Greenfield Running Trails and Maps

536 Reviews

Looking for the best Running trails around Greenfield?

Find the top rated running trails in Greenfield, whether you're looking for an easy short running trail or a long running trail, you'll find what you're looking for. Click on a running trail below to find trail descriptions, trail maps, photos, and reviews.

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Activities
Length
Surfaces
Type
42 Results
Activities
Length
Surfaces
Type

Appel Way Trail

1.3 mi
State: NH
Asphalt

Ashburnham Rail Trail

1.3 mi
State: MA
Dirt

Ashuelot Recreational Rail Trail

21.5 mi
State: NH
Asphalt, Ballast, Cinder, Crushed Stone, Dirt

Ashuwillticook Rail Trail

11.9 mi
State: MA
Asphalt

Blackstone River Greenway (MA)

3 mi
State: MA
Asphalt

Bridge of Flowers

0.1 mi
State: MA
Concrete

Canalside Rail Trail

3.6 mi
State: MA
Asphalt

Cheshire Rail Trail (Cheshire Branch Rail Trail)

32.9 mi
State: NH
Asphalt, Ballast, Cinder, Dirt, Gravel, Sand

Chicopee River Canal Rail Trail

0.21 mi
State: MA
Asphalt

Columbia Greenway Rail Trail

2.4 mi
State: MA
Asphalt

Common Pathway

5.5 mi
State: NH
Asphalt, Crushed Stone

Connecticut Riverwalk and Bikeway

5.4 mi
State: MA
Asphalt

Corkscrew Rail Trail

3.8 mi
State: NY
Dirt

East Branch Trail (VT)

