Best Rail Trails In Massachusetts: Ranking The Good, Great, God Tier

MASSACHUSETTS — This is an article for rail trail freaks only. If you don't daydream about little bike trips and walks along rail trails, you won't like the rest of this article.

Since moving back to Massachusetts in 2019, I've tried to visit as many local rail trails as possible. I've found them to be the best way to explore hidden parts of the state, allowing you to get fresh air and exercise while avoiding the hassle of driving and parking.

My love of these trails has gotten to the point where I often fantasize about having billions of dollars to build new rail trails wherever I want. Some of that cash would undoubtedly be spent defending trails in court, unfortunately. I have become a true rail trail freak, and I don't care who knows it.

As summer turns to fall, I think it's time to compile all my rail trail experiences into some type of ranking so first-time users can prioritize where to go during leaf season. Keep in mind, I think every rail trail is great, so the ones on this list are all No. 1, with some caveats. I'm only including trails I've used, so this is an incomplete ranking. Also, the term “rail trail” really just means any relatively flat path that excludes motorized vehicles. The previous existence of railroad tracks is not required.

19) Quinebaug River Trail (Dudley)

The Quinebaug is a little odd. The short section in Dudley offers some woodsy scenery, plus a look at the French River. It's not paved, and there are a couple of road crossings. Best by foot rather than bike.

18) Quinebaug River Trail (Southbridge)

I think the goal is to connect the Dudley and Southbridge sections via an old rail line that dips into Connecticut in Dudley, then loops around into Southbridge. Heading south from the parking area at the Quinebaug River Reservoir, you get a couple miles of unpaved trail that passes by the closed Southbridge landfill, a terribly toxic scrap of land that you should probably avoid walking on (I climbed up on it before knowing what it was).

If you head north from the reservoir, you get a much shorter path that ends at a stinky section of the river due to outflow from a nearby sewage treatment plant. This section needs some work to shine. But when I was there in December, a local resident was out with a chainsaw clearing a downed tree, so the trail has its boosters.

17) Depot Rail Trail (Spencer)

I was surprised to find Spencer had a trail. This one starts just a little south of the downtown area and travels unpaved for about 2 miles before ending at Spencer Road. Near the southern terminus, you can hop off the trail and explore Howe State Park.

16) MA Central Rail Trail (Gilbertville)

This is one of the newer sections of the planned 104-mile Mass Central Rail Trail. It's short, but offers some cool sights like a covered bridge, and the option to visit Lost Towns Brewing or Hardwick House of Pizza. Great views of the Ware River.

15) Connecticut River Walk (West Springfield, Springfield)

These two sections aren't connected, and probably should be considered separate. The West Springfield section travels between the river and an imposing levee. It's paved, so best for a quick bike ride or jog. The Springfield section starts downtown near the Basketball Hall of Fame. A good chunk of the trail is secluded by various pieces of infrastructure, including a wall that runs alongside the trail at the northern end. Good for a bike ride.

14) MA Central Rail Trail (Rutland, Barre)

This is one of the longest stretches of the trail in central Massachusetts. It's unpaved, but offers a great hiking experience. At close to 9 miles, it’s a great workout. There aren't any facilities along the way, so pack accordingly. Bonus: it intersects with the Mid-State Trail in Rutland for more hiking adventures.

13) Blackstone River Bikeway (Worcester, Millbury)

This surprisingly hilly, paved trail is Worcester's only rail trail. It's also the northern point of a planned trail between Worcester and Providence, although the full route likely won't happen any time soon due to challenges acquiring land. My biggest criticism of this section is its location. It's in the state's second-largest city, but doesn't really have any amenities or major sights along the way, unless you count Walmart and Olive Garden. The trail also has an unpleasant section along Route 146, and travels through some stinky industrial areas, including the Upper Blackstone Clean Water treatment plant. A connection to either Worcester's Canal District or downtown Grafton (tantalizingly close to the trail's southern terminus) could turn this into one of the best trails around.

12) MA Central Rail Trail (West Boylston)

I would rank this one higher because it's long and scenic, but it's also very busy. For good reason: it offers at least 6 miles (round trip) of walking, biking or hiking. There are two generous parking lots at either end. Keep in mind, dogs are not allowed along the section west of the I-190 overpass.

11) Ware River Rail Trail (Winchendon, Barre)

The sheer length of this trail (15 miles) makes it worth a visit. Starting in Winchendon at the north end offers some dining opportunities before the trail plunges into the depths of rural north-central Massachusetts. The entire length is probably doable in one day on a bike if you’re up for it (I’ve never attempted).

10) MA Central Rail Trail (Wayland, Weston)

This section is great, but it's so close to being so much better. The east end terminates just before the Waltham line in Weston at an old rail bridge. Waltham is so close, but not quite reachable yet. Thankfully, construction on that connection got underway last spring. At the west end of this section, the trail ends just shy of the Sudbury line. Plans are underway to add a section into Sudbury and to Hudson, which will also intersect with the under-construction Bruce Freeman Rail Trail. The completion of those sections will open a new universe of trails, perhaps even making bike commuting to Boston possible from the MetroWest 'burbs.

