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Find Trails > Connecticut > Windham > Windham Dog Walking Trails

Windham, CT Dog Walking Trails and Maps

1438 Reviews

Looking for the best Dog Walking trails around Windham?

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

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Activities
Length
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Type
60 Results
Activities
Length
Surfaces
Type

Air Line State Park Trail
60.3 mi
State: CT
Ballast, Crushed Stone, Dirt, Gravel

Blackstone River Greenway
31.6 mi
State: MA, RI
Asphalt, Boardwalk, Crushed Stone, Dirt

Bloomfield Greenway Multi-Use Trail
1.8 mi
State: CT
Asphalt

Branford Trolley Trail
0.6 mi
State: CT
Concrete, Crushed Stone, Gravel

Center Trail
0.6 mi
State: MA
Crushed Stone

Cheney Rail Trail
1.7 mi
State: CT
Crushed Stone

Columbia Greenway Rail Trail
3.1 mi
State: MA
Asphalt

East Bay Bike Path (RI)
14.3 mi
State: RI
Asphalt, Boardwalk

Farmington Canal Heritage Trail
49.1 mi
State: CT
Asphalt

Farmington River Trail
16.5 mi
State: CT
Asphalt, Concrete, Crushed Stone

Fred Lippitt Woonasquatucket River Greenway
6.8 mi
State: RI
Asphalt

Grand Trunk Trail
6.9 mi
State: MA
Crushed Stone, Dirt, Gravel

Hanover Pond Trail

1 mi
State: CT
Asphalt

Hartford Riverwalk
1.7 mi
State: CT
Asphalt

Hop River State Park Trail
20 mi
State: CT
Crushed Stone

Manhan Rail Trail
9.5 mi
State: MA
Asphalt

Mass Central Rail Trail
64 mi
State: MA
Asphalt, Cinder, Crushed Stone, Dirt, Gravel

Phenix-Harris Riverwalk
0.3 mi
State: RI
Dirt

Quinebaug River Trail
4.8 mi
State: CT
Asphalt

Quinebaug Valley Rail Trail
5.7 mi
State: MA
Ballast, Cinder, Dirt, Grass
Accordion

Quinnipiac River Gorge Trail
1.3 mi
State: CT
Asphalt

Quonset Point Bike Path
2.5 mi
State: RI
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

Sue Grossman Still River Greenway
3.4 mi
State: CT
Asphalt

Ten Mile River Greenway
3 mi
State: RI
Asphalt

Upper Charles Trail
13.9 mi
State: MA
Asphalt, Crushed Stone

Warren Bike Path
0.9 mi
State: RI
Asphalt

Washington Secondary Bike Path
19.2 mi
State: RI
Asphalt

Westville Lake Community Trail
0.7 mi
State: MA
Crushed Stone

William C. O'Neill Bike Path
7.2 mi
State: RI
Asphalt

Windsor River Trail

0.8 mi
State: CT
Asphalt

Arkwright Riverwalk
0.8 mi
State: RI
Dirt, Woodchips

Burrillville Bike Path
1.2 mi
State: RI
Asphalt

CTfastrak Multi-Use Trail
4.4 mi
State: CT
Asphalt, Concrete

Captain John Bissell Trail
4.5 mi
State: CT
Asphalt

Charter Oak Greenway
16.5 mi
State: CT
Asphalt

Connecticut Riverwalk and Bikeway
7.8 mi
State: MA
Asphalt

G & S Trolley trail
1.6 mi
State: CT
Asphalt, Crushed Stone

JAYCEE Arboretum & Senator Roch Riverwalk
1.3 mi
State: RI
Asphalt, Dirt, Gravel

Larkin State Park Trail
10.8 mi
State: CT
Cinder, Crushed Stone, Dirt, Gravel

Mattabassett Trolley Trail

2.9 mi
State: CT
Asphalt

Middlebury Greenway
4.5 mi
State: CT
Asphalt

Niantic Bay Boardwalk
1.1 mi
State: CT
Boardwalk, Concrete, Gravel

Putnam River Trail
2 mi
State: CT
Asphalt

Quinnipiac Linear Trail

2.1 mi
State: CT
Asphalt, Gravel

Shoreline Greenway Trail
4.6 mi
State: CT
Crushed Stone, Dirt

Southern New England Trunkline Trail
21.8 mi
State: MA
Asphalt, Ballast, Crushed Stone

Stillwater Scenic Walkway
1 mi
State: RI
Crushed Stone, Dirt

URI Bike Path
2 mi
State: RI
Asphalt

Vernon Rails-to-Trails (Hop River State Park Rockville Spur)
4.2 mi
State: CT
Crushed Stone, Dirt

