Middletown Cross Country Skiing Trails and Maps

501 Reviews

Looking for the best Cross Country Skiing trails around Middletown?

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

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Activities
Length
Surfaces
Type
21 Results
Activities
Length
Surfaces
Type

Air Line State Park Trail

54.6 mi
State: CT
Ballast, Dirt, Gravel

Arkwright Riverwalk

0.8 mi
State: RI
Dirt, Woodchips

Bay Colony Rail Trail

1.7 mi
State: MA
Crushed Stone

Blackstone River Greenway (RI)

11.8 mi
State: RI
Asphalt

Burrillville Bike Path

1.2 mi
State: RI
Asphalt

Center Trail

0.6 mi
State: MA
Crushed Stone

East Bay Bike Path

14.3 mi
State: RI
Asphalt

Hanover Branch Rail Trail

2.6 mi
State: MA
Asphalt, Crushed Stone

Mattapoisett Rail Trail

1.1 mi
State: MA
Asphalt

Moosup Valley State Park Trail

5.8 mi
State: CT
Ballast, Crushed Stone, Dirt, Grass, Gravel, Sand

Neponset River Greenway

8.2 mi
State: MA
Asphalt

Phenix-Harris Riverwalk

0.3 mi
State: RI
Dirt

Putnam River Trail

2 mi
State: CT
Asphalt

Shining Sea Bikeway

10.7 mi
State: MA
Asphalt

Southern New England Trunkline Trail

21 mi
State: MA
Asphalt, Ballast, Crushed Stone

Ten Mile River Greenway

3 mi
State: RI
Asphalt

Trolley Trail (CT)

0.75 mi
State: CT
Asphalt

Upper Charles Trail

12.3 mi
State: MA
Asphalt, Crushed Stone

Washington Secondary Bike Path

19.2 mi
State: RI
Asphalt
Accordion

William C. O'Neill Bike Path

7.2 mi
State: RI
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
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
The Bay Colony Rail Trail will one day span 7 miles connecting the Boston suburbs of Newton, Needham, Dover, and Medfield along tracks once used by the Massachusetts Bay Transit Authority. In May...
MA 1.7 mi Crushed Stone
The Blackstone River Greenway (previously known as the Blackstone River Bikeway) represents a big undertaking in this tiny state: The 11.8-mile trail running between Woonsocket and the outskirts of...
RI 11.8 mi Asphalt
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
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
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
With spectacular maritime views and an abundance of coastal wildlife, the East Bay Bike Path offers a spectacular New England experience. Inducted into the Rail-Trail Hall of Fame in 2009, the route...
RI 14.3 mi Asphalt
In the southeastern outskirts of Boston, the Hanover Branch Rail Trail connects the communities of Abington and Rockland. (Locally, the trail’s east and west halves are sometimes referred to as the...
MA 2.6 mi Asphalt, Crushed Stone
The Mattapoisett Rail Trail is a work in progress. As of autumn 2011, it runs for just more than 1 mile between Reservation Road at Mattapoisett Harbor and the Phoenix Bike Trail in Fairhaven, joining...
MA 1.1 mi Asphalt
This 5.8-mile trail is part of the planned East Coast Greenway, an off-road path that will eventually run from Calais, Maine, to Key West, Florida. The Moosup Valley State Park Trail will connect with...
CT 5.8 mi Ballast, Crushed Stone, Dirt, Grass, Gravel, Sand
The Neponset River Greenway totals just over 8 miles in length on the southern outskirts of Boston. The trail is paved and provides a variety of scenery from urban wilderness through a mill village...
MA 8.2 mi Asphalt
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 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
Curling nearly 11 miles past woodlands, marshes, salt ponds and seascape, the Shining Sea Bikeway is the only bikeway on Cape Cod to skirt the shore. Also called the Shining Sea Bike Path, the paved...
MA 10.7 mi Asphalt
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 mi Asphalt, Ballast, Crushed Stone
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
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 Upper Charles Trail will one day span more than 20 miles, connecting the communities of Milford, Ashland, Hopkinton, Sherborn and Holliston along a former CSX rail bed. The trail is being...
MA 12.3 mi Asphalt, Crushed Stone
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
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

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Trails by activity

Upper Charles Trail

MA - 12.3 miles

The Upper Charles Trail will one day span more than 20 miles, connecting the communities of Milford, Ashland, Hopkinton, Sherborn and Holliston along a former CSX rail bed. The trail is being...

