Explore the best rated trails in Windsor, VT. Whether you're looking for an easy walking trail or a bike trail like the South Barre Bike Path and Stevens Rail Trail. With more than 33 trails covering 294 miles you’re bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.
_182873_st.jpg)
_20906_st.jpg)
_0_st.jpg)
In Woodsville the trail starts across from the Subway Restaurant across from the the Oceans Job Lot Store and next to the Woodsville Machine Shop and YES Yankee Electrical Supply up and down a short...
The WOW Trail is named after the three bodies of water that can be seen from this rail-trail: Lake Winnipesaukee, Opechee Bay, and Lake Winnisquam. This picturesque 2.7-mile trail shares a corridor...
About a dozen miles west of Concord, the Stevens Rail Trail offers a quiet, wooded route along the former Concord-Claremont rail line in Contoocook Village. It starts off Krzyzaniak Road and continues...
The Millstone Hill West Bike Path connects the charming communities of Graniteville and Websterville in central Vermont. The trail is part of the Central Vermont Path, a proposed trail network to...
The Toonerville Rail-Trail shadows the Black River for most of its 3.2-mile length in eastern Springfield to the border with New Hampshire across the Connecticut River. The route originally carried an...
Spanning 57.6 miles from Lebanon to Boscawen, the Northern Rail Trail is New Hampshire’s longest rail-trail conversion. It weaves through Grafton and Merrimack counties and is less than a 2-hour drive...
The Common Pathway travels 5.5 miles from the outskirts of Peterborough south to downtown’s Noone Falls area, paralleling US 202 and the Contoocook River for most of its journey. The small town of...
The Mascoma River Greenway is a planned 4-mile non-motorized pathway through the heart of Lebanon. The trail is envisioned to link West Lebanon to the Northern Rail Trail, which spans more than 50...
The Keene Industrial Trail links the county's Cheshire Rail-Trail in the city of Keene. The paved path is a 1-mile segment through downtown Keene, which passes among some of the city's old mill...
Built in the 1910s by the Boston and Maine Railroad (B&M) as part of the Connecticut River Division Main Line, the route introduced daily service to the B&M Fort Hill Branch in the early 1920s to meet...
Lake Winnisquam is New Hampshire’s fourth largest lake, and taking the Lake Winnisquam Scenic Trail is one of the best ways to experience it. Meaning “pleasant waters,” Lake Winnisquam provides...
The Old Railroad, as its name suggests, is a multi-use trail that occupies a former Boston & Maine Railroad corridor. The trail picks up at the northern trailhead of the Common Pathway, a paved...
The Harrisville Rail Trail runs for just under two miles between the outskirts of Harrisville and Hancock in rural New Hampshire. The former railroad bed is located on lands conserved by the Harris...
Appel Way Trail offers a paved route of about a mile through woodlands on the north end of Keene. Most notably, it offers a connection between Wheelock Park on the trail's west end and Ashuelot River...
Jonathan Daniels Trail travels the length of Ashuelot River Park through Keene. Along the stone-dust trail, you can enjoy the park’s beautiful natural backdrop and flower garden. The trail was named...
The scenic Valley Trail spans 9 miles connecting Dover and Wilmington in southern Vermont along the Green Mountain National Forest. It provides a critical off-road pathway for bypassing State Route...
The Ashuelot Recreational Rail Trail passes such scenic and historical landmarks as covered bridges, abandoned mills, and postcard-perfect towns. Starting on asphalt in Keene, the rail-trail can be...
The Winnipesaukee River Trail runs along a rail line that previously connected the paper industry between Franklin and Tilton. Nicknamed the Paper City, Franklin saw the industry boom from the 1900s...
The South Barre Bike Path is a paved trail approximately 1 mile long, running from Bridge Street in south Barre to Fairview Street in Barre City. The path passes the Barre City Elementary and Middle...
The Winnipesaukee River Trail runs along a rail line that previously connected the paper industry between Franklin and Tilton. Nicknamed the Paper City, Franklin saw the industry boom from the 1900s...
Jonathan Daniels Trail travels the length of Ashuelot River Park through Keene. Along the stone-dust trail, you can enjoy the park’s beautiful natural backdrop and flower garden. The trail was named...
The Ashuelot Recreational Rail Trail passes such scenic and historical landmarks as covered bridges, abandoned mills, and postcard-perfect towns. Starting on asphalt in Keene, the rail-trail can be...
The Mascoma River Greenway is a planned 4-mile non-motorized pathway through the heart of Lebanon. The trail is envisioned to link West Lebanon to the Northern Rail Trail, which spans more than 50...
