

Parking and Trail Access

The Upper Charles Trail runs between Whitney St & Mill Stone Dr (Sherborn) and 480 Cedar St. (SR 85) (Milford) with parking available at both endpoints. 

Parking is also available: 

  • 15 Dilla St (Milford) 
  • 229 1/2 E. Main St (Milford)
  • 600 Mayflower Landing (Holliston)

There are numerous parking options along this route, see TrailLink Map for all parking options and detailed directions.

Upper Charles Trail Reviews

needs paving…

Nice trail with lots of great views, but unless you’re a trail bike enthusiast, who loves coming home with an encrusted bike, make sure your bike has big fenders. Especially after it rains, because the bike will get covered with stone chips and dust in the form of slurry. The trail will be even better when it gets completed and asphalt paved the entire way.

nice ride

This is an interesting trail. I started at Fino park, and went towards Milford. It was actually an enjoyable ride given it was not just straight and level. Turned around and took the other side. Straight as and arrow and not very exciting. Though it was hot most of it is under the tree canopy. It’s a little confusing in the middle. However, I think that was more me than the trail. I’d definitely do it again and did have a good time. It’s worth the drive.

4m Trail?

Good trail, nice but it is 4-5 miles of asphalt. If anyone knows were it extends to LMK.

wow, fantastic trail section

Since our last visit here the bridge north of Holliston has been paved and beautiful railings with info signage. A 12 foot wide hard packed stone trail with breathtaking views. The town deserves two thumbs up! The trail head at Holliston has been really spruced up with a coffee shop/bakery across the street and a railroad depot dinner with paved parking.Small parking area at Whitney street. The entire trail all the way is a gem.


Improved trail end at Whitney street

As of August 2021, the end of the trail at Whitney Street in Holliston has been improved. It no longer just dead ends in the swamp without a connection. Instead, a short new segment connects to a tiny parking lot, giving direct access to Whitney Street.

Pleasant Ride

Parked and road the trail from Fino Field in Milford. No usable facilities at the field likely due to Covid. The trail is mostly level with small grades in parts. It passes through urban, residential and forested areas. The surface is paved to the Milford line on both legs, where it then becomes hard packed process stone. Road bikes (25 mm tires) can negotiate the trail. The leg from Fino Field to Holliston is about 9.5 miles to the unimproved section, which had considerable standing water preventing further exploration. The trail passes through Holliston at the 7.5 mile mark where there are some small eateries and a town greenspace. Phipps Tunnel is noteworthy. The leg from Fino Field to Hopkington is about 4 miles to the trail terminus. The trail passes through Louisa Lake Park (picnicing and fishing). Foundations from early granite cutting sheds served by the former Hopkington RR of the late 19th century are visible on the left near the terminus of this leg.

Unexpected Surprise!

My husband and I rode the Upper Charles Trail from the Hopkinton start to the near end in Holliston this last Saturday in November 2020. What a pleasant surprise! We enjoyed very pretty scenery in Hopkinton, a great lunch at Oliva's Market in Milford, visited the brand new Boston Honey Company store in Holliston, and marveled at the historic Phipps Railroad Tunnel under Highland Street. The trail changes from asphalt to very rideable stonedust in Holliston. At just over 13 miles one-way, the trail is a great way to enjoy being outside and getting some great exercise to boot! I thoroughly recommend this trail to anyone who likes pretty scenery, and great stops along the way.

great trail

Flat surface with a places you can sit if need be. Beautiful this time of year.(OCT) can’t wait to explore the rest! Great for families, bikes and walkers.

Excellent trail

Excellent condition, beautiful landscapes, bridges and tunnels - this trail is amongst the very best we’ve done. Good for any level, from family riding to faster-type work-out. Highly recommended.

Upper Charles on my bike

This was my first time on this trail, despite driving by it more times than I can count. What a wonderful ride. Mostly flat, but some low grade rises. Can’t wait to come back again- maybe tomorrow!

loved it

It was exactly what I was looking for in a bike trail. I started on the Milford/Hopkinton line and ended up in the small dirt trail in Sherborn. I’m coming back in the fall! I also recorded my journey Christos Rad Bike Trails

Excellent Ride

We started in Milford and first rode to Holliston. The trail starts paved and then turns into a crushed stone but is well maintained throughout. Returning to Milford we then rode the other side of the trail which is paved throughout. Overall the trail is quite nice and a great option for two shorter rides or one long ride. Road crossings were easy and the traffic was quite kind. We have ridden in 33 states now and can easily give this trail a 9 out of 10. I will be posting a YouTube video of our ride using the username PedalPushin AK.

