Winchester Horseback Riding Trails and Maps

1022 Reviews

Looking for the best Horseback Riding trails around Winchester?

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

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  • Length
Activities
Length
Surfaces
Type
21 Results
Activities
Length
Surfaces
Type

Air Line State Park Trail

54.6 mi
State: CT
Ballast, Dirt, Gravel

Barker Road Trail

0.9 mi
State: MA
Dirt, Grass

Bridle Trail

3 mi
State: MA
Dirt, Sand

Derry Rail Trail

3.6 mi
State: NH
Asphalt

Granite Town Rail-Trail

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

Haggetts Rail Trail

2 mi
State: MA
Crushed Stone

Jay McLaren Memorial Trail

2 mi
State: MA
Dirt, Grass, Gravel

Marblehead Rail-Trail

4 mi
State: MA
Asphalt, Dirt, Gravel, Sand

Martin H. Burns Wildlife Management Area Trail

3.4 mi
State: MA
Dirt, Gravel, Sand

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

Nashua River Rail Trail

12.3 mi
State: MA, NH
Asphalt

New Boston Rail Trail

3.9 mi
State: NH
Dirt

Rockingham Recreational Rail Trail (Portsmouth Branch)

28.1 mi
State: NH
Crushed Stone, Dirt, Grass, Gravel, Sand

Southern New England Trunkline Trail

22 mi
State: MA
Asphalt, Ballast, Crushed Stone

Topsfield Linear Common and Wenham Rail-Trail

4.9 mi
State: MA
Crushed Stone, Dirt

Washington Secondary Bike Path

19.2 mi
State: RI
Asphalt
Accordion

Windham Rail Trail

4.3 mi
State: NH
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
Barker Road Trail begins on the town line between North Andover and Boxford in northern Massachusetts, not far from the New Hampshire border. From there, the pathway continues through dense woodlands...
MA 0.9 mi Dirt, Grass
The Blackstone River and Canal Heritage State Park recalls the role of canals in transporting raw materials and manufactured goods between emerging industrial centers. Walk along restored sections of...
MA 3.5 mi Dirt
The abandoned rail bed is predominantly owned by the Town of Marshfield. Sections of the abandoned rail bed are open to the public and actively used for recreational uses such as walking, running,...
MA 3 mi Dirt, Sand
This exquisitely maintained trail slices through forested areas and wetlands for a wonderful experience in southern New Hampshire. The trail will eventually be part of the Granite State Rail Trail,...
NH 3.6 mi Asphalt
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 Haggetts Rail Trail is a short, but sweet unpaved trail located on the periphery of Haggetts Pond, the local reservoir for the nearby town of Andover. Built on part of the former line of the...
MA 2 mi Crushed Stone
Nestled in the woodlands on the northern end of Merrimac in the far northeastern corner of Massachusetts, lies the beautiful Jay McLaren Memorial Trail. The town, once known as West Amesbury, had a...
MA 2 mi Dirt, Grass, Gravel
The Marblehead Rail-Trail appears on maps as a Y resting on its side, connecting Marblehead and Salem in the north and the city limits of Swampscott in the west. The 4-mile trail knits together a...
MA 4 mi Asphalt, Dirt, Gravel, Sand
The rail-trail through the Martin H. Burns Wildlife Management Area begins at the Massachusetts Bay Transportation Authority (MBTA) commuter rail station near downtown Newburyport, a coastal...
MA 3.4 mi Dirt, Gravel, Sand
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
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 Nashua River Rail Trail stretches from southern Nashua, New Hampshire, to downtown Ayer, Massachusetts, connecting to the towns of Pepperell and Groton. The trail is built on the former rail...
MA, NH 12.3 mi Asphalt
The New Boston Rail Trail follows the former railroad corridor of the same name for 3.9 miles through densely wooded areas in the town of New Boston. The railroad was in operation from 1893 to 1931,...
NH 3.9 mi Dirt
Crossing through wooded areas and featuring magnificent wetland vistas, the Rockingham Recreational Rail Trail (Fremont Branch) offers an 18.3-mile trail adventure from Epping to Windham. The northern...
NH 18.3 mi Dirt, Sand
The Rockingham Recreational Rail Trail brings at least two superlatives to mind: it’s one of New Hampshire’s longest rail-trails at just more than 28 miles, and it begins in Manchester, the state’s...
NH 28.1 mi Crushed Stone, Dirt, Grass, Gravel, Sand
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 trail begins in the small town of Boxford, about 25 miles north of Boston. For just shy of 5 miles, the hard-packed stone-dust pathway follows a former rail bed through Topsfield, meandering...
MA 4.9 mi Crushed Stone, Dirt
The Washington Secondary Bike Path offers just over 19 miles of paved trail from Cranston (Providence’s southwestern neighbor) to Coventry. The rail-trail, Rhode Island’s longest, follows the former...
RI 19.2 mi Asphalt
Accordion
The Windham Rail Trail passes through the woodsy periphery of Windham in southern New Hampshire, but it sits in the heart of the future cross-state Granite State Rail Trail. Its connections to the...
NH 4.3 mi Asphalt