9) Canalside Rail Trail (Montague, Turners Falls)

This one gets my vote for best trip through history. The trail takes you past the Turners Falls dam, which was built to divert water through the Montague Power Canal. Along the way you have the chance to visit the state's Great Falls Discovery Center museum, shop and dine in downtown Turners Falls, or continue exploring a trail with views of the old factories and neighbors shaped decades ago by the building of the canal.

8) Twin Cities Rail Trail (Leominster, Fitchburg)

This trail just opened a few years ago, connecting, well, the twin cities of Fitchburg and Leominster. The centerpiece is a bridge over Route 2, and it doesn't hurt that Sookie's Burgers and Fried Chicken is off the trail for a quick bite. There's a new section coming soon, lengthening the trail a little bit along Middle Street in Fitchburg. Beyond that, plans call for the trail to someday cross the MBTA tracks into downtown Fitchburg.

7) Blackstone River Bikeway (Uxbridge, Blackstone)

This is the second paved Massachusetts section of the planned bikeway between Worcester and Providence. The trail offers a nice, shady jaunt into downtown Blackstone with some of the best views of the Blackstone River anywhere. A new section under construction right now — likely opening in the fall — will extend the trail from the town of Blackstone to Cold Spring Park in Woonsocket, RI. It's a short but important extension that will allow trail users to access the incredible section of trail that starts at River's Edge Park in Woonsocket and travels all the way to Pawtucket. From there, you can ride along city streets to get to Providence.

6) Cochituate Rail Trail (Framingham, Natick)

I think this is the only rail trail around that offers the opportunity to visit a shopping mall. But apart from that, this is one of the region’s premier trails. It travels from Framingham's historic Saxonville neighborhood south across Route 9 and into downtown Natick. The trail will soon connect to a new Commuter Rail station in Natick, offering the chance for car-free trips to Boston or Worcester.

5) Assabet River Rail Trail (Marlborough, Hudson)

People rave about downtown Hudson. I've heard multiple elected officials in the MetroWest area question why their downtowns don't bustle like Hudson. The shops and restaurants there are a big part. But I think the Assabet trail is a bigger factor, offering a way for people to congregate in a downtown area without dealing with traffic and parking. After a recent update, the trail now starts in downtown Marlborough, ambling through woods, past office parks and over wetlands and through downtown Hudson. Leave your car at one of the many parking areas and bike or walk to Hudson. You will not regret it.

4) MA Central Rail Trail (Amherst, Northampton)

The grandaddy of all rail trails. This paved path, called the Norwottuck Rail Trail, was built in the early 1990s. You’ll notce the path is pretty narrow in some sections due to the outdated trail design standards of 30 years ago. Nevertheless, it travels 11 miles from Belchertown through Amherst, Hadley and into downtown Northampton. This was one of the first sections of the Mass Central Rail Trail ever built, and has grown into a sort of human highway in that part of the state. You'll find scores of people using it to commute each day alongside people using it for leisure. The trail also offers a huge variety of scenery, from collegiate downtown Amherst to sweeping views of farms in Hadley to a long Connecticut River crossing before Northampton.

3) Upper Charles Trail (Milford, Holliston)

A real hidden treasure, unless you're one of the thousands of people who have used it. The trail offers two very cool experiences. The stone dust section in Holliston travels by horse farms, 200-year-old homes and across an old aqueduct. The section in Milford is more urban, crossing through downtown and newer commercial areas. The changing scenery is an invitation to go farther. The first time I biked this, I only set out to explore the few miles in Dover and Holliston. I ended up riding all the way to the end in Milford near the Hopkinton line and back.

2) Southern New England Trunkline Trail (Douglas)

This one is a real sleeper. It's an enormously long trail that travels from downtown Franklin all the way to the tri-state border with Rhode Island and Connecticut in Douglas. Some sections aren't complete, but the ones that are offer incredible recreation opportunities in all seasons. If there's snow, you can cross-country ski or snowshoe — or just walk in the footprints of trail users who came before you. The trail also gives you the opportunity to continue into Connecticut along the Air Line State Park Trail — a 50-mile trail from Thompson to Portland. SNETT is the trail I return to most frequently because of how easy it is to get to and to use. Even in the depths of January, it's a great place to be outdoors.

1) Manhan Rail Trail (Easthampton)

To me, this is the best example of what a rail trail can do for a community. Manhan truly feels like the aorta of Easthampton, transporting people to work, school and leisure activities. You can get beer, ice cream, go record shopping or watch a high school football game right off the trail. The Manhan works together with a town that's already very alive with shops and restaurants, and with nature. Mt. Tom looms in the background as big herons land on the pond downtown. And the trail offers many more possibilities. A connection into Southampton has been brewing for ages and is now in the design stage. It also connects to the Norwottuck trail, making Northampton and the towns beyond reachable. The Manhan also ends just north of the beginning of the Farmington Canal Heritage Trail, a partially complete trail that ends in New Haven, Conn.

That billionaire fantasy of mine would be put to use here first, helping to complete the Mass Central Rail Trail and Farmington trail, creating a link between Boston, central Massachusetts, the Pioneer Valley and New Haven — a truly wicked vision for all my fellow rail trail freaks. Or for anyone who just enjoys a nice walk or bike ride.