Explore the best rated trails in Dennis, MA. Whether you're looking for an easy walking trail or a bike trail like the Old Colony Nature Pathway and Bridle Trail . With more than 18 trails covering 91 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.
The Old Colony Rail Trail, named after the eponymous railroad line that operated in Massachusetts and Rhode Island, offers a serene journey through quiet Cape Cod beach towns. At 8 miles, the trail is...
The Nauset Trail offers a winding route through dense Cape Cod woodlands, providing a pleasant respite from the oft-crowded seashore and tourist hubs. The trail is entirely paved, with the notable...
The Goose Pond Path, also known as the In-Town Bike Path, offers a short paved route on the charming island of Nantucket, which lies south of Cape Cod. The trail overlooks The Creeks area of Nantucket...
The Phoenix Bike Trail cruises through a mixture of surroundings on its relatively short 4-mile journey from the heart of the historical Fairhaven seaport to woodlands and farms on the outskirts of...
The Shining Sea Bikeway follows the route of a former railroad line run by the New York, New Haven and Hartford Railroad Company, which ran service to New York and Boston from 1872 to 1965. After the...
The Alfred J. Lima Quequechan River Rail Trail, which was formally known simply as Quequechan River Rail Trail travels along the northern shore of scenic South Watuppa Pond. The project created a...
The Head of the Meadow Trail offers a pleasant winding route through woodlands and marshlands tantalizingly close to the Atlantic Ocean in Truro. In fact, direct access to two of the Cape Cod National...
The New Bedford Covewalk, like the HarborWalk further east, sits atop the hurricane barrier built to protect New Bedford residents from storm surges during extreme weather. Even when it's nice out...
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...
Closure Notice: Starting March 15, 2021, the Lecount Hollow trailhead and parking lot will be closed as the DCR works on extending the trail; please consult the official project site for the latest...
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...
Constructed in 1967, the Province Lands Bike Trail is the first bike trail ever built by the National Park Service. The trail, located at the northern tip of Cape Cod, features steep hills, sharp...
Though the idea for a Cape Cod Canal goes back to the settlers of Plymouth Colony, the waterway didn’t begin construction until 1909. The U.S. Army Corps of Engineers took over operation and...
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...
Norwell is a suburb about 30 minutes' drive south of Boston, Massachusetts. It is home to the Norwell Pathway, a 2-mile non-motorized trail that was constructed to give residents an alternative way to...
The New Bedford Hurricane Barrier was built to protect New Bedford and nearby villages from storm surge during hurricanes, but also ended up cutting off residents from the water that lay just beyond...
The Old Colony Nature Pathway is a short trail open on a former Old Colony Railroad corridor in Provincetown, a picturesque vacation destination at the tip of Cape Cod. While a longer portion of the...
Closure Notice: Starting March 15, 2021, the Lecount Hollow trailhead and parking lot will be closed as the DCR works on extending the trail; please consult the official project site for the latest...
The Phoenix Bike Trail cruises through a mixture of surroundings on its relatively short 4-mile journey from the heart of the historical Fairhaven seaport to woodlands and farms on the outskirts of...
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...
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...
The Head of the Meadow Trail offers a pleasant winding route through woodlands and marshlands tantalizingly close to the Atlantic Ocean in Truro. In fact, direct access to two of the Cape Cod National...
The New Bedford Covewalk, like the HarborWalk further east, sits atop the hurricane barrier built to protect New Bedford residents from storm surges during extreme weather. Even when it's nice out...
Norwell is a suburb about 30 minutes' drive south of Boston, Massachusetts. It is home to the Norwell Pathway, a 2-mile non-motorized trail that was constructed to give residents an alternative way to...
Constructed in 1967, the Province Lands Bike Trail is the first bike trail ever built by the National Park Service. The trail, located at the northern tip of Cape Cod, features steep hills, sharp...
The Alfred J. Lima Quequechan River Rail Trail, which was formally known simply as Quequechan River Rail Trail travels along the northern shore of scenic South Watuppa Pond. The project created a...
The Nauset Trail offers a winding route through dense Cape Cod woodlands, providing a pleasant respite from the oft-crowded seashore and tourist hubs. The trail is entirely paved, with the notable...
The Old Colony Rail Trail, named after the eponymous railroad line that operated in Massachusetts and Rhode Island, offers a serene journey through quiet Cape Cod beach towns. At 8 miles, the trail is...
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 New Bedford Hurricane Barrier was built to protect New Bedford and nearby villages from storm surge during hurricanes, but also ended up cutting off residents from the water that lay just beyond...
The Shining Sea Bikeway follows the route of a former railroad line run by the New York, New Haven and Hartford Railroad Company, which ran service to New York and Boston from 1872 to 1965. After the...
Marshfield's Bridle Trail follows a former railroad bed through a tree-lined corridor. It begins at the town's Dandelion Park and heads north. Its compacted dirt surface is best suited for walking,...
Though the idea for a Cape Cod Canal goes back to the settlers of Plymouth Colony, the waterway didn’t begin construction until 1909. The U.S. Army Corps of Engineers took over operation and...
The Goose Pond Path, also known as the In-Town Bike Path, offers a short paved route on the charming island of Nantucket, which lies south of Cape Cod. The trail overlooks The Creeks area of Nantucket...
The Shining Sea Bikeway follows the route of a former railroad line run by the New York, New Haven and Hartford Railroad Company, which ran service to New York and Boston from 1872 to 1965. After the...