0.5 mi
State: VT
Gravel

Farmington Canal Heritage Trail

48.3 mi
State: CT
Asphalt

Fort Hill Recreational Rail Trail

7 mi
State: NH
Ballast, Cinder, Dirt, Gravel, Sand

Fort Hill Recreational Rail Trail

7 mi
State: NH
Ballast, Cinder, Dirt, Gravel, Sand

Grand Trunk Trail

6.2 mi
State: MA
Crushed Stone, Dirt, Gravel

Granite Town Rail-Trail

3 mi
State: NH
Ballast, Cinder, Dirt, Grass, Gravel, Sand

Harrisville Rail Trail

1.6 mi
State: NH
Dirt
Accordion

Hillsborough Recreational Rail Trail

7.8 mi
State: NH
Crushed Stone, Dirt

Hoosic River Greenway

2.5 mi
State: NY
Gravel

Hoot, Toot and Whistle Trail

0.5 mi
State: VT
Dirt

Jonathan Daniels Trail

0.9 mi
State: NH
Crushed Stone

Keene Industrial Heritage Trail

1 mi
State: NH
Asphalt

Lye Brook Falls Trail

2.2 mi
State: VT
Gravel

Manhan Rail Trail

9.6 mi
State: MA
Asphalt

Mason Railroad Trail

6.7 mi
State: NH
Ballast, Gravel, Sand

Mass Central Rail Trail

38 mi
State: MA
Crushed Stone, Dirt, Grass

Monadnock Recreational Rail Trail

7.5 mi
State: NH
Asphalt, Gravel

North Central Pathway

8.9 mi
State: MA
Asphalt

Redstone Rail Trail

1.4 mi
State: MA
Asphalt

South Spencer Rail Trail

1.62 mi
State: MA
Crushed Stone

Southwick Rail Trail

6.5 mi
State: MA
Asphalt

Toonerville Rail-Trail

3.2 mi
State: VT
Asphalt

Valley Trail

9.1 mi
State: VT
Asphalt

Ware River Rail-Trail

12 mi
State: MA
Ballast, Dirt, Grass, Gravel

West River Trail

16.1 mi
State: VT
Asphalt, Dirt, Gravel, Sand

Westville Lake Community Trail

0.7 mi
State: MA
Crushed Stone
Trail Image Trail Name States Length Surface Rating
Appel Way Trail offers a paved route of about a mile through woodlands on the north end of Keene. Most notably, it offers a connection between Wheelock Park on the trail's west end and Ashuelot River...
NH 1.3 mi Asphalt
More than a mile of the Ashburnham Rail Trail opened in 2015 from a point just south of Ashburnham's center to Turnpike Road. The rustic route, planned to be paved in the future, offers a...
MA 1.3 mi Dirt
The Ashuelot Recreational Rail Trail passes such scenic and historical landmarks as covered bridges, abandoned mills, and postcard-perfect towns. Starting on asphalt in Keene, the rail-trail can be...
NH 21.5 mi Asphalt, Ballast, Cinder, Crushed Stone, Dirt
Nestled in the Hoosic River Valley, between Mount Greylock and the Hoosac Mountains in Berkshire County, the Ashuwillticook Rail Trail takes its name from a Native American word meaning "the pleasant...
MA 11.9 mi Asphalt
The Blackstone River Greenway (previously known as the Blackstone River Bikeway) is a 3-mile trail that represents the first open segment of the Massachusetts portion of a pathway that will eventually...
MA 3 mi Asphalt
The Bridge of Flowers is a 400-foot-long former trolley line bridge that has been converted into a garden pathway. Open from April 1 to October 31, the bridge spans the Deerfield River between...
MA 0.1 mi Concrete
Canalside Rail Trail begins at McClelland Farm Road in Deerfield and heads north on the former NYNH&H Railroad, crossing the Connecticut River near its confluence with Deerfield River. Approximately a...
MA 3.6 mi Asphalt
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...
NH 32.9 mi Asphalt, Ballast, Cinder, Dirt, Gravel, Sand
The Chicopee Center Canal Walk offers a short pleasant route in Chicopee, a small city on the outskirts of Springfield in southern Massachusetts. The pathway closely follows the slow-moving canal and...
MA 0.21 mi Asphalt
The Columbia Greenway Rail Trail offers just over 2 miles of paved, tree-lined pathway through Westfield in southwestern Massachusetts. The trail runs from Main Street, across the Great River Bridge...
MA 2.4 mi Asphalt
The Common Pathway travels 5.5 miles from the outskirts of Peterborough south to downtown’s Noone Falls area, paralleling US 202 and the Contoocook River for most of its journey. The small town of...
NH 5.5 mi Asphalt, Crushed Stone
The Connecticut River Walk and Bikeway, which will one day run 21 miles along the river, currently has two open segments. The longest stretches 3.7 miles from the Chicopee town line to the South End...
MA 5.4 mi Asphalt
The first section of the Corkscrew Rail Trail opened in June 2015. It begins at Knapp Road in Stephentown and heads south under a shady tree canopy towards New Lebanon, near the New York/Massachusetts...
NY 3.8 mi Dirt
The East Branch Trail is a 0.5-mile ungroomed, backcountry pathway built on a former logging railroad bed in southern Vermont's Windham County. The remote, heavily wooded trail lies just north of the...
VT 0.5 mi Gravel
First a canal, then a railroad, and now a trail define the history of the Farmington Canal Heritage Trail. Completed segments span Connecticut south to north, from New Haven to the Massachusetts...
CT 48.3 mi Asphalt
Built in the 1910s by the Boston and Maine Railroad (B&M) as part of the Connecticut River Division Main Line, the route introduced daily service to the B&M Fort Hill Branch in the early 1920s to meet...
NH 7 mi Ballast, Cinder, Dirt, Gravel, Sand
Built in the 1910s by the Boston and Maine Railroad (B&M) as part of the Connecticut River Division Main Line, the route introduced daily service to the B&M Fort Hill Branch in the early 1920s to meet...
NH 7 mi Ballast, Cinder, Dirt, Gravel, Sand
Grand Trunk Trail is part of a larger trail network, the Titanic Rail Trail, which will stretch more than 60 miles through south-central Massachusetts and the northeastern corner of Connecticut along...
