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 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...
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 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 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 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 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 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 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...
Cape Cod’s briny seaports, sandy beaches, delectable seafood, and diverse landscape of salt marshes, pine forests, and cranberry bogs can all be experienced from the 27.5-mile Cape Cod Rail Trail....
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...
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...
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...
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...
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 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...
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 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...
Cape Cod’s briny seaports, sandy beaches, delectable seafood, and diverse landscape of salt marshes, pine forests, and cranberry bogs can all be experienced from the 27.5-mile Cape Cod Rail Trail....
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 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 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 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 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 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 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 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...
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,...
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...
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 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...
Cape Cod’s briny seaports, sandy beaches, delectable seafood, and diverse landscape of salt marshes, pine forests, and cranberry bogs can all be experienced from the 27.5-mile Cape Cod Rail Trail....
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...
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...
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 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...
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 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...
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,...
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 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 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 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 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 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 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...
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...
Did this trail 3 times in two days that is how great it is!
This is one of my favorite trails. It’s a nice paved trail that crosses a few streets, an intersection, The Rockland Police Dept, and is surrounded mostly by trees.
Great walk. It was 4 miles round trip to go to the end by Lepages seafood. Very scenic. Watch out for the Fiesta duck in the beginning with the red head. He gives you a hard stare down and will chase you. But lots of artwork along the way.
The trail has been completely paved and nearly flat. Wonderful ride for the whole family.
I’m not use to long distance riding, I parked in wellfleet and rode all the way to Dennis and back. Beautiful trail especially near the Brewster area where you can go swimming and plenty of places to eat along the way
Sand dunes and beach need I say more! There are definitely some hills, I’m going back in the fall to check out the beach Forrest
...for strolling through the woods solo, with a friend, a family, or your dog. Shaded and flat, well maintained and feels almost private. A great find.
Really lovely trail. Beautiful scenic views. Definitely a hilly ride but definitely worth it if you have a little experience. Easier with a road bike!
Perfect place for bike riding. I’m one who does not like to bike on streets and this is the perfect place. Two paths on both sides of canal. Biked both and they’re both great. Parking at either end on both sides. Will definitely be back.
Easily my favorite set of trails, the Provinceland Trails never fail to disappoint. A roller coaster of a trail, with constant up and downs and tight curves, a skilled rider could easily hit 20 mph (30 km/h). And there’s no shame in walking the bike up a few of the hills, since in the end the views are worth it. Can’t wait to do it again!
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