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Trails by activity

Granite Town Rail-Trail

NH - 3 miles

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...

Topsfield Linear Common and Wenham Rail-Trail

MA - 4.9 miles

The trail begins in the small town of Boxford, about 25 miles north of Boston. For just shy of 5 miles, the hard-packed stone-dust pathway follows a former rail bed through Topsfield, meandering...

Washington Secondary Bike Path

RI - 19.2 miles

The Washington Secondary Bike Path offers just over 19 miles of paved trail from Cranston (Providence’s southwestern neighbor) to Coventry. The rail-trail, Rhode Island’s longest, follows the former...

Haggetts Rail Trail

MA - 2 miles

The Haggetts Rail Trail is a short, but sweet unpaved trail located on the periphery of Haggetts Pond, the local reservoir for the nearby town of Andover. Built on part of the former line of the...

Accordion

Windham Rail Trail

NH - 4.3 miles

The Windham Rail Trail passes through the woodsy periphery of Windham in southern New Hampshire, but it sits in the heart of the future cross-state Granite State Rail Trail. Its connections to the...

Nashua River Rail Trail

MA,NH - 12.3 miles

The Nashua River Rail Trail stretches from southern Nashua, New Hampshire, to downtown Ayer, Massachusetts, connecting to the towns of Pepperell and Groton. The trail is built on the former rail...

Marblehead Rail-Trail

MA - 4 miles

The Marblehead Rail-Trail appears on maps as a Y resting on its side, connecting Marblehead and Salem in the north and the city limits of Swampscott in the west. The 4-mile trail knits together a...

Derry Rail Trail

NH - 3.6 miles

This exquisitely maintained trail slices through forested areas and wetlands for a wonderful experience in southern New Hampshire. The trail will eventually be part of the Granite State Rail Trail,...

Mass Central Rail Trail

MA - 38 miles

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....

Topsfield Linear Common and Wenham Rail-Trail

MA - 4.9 miles

The trail begins in the small town of Boxford, about 25 miles north of Boston. For just shy of 5 miles, the hard-packed stone-dust pathway follows a former rail bed through Topsfield, meandering...

Air Line State Park Trail

CT - 54.6 miles

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...

Martin H. Burns Wildlife Management Area Trail

MA - 3.4 miles

The rail-trail through the Martin H. Burns Wildlife Management Area begins at the Massachusetts Bay Transportation Authority (MBTA) commuter rail station near downtown Newburyport, a coastal...

Accordion

New Boston Rail Trail

NH - 3.9 miles

The New Boston Rail Trail follows the former railroad corridor of the same name for 3.9 miles through densely wooded areas in the town of New Boston. The railroad was in operation from 1893 to 1931,...

Haggetts Rail Trail

MA - 2 miles

The Haggetts Rail Trail is a short, but sweet unpaved trail located on the periphery of Haggetts Pond, the local reservoir for the nearby town of Andover. Built on part of the former line of the...

Granite Town Rail-Trail

NH - 3 miles

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...

Barker Road Trail

MA - 0.9 miles

Barker Road Trail begins on the town line between North Andover and Boxford in northern Massachusetts, not far from the New Hampshire border. From there, the pathway continues through dense woodlands...

Washington Secondary Bike Path

RI - 19.2 miles

The Washington Secondary Bike Path offers just over 19 miles of paved trail from Cranston (Providence’s southwestern neighbor) to Coventry. The rail-trail, Rhode Island’s longest, follows the former...