MA 6.2 mi Crushed Stone, Dirt, Gravel
Mile 0.0 - DPW Garage  Cross the bridge in the parking area, the trail starts behind the fence, crossing over Great Brook on a old dam. Mile 0.53 - After crossing Union St. you will come to a...
NH 3 mi Ballast, Cinder, Dirt, Grass, Gravel, Sand
The Harrisville Rail Trail runs for just under two miles between the outskirts of Harrisville and Hancock in rural New Hampshire. The former railroad bed is located on lands conserved by the Harris...
NH 1.6 mi Dirt
Accordion
Hillsborough Recreational Rail Trail connects three communities in south-central New Hampshire: Hillsborough, Deering, and Bennington. The unpaved trail winds along the Contoocook River through rural...
NH 7.8 mi Crushed Stone, Dirt
The Hoosic River Greenway spans 2.5 miles along the river’s east bank through the Village of Hoosick Falls. The gravel pathway follows the former route of the Boston Hoosac Tunnel & Western Railway,...
NY 2.5 mi Gravel
Although short, the Hoot, Toot and Whistle Trail provides an enjoyable journey through peaceful woodlands on Wilmington's west end. As you might guess, the rail-trail gets its name from the former...
VT 0.5 mi Dirt
Jonathan Daniels Trail travels the length of Ashuelot River Park through Keene. Along the stone-dust trail, you can enjoy the park’s beautiful natural backdrop and flower garden. The trail was named...
NH 0.9 mi Crushed Stone
The Keene Industrial Trail links the county's Cheshire Rail-Trail in the city of Keene. The paved path is a 1-mile segment through downtown Keene, which passes among some of the city's old mill...
NH 1 mi Asphalt
The heavily wooded Lye Brook Falls Trail runs for 2 miles through the Lye Brook Wilderness of the Green Mountain National Forest near Manchester. The blue-blazed hiking trail follows the bed of a...
VT 2.2 mi Gravel
The Manhan Rail Trail wends its way between Easthampton and Northampton, with a spur trail leading out The Oxbow near Mt. Tom. Easthampton is a typical New England factory town brimming with commerce...
MA 9.6 mi Asphalt
The Mason Railroad Trail runs for nearly 7 miles from near the New Hampshire–Massachusetts border (nr. Townsend, MA) to Greenville, NH. The trail follows a heavily wooded corridor through Russell...
NH 6.7 mi Ballast, Gravel, Sand
A 104-mile rail line was shattered by hurricane in 1938. Today, the corridor is being developed as the Mass Central Rail Trail to be enjoyed by bicyclists, walkers, joggers, and cross-country skiers....
MA 38 mi Crushed Stone, Dirt, Grass
Stretching east from Northampton, the 10-mile Norwottuck Branch of the Mass Central Rail Trail connects the towns of Northampton, Hadley, and Amherst. Part of the Connecticut River Greenway State...
MA 10 mi Asphalt
The Monadnock Recreational Rail Trail is a great example of a repurposed rail route that provides safe commuting opportunities while also allowing trail users to escape into forest environments for...
NH 7.5 mi Asphalt, Gravel
The North Central Pathway will one day stretch 16 miles between the cities of Winchendon and Gardner in northern Massachusetts, primarily along a former railroad right-of-way. Three open sections...
MA 8.9 mi Asphalt
In central Massachusetts, the Norwottuck Rail-Trail (formerly the Northampton Bikeway) runs between New South Street in Northampton and the neighborhood north of Look Memorial Park in Florence....
MA 4.9 mi Asphalt
The Redstone Rail Trail is built on the former New York, New Haven & Hartford Armory Branch, which in turn is a former branch line of the New York & New England RR. Its name comes from the numerous...
MA 1.4 mi Asphalt
The South Spencer Rail Trail runs for less than 2 miles from downtown Spencer to an area south of town near Spencer State Forest. The path, which is also known as the Depot Trail, occupies a former...
MA 1.62 mi Crushed Stone
The Southwick Rail Trail extends from the Massachusetts–Connecticut state line north to the Westfield town line and connects to the Columbia Greenway Rail Trail. Along the way, it travels through...
MA 6.5 mi Asphalt
The Toonerville Rail-Trail shadows the Black River for most of its 3.2-mile length in eastern Springfield to the border with New Hampshire across the Connecticut River. The route originally carried an...
VT 3.2 mi Asphalt
The scenic Valley Trail spans 9 miles connecting Dover and Wilmington in southern Vermont along the Green Mountain National Forest. It provides a critical off-road pathway for bypassing Route 100....
VT 9.1 mi Asphalt
This unpaved state-owned trail is open for public use from Coldbrook to Baldwinville. An on-road detour is necessary through the village of Baldwinville, but the right-of-way is open for public use on...
MA 12 mi Ballast, Dirt, Grass, Gravel
The West River Railroad, which once followed its namesake river for 36 miles, began passenger service in the late 1800s as a way to trim the two-day voyage between Brattleboro and South Londonderry to...
VT 16.1 mi Asphalt, Dirt, Gravel, Sand
The Westville Lake Community Trail offers a short, scenic excursion along the east bank of Westville Lake in Southbridge. Much of the crushed-stone pathway is under a lush tree canopy. Along the way,...
MA 0.7 mi Crushed Stone
Note:Note: Per the State of Connecticut's website, the trail is open from dawn to dusk April 1–November 14. Eagle nesting activities can delay the opening of the southern trail head in Windsor Locks....
CT 5.4 mi Asphalt