Windsor Locks Canal State Park Trail
5.4 mi
State: CT
Asphalt

Chicopee River Canal Rail Trail
0.21 mi
State: MA
Asphalt

Moosup Valley State Park Trail
5.8 mi
State: CT
Crushed Stone, Grass, Gravel

Naugatuck River Greenway
7.4 mi
State: CT
Asphalt

Stratton Brook State Park Trail
1.2 mi
State: CT
Asphalt, Cinder, Crushed Stone

Ware River Rail-Trail
15 mi
State: MA
Ballast, Dirt, Grass, Gravel

Trolley Trail (CT)
0.75 mi
State: CT
Asphalt

Middletown Westlake Area Bikeway

2.2 mi
State: CT
Asphalt
Trail Image Trail Name States Length Surface Rating
The Air Line State Park Trail winds 60.3 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 nearly...
 CT 60.3 mi Ballast, Crushed Stone, Dirt, Gravel
Throughout history, the Blackstone River has been an important waterway, from its use by American Indians who fished its once-abundant salmon to its role as a major artery for the transportation of...
 MA, RI 31.6 mi Asphalt, Boardwalk, Crushed Stone, Dirt
The Bloomfield Greenway Multi-Use Trail currently runs 1.8 miles between Bloomfield and village of Tariffville in the Town of Simsbury. The paved rail-trail passes through woods and fields with...
 CT 1.8 mi Asphalt
The Branford Trolley Trail is essentially a 0.6-mile footbridge occupying an old bridge along the route of an abandoned trolley track. About the Route The long bridge links nature trails on both...
 CT 0.6 mi Concrete, Crushed Stone, Gravel
The Center Trail runs for less than a mile from Hopkinton's downtown to its high school and middle school, providing a safe route to school for thousands of students. The wooded trail, which once...
 MA 0.6 mi Crushed Stone
The Cheney Rail Trail is a 1.7-mile trail with a crushed stone surface in downtown Manchester. About the Route The trail is mostly shaded and a pleasant walk any time of the year. The terrain is...
 CT 1.7 mi Crushed Stone
The Columbia Greenway Rail Trail offers just over 3 miles of paved, tree-lined pathway through Westfield in southwestern Massachusetts. About the Route The rail-trail runs between the Westfield...
 MA 3.1 mi Asphalt
Offering spectacular maritime views and an abundance of coastal wildlife, the East Bay Bike Path is a 14.3-mile trail that connects historic New England waterfronts along several river mouths of the...
 RI 14.3 mi Asphalt, Boardwalk
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 49.1 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, Concrete, Crushed Stone
The Fred Lippitt Woonasquatucket River Greenway provides a valuable crosstown connector of nearly 7 miles from downtown Providence to the city’s western neighborhoods and the nearby town of Johnston....
 RI 6.8 mi Asphalt
The overall goal of the Grand Trunk Trail in south-central Massachusetts is to connect the communities of Brimfield, Sturbridge, and Southbridge by trail. There are two longer sections of trail, in...
 MA 6.9 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
The Hartford Riverwalk is a charming network of paved pathways for cyclists and pedestrians that runs along the banks of the Connecticut River through the state capital. The trail provides an off-road...
 CT 1.7 mi Asphalt
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 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 9.5 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. The Mass Central Rail Trail runs for 36.36 miles from...
 MA 64 mi Asphalt, Cinder, Crushed Stone, Dirt, Gravel
The Phenix-Harris Riverwalk, a short trail built on a former rail bed purchased from Penn Central Railroad, connects West Warwick and Coventry, two towns on the outskirts of Providence. The dirt...
 RI 0.3 mi Dirt
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 Quinebaug Valley Rail Trail runs on the corridor once occupied by the Southbridge & Blackstone line of the Providence & Worcester Railroad, transforming a corridor once designed to link rural...
 MA 5.7 mi Ballast, Cinder, Dirt, Grass
Accordion
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
Beginning from Calf Pasture Point Beach, the Quonset Point Bike Path offers a short-but-sweet path across North Kingstown on Rhode Island's eastern coastline. The 2.5-mile paved pathway is ideal for...
 RI 2.5 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 for 6.5 miles between the Westfield town line south and the Massachusetts–Connecticut state line. About the Route Along the way, the Southwick Rail Trail travels...
 MA 6.5 mi Asphalt
Just over 3 miles long, the Sue Grossman Still River Greenway is anchored by Winsted to the north and Torrington to the south. It occupies the right-of-way of the Naugatuck Division of the New York,...
 CT 3.4 mi Asphalt