Rockingham Recreational Rail Trail (Fremont Branch)

NH - 18.3 miles

Crossing through wooded areas and featuring magnificent wetland vistas, the Rockingham Recreational Rail Trail (Fremont Branch) offers an 18.3-mile trail adventure from Epping to Windham. The northern...

Windham Rail Trail

NH - 4.3 miles

The Windham Rail Trail passes through the woodsy periphery of Windham in southern New Hampshire, but it sits in the heart of the future cross-state Granite State Rail Trail. Its connections to the...

Nashua River Rail Trail

MA,NH - 12.3 miles

The Nashua River Rail Trail stretches from southern Nashua, New Hampshire, to downtown Ayer, Massachusetts, connecting to the towns of Pepperell and Groton. The trail is built on the former rail...

Southern New England Trunkline Trail

MA - 22 miles

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...

Derry Rail Trail

NH - 3.6 miles

This exquisitely maintained trail slices through forested areas and wetlands for a wonderful experience in southern New Hampshire. The trail will eventually be part of the Granite State Rail Trail,...

Mason Railroad Trail

NH - 6.7 miles

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...

Blackstone River and Canal Heritage State Park Trail

MA - 3.5 miles

The Blackstone River and Canal Heritage State Park recalls the role of canals in transporting raw materials and manufactured goods between emerging industrial centers. Walk along restored sections of...

Marblehead Rail-Trail

MA - 4 miles

The Marblehead Rail-Trail appears on maps as a Y resting on its side, connecting Marblehead and Salem in the north and the city limits of Swampscott in the west. The 4-mile trail knits together a...

Rockingham Recreational Rail Trail (Portsmouth Branch)

NH - 28.1 miles

The Rockingham Recreational Rail Trail brings at least two superlatives to mind: it’s one of New Hampshire’s longest rail-trails at just more than 28 miles, and it begins in Manchester, the state’s...

Monadnock Recreational Rail Trail

NH - 7.5 miles

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...

Jay McLaren Memorial Trail

MA - 2 miles

Nestled in the woodlands on the northern end of Merrimac in the far northeastern corner of Massachusetts, lies the beautiful Jay McLaren Memorial Trail. The town, once known as West Amesbury, had a...

Granite Town Rail-Trail

NH - 3 miles

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...

Bridle Trail

MA - 3 miles

The abandoned rail bed is predominantly owned by the Town of Marshfield. Sections of the abandoned rail bed are open to the public and actively used for recreational uses such as walking, running,...

Southern New England Trunkline Trail

MA - 22 miles

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...

Blackstone River and Canal Heritage State Park Trail

MA - 3.5 miles

The Blackstone River and Canal Heritage State Park recalls the role of canals in transporting raw materials and manufactured goods between emerging industrial centers. Walk along restored sections of...

Accordion

Windham Rail Trail

NH - 4.3 miles

The Windham Rail Trail passes through the woodsy periphery of Windham in southern New Hampshire, but it sits in the heart of the future cross-state Granite State Rail Trail. Its connections to the...

Mason Railroad Trail

NH - 6.7 miles

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...

Rockingham Recreational Rail Trail (Portsmouth Branch)

NH - 28.1 miles

The Rockingham Recreational Rail Trail brings at least two superlatives to mind: it’s one of New Hampshire’s longest rail-trails at just more than 28 miles, and it begins in Manchester, the state’s...

Barker Road Trail

MA - 0.9 miles

Barker Road Trail begins on the town line between North Andover and Boxford in northern Massachusetts, not far from the New Hampshire border. From there, the pathway continues through dense woodlands...

Air Line State Park Trail

CT - 54.6 miles

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...

Topsfield Linear Common and Wenham Rail-Trail

MA - 4.9 miles

The trail begins in the small town of Boxford, about 25 miles north of Boston. For just shy of 5 miles, the hard-packed stone-dust pathway follows a former rail bed through Topsfield, meandering...

Rockingham Recreational Rail Trail (Fremont Branch)

NH - 18.3 miles

Crossing through wooded areas and featuring magnificent wetland vistas, the Rockingham Recreational Rail Trail (Fremont Branch) offers an 18.3-mile trail adventure from Epping to Windham. The northern...