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Trails by activity

Recent Trail Reviews

Mason Railroad Trail

Lovely hike from Abbot Hill Rd.

May, 2018 by jimtylerwall

Don't bother with the trailhead behind the restaurant in Greenville (currently the King House) marked on the map---it's a dead end about 1/4 to 1/2 mile in. Someone has piled Jersey Barriers, concrete blocks and old storm drains to block the trail behind Pilgrim Plastic. That and the numerous NO TRESPASSING signs make it pretty clear that they don't want people hiking, biking or anything else up there.

Start from Abbot Hill Road where it crosses the trail, it's a nice hike from there. There isn't a lot of parking available there, but I've never seen it too crowded. The day we went we didn't see anyone on the trail and once we got away from the road noise of Rte. 31 it was birdsong and peepers to accompany our hike.

One other thing---bring bug spray! We were swarmed by mosquito's and blackflies for most of the hike. I was glad I wore a long sleeve shirt and long hiking pants, so all I had to defend was my head and neck (yes, I forgot bug spray!)

Cheshire Rail Trail (Cheshire Branch Rail Trail)

North End - Walpole trail head

May, 2018 by ryoung_tl

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.

Blackstone River Greenway (MA)

Trash

May, 2018 by jruggieri6568

I’ve been walking the millbury Worcester trail since it opened. It’s so sad what’s become of it. Loaded with trash and broken glass. The trail is now under construction to include a center and lengthening the trail! Why bother if it’s not going to be maintained.

Accordion

Corkscrew Rail Trail

Not that long then

April, 2018 by russnelson_tl

When I rode it in September 2016, it stopped a short way into the town of New Lebanon, dead-ending before it reached the village. It's a nice ride as far as it goes. Hopefully it's now as long as the map says it is.

Farmington Canal Heritage Trail

Farmington Canal Heritage Trail, New Haven Ct to Massachussettes

November, 2017 by peasenh

My wife and I rode the trail in five segments, each approximately 20 miles each. My wife rode her 3-wheeled recumbent and I my Mt Bike. The trail is very level and has only a very few hills. Due to Autumn leaves and the wonderful foliage along the entire route, there was a considerable amount of leaves and other debris on the trail. In Cheshire and Hamden, the Parks and Recreation Dept personnel were cleaning and maintaining the trail every day we were there. The trail is well used by all, the surface is almost completely asphalt; unfortunately, rest room facilities are somewhat lacking...be sure to plan accordingly and take advantage when the occasion arises. WE LOVED THE RIDES!!