_0_sc.jpg)
The East Branch Trail is a 0.5-mile ungroomed, backcountry pathway built on a former logging railroad bed in southern Vermont's Windham County. The remote, heavily wooded trail lies just north of the...
Hillsborough Recreational Rail Trail connects three communities in south-central New Hampshire: Hillsborough, Deering, and Bennington. The unpaved trail winds along the Contoocook River through rural...
Built in the 1910s by the Boston and Maine Railroad (B&M) as part of the Connecticut River Division Main Line, the route introduced daily service to the B&M Fort Hill Branch in the early 1920s to meet...
About a dozen miles west of Concord, the Stevens Rail Trail offers a quiet, wooded route along the former Concord-Claremont rail line in Contoocook Village. It starts off Krzyzaniak Road and continues...
Many rail-trails start at a vintage depot, an old caboose, or a rusty locomotive acquired by the local historical society. The Warren to East Haverhill Railroad Grade Trail, however, starts at the...
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,...
_182873_sc.jpg)
Formerly comprising two separate segments—one running northward from Keene to Walpole, and the other running southward from Keene to Fitzwilliam—the Cheshire Rail Trail now runs a continuous 32.9...
The WOW Trail is named after the three bodies of water that can be seen from this rail-trail: Lake Winnipesaukee, Opechee Bay, and Lake Winnisquam. This picturesque 2.7-mile trail shares a corridor...
Although short, the Hoot, Toot and Whistle Trail provides an enjoyable journey through peaceful woodlands on Wilmington's west end. As you might guess, the rail-trail gets its name from the former...
The West River Railroad, which once followed its namesake river for 36 miles, began passenger service in the late 1800s as a way to trim the two-day voyage between Brattleboro and South Londonderry to...
The Cross Vermont Trail (CVT) is a statewide route that links a number of Vermont trails and includes on-road sections. As of January 2016, 87 miles of trail are built and scattered across the state....
Spanning 57.6 miles from Lebanon to Boscawen, the Northern Rail Trail is New Hampshire’s longest rail-trail conversion. It weaves through Grafton and Merrimack counties and is less than a 2-hour drive...
The heavily wooded Lye Brook Falls Trail runs for 2 miles through the Lye Brook Wilderness of the Green Mountain National Forest near Manchester. The blue-blazed hiking trail follows the bed of a...
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...
The Common Pathway travels 5.5 miles from the outskirts of Peterborough south to downtown’s Noone Falls area, paralleling US 202 and the Contoocook River for most of its journey. The small town of...
The Delaware and Hudson Rail-Trail follows the flowing contours of the western Vermont countryside, rambling in and out of New York state, where you’ll find a 4-mile gap. This border area is known as...
Spanning 57.6 miles from Lebanon to Boscawen, the Northern Rail Trail is New Hampshire’s longest rail-trail conversion. It weaves through Grafton and Merrimack counties and is less than a 2-hour drive...
Many rail-trails start at a vintage depot, an old caboose, or a rusty locomotive acquired by the local historical society. The Warren to East Haverhill Railroad Grade Trail, however, starts at the...
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...
The scenic Valley Trail spans 9 miles connecting Dover and Wilmington in southern Vermont along the Green Mountain National Forest. It provides a critical off-road pathway for bypassing State Route...
The Millstone Hill West Bike Path connects the charming communities of Graniteville and Websterville in central Vermont. The trail is part of the Central Vermont Path, a proposed trail network to...
The Ashuelot Recreational Rail Trail passes such scenic and historical landmarks as covered bridges, abandoned mills, and postcard-perfect towns. Starting on asphalt in Keene, the rail-trail can be...
The Cross Vermont Trail (CVT) is a statewide route that links a number of Vermont trails and includes on-road sections. As of January 2016, 87 miles of trail are built and scattered across the state....
The WOW Trail is named after the three bodies of water that can be seen from this rail-trail: Lake Winnipesaukee, Opechee Bay, and Lake Winnisquam. This picturesque 2.7-mile trail shares a corridor...
The East Branch Trail is a 0.5-mile ungroomed, backcountry pathway built on a former logging railroad bed in southern Vermont's Windham County. The remote, heavily wooded trail lies just north of the...
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,...
The Old Railroad, as its name suggests, is a multi-use trail that occupies a former Boston & Maine Railroad corridor. The trail picks up at the northern trailhead of the Common Pathway, a paved...
The West River Railroad, which once followed its namesake river for 36 miles, began passenger service in the late 1800s as a way to trim the two-day voyage between Brattleboro and South Londonderry to...
The Mascoma River Greenway is a planned 4-mile non-motorized pathway through the heart of Lebanon. The trail is envisioned to link West Lebanon to the Northern Rail Trail, which spans more than 50...
