Southwick, MA Running Trails and Maps

861 Reviews

Looking for the best Running trails around Southwick?

Find the top rated running trails in Southwick, 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.

  • Relevance
  • Name
  • Length
  • Most Popular
Activities
Length
Surfaces
Type
45 Results
Activities
Length
Surfaces
Type

Air Line State Park Trail

54.6 mi
State: CT
Ballast, Dirt, Gravel

Ashuwillticook Rail Trail

11.9 mi
State: MA
Asphalt

Billings Trail

3.3 mi
State: CT
Dirt

Bridge of Flowers

0.1 mi
State: MA
Concrete

CTfastrak Multi-Use Trail

4.4 mi
State: CT
Asphalt, Concrete

Canalside Rail Trail

3.6 mi
State: MA
Asphalt

Captain John Bissell Trail

4.5 mi
State: CT
Asphalt

Charter Oak Greenway

16.6 mi
State: CT
Asphalt

Cheney Rail Trail

1.7 mi
State: CT
Crushed Stone

Chicopee River Canal Rail Trail

0.21 mi
State: MA
Asphalt

Columbia Greenway Rail Trail

2.4 mi
State: MA
Asphalt

Connecticut Riverwalk and Bikeway

5.4 mi
State: MA
Asphalt

Corkscrew Rail Trail

3.8 mi
State: NY
Dirt

Farmington Canal Heritage Trail

48.3 mi
State: CT
Asphalt

Farmington River Trail

16.5 mi
State: CT
Asphalt, Crushed Stone

Grand Trunk Trail

6.2 mi
State: MA
Crushed Stone, Dirt, Gravel

Hanover Pond Trail

1 mi
State: CT
Asphalt

Harlem Valley Rail Trail

17.2 mi
State: NY
Asphalt, Crushed Stone

Hop River State Park Trail

20 mi
State: CT
Crushed Stone

Kress Family Trail

3.1 mi
State: CT
Dirt
Accordion

Larkin State Park Trail

10.8 mi
State: CT
Cinder, Crushed Stone, Dirt, Gravel

Manhan Rail Trail

9.6 mi
State: MA
Asphalt

Mass Central Rail Trail

38 mi
State: MA
Asphalt, Cinder, Crushed Stone, Dirt, Gravel

Mattabassett Trolley Trail

2.9 mi
State: CT
Asphalt

Middlebury Greenway

4.5 mi
State: CT
Asphalt

Middletown Westlake Area Bikeway

2.2 mi
State: CT
Asphalt

Naugatuck River Greenway

5.4 mi
State: CT
Asphalt

New Milford River Trail

5 mi
State: CT
Asphalt, Crushed Stone, Dirt

Putnam River Trail

2 mi
State: CT
Asphalt

Quinebaug River Trail

4.8 mi
State: CT
Asphalt

Quinnipiac Linear Trail

1.25 mi
State: CT
Asphalt, Gravel

Quinnipiac River Gorge Trail

1.3 mi
State: CT
Asphalt

Railroad Ramble

1.7 mi
State: CT
Asphalt, Dirt, Grass

Redstone Rail Trail

1.4 mi
State: MA
Asphalt

South Spencer Rail Trail

1.62 mi
State: MA
Crushed Stone

Southern New England Trunkline Trail

22 mi
State: MA
Asphalt, Ballast, Crushed Stone

Southwick Rail Trail

6.5 mi
State: MA
Asphalt

Stratton Brook State Park Trail

1.2 mi
State: CT
Asphalt, Cinder, Crushed Stone

Sue Grossman Still River Greenway

2.9 mi
State: CT
Asphalt

Trolley Trail (CT)

