Find the top rated trails in Winchester, whether you're looking an easy walking path or a long bike trail, you'll find what you're looking for. Click on a trail below to find trail descriptions, trail maps, photos, and reviews.
The Clipper City Rail Trail is part of the Coastal Trails Coalition, which is developing in the four towns of Amesbury, Newbury, Newburyport, and Salisbury along the Merrimack River and will...
The smooth paved surface of the Londonderry Rail Trail offers a pleasant, tranquil 3.3-mile adventure for trail users in south-central New Hampshire. Its route follows a corridor once used by the...
The Whitney Spur Rail Trail runs from just north of the MBTA’s Cohasset Station through dense woodlands to the edge of Wompatuck State Park. The corridor was originally a spur off the Old Colony...
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...
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,...
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....
The Massachusetts Central Railroad was destroyed by a hurricane in 1938, but the 104-mile corridor is being reborn as a cross-state rail-trail. Currently, nearly 40 miles from Boston to Northampton...
The Northern Strand Community Trail is part of the visionary and almost-complete Bike to the Sea plan to link Boston and the Mystic River to the seashore in Lynn, north of Boston. It currently runs...
Although less than a mile, the trail running through Salisbury Beach State Reservation offers lovely views of the beaches off the northeastern coast of Massachusetts, just a few miles south of the New...
Bruce N. Freeman was a Massachusetts state representative from 1969 to 1986. Beginning in 1985, he championed the creation of a bike path that would run along the former Penn Central railroad line...
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...
The Neponset River Greenway is a south Boston jewel, utilizing the best in design and construction standards as it winds through the Neponset River valley, offering a low-stress, high-quality...
Although short, the scenic Gloria Braunhardt Bike Path travels through forests and pastures full of birds and wildlife. The asphalt pathway parallels the eastern side of the present-day Interstate 95...
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The Heritage Trail is managed by the state of New Hampshire to provide access to recreational and historical attractions across the state. Eventually, the north-south route along the former Boston and...
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Although only a grassy, hard-packed dirt pathway, the route along the Salem-Beverly Canal (also known as the Grand Wenham Canal), is scenic and peaceful. The old canal, built in 1917, lies between two...
The Upper Falls Greenway is a short rail-trail that cuts through the charming village of Newton Upper Falls in Newton, Massachusetts. The trail occupies the same former rail corridor as the developing...
The South Manchester Rail Trail is a proposed bike/pedestrian path that would connect the downtown Millyard area of Manchester to the Town on Londonderry. The South Manchester Rail Trail will utilize...
Currently 1.8 miles, the Salisbury Point Ghost Trail provides a peaceful walk or bike ride through the woods on a well-maintained stone-dust trail. The route is one part of the larger Coastal Trails...
The health and fortunes of Lowell have been intimately tied to the Concord River for hundreds of years. This tributary of the more well-known Merrimack River continues to be at the heart of the local...
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The Southwest Corridor Park (Pierre Lallement Bike Path) knits together neighborhoods in southern Boston from the Back Bay to Jamaica Plain. Popular as a route for commuters as well as casual walkers,...
The Piscataquog Trail, though only about 2 miles long, provides a vital off-road link between the communities on the western side of the Merrimack River (the West Side of Manchester) to several parks...
The Border to Boston Trail connects the communities of West Peabody, Peabody, Danvers, Topsfield, and Boxford in northeastern Massachusetts. The long-term goal for the trail is to continue it north to...
The Clipper City Rail Trail is part of the Coastal Trails Coalition, which is developing in the four towns of Amesbury, Newbury, Newburyport, and Salisbury along the Merrimack River and will...
The 5.3-mile Independence Greenway makes for a pleasant ride, providing access to lakes, parks, and nature preserves. The paved pathway is located in the town of Peabody (pronounced by locals as...
More and more, airport lands near previously under-used rail corridors are being transformed from largely neglected vacant lands into urban greenways. These new vibrant spaces are used not only by...
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...
The Salisbury Rail Trail Connector, also known as the Gillis Rail Trail Connector, is a 0.3-mile link between two rail-trails: Salisbury's Old Eastern Marsh Trail and Newburyport's Clipper City Rail...
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...
Methuen Rail Trail connects three communities in northeastern Massachusetts as it follows the route of the former Manchester and Lawrence Branch of the Boston and Maine Railroad. The rail-trail's...
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...
The smooth paved surface of the Londonderry Rail Trail offers a pleasant, tranquil 3.3-mile adventure for trail users in south-central New Hampshire. Its route follows a corridor once used by the...