Farmington Canal Heritage Trail

New Haven Ct. to Southwick MA

October, 2017 by peasenh

We completed the ride during 5 different segments during Autumn 2017 and each ride approx. 20 miles. Hands down the Cheshire and Hamden segments were best maintained in terms of leaves/branches/acorns/etc being cleared from trail. Each time we rode those two city segments we saw city parks and recreation employees working on the trail and/or performing nearby grounds maintenance; BIG ATTA-BOY to those 2 towns. Our last segmented ride was Simsbury to Southwick MA; the trail was covered in leaves in most areas but didn't limit our travel. Of all the miles we rode, there was only one rest room facility (Cheshire), the remainder of the ride had portalets (pretty clean). We HIGHLY recommend this trail. Southington and Plainville are very near completing their final designs to make the trail complete.

Mason Railroad Trail

Autumn Trail Ride

October, 2017 by ryoung_tl

10/27/2017
Easy to locate by following directions on the trail page.
Park on Rt 23, Mason Rd.- dirt lot on the left. It is a half mi to trailhead on Morse Rd. The orange barrier is about 100 yards in from the road on the left, so if the leaves have not yet fallen, it may be difficult to see, but it should be rather obvious that the trail is there. A very short section also goes further south towards Townsend.
10.4 miles to the Mason Village depot. Average grade 2.8% going northbound. Therefore, you are going up hill, but you hardly notice. The road surface of crushed gravel, as a base, is very flat. With each crossing of a motor vehicle roadway, there are barriers and signs to warn you.
The trail is in excellent shape with some water across the trail, probably collecting in depressions caused by ATVs. This occurs beyond Pratt Pond at the top of the hook, but not so difficult that one cannot get around them. It was probably more obvious due to severe rain over the past 48 hrs.
Nice vistas and scenery along the way. At approximately 4 miles from the trailhead, there is a granite quarry loop on the left. I did not take it, so can offer no report.
At the end of the trail (9 miles), you will encounter a barricade that marks the intersection with Rt. 31. You should walk down to the highway and then you can ride on Rt 31 (take a left) to reach Old Wilton Road on your right. There is a bridge to cross. It is one more mile to the old depot in the center of town. Be careful on Rt. 31. Large trucks go very fast.
This trail is historically significant in that Henry David Thoreau, on September 6, 1852, rode this line (Peterboro’ & Shirley Railroad) from Ayer (Groton Junction at the time) [after riding the Fitchburg line from Concord to Ayer]. Reaching Mason Village (Greenville), he walked to Peterborough, stayed the night and continued on to the summit of Grand Monadnock, on foot. Later in the day, he descended to Troy, NH, and returned the same day to Concord, via the Cheshire RR, and, at Fitchburg, the Fitchburg RR.

Hillsborough Recreational Rail Trail

Bennington rail trail

October, 2017 by k8sl

Abominable surface, where you can pass, is very narrow and obstructed. A real waste of time and a disappointment.

Hillsborough Recreational Rail Trail

bennington rail trail

October, 2017 by k8sl

Terrible for bikes. Lots of dead fall, trash and railroad ties. 1/2 mile from "trailhead" there is a huge locked gate (chain link) which means you back track and ride through town to get to the other side of the river

Cheshire Rail Trail (Cheshire Branch Rail Trail)

Nice ride in the fall

October, 2017 by albern36

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.

Ashuelot Recreational Rail Trail

Not for road, hybrid, cyclocross!

October, 2017 by truedoc

Very much disappointed. From Keen, I both tried for this trail and Cheshire trail, too. Compared to other trails in other states, these two rails are both so poor in views and surface conditions except first 5 miles. Only good for MTB!

Mass Central Rail Trail

Beautiful soft running trail

October, 2017 by alicemark.md

This is a lovely quiet running trail with a smooth, wide, soft dirt surface. Park in the lot off of Thomas Street and then run - it's a slight incline going up that you don't notice until you turn around and come back and are cooking. An absolutely beautiful run through the forest and next to water!! No dogs allowed in some sections so leave the pupper at home.

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