0.75 mi
State: CT
Asphalt

Ware River Rail-Trail

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

Westville Lake Community Trail

0.7 mi
State: MA
Crushed Stone

Windsor River Trail

0.8 mi
State: CT
Asphalt
Trail Image Trail Name States Length Surface Rating
The Air Line State Park Trail winds nearly 55 miles from the northeast corner of Connecticut, where the state borders Massachusetts, down to East Hampton in the heart of the state. The pathway is...
CT 54.6 mi Ballast, Dirt, Gravel
Visitors to the Ashuwillticook Rail Trail will find the full splendor of the scenic Berkshires along this nearly 12-mile-long paved trail. The Ashuwillticook (ash-oo-will-ti-cook) follows MA 8 through...
MA 11.9 mi Asphalt
Open in several disconnected segments, the Billings Trail is a dirt path that traverses a lovely scenic and wooded landscape outside Norfolk in northern Connecticut. Built on the abandoned railbed of...
CT 3.3 mi Dirt
The Bridge of Flowers delights the senses of visitors walking among the trees and blossoms on the old trolley bridge spanning the Deerfield River, which connects two communities in northwestern...
MA 0.1 mi Concrete
A part of Connecticut's first bus rapid transit line, the CTfastrak Trail serves as recreational and multi-use path for walking and bicycling between Downtown New Britain and Newington Junction. The...
CT 4.4 mi Asphalt, Concrete
The well-maintained Canalside Rail Trail provides users with a variety of trestle bridges, views of waterbirds stalking fish and frogs, and gentle grades that alternate between open sky and forested...
MA 3.6 mi Asphalt
The Bissell name looms large in this part of New England, and has been immortalized in multiple ways, including the Bissell Ferry, the Bissell Memorial Bridge and now, the Captain John Bissell trail,...
CT 4.5 mi Asphalt
The Charter Oak Greenway offers more than 16 miles of paved pathway through Hartford and its eastern suburbs. At first glance, the trail looks as if it is simply a highway side path, but the journey...
CT 16.6 mi Asphalt
The Cheney Rail Trail follows part of the corridor of the South Manchester Railroad, built by the Cheney brothers in 1869. The line was a 2.5-mile spur from the main Hartford, Providence, and Fishkill...
CT 1.7 mi Crushed Stone
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 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
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
A dozen miles west of Connecticut’s capital of Hartford, the Farmington River Trail forms a 16.5-mile arc that connects to the larger Farmington Canal Heritage Trail on both ends. The rail-trail was...
CT 16.5 mi Asphalt, Crushed Stone
The overall goal of the Grand Trunk Trail in south-central Massachusetts is to connect the communities of Brimfield, Sturbridge, and Southbridge by trail. Currently, two sections of the trail are...
MA 6.2 mi Crushed Stone, Dirt, Gravel
The Hanover Pond Trail is a mile-long rail-trail in Meriden, Connecticut offering scenic natural escape combined with historical exploration. The smooth asphalt trail is open to a diverse range of...
CT 1 mi Asphalt
Paralleling the Connecticut and Massachusetts borders, which lie only a few miles away, the Harlem Valley Rail Trail is a beautiful paved wooded pathway along the former New York & Harlem Railroad...
NY 17.2 mi Asphalt, Crushed Stone
It’s hard to pick a favorite season to experience the Hop River State Park Trail, set amid the dense forests of Eastern Connecticut. Sections of the 20-mile rail-trail dive through steep rock cuts...
CT 20 mi Crushed Stone
The 3.1-mile Kress Family Trail in Roxbury occupies the former route of the Shepaug Valley Railroad (the Shepaug, Litchfield and Northern Railroad). The railroad was famously known as the “crookedest...
CT 3.1 mi Dirt
Accordion
The Larkin State Park Trail meanders 10.8 miles through the woods and around the lakes and low hills of southwestern Connecticut. The rail-trail follows the route of the New York & New England...
CT 10.8 mi Cinder, Crushed Stone, Dirt, Gravel
The Manhan Rail Trail, well integrated into the local communities it serves, offers a pleasant ride or stroll. It conveniently weaves together parks, community points of interest, neighborhoods, and...
MA 9.6 mi Asphalt
The Massachusetts Central Railroad was destroyed by a hurricane in 1938, but the 104-mile corridor is being reborn as a cross-state rail-trail. Currently, nearly 40 miles from Boston to Northampton...
MA 38 mi Asphalt, Cinder, Crushed Stone, Dirt, Gravel
Where a trolley once ran, now you can too on the south bank of the Mattabessett River. The electrified trolley shuttled passengers from Berlin to Middletown and beyond. The smooth blacktop and an easy...
CT 2.9 mi Asphalt
The Middlebury Greenway provides a paved, off-road option for a self-propelled journey across suburban Middlebury. The trail touches on several business districts and parks, ending at an amusement...
CT 4.5 mi Asphalt
Over 2 miles from start to finish, this U-shaped trail meets both the commuting and the recreational needs of local residents in Middletown. The trail begins on Middle St, marked by a trailhead with a...
CT 2.2 mi Asphalt
The Naugatuck River Greenway will one day span 44 miles from Torrington to Derby in western Connecticut, but is currently open in a few short disconnected segments totaling just over 5 miles. The...
CT 5.4 mi Asphalt
The first phase of the New Milford River Trail runs southeast from Gaylordsville via the scenic but lightly traveled River Road, through Sega Meadows to Boardman Bridge, a distance of about 5 miles....
CT 5 mi Asphalt, Crushed Stone, Dirt
The Putnam River Trail extends between Arch Street in the Putnam District and Providence Street to the south. The trail follows the east bank of the Quinebaug River between the river and Kennedy...
CT 2 mi Asphalt
The Quinebaug River Trail exists in two segments in northwest Connecticut. The northern section parallels Park Road and Tracy Road for about 2 miles in an industrial section of Putnam with few trail...
CT 4.8 mi Asphalt
The Qunnipiac Linear Trail is an easy multipurpose path in Wallingford, Connecticut. The trail skirts Community Lake while traveling a heavily wooded corridor along the Quinnipiac River. It is one of...
CT 1.25 mi Asphalt, Gravel
The Quinnipiac River Gorge Trail is a 1.3-mile rail-trail in Meridan, Connecticut. The trail occupies the former railbed of the Meriden, Waterbury & Connecticut River Railroad, a 17-mile line which...
CT 1.3 mi Asphalt
The Railroad Ramble occupies a corridor abandoned by the Central New England Railroad, which provided service from 1871 through 1967. In Lakeville, the trail can be found just off of Route 41 behind...
CT 1.7 mi Asphalt, Dirt, Grass
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 Southern New England Trunk Line Trail (aka the "SNETT") was designated as a National Recreation Trail in 1994. It is built upon a segment of the former right-of-way of the New Haven Railroad's...
MA 22 mi Asphalt, Ballast, 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 Stratton Brook State Park Trail presents a great way to work up an appetite for a picnic at Stratton Brook State Park, the first state park in Connecticut to be entirely wheelchair accessible. The...
CT 1.2 mi Asphalt, Cinder, Crushed Stone
Coming in at just under 3 miles, the Sue Grossman Still River Greenway is anchored by the towns of Winchester to the north and Torrington to the south. It occupies the right-of-way of the Naugatuck...
CT 2.9 mi Asphalt
The Trolley Trail runs through Plainfield and is a key link the East Coast Greenway. Plans are to use this trail as a link between the Moosup Valley State Park Trail and the Airline State Park...
CT 0.75 mi Asphalt
The Rockville Spur, a section of Vernon Rails-to-Trails, is a stone-dust rail-trail stretching 4.2 miles into the heart of historical Rockville. The trail begins on Warren Avenue in Vernon, but you’ll...
CT 4.2 mi Crushed Stone, Dirt
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 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: 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. Due...
CT 5.4 mi Asphalt
The Windsor River Trail is a paved trail along the Connecticut River in Windsor Meadows State Park. The trail begins at the state park’s parking lot on E Barber St. The Captain John Bissell Trail,...
CT 0.8 mi Asphalt