Ten Mile River Greenway, named for the waterway it parallels and not its length, runs 3 miles through a serene and green corridor connecting the City of East Providence and Pawtucket. The southern end...
 RI 3 mi Asphalt
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...
 MA 13.9 mi Asphalt, Crushed Stone
The pleasantly tree-lined Warren Bike Path, built along the former Warren-Fall River Railroad, runs just under a mile from Long Road west to the Kickemuit River. The trail ends in an 18-acre park...
 RI 0.9 mi Asphalt
The Washington Secondary Bike Path offers just over 19 miles of paved trail from Cranston (Providence’s southwestern neighbor) to Coventry. About the Route The rail-trail, Rhode Island’s...
 RI 19.2 mi Asphalt
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
Imagine a wealthy 19th-century textile mill owner building an 8-mile railroad to get coal to his plant or products to market, and then adding accommodations to carry vacationers to beach resorts or...
 RI 7.2 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
The Arkwright Riverwalk, founded on a former rail bed purchased from Penn Central Railroad, is located in Coventry, a rural central Rhode Island town that was built around textile mills. The one-mile...
 RI 0.8 mi Dirt, Woodchips
Burrillville Bike Path runs for just over a mile through its namesake rural community in northwest Rhode Island. It connects the villages of Pascoag and Harrisville through a corridor that once...
 RI 1.2 mi Asphalt
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 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 pathways 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 16.5 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 7.8 mi Asphalt
At the turn of the 20th century, Groton & Stonington Railway Company began to move passengers between Groton to Mystic via electric trolleys. But in 25 years, the line had been discontinued due to...
 CT 1.6 mi Asphalt, Crushed Stone
Riverpoint Park sits nestled into a bend of the Pawtuxet River in West Warwick, Rhode Island. The park accommodates the 400-ft arboretum which leads to 1.3-mile riverside path known as the Senator...
 RI 1.3 mi Asphalt, Dirt, Gravel
The Larkin State Park Trail meanders 10.8 miles through the woods and around the lakes and low hills of southwestern Connecticut. About the Route Horseback riders use this trail frequently and...
 CT 10.8 mi 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 4.5-mile 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...
 CT 4.5 mi Asphalt
Bookended by beaches and offering gorgeous vistas of Niantic Bay, the Niantic Bay Boardwalk is a must-do excursion in the small Connecticut village of Niantic, part of the larger Town of East Lyme....
 CT 1.1 mi Boardwalk, Concrete, Gravel
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 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 2.1 mi Asphalt, Gravel
When complete, Connecticut’s Shoreline Greenway Trail will be a scenic 25-mile route through four quaint New England towns off Long Island Sound. From Lighthouse Point to Hammonasset Beach State Park,...
 CT 4.6 mi Crushed Stone, Dirt
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 21.8 mi Asphalt, Ballast, Crushed Stone
The Stillwater Scenic Walkway is a short trail that follows an old railroad bed between Capron Road and State Route 104 (Farnum Pike) south of Smithfield. The trail passes through a wooded area along...
 RI 1 mi Crushed Stone, Dirt
The URI (University of Rhode Island) Bike Path provides a safe conduit for students, faculty and staff to commute to and from school via the William C. O'Neill Bike Path. The asphalt, two-lane path...
 RI 2 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 trail...
 CT 4.2 mi Crushed Stone, Dirt
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...
 CT 5.4 mi Asphalt
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
This 5.8-mile trail runs between Moosup and the Rhode Island/Connecticut border. Wide and flat, this rail-trail is suitable for riders of all levels. The surface is a mix of paved asphalt and granular...
 CT 5.8 mi Crushed Stone, Grass, Gravel
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 7 miles. The...
 CT 7.4 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
The Ware River Rail-Trail is an unpaved 15-mile rail-trail that stretches between Barre and Baldwinville, running through Hubbardston and Templeton along the way.  Following along the Burnshirt...
 MA 15 mi Ballast, Dirt, Grass, Gravel
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
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

Recent Trail Reviews

Naugatuck River Greenway

Naugatuck River Greenway-Torrington CT Section(s)