The Alfred J. Lima Quequechan River Rail Trail, which was formally known simply as Quequechan River Rail Trail travels along the northern shore of scenic South Watuppa Pond. The project created a...
Though the idea for a Cape Cod Canal goes back to the settlers of Plymouth Colony, the waterway didn’t begin construction until 1909. The U.S. Army Corps of Engineers took over operation and...
Constructed in 1967, the Province Lands Bike Trail is the first bike trail ever built by the National Park Service. The trail, located at the northern tip of Cape Cod, features steep hills, sharp...
The New Bedford Covewalk, like the HarborWalk further east, sits atop the hurricane barrier built to protect New Bedford residents from storm surges during extreme weather. Even when it's nice out...
The New Bedford Hurricane Barrier was built to protect New Bedford and nearby villages from storm surge during hurricanes, but also ended up cutting off residents from the water that lay just beyond...
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 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...
The Goose Pond Path, also known as the In-Town Bike Path, offers a short paved route on the charming island of Nantucket, which lies south of Cape Cod. The trail overlooks The Creeks area of Nantucket...
Closure Notice: Starting March 15, 2021, the Lecount Hollow trailhead and parking lot will be closed as the DCR works on extending the trail; please consult the official project site for the latest...
The Head of the Meadow Trail offers a pleasant winding route through woodlands and marshlands tantalizingly close to the Atlantic Ocean in Truro. In fact, direct access to two of the Cape Cod National...
The Old Colony Nature Pathway is a short trail open on a former Old Colony Railroad corridor in Provincetown, a picturesque vacation destination at the tip of Cape Cod. While a longer portion of the...
The Phoenix Bike Trail cruises through a mixture of surroundings on its relatively short 4-mile journey from the heart of the historical Fairhaven seaport to woodlands and farms on the outskirts of...
The Old Colony Rail Trail, named after the eponymous railroad line that operated in Massachusetts and Rhode Island, offers a serene journey through quiet Cape Cod beach towns. At 8 miles, the trail is...
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...
Norwell is a suburb about 30 minutes' drive south of Boston, Massachusetts. It is home to the Norwell Pathway, a 2-mile non-motorized trail that was constructed to give residents an alternative way to...
The Nauset Trail offers a winding route through dense Cape Cod woodlands, providing a pleasant respite from the oft-crowded seashore and tourist hubs. The trail is entirely paved, with the notable...
Marshfield's Bridle Trail follows a former railroad bed through a tree-lined corridor. It begins at the town's Dandelion Park and heads north. Its compacted dirt surface is best suited for walking,...
My wife and I rode the full 27.5 miles on 10/15/21. We started at the western most trailhead (near Homer Park) and rode to Wellfleet and made a delightful stop at PB Boloulangerie Bistro for a treat before heading back to the Home Park trailhead. 55+ miles and the only criticism would be that the asphalt may not have been put in think enough to withstand the tree roots that are undermining the trail. The jarring from the roots becomes somewhat annoying after a while. We would ride it again though!
Newly built on top of hurricane barrier, wonderful views of Clarks Cove. Connects to Fort Taber park at end of penninsula and to tbe new bike path on the outer New Bedford harbor.
First and not last ride on this historic trail. Well maintained, but keep your eye out for some upward pressing roots. Not too crowded and plenty of scenic vistas. A joy.
Be very aware that the last mile of the trail in the town of Chatham is on city streets with very heavy car and truck traffic. This is absolutely not safe for families that are traveling with little kids on bikes. Suggest parking at the airport or another place and begin the travel westward from there.
Flat, winding trail on brand new smooth asphalt. Not a single crack or root bump. Wish it was longer! Parked at Head of Meadow beach lot, did this as short bike before heading to the beach.
Great trail with flats and rollers…if you do not ride you may have issues as the dunes can be steep. Pay attention to sand on curves and watch your speed. Be respectful of others by pulling to the outside of the path when taking in the scenery. Look back as you will see the scenic vistas from a different perspective- If your hungry head over to Cosmos to Go as they have great food and cold drinks as well as cookies!!!
Can’t ask for a better trail to ride. I love the coastal views!
Way too many 2 to 4 inch root bumps.
Bring a mountain Bike.
Or one with massive shocks.
Be careful of your wrists
From Orleans to Wellfleet there must be over 250. Maybe MA should give some Fed funds to removal and steel root barriers
Rented bikes and rode this trail from the terminus in Chatham. What a great trail. Completely paved and well maintained. Mostly level with some slight inclines here and there. Nice leisurely ride. Going past the airport was neat because I was able to see a plane takeoff and another land on the different legs of the ride.
June 2021: Jumped on the trail at the parking lot at Rt 137 and Rt 28 in Chatham, which about the midpoint of this trail. Went west to the terminus, the junction with the CCRT, about 3.7 miles, mostly flat, very scenic and quiet. From there, I turned around and did the 8 miles to Chatham, then back ~4 miles to my car. Highlights: many well marked road crossings, and just short hops on roads. For my ride, at about the 12 mile point, returning from Chatham, there is a nice breakfast stop at the Chatham airport (Hanger B) I didn't go all the way to the Chatham terminus, since the traffic was building this Saturday morning. Kudos for the air and tool station that is situated at the midpoint, where I parked, at RT 137 and Rt 28 junction!
Lovely trail excellent weather. Rosie on a Thursday before Memorial Day weekend Need more bathroom stops. One is not enough. Currently a portion of the trail is closed due to construction with no mention when it will be completed.
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