Register for free!

Register for free with TrailLink today!

We're a non-profit all about helping you enjoy the outdoors
  • View over 30,000 of trail maps
  • Share your trail photos
  • Save your own favourite trails
  • Learn about new trails near you
  • Leave reviews for trails
  • Add new and edit existing trails

Trails by activity

Recent Trail Reviews

Redstone Rail Trail

Beginners- short flat trail

July, 2019 by godsmelissa

We enjoyed this short path to cap off the weekend after having ridden in the cape. Loved the train stop building, wish you could go in and read up and see pictures of the history; instead they had picture signs dotting the ride. Also there were some stone benches along the way and a bike shop I’d say at the halfway point. We saw bunnies too.

Mass Central Rail Trail

Norwottuck Branch (Belchertown to Northampton)

July, 2019 by lughnerson

Tuesday July 09, 2019, 5:30 pm.
Weather 88' F, low humidity, very light clouds.

Great weather for riding this great trail. Massachusetts really sets the bar for bike trails. This one has a line down the middle to help the careless riders better their performance. There are benches near view spots with poems and examples of flora and fauna carved into boulders. There are granite mile markers on both poles and pavement stones at the side of the trail. The pavement was very smooth and there are only some slight inclines. Tunnels and bridges, a variety of scenery, this is both a community trail and a destination trail. I drove 2.5 hours for this one and the much shorter Canalside trail a half hour away in Turner Falls, doing both on the same day with a mid-trip visit to the Bridge of Flowers in Shelburne Falls. All 3 places worth the trip, but now I have to complete the other sections of the Mass Central Greenway. Good job Massachusetts!

Canalside Rail Trail

Combine with the Bridge of Flowers

July, 2019 by lughnerson

Tuesday, July 09, 2019. Weather 88' F, few whisps of clouds, and low humidity.

It was a great weather for riding and a great trail to ride. The photos here are exactly what you see, except for the very nice park at the beginning of the trail. The village of Turner Falls is quite nice to visit also.

Only 15 minutes away in Shelburne Falls is the Bridge of Flowers, which is a beautiful short walk with a pub at one end. Combine these two activities into one great outing.