New Boston Rail Trail

NH - 3.9 miles

The New Boston Rail Trail follows the former railroad corridor of the same name for 3.9 miles through densely wooded areas in the town of New Boston. The railroad was in operation from 1893 to 1931,...

Monadnock Recreational Rail Trail

NH - 7.5 miles

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...

Jay McLaren Memorial Trail

MA - 2 miles

Nestled in the woodlands on the northern end of Merrimac in the far northeastern corner of Massachusetts, lies the beautiful Jay McLaren Memorial Trail. The town, once known as West Amesbury, had a...

Marblehead Rail-Trail

MA - 4 miles

The Marblehead Rail-Trail appears on maps as a Y resting on its side, connecting Marblehead and Salem in the north and the city limits of Swampscott in the west. The 4-mile trail knits together a...

Washington Secondary Bike Path

RI - 19.2 miles

The Washington Secondary Bike Path offers just over 19 miles of paved trail from Cranston (Providence’s southwestern neighbor) to Coventry. The rail-trail, Rhode Island’s longest, follows the former...

Martin H. Burns Wildlife Management Area Trail

MA - 3.4 miles

The rail-trail through the Martin H. Burns Wildlife Management Area begins at the Massachusetts Bay Transportation Authority (MBTA) commuter rail station near downtown Newburyport, a coastal...

Mass Central Rail Trail

MA - 38 miles

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....

Nashua River Rail Trail

MA,NH - 12.3 miles

The Nashua River Rail Trail stretches from southern Nashua, New Hampshire, to downtown Ayer, Massachusetts, connecting to the towns of Pepperell and Groton. The trail is built on the former rail...

Haggetts Rail Trail

MA - 2 miles

The Haggetts Rail Trail is a short, but sweet unpaved trail located on the periphery of Haggetts Pond, the local reservoir for the nearby town of Andover. Built on part of the former line of the...

Recent Trail Reviews

Minuteman Commuter Bikeway

Wonderful Commuter Trail

August, 2018 by heochief

We are from Chicago and rode this trail. We found it very pleasant even dodging rain drops. The trail is clean and smooth with a moderate amount of traffic. Most traffic seemed to be commuter traffic. We enjoyed the historic portions of the trail and loved Lexington along the way. The old commuter coach at the Bedford Station is a nice touch of the days the trail served as a rail line. We did ride the trail from end pint to end point however after the Bedford Station the trail seems to be less marked and resorts to street traffic. All in all a great inter urban commuter trail.

East Bay Bike Path

Brand new east bay bike path

August, 2018 by srinisankar

New asphalt, lane markers and mile markers. Our tax dollars at work

Washington Secondary Bike Path

Longest path in the state

August, 2018 by smt42

It's an excellent path, especially the more rural Coventry section. I can't wait for the final 5-mile extension to Connecticut to be done in a few years! There's also a possible mile or so extension into Providence coming in the next several years.
The trail surface needs a little attention along some of the older parts in Cranston through West Warwick, like the East Bay had earlier this year, but overall not too bad.

Accordion

East Bay Bike Path

Beautiful

July, 2018 by vikkb34

The trail has such beautiful views.. Water ,woods & residential..We parked around Mercer st...There is a bunch of parking..Next time I would go to the parking lot a little further down the road. There is a slight hill there,u go down. Coming back u go up. We were tired rode 27 miles & that was the last leg...we managed to get up the hill...lol.. Really the trail is pretty flat .. It is a narrow trail & can get very busy,so u have to pay attention. But most people were great...There r plenty of places to get off & grab something to eat,drink.. Bathrooms didn't see.. Bristol was a nice town..

Southern New England Trunkline Trail

Poor Franklin Leg

July, 2018 by marksbono


Having just tried the SNETT for the 1st time, I was very disappointed. The review from July last year is still the situation ... the trail was amazing for a few miles, quite stunning all around though for this section the path was clear and maintained. While no standing water, the trail narrowed to a walking path at best in many places. I also abandoned somewhere in Bellingham. I'll try another leg next time.

I've used the Hopkinton/Milford/Holliston trails that have great trails - wide, gravel or paved, & no obscure entry/exits - so my benchmark is quite high. Hoping for another good local option!