Putnam River Trail

CT - 2 miles

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...

Center Trail

MA - 0.6 miles

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...

Blackstone River Greenway (RI)

RI - 11.8 miles

The Blackstone River Greenway (previously known as the Blackstone River Bikeway) represents a big undertaking in this tiny state: The 11.8-mile trail running between Woonsocket and the outskirts of...

Accordion

East Bay Bike Path

RI - 14.3 miles

With spectacular maritime views and an abundance of coastal wildlife, the East Bay Bike Path offers a spectacular New England experience. Inducted into the Rail-Trail Hall of Fame in 2009, the route...

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...

William C. O'Neill Bike Path

RI - 7.2 miles

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...

Phenix-Harris Riverwalk

RI - 0.3 miles

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...

Bay Colony Rail Trail

MA - 1.7 miles

The Bay Colony Rail Trail will one day span 7 miles connecting the Boston suburbs of Newton, Needham, Dover, and Medfield along tracks once used by the Massachusetts Bay Transit Authority. In May...

Ten Mile River Greenway

RI - 3 miles

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...

Neponset River Greenway

MA - 8.2 miles

The Neponset River Greenway totals just over 8 miles in length on the southern outskirts of Boston. The trail is paved and provides a variety of scenery from urban wilderness through a mill village...

Burrillville Bike Path

RI - 1.2 miles

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...

Hanover Branch Rail Trail

MA - 2.6 miles

In the southeastern outskirts of Boston, the Hanover Branch Rail Trail connects the communities of Abington and Rockland. (Locally, the trail’s east and west halves are sometimes referred to as the...

Shining Sea Bikeway

MA - 10.7 miles

Curling nearly 11 miles past woodlands, marshes, salt ponds and seascape, the Shining Sea Bikeway is the only bikeway on Cape Cod to skirt the shore. Also called the Shining Sea Bike Path, the paved...

Mattapoisett Rail Trail

MA - 1.1 miles

The Mattapoisett Rail Trail is a work in progress. As of autumn 2011, it runs for just more than 1 mile between Reservation Road at Mattapoisett Harbor and the Phoenix Bike Trail in Fairhaven, joining...

Trolley Trail (CT)

CT - 0.75 miles

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...

Bay Colony Rail Trail

MA - 1.7 miles

The Bay Colony Rail Trail will one day span 7 miles connecting the Boston suburbs of Newton, Needham, Dover, and Medfield along tracks once used by the Massachusetts Bay Transit Authority. In May...

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...

Upper Charles Trail

MA - 12.3 miles

The Upper Charles Trail will one day span more than 20 miles, connecting the communities of Milford, Ashland, Hopkinton, Sherborn and Holliston along a former CSX rail bed. The trail is being...

Arkwright Riverwalk

RI - 0.8 miles

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...

Accordion

Putnam River Trail

CT - 2 miles

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...

Southern New England Trunkline Trail

MA - 21 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 Greenway (RI)

RI - 11.8 miles

The Blackstone River Greenway (previously known as the Blackstone River Bikeway) represents a big undertaking in this tiny state: The 11.8-mile trail running between Woonsocket and the outskirts of...

Ten Mile River Greenway

RI - 3 miles

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...

Burrillville Bike Path

RI - 1.2 miles

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...

Mattapoisett Rail Trail

MA - 1.1 miles

The Mattapoisett Rail Trail is a work in progress. As of autumn 2011, it runs for just more than 1 mile between Reservation Road at Mattapoisett Harbor and the Phoenix Bike Trail in Fairhaven, joining...

William C. O'Neill Bike Path

RI - 7.2 miles

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...

Shining Sea Bikeway

MA - 10.7 miles

Curling nearly 11 miles past woodlands, marshes, salt ponds and seascape, the Shining Sea Bikeway is the only bikeway on Cape Cod to skirt the shore. Also called the Shining Sea Bike Path, the paved...

Trolley Trail (CT)

CT - 0.75 miles

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...

Phenix-Harris Riverwalk

RI - 0.3 miles

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...

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...

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...