The Keene Industrial Trail links the county's Cheshire Rail-Trail in the city of Keene. The paved path is a 1-mile segment through downtown Keene, which passes among some of the city's old mill...
Built in the 1910s by the Boston and Maine Railroad (B&M) as part of the Connecticut River Division Main Line, the route introduced daily service to the B&M Fort Hill Branch in the early 1920s to meet...
Hillsborough Recreational Rail Trail connects three communities in south-central New Hampshire: Hillsborough, Deering, and Bennington. The unpaved trail winds along the Contoocook River through rural...
The Bobby Woodman Rail Trail, a hard-packed dirt and gravel pathway, begins off a quiet street at the southern end of Claremont and quickly dives under pleasant tree cover. After about a half mile,...
The Toonerville Rail-Trail shadows the Black River for most of its 3.2-mile length in eastern Springfield to the border with New Hampshire across the Connecticut River. The route originally carried an...
The Ammonoosuc Rail Trail carries its users for 19.2 miles along the scenic river that shares its name and is itself a destination for fishing, kayaking, and canoeing. The trail passes through a...
Appel Way Trail offers a paved route of about a mile through woodlands on the north end of Keene. Most notably, it offers a connection between Wheelock Park on the trail's west end and Ashuelot River...
I have ridden this trail in increments, in 10ish mile out and back segments, and have enjoyed each ride a great deal. I have the last bit to finish still, a section in the middle where parking was not as clear to me initially. I hope to repeat it as a full ride at some point just to say I did it. Spring, Summer, Fall, all beautiful, and the covered bridges and historic areas are a nice surprise. The incline is so gradual, you don't realize it until you turn around and head back and finish a bit quicker on the return. It's busier at the Lebanon end but not packed by any means, and the Loons were a real treat.
The is was my first event with the MeetUp organization. It was a 40 mile ride with a great group of people. I was the “geezer” and everyone was extremely friendly and helpful. And as soon as Winter is over, I want to do more of these trips.
Took our ATVS down this trail today. Very well groomed, mainly flat surface (dirt and gravel). There is a large parking lot to unload. The trail signage was a bit confusing at times—one sign saying ATVS were permitted and others saying prohibited. If you park at the Fish and Game Road the trail head on the right takes you down a pretty short trail—so I would recommend starting on the left trail head which is decent in length. V
I just went to Black Jack Crossing road. There is no parking. Where is someone parking a horse trailer to get on this side of the trail?
Lots of stop signs involving crossing streets and Frost heaves on the trail. Not a terribly wide trail, expect to go over bricks and wooden Bridges also which are pretty bumpy unless you’re on a bike or something. The other nearby scenic trail is much better
A little more hilly than anticipated but a lot of fun.
Short trail but gorgeous trail along the river. Mallard ducks, beautiful fall colors and peaceful at dawn on October 11.
This isn’t really a rail trail. It is a trail that parallels a working rail. A lot of the trail goes through commercial areas, and it is likely you will see homeless people and the less desirable parts of town. More an urban passage. Given where the trail goes, the views are unremarkable.
Just did this yesterday (9/14/20) starting from Woods Crossing to the northern terminus at the American Legion then back, going past my parking location to the MA line. From the border up to I'd say the Rt. 202 section, it was quiet, saw 2 people but mainly around the Rt. 202 starting point. Comparing to sections north of it, the southern area is more wooded and a narrower trail but easily ridden with a hybrid bike. Anything with skinnier tires would probably have a harder time for the whole length of it. The northern section was quite busy, many walking, enjoying the weather. It is a little more scenic and the trail is wider. Trail is mainly gravel or hard packed dirt throughout though a little loose sand in the southern section in a few spots but not much. At some trail entrances, there is a sign which gives you some pointers as to what you will see along that stretch, gives you something to to try and see instead of just staring down the path.
Wonderful trail. Nine miles of crushed stone and hard pack dirt from southern end to Castleton University parking lot. I would not use a thin tire road bike. Beware: the southern end is a dead end 2 miles from Poultney and does not have a parking lot as indicated on the trail map. You must park in Poultney in a well marked lot off of Bentley Ave.
We started in Walpole at Blackjack Crossing. First few miles were tough! But the remaining 12 miles into Keene were great. Some great views and remnants of the railroad. Some beautiful cuts in the stone. Highly recommend!
TrailLink is a free service provided by Rails-to-Trails conservancy
(a non-profit) and we need your support!
TrailLink is a free service provided by Rails-to-Trails Conservancy (a non-profit) and we need your support!
Map Search