Great Trail

Very shady in most sections. Very well marked and the areas that involve streets are very few and very easy to navigate. Do not let this stop you from enjoying this great path. Hopefully they keep adding on!

Nice trail but not 5 stars

If the entire trail were like the section in Holliston, I would have given this a 5 star. The Holliston section is the high point of the trail. It's well maintained and does not have too many busy street crossings and has a nice canopy to block the sun. The paved section in Milford has a busy cross by 495 and is a bit weird as you head into downtown. At one point a narrow sidewalk has a painted divider and you also need to head behind a shopping center to catch the trail as it has a small break. The Milford section has its nice spots though, by the lake and the park, but the 495 section isn't a highlight nor the downtown break. Also the map shows the trail ending in Sherborn at a street. If you have a road bike or a hybrid you'll probably end at the Sherborn line, which is in the woods. The last .3 miles of the trail is single track better for mountain bikes that will take you to the road.

Easy, Comfortable Ride

Got there early Sunday morning with just a couple of walkers and a jogger or two. Riding my road bike was easy but the gravel section from Holliston soon threw sand into the drivetrain. After 4.25 miles it changed to paved and I washed out the sand. The rest of the ride was easy and most pleasant. The map shows an extension North of Holliston but this did not look inviting so did not go.

Have been riding this trail before the 7 arch bridge was repaired. Even better now, the ride is longer and very shady. One of my favorite trails in Mass.

Have been riding this trail before the 7 arch bridge was repaired. Even better now, the ride is longer and very shady. One of my favorite trails in Mass.

Upper Charles

Great trail did 27 miles. Part is paved and smooth - a traffic crossing at highway on/off ramps to watch out at - otherwise awesome section. 2nd half stone dust portion was awesome as well. Excellent condition and peaceful. The only reason I did not give it 5 stars is I only saw one bathroom-ports potty in my 27 miles. Could have been more but I didn’t see them

Nice easy ride

Nice easy ride. After Washington Secondary and East Bay, this is a nice relaxing ride.

Great walking trail

Today was the fourth time I walked this trail from holliston walked 2.5 miles and back.

Very easy walking the packed stone and dust pavement. I walk the Henry Hudson trail in NJ nearly every day 5 miles and both these trails provide some of the most interesting sites.

When visiting my family here this provides me a great walk. Wonderful

A great long trail in very good condition

Rode the trail this morning (a Wednesday). Very light and friendly walkers with few bikers. Trail is in very good condition -- both the gravel portion in Holliston and the paved portion in Milford. Plenty of benches to pull over and rest if you want...but the trail is about as flat as you get so the riding is easy. Will return many times.

Trail in good shape

The improved section of the trail has been extended further at the Holliston end. There is now an nice packed stone dust surface starting across the street from the Sam Placentino school in Holliston and running all the way to the paved portion that starts at the Milford town line.

A great rail trail

Start is still at Holliston, where the trail is hard pack and gravel in places. It changes to tarmac at the Milford town line. It is not road bike friendly until you get to the town line.

The scenery is really nice and the only interruption to this is when you reach route 495. The section from Milford north us a beautiful ride. Really enjoyable and suitable for all bikes. The latter section is fully paved, about 3.5 miles one way.

A great rail trail.

Very good trail for senior riders

My wife and I are in our mid-60's and enjoy bike-trail rides that are about 25 miles roundtrip. We recommend this trail!

Upper CharlesTrail from Sherborn to Holliston to Milford

I use the trail from Sherborn (unfinished but ok with thick soled shoes) and walk towards Milford a couple of times a week. The trails in Holliston from Exchange Street towards Milford are wonderful! With any luck, some donors and workers will get this trail finished! The trail is used extensively and it is a joy to connect with people I normally would not even see! The celebration on the Holliston section first night last December was terrific!

Nice trail

The asphalt part in Milford is really nice. The stone dust in Holliston is good.

It is easy to lose your way when the trail turns at the field, but there is a map posted on a board in the parking lot at Lake Louisa and friendly people at the Milford Bicycle store right near where the trail turns.

Many beautiful areas on the trail. Extraordinarily polite motorists with very cool light systems at some of the intersections. Good parking at the north end.