Hanover Branch Rail Trail

MA - 2.6 miles

In the southeastern outskirts of Boston, the Hanover Branch Rail Trail connects the communities of Abington and Rockland. (Locally, the trail’s east and west halves are sometimes referred to as the...

Center Trail

MA - 0.6 miles

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...

Moosup Valley State Park Trail

CT - 5.8 miles

This 5.8-mile trail is part of the planned East Coast Greenway, an off-road path that will eventually run from Calais, Maine, to Key West, Florida. The Moosup Valley State Park Trail will connect with...

East Bay Bike Path

RI - 14.3 miles

With spectacular maritime views and an abundance of coastal wildlife, the East Bay Bike Path offers a spectacular New England experience. Inducted into the Rail-Trail Hall of Fame in 2009, the route...

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...

Upper Charles Trail

MA - 12.3 miles

The Upper Charles Trail will one day span more than 20 miles, connecting the communities of Milford, Ashland, Hopkinton, Sherborn and Holliston along a former CSX rail bed. The trail is being...

William C. O'Neill Bike Path

RI - 7.2 miles

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...

Burrillville Bike Path

RI - 1.2 miles

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...

Accordion

Mattapoisett Rail Trail

MA - 1.1 miles

The Mattapoisett Rail Trail is a work in progress. As of autumn 2011, it runs for just more than 1 mile between Reservation Road at Mattapoisett Harbor and the Phoenix Bike Trail in Fairhaven, joining...

Shining Sea Bikeway

MA - 10.7 miles

Curling nearly 11 miles past woodlands, marshes, salt ponds and seascape, the Shining Sea Bikeway is the only bikeway on Cape Cod to skirt the shore. Also called the Shining Sea Bike Path, the paved...

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...

Hanover Branch Rail Trail

MA - 2.6 miles

In the southeastern outskirts of Boston, the Hanover Branch Rail Trail connects the communities of Abington and Rockland. (Locally, the trail’s east and west halves are sometimes referred to as the...

Blackstone River Greenway (RI)

RI - 11.8 miles

The Blackstone River Greenway (previously known as the Blackstone River Bikeway) represents a big undertaking in this tiny state: The 11.8-mile trail running between Woonsocket and the outskirts of...

Neponset River Greenway

MA - 8.2 miles

The Neponset River Greenway totals just over 8 miles in length on the southern outskirts of Boston. The trail is paved and provides a variety of scenery from urban wilderness through a mill village...

Ten Mile River Greenway

RI - 3 miles

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...

Bay Colony Rail Trail

MA - 1.7 miles

The Bay Colony Rail Trail will one day span 7 miles connecting the Boston suburbs of Newton, Needham, Dover, and Medfield along tracks once used by the Massachusetts Bay Transit Authority. In May...

Southern New England Trunkline Trail

MA - 21 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...

Arkwright Riverwalk

RI - 0.8 miles

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...

Trolley Trail (CT)

CT - 0.75 miles

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...

Putnam River Trail

CT - 2 miles

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...

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...

Center Trail

MA - 0.6 miles

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...

Phenix-Harris Riverwalk

RI - 0.3 miles

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...

East Bay Bike Path

RI - 14.3 miles

With spectacular maritime views and an abundance of coastal wildlife, the East Bay Bike Path offers a spectacular New England experience. Inducted into the Rail-Trail Hall of Fame in 2009, the route...

Recent Trail Reviews

Burrillville Bike Path

Peaceful, relaxing!

May, 2018 by jimalix54

Yes, the trail is short, but it's very near my home and so great for daily exercise. I'm just beginning to ride my recumbent trike in a serious way, and so I do 3-4 laps every day. It's quiet, peaceful, and very well-maintained.

Upper Charles Trail

Great walking trail

May, 2018 by vito709

Today was the fourth time I walked this trail from holliston walked 2.5 miles and back.

Very easy walking the packed stone and dust pavement. I walk the Henry Hudson trail in NJ nearly every day 5 miles and both these trails provide some of the most interesting sites.

When visiting my family here this provides me a great walk. Wonderful

Upper Charles Trail

A great long trail in very good condition

May, 2018 by davidbornstein302

Rode the trail this morning (a Wednesday). Very light and friendly walkers with few bikers. Trail is in very good condition -- both the gravel portion in Holliston and the paved portion in Milford. Plenty of benches to pull over and rest if you want...but the trail is about as flat as you get so the riding is easy. Will return many times.