The Spicket River begins in Derry, New Hampshire, through Methuen and Lawrence, Massachusetts, before draining into the Merrimack River. Like many mill towns of the late 19th and 20th centuries, the...
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...
This unpaved state-owned trail is open for public use from Coldbrook to Baldwinville. An on-road detour is necessary through the village of Baldwinville, but the right-of-way is open for public use on...
The developing Upper Charles Trail will one day total 24 miles, linking the communities of Milford, Ashland, Sherborn, Holliston, Framingham, and Hopkinton along a former railroad bed. As of 2018,...
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...
Currently 1.8 miles, the Salisbury Point Ghost Trail provides a peaceful walk or bike ride through the woods on a well-maintained stone-dust trail. The route is one part of the larger Coastal Trails...
The Assabet River Rail Trail connects five old mill towns that owe their revitalization to present-day high-tech industries. A midpoint gap splits the 8.6-mile paved trail, though long-range plans...
The Northern Strand Community Trail is part of the visionary and almost-complete Bike to the Sea plan to link Boston and the Mystic River to the seashore in Lynn, north of Boston. It currently runs...
The World War II Veterans Memorial Trail opened in Mansfield in 2004 after several decades of advocacy by local rail-trail supporters. The trail rests on an abandoned corridor once served by the Old...
The Quarries Foot Path offers a wooded 1-mile hiking route in western Quincy, about 10 miles south of Boston. Begin your adventure on the south side of Ricciuti Drive, which borders Quincy Quarries...
The Spicket River begins in Derry, New Hampshire, through Methuen and Lawrence, Massachusetts, before draining into the Merrimack River. Like many mill towns of the late 19th and 20th centuries, the...
The North Bank Bridge, which opened in 2012, provides a safe and convenient pedestrian and bicycle connection between Cambridge's North Point Park and Paul Revere Park in Charlestown. Spanning 690...
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...
The Salisbury Rail Trail Connector, also known as the Gillis Rail Trail Connector, is a 0.3-mile link between two rail-trails: Salisbury's Old Eastern Marsh Trail and Newburyport's Clipper City Rail...
This unpaved state-owned trail is open for public use from Coldbrook to Baldwinville. An on-road detour is necessary through the village of Baldwinville, but the right-of-way is open for public use on...
The newly open Bradford Rail Trail occupies the former Pan Am rail lines, beautifying an area that once lay strewn with garbage and weeds. The city and numerous dedicated volunteers created the...
The 5.3-mile Independence Greenway makes for a pleasant ride, providing access to lakes, parks, and nature preserves. The paved pathway is located in the town of Peabody (pronounced by locals as...
The Neponset River Greenway is a south Boston jewel, utilizing the best in design and construction standards as it winds through the Neponset River valley, offering a low-stress, high-quality...
Many commuters choose the Minuteman Commuter Bikeway for freedom from congested traffic in the northwest Boston suburbs. For others, the 10.1-mile paved trail between Cambridge and Bedford serves as a...
The Charles River Bike Path, also referred to as the Charles River Greenway, offers a paved, 22-mile route from Boston to its western suburbs. The trail is also part of a larger, developing network...
Mine Falls Park in Nashua is a 300-acre-plus urban park with a network of approximately 9.7 miles of a variety of trail types. This forested park offers an extraordinary nature experience in the heart...
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...
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...
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...
The South Manchester Rail Trail is a proposed bike/pedestrian path that would connect the downtown Millyard area of Manchester to the Town on Londonderry. The South Manchester Rail Trail will utilize...
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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...
The health and fortunes of Lowell have been intimately tied to the Concord River for hundreds of years. This tributary of the more well-known Merrimack River continues to be at the heart of the local...
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...
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...
The Worcester and Nashua RR is long gone but the end of the trail in Ayer is still served by MBTA Commuter Rail which provides daily service. You can take your bike aboard all off-peak trains. Enjoy the currently-offered $10.00 unlimited weekend pass to get you there.