October, 2025 by marieperriello86

Currently there is a couple of sections that are really nice for the work thats been completed, but will be a fantastic trail once they have completed the sections necessary to connect them into one long trail. All the sections completed are mostly all paved and are great for walking/jogging/biking & wheelchair/stroller friendly. The only exception is tgr Naugatuck River Greenway section that starts at the Sullivan Senior Center, which has a paved trail that runs parallel to the the river and ends at the side road which you continue down a one way street that almost zig zags until you reach palmer bridge. Crossing the bridge and crossing to the paved trail that goes behind a condominium and continues until the end of the dirt parking lots (trail is paved) of John Toro Sports Complex, where the pavement ends towards the actual field. Then it transitions to the field with no defined trail. The Trail at that point isnt really distinct. I lived here most of my life and I didnt know until I saw a news article about The Rainbow Bridge and found that the trail in fact extended past where the pavement ends and continues straight past the dog park past both the first baseball field, the soccer field, and then about halfway through the 2nd baseball field there is a wide opening in the forest, where you then see the entrance to the Rainbow Bridge Trail. Which is an amazing small half looped trail, with some of the most beautiful works of art, and tributes to various pets (photos, stepping stones/memorial rock garden, a memorial fence, k-9 officers memorial bulletin board(s), sculptures, poems, signs, chairs, then the rainbow Bridge which is adorned with photos, momentos, stories, collars & tributes to pets of those who came to place their beloved pets memorials. After you find the exits shortly after that you can see the wide open pathway continues for a while on but ends at a fenced off area that currently is a business/underutilized "Sports park" that will eventually be replaced with a connector trail that will connect with other nearby trails.

read more …

Washington Secondary Bike Path

Not a bad ride

October, 2025 by trainman1957

This trail needs open parking spaces! Most of the parking spots are blocked off!

read more …

East Bay Bike Path (RI)

Where is the bathroom if starting from Providence RI ?

October, 2025 by ningji

don't see bathroom in the parking lot

read more …
Accordion

Washington Secondary Bike Path

No e-bikes allowed

October, 2025 by dwxchcmrzk

This is a multi use bike trail for everyone to enjoy.

read more …

Farmington Canal Heritage Trail

ok

October, 2025 by deceived

Rode a portion from Milldale north to Southington. All paved in fairly decent shape. A few bumps but no broken pavement. At the point in Southington the trail just ends with no information as to where to go. No signs or arrows. The trail picks up somewhere a few miles away but I couldn’t find out how to get there. On the portion I rode it was flat and easy, but not much to see other than woods and backs of buildings.

read more …

Upper Charles Trail

lots of street crossings

September, 2025 by chleary11

This is a good trail, but if you start in Milford and do the entire checkmark there are a lot of street crossings. The pretty parts of the trail are nice and shady and wooded, but there is a fair amount of commercial areas that you have to get through. It’s nice and flat and there are lots of parking areas along the way. My gps did not take me to a parking lot but when I put the trail into AllTrails I got accurate directions.

read more …

Hop River State Park Trail

Truly Amazing

September, 2025 by mtheis.45

Was visiting the area and am so happy I got my gravel bike out to do this trail. As others have mentioned, it is very, very well maintained and quite smooth, enabling fast riding (I rode the entire trail as listed). As a former rail, this trail has nice and gradual elevation changes and has cool features like the tunnels and bridges. I'd highly recommend and hope to be back for another spin soon.

read more …

Windsor Locks Canal State Park Trail

Nice Biking spot for a 10-ish mile ride

September, 2025 by mtheis.45

Had a great evening bike ride out at the Windsor Locks Canal trail earlier this month (Aug, '25). The trail is paved, and as others have mentioned, it is not super smooth in some areas where the tree roots are pushing the asphalt up but can be navigated pretty easily. I was riding my gravel bike setup with 42mm tires and was able to go quite fast - averaging 15mph on the ride so it really was not that beat up / bad.

The scenery on the river is very nice, and the canal on the other side was also fun - lots of wildlife to see. Would recommend if in the area!

read more …

Farmington Canal Heritage Trail

Rode the entire trail…

September, 2025 by willipar

Rode the entire Farmington Canal Heritage Trail as part of a 2 day ride from Northampton to New Haven. What a fabulous experience! So much variety and New England splendor packed into one journey. It was very interesting to see how each of the towns maintained the trail differently. Everything from the paving to the signage changed as you moved from one village to the next. What an amazing treasure!

read more …

Columbia Greenway Rail Trail

Beautifully Designed and Maintained

September, 2025 by willipar

A pleasure to ride!

read more …

Connecticut Riverwalk and Bikeway

River trail

August, 2025 by dawgpound99

Short for bike, nice views, benches and even a real train.

read more …

Mass Central Rail Trail

A Delightful Ride on The Norwottuck Section

August, 2025 by gettinlate

June 6th 2025
The Mrs and I rode this beautiful trail from North Hampton to just short of Belchertown, and back.
The weather was great and the trail is mostly shaded, so the ride was superb.
I'd have no objection to doing it again.

read more …
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Explore by Activity

ATV
Bike
Birding
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Fishing
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Horseback Riding
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Running
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Walking
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