Northern Strand Community Trail

mediocre

July, 2018 by albern36

As mentioned, the section in Saugus is rock not crushed stone. I rode this on a hybrid and luckily didn't get a flat. The trail is not that interesting, goes behind some ugly industrial developments, and crosses too many busy intersections. This is a one and done for me. I could see the value of the trail for commuters/walkers, but this trail held very little interest for me. I started going on a bit through unimproved section that goes into Lynn. I saw some broken glass, thought better of it, and turned around.

Rockingham Recreational Rail Trail (Portsmouth Branch)

too rough

July, 2018 by kjands

Tried it out with dat wheel bike- I like a smoother ride for relaxation and to enjoy scenery.

Danvers Rail Trail

Flat and dry even after a rain. But not much shade

July, 2018 by engsurplus

Danvers trail is flat (like it was rolled recently) and very well maintained. Packed small cinder/gravel, it was already drained and dry less then 24 hours after a rain. South 2 miles does cross a lot of roads, though crossings are well marked and the cars are polite enough to stop. Personally, I'd skip the southern 2 miles and instead just keep going into the 'Topsfield Linear' trail. Both trails have a lot of sun....they're not very shady so consider that on a hot sunny day. My ride was during the week...very little traffic.

Alewife Linear Park/Somerville Community Path

Community Portion is Excellent - Way too short though

July, 2018 by pwhitmer8

I love the community path - the art, the kids, the people hanging out. It seems really well used.

Of course the path just ends. There's a not totally horrible way (with kids) to get to the Museum of Science aka the Charles River Path from the end of the community path. We took a side street to Central Ave., then the bike line on Somerville to Union Sq., crossing via sidewalks. Then the bike lane on Somerville Ave, with a RT on Medford, to School, to Thorndike. The Medford Street portion goes underneath a train bridge with fast traffic, but there is a bike lane. Considered Webster > Cambridge St. to get around that, but the last part of Webster is a Show for kids.

Narrow-Gauge Rail-Trail

Short, quiet, great for kids

July, 2018 by pwhitmer8

Started on this trail (by the noted parking), with a goal of connecting to the MBT. We found the trail very smooth and well maintained, not crowded (even on a weekend) and very pleasant. Not long enough for a ride by itself, but definitely a more interesting way to start your Minuteman experience.

East Bay Bike Path

Yup, it's all that and a bag of chips

July, 2018 by lughnerson

Or ice cream, from one of the vendors you can visit along the way.

Dateline: Monday June 25, 2018.
Beautiful sunny day, temps in the upper 80's

I came for 3 days of biking in Rhode Island just for this trail and it did not let me down. Do it. It's worth a long drive (3.5 hours for me) and repeat visits. I used a municipal parking lot in Bristol for the round trip, which was about a quarter mile down the same street as the endpoint of the trail. Every other parking area was too busy.

Caution. After visiting many bike trails thanks to TrailLink, my only complaint is that some of the parking areas need to be reviewed more carefully. In this case the first parking area in East Providence did not encourage me to leave my car there for 3 hours. Always take the address/directions/GPS to more than one parking lot and visit the TrailLink site just before departing for any updates. I drove 2.5 hours to Windsor Locks, CT to find out the entire trail was closed temporarly, and my only parking lot address closed for the entire year. But I will go back, because the trails themselves have not let me down.

Blackstone River Greenway (RI)

Maybe the Most Beautiful Trail in Rhode Island

July, 2018 by lughnerson

Dateline: Tuesday, June 26, 2018.
Beautiful sunny day, about 85 F.

I started from the Traillink suggested parking lot in the East Providence. The first 3 to 4 miles were in suburban street bike lanes until I got to Lonsdale. Then the trail became wonderful and completely off-road. So choose your parking area carefully. This trail is definitely worth a long drive (3.5 hours for me) and a repeat visit. As much as I love the ocean views of the East Bay Bike Path, I liked this trail better. Nice job Rhode Island.

Caution. After visiting many bike trails thanks to TrailLink, my only complaint is that some of the parking areas need to be reviewed more carefully. Always take the address/directions/GPS to more than one parking lot and visit the TLink site just before departing for any updates. I drove 2.5 hours to Windsor Locks, CT to find out the entire trail was closed temporarly, and my only parking lot address closed for the entire year. But I will go back, because the trails themselves have not let me down.

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