Can't Complain

Brought my black lab to this lovely trail, and I think I enjoyed it more than her. It has a nice paved path, and starts right at the Milford/Hopkinton line. Lots of history, and active almost everyday. No matter which you go you won't get lost. In general, its a hidden diamond and I love that its so close to my house!

nice trail..not too long

I recently tried this trail. I started in Hopkinton and ended in Milford.. trail was ok although there were quite a few major roads to cross ..though did have lights etc... the bad part was just getting to the trail parking in Hopkinton with the heavy afternoon traffic, its a very wooded path... paved..was ok..not very long though...worth a try

beware of children

This is a beautiful trail, shared by bikers, dog people, runners etc. Everyone is friendly, but many small children weave across the trail unaware that they are in the way and as they are unpredictable, a bit scary. They were accompanied by oblivious parents. Give me dogs any day.

Ridden 6/16/13

I parked in the Fino Field park, Main St in Milford. This is adjacent to the Commuter Parking lot in Milford, which is a slightly more centrally located spot. I rode both parts of this trail (the Hopkinton part and the Holliston part), starting with the Hopkinton part. It's about 4.5 miles to the northern end, all very beautifully paved, and landscaped. There are a couple of busy street crossings - I found all the drivers to be very polite at the crossings - very welcoming! Northbound, passing Louisa Lake park there are lots of people, so be attentive. From there to the northern end of pavement, the trail is very pretty, rambling through woods, with some historical sights on the way to the northern terminus at a parking lot on what is Rte 85, I think.

I also rode the other section which heads for Holliston. The two section of this trail can be done together, but that requires riding through the busy traffic sections of Milford - OK for experienced cyclists, shouldn't be attempted with inexperienced riders. The roads and signals through Milford are fine however. Again - very polite drivers in the city traffic in Milford! The Holliston section starts in back of Friendly's on Medway Rd, rte 109 about 1/4 mi east of the split with 126. Friendly's has designated a signed parking area (thank you very much!). The trail northbound is actually paved about 2 miles north, and then it is unimproved. I also rode the portion from there to Holliston, varying from muck holes to sections with nice stone dust - not really recommended for road bikes, but fine for a cyclocross or mountain bike, if you are OK with getting dirty. Just slightly south of Holliston there is a magnificent (and short) tunnel definitely worth seeing - the stonework is beautiful

Overall - a nice afternoon - this would be a great ride for the kids, just be careful crossing the roads, although I'm sure the drivers will treat you right. Both sections end to end with the city ride about 9 miles, one way.

Rough ride through Holliston...for now!

April 13, 2013: Did some trail work (with some very nice people) on the Holliston section near the Milford line and in the afternoon rode into Holliston on the unimproved section. There's .9 miles of nice stone dust at South St. (hint of what's coming!), and that turns into cinder, later gravel, some single-track through grass, and finally ballast as you go along. At one point (depending on conditions), you need to hop up on the side onto a single track for about 1/4 mile to get around some significant water (this was April, so...). There's an unimproved bridge over a road not far from the Phipps Tunnel--be careful, you can't just "bomb through" on this trail! The ballast used on this railbed is large, sharp chunks of rock I didn't want to ride my bike on, so I walked from time to time, finishing my ride-walk at the Dopping Brook Water Treatment Plant, returning on-road to South St.

In stark contrast with the paved Milford side, the Holliston section is a work in progress. But don't write it off entirely. The humps in the cinder created by the ATVs are fun, the trail goes through Holliston Conservation Land where there are walking trails, through the Phipps Tunnel (must see!), and over an 8-arch bridge. You can make it from the Milford line to the Phipps Tunnel at Highland St. fairly well, but the 8-arch bridge (for now) is in a ballast section where I did a lot of walking. And because there are no railings on the 8-arch bridge, I recommend walking anyway.

The plan is to clear the trail and put down stone dust, then make it part of a 20+ mile Upper Charles loop with surrounding towns. I think they have a great start and some must-see items like the Phipps Tunnel that will shine as more of the trail is completed. Really looking forward to this in the coming years!

Upper Charles is mostly a smooth ride and worth it.

You can access the Upper Charles Trail on South Street in Holliston where is joins up with an unimproved section of the Milford Upper Charles Trail. Although it says the trail ends at Cross Street, you can ride it all the way into downtown Holliston. The surface is everything from smooth cinder to dirt/mud to some pretty rough ballast. There are a couple overpasses that require care, and plenty of moguls that are spaced part enough apart to be fun. The crushed cinder section at South Street can be ridden on almost any bike but after Hopping Brook Industrial park you'll need off road tires and front shocks. About 13 miles round trip. Some of the road crossings are very busy, but you can't lose your way on this trail.