This is a city trail with views of the seashore. It goes through the Bremen St. Park which is used by children and adults skating, running and walking. At one terminus is a stunning view of Boston over the harbor, with easy access to the harbor walk and Piers Park. The other end is at Constitution Beach, from which you can watch airplanes take-off and get pizza or a hot dog in the summer. There is also a stopping point overlooking the wetlands. Lots of local restaurants around: Italian, Salvadorian, and more. If you’re a cyclist don’t expect a long, fast experience. It is scenic and gives you a great sense of “Easty”
It's early fall and a great time to ride this trail. The leaves are turning, the surface is dry and flat. There are many street crossings, most of them easy. We started in Raymond, off Onway Lake Road. If you map this using the RTC map, it gives you the address for the Gordon Cammett Recreation Area. If you turn in here, it takes you to a large parking lot and ball fields. This is where we started. The trail runs parallel to the ball fields but you can't see it from the parking lot. If you ride your bikes back up the hill you drove down, to the left at the top of the hill, there's a small cut-through. The trail is right there. If you look to your right, you'll see a tunnel (Manchester, or westbound). We rode to our left (Newfields, or eastbound). This is a 30-mile roundtrip ride. The trail has a few different surfaces, most well-packed and rideable with a hybrid. Some of the sandy patches and looser gravel (not many) might be more difficult with road bike tires. In Raymond, there is an old train station with train cars, a one-room schoolhouse, as well as stocks and a jail cell. There are 2 or 3 street crossings near various services if you need a drink or bite to eat. The trail ends at a parking lot, and fittingly, at the railroad tracks. There are no mileage markers along the trail. A trail kiosk in Epping will tell you the mileage to your destination in both directions.
Beautiful trail nice even gravel and sand walkway but WAY WAY WAY too much broken glass along the trail someone didn’t want dogs on the trail !!!
My wife and I parked at the Lowell St end in a large lot. We rode about 5-6 miles north. This trail is great. Nice scenery. Good places to stop. Water fountains, jiffy Johnny's, bike shops along the way. In one park, there is a station with tethered tools to do repairs.
Highly recommend.
So far, I've ridden this trail through Everett and Malden a couple of times. I love that section. It's very convenient when I ride from Boston to Lynnfield on my home commute.
This week, I rode from Malden through Revere and Saugus to Lynn. When you get to the Rowe's Quarry apartments, the surface becomes thick loose gravel. In some places, there are larger rocks hiding in the gravel. It's unsteady and a little hard to ride on. I could not keep up my usual commuting speed. My bike has hybrid tires, but this is a trail better suited for a mountain bike.
I might take this trail again, but this is not a trail that my wife would appreciate.
We parked in Newton and rode out bikes all the way to the Cambridge Galleria and had lunch. Then we rode back to Newton, was just over 27 miles round trip. Mostly along the river. The trail is broken up and we crossed the river about 3 times in Watertown to Waltham, but what an amazing ride. Some dirt sections, but our Trek hybrids did not have trouble. Be careful crossing streets, espcially in the city. Also, don't go full speed as there are a lot of people walking and enjoying the trail, so take your time and enjoy!
A brand new bridge has been constructed which crosses 2A seamlessly connecting this (at present) Chelmsford to Acton path. A fully paved, and at times exceptionally wide, path passes through marshland and lovely new wood feel ferns, lovely ponds/small beaches. It was a pleasure taking this 12.5 mile ride which had plenty of canopy covering on a sunny day. The description may be a little outdated b/c we saw newer looking parking on various parts of the trail and actually started in Acton. As always a bunch of street crossings to be cautious about with older style raised brick stanchions at these intersections to encourage reduced speed.
We started in Providence at India Point Park. It was a beautiful blue bird day in the high 70's with little to no wind. A perfect day for a bike ride. However, after riding the entire length of the trail from Providence to Bristol and back, we feel this is another Hall of Fame Trail that is so over hyped it is almost criminal. First, there are no facilities anywhere on the trail. Be prepared to buy lunch somewhere if you need to go to the bathroom. The trail surface is paved and in excellent condition with lane markers dividing the trail. It is probably the best trail surface we've ever ridden on. It is very flat, but it is also very narrow. You will have to watch out for walkers and runners, ALL of whom ignore the trail signs and walk against the flow of bike traffic. Be prepared to do a lot of weaving in and out of traffic. When it comes to scenery, the bridge that you cross when leaving India Point Park from the Providence trail head is beautiful. Then there is one small section of trail about a half a mile long where the trees form a very pretty tunnel you ride through. As you get into Bristol, you get some views of the bay, (which are for the most part obscured by chain link fencing). However, for the most of the trails length, there is nothing to see except the small trees and scrub brush that lines both sides of the trail. There really isn't anything to see. For as much as this trail is hyped as a Hall of Fame Trail, we expected much more, and to be honest, were thoroughly disappointed, and left wishing we had just ridden one of our local trails instead.
In April 2018 the Windham Town Council approved $1,300,000 for rehabilitation on the Willimantic River bridge behind Mackeys. This would include 800 feet of trail. It was put out for bids due on July 26th. I haven't seen any work yet. There is still the bridge over the Hop River which looks to be in terrible shape and may never be repaired.
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