Accordion

Harlem Valley Rail Trail

A beautiful trail

July, 2019 by john.dischinger

We biked south to north from Wassaic to Millertown(?)....a great way to spend the 4th of July on an absolutely beautiful trail having lunch in the diner then turning around and going back...21 miles felt like 5....

Canalside Rail Trail

Great paved path- short distance ride

June, 2019 by godsmelissa

This trail was nice and flat. We got misdirected when we came to the main rd. The bike route follows straight across but we got confused as the sign said road closed, bridge out- but that was exactly where we needed to go. Then you turn to the right and follow thru old brick buildings that are mostly un-occupied. There is road crossings as others stated and they are marked. The cool trestle bridge was a nice view of the river. Past the bridge is a straight way then a few turns as you go slight uphill before it ends at the rail yard. There is a few picnic tables an benches along the entire bike route. Weather was good and cloudy also a nice breeze or it may have been hot along the open canal. We brought the kids to the amazing playground after. There is also a skate park too and you can fish as we saw ppl do- I assume state license needed; we were from CT.

Windsor Locks Canal State Park Trail

very nice 5 mile trail. great for walking. surface is rather bumpy even on my hybrid. can't beat the views. lots of wildlife.

June, 2019 by klinonis

very nice 5 mile trail. great for walking. surface is rather bumpy even on my hybrid. can't beat the views. lots of wildlife.

Farmington Canal Heritage Trail

Trail Status New Haven to Northampton

June, 2019 by petesalomone

Long Wharf to Yale is partially on-road, busy and tricky. Agreements with landowners have been completed and future construction will eliminate some of the on-road. 2018 trail completions in Cheshire and Southington make the trail continuous for 23 miles.
The remaining section in Southington is scheduled for construction in 2020. The Plainville section is currently in design. Construction could start in 2021. It might be phased, so construction might be complete in 2024 or later. When the Southington section is complete it will be relatively safe to ride on-road across Plainville.
From Northwest Dr on the Plainville/Farmington border the trail goes continuously to Main St Westfield about 34 miles. A few railroad bridges in Westfield have to be rebuilt to complete the trail to the Westfield River
North of the Westfield River the railroad is active. The best on-road routes include hilly and traffic. In Southampton the trail will be on the abandoned railroad right of way, but the right of way has not yet been purchased.
Getting to the trail in Easthampton requires about 10 miles of on-road. The last 7 miles of the trail to Northampton are complete

Ashuwillticook Rail Trail

Super Trail

June, 2019 by tbobinsky_tl

Beautiful scenery, good asphalt surface with big bumps well marked. Not much at the south end but great food and ale at the north end...plan accordingly. May also want to plan camping at Clarksburg State Park...about 15 minutes from the trail head. Met a few RTC members. So far for me, this is the best trail in Massachusetts. Please support - and a big thank you to - the Conservation Trust! Signed, one happy biker from New Hampshire.

Ashuwillticook Rail Trail

Great Trail

June, 2019 by coachmrpaul

Found this gem while visiting the Berkshire’s. Well maintained and a pleasure to ride. I went from Adams to Lanesborough. I appreciate the markings for the rises in the pavement (very few) due to roots coming up. Bravo Berkshire area for taking care of this one.

Captain John Bissell Trail

Great hard surface trail, light-traffic roads

June, 2019 by kathleenpwood

We love all of Main St, South Windsor, and it's perfect for a bike ride. I recommend starting at the top of Main St rather than by Chapel Rd as suggested here. It's a sample of old New England with lots of well-maintained vintage homes (including the birthplace of Jonathan Edwards), tobacco barns, fields, & farms. The road itself is a very moderate incline, similar to rails-to-trails. The bike trail alongside I291 is also very easy biking. We only had time to go about halfway on that portion before we needed to head back. An absolutely perfect ride!

Ashuwillticook Rail Trail

Well Maintained and Peaceful Ride

June, 2019 by tnjgronberg

Great scenery along the entire route. We started at the south end and rode all the way to the north end and back.

Farmington River Trail

Excellent

June, 2019 by yiwang100

This is the 1st trail I rode since started biking 7 years ago. It is still one of my favorites. Close to the north end there is a small town with nice restaurants and a surprisingly good small museum displaying local history. It is well worth a visit.

Find Nearby City trails

Accordion

Explore by City

Explore by City

Explore by Activity

Explore by Activity

Log in to your account to:

  • View trail paths on the map
  • Save trails to your account
  • Add trails, edit descriptions
  • Share photos
  • Add reviews

Log in with Google

OR

Register for free!

Join TrailLink (a non-profit) to view more than 30,000 miles of trail maps and more!

Register with Google

OR