My husband and I packed up our bikes & traveled to the Upper Charles Trail expecting a round trip ride of over 12 miles. It was a lovely trail with great water views, but we were quite surprised that we reached the end (in the Senior Center parking lot - after Dunkin's) so quickly. The return trip has mile markers & we discovered that we had only traveled a bit over three miles (over 6 round trip). Not sure why this trail is marked as an over 6 mile trail. Each end was clearly marked "end of the trail". What did we miss???

We rode this trail on a Saturday morning under the threat of rain. Despite the forecast, there were many people out enjoying this pleasant trail. The trail features interesting water views and some abandoned quarry artifacts. There are numerous benches and pullouts for those wanting to spend time exploring the scenery of the parks through which the trail traverses. We started at the parking area on Main Street and rode up through the Fino Field area to the trail head parking at the north end enjoying views of Milford Pond, Louisa Lake and Wildcat Pond along the way. On our return we took the Senior Center Spur and via the senior center parking lot reached Center Street where we saw the end of active rail and handsome train station. The trail surface is excellent and the signs are very good. We did not do the isolated section of trail east of Route 109. We are from Connecticut and hope to come back and ride this trail again especially if they construct the missing link. I would definatley drive up from Mystic, CT to ride this one a gain!

My new favorite!

Rode half the trail last night. I work in downtown Milford, and finally packed the bike to work. It was well worth it. I rode from the Dunkin' Donuts to the highway and then doubled back. This trail is exceptionally well kept. I was surprised that it is suitable for road cyclists. My only obstacles were in downtown Milford itself- I had decided to park in the municipal lot between Central St. and Jefferson St, as that is where I can access my place of employment. Beware, there is much construction in downtown at the moment, and that resulted in my walking the bike the 1/4 mile or so to the trail head. It was so worth it- the trail was beautifully kept. There was traffic on the trail, but not so much that I couldn't keep pace. Other cyclists smiled and waved or nodded. ONE MINOR COMPLAINT: Dear dog people: Because you bought a retractable leash for your dog does not mean that you should give Fido the entire 50 feet of leash to wander. (I had to dodge more than a few retractable leash people.) This trail has a painted center line, and it would really be nice if you could keep yourself and your dog to one side of that line. When we cyclists come up behind you and YELL "On your left!" it means that we intend to pass you on YOUR left side. We (Bicycle people) aren't trying to scare you or be rude, we are just trying to communicate in as few words as possible so as not to disturb the trail. On my ride, I saw runners, walkers, and many young cyclists. I was pleased at how bike friendly this trail really is! All the crossings were super safe- only one car failed to stop. I hope to ride this trail for weeks to come. Thanks to all that shared the trail with me today!

Perfect family bike ride

We started at the north end. Biked into downtown Milford. Picked up some snacks at Dunkin Donuts (right at the end of the trail) and returned to the picnic tables at the lake for a picnic. Sports Authority at 495 exit has bike supplies if you need something last minute.

Upper Charles Trail Milford

This is a short, flat, paved trail great for young children on bikes, rollerblades or in strollers and for walking your dog. It is accessible from a large parking lot located on Milford's Main Street. The trail passes Fino Field, which has a community pool and ball fields, crosses Dilla Street to a small park on Louisa Lake, and continues on through scenic woodland to an intersection where you can enjoy lunch or an ice cream treat at Wendy's before heading back (trail currently ends right about there). All sorts of wildlife can be seen on or near trail (mostly on the Lousia Lake side); swans, mallards, turkey, heron, baby snapping turtles, garter snakes, turkey vulture, wood chucks, the remains of a beaver dam/activity. The trail can get crowded on sunny weekends. Expect to see lots of dog walkers.

Upper Charles Trail

I've walked and biked this trail from Main Street near downtown Milford to Route 495. It is a pretty straight, nicely paved route that runs through a nice water plain before it comes to Louisa Lake across Dilla Street. From here the trail gets very crowded and winds through a hilly area before it comes to Route 495. If you are adventurous and willing to get off the beaten path, there are several side paths. My favorite is a left turn about 3/4 of a mile northeast and up from the Dilla Street parking lot. A bar runs across a dirt path and can be used as marker to find it. If you travel up the path for a 1/4 mile or so you will come to an area that was used as a quarry complete with a water-filled quarry (the water is an unusual green color and quite filthy), old cables and pulleys anchored in the stone that were used by machinery to mine the area and piles and piles of broken stone of all shapes and sizes. This quarry area is a wonderful place to scout around. Overall, the Upper Charles Trail is a pretty good route for families and others hiking or biking.

upper charles trail

This is a very nice paved trail. There is a small parking lot at Louise Lake. The trail goes across a few streets. Expect to stop and walk your bike a few times. It is great for the kids. Mostly flat. Very populated.

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