Accordion

Air Line State Park Trail

Flooded trail

April, 2018 by blueskye

After heavy rain on April 16th, the trail along the Willimantic River is temporarily flooded and impassable,

Washington Secondary Bike Path

hard to find

April, 2018 by fourperch

Hard to find and not well maintained

Fred Lippitt Woonasquatucket River Greenway

The western half of the trail is an easy ride, suitable for kids.

April, 2018 by laurastark

We started our ride in Riverside Park, which has a parking lot, a great playground, and river overlooks. Heading west from there, it's a pleasant trail experience, mostly lined with trees and wildflowers.

William C. O'Neill Bike Path

The wife and I are getting back into biking and this trail is great for the beginner/novice. There are slight inclines which reminded us on why we are taking it slow to get back into shape for more challenging trails as the weather improves.

April, 2018 by brian schreiber

The wife and I are getting back into biking and this trail is great for the beginner/novice. There are slight inclines which reminded us on why we are taking it slow to get back into shape for more challenging trails as the weather improves.

Putnam River Trail

Great trail for many purposes

April, 2018 by fencinggirl93

I have used this trail for many purposes. First off, I love finding dog parks and having one right on this trail is a great asset. While it is not my favorite, and dogs being there is rather hit or miss most days, it is still functional for what it is and my dog enjoys going there before or after our walks. There are also a few places where the dogs can access the water if they are into swimming.

Second, it is a pleasant walking trail that is both scenic and urban. It leads from the dog park, follows the river, and into downtown Putnam where lots of shops, restaurants, and more await. As a dog trainer, I highly recommend the trail because you get all kinds of training done in one location (dog on dog greeting, urban walking, trail walking, and socialization with all kinds of people and places).

Also, I recently took up Inline Skating, and this trail is perfect for it! It is smooth all the way, and while there are a couple hills, they aren't very hard to go up or down. I couldn't be happier with my skating experience here.

Lastly there is always a lot of available parking at various points along the trail: at the dog park, near two river access points, near picnic areas, near a band stand, and of course in downtown Putnam itself. It is so convenient! I love this trail and visit it often.

Quinebaug River Trail

Quinebaug River Trail behind Delta Rubber Segment

March, 2018 by mbenitez_tl

It's a fantastic trail. I went after a snowstorm a few days after and to my surprise the trail itself was nice and clean, snow cleared! It runs along the Quinebaug River and it is a very peaceful place for a walk. I have not completed this trail seeing how we just started walking but will look forwarded to completing this trail. Great place for a bike ride, Walk, Run, skate, strollers. All paved once you get to the trail.

Neponset River Greenway

really hope for some expasion

January, 2018 by graftderf

as i live in this area and bike often as possible to reduce my carbon footprint, i like the newponset riverway but i feel its lacking one trail that could be very beneficial, its an unofficial hidden trail running parallel to President golf course that connects Harriet street to Granite street, currently its very rocky and borderline dangerous but im sure its public access road?..? anyway just my 2cents

i had a vision of a foot/bike bridge over to the Newponset river greenway from that unofficial trail would really sweeten the biking commute from east milton to greenway...oh the possibilities

Bay Colony Rail Trail

Map error

December, 2017 by 23rock

This is a delightful section of trail. But, the map does not match the description. The map only shows a piece between Fisher St. and Charles River St. in Needham. But, the trail (as per the description) extends from the Needham / Dover town line at the Charles River, west of Fisher Road, to just west of High Rock St. I particularly like the railroad cross bucks at the street crossings, which have been changed to read "rail trail crossing" and the crosswalk painting which has the cross bars longer to look line cross ties.

Air Line State Park Trail

Airline Trail - South

November, 2017 by CW4

A note to everyone: The 1 mile section of the Airline Trail From Route 149 in Colchester to the Blackledge River bridge is now resurfaced. The trail is now finished from Alden's Crossing in East Hampton to South Brook Road in Hampton, where a 3.5 mile stretch of rough gravel slows you down, before the trail finishes in Promfret Station at Route 169. Get out and ride!!

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