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 20 trails covering 161 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.
Overview The Old Colony Rail Trail is named after the railroad line that operated in Massachusetts and Rhode Island. At 8 miles, the trail offers a serene journey through quiet Cape Cod beach towns. The trail is suitable for a short ride out and back, or a longer journey when combined with the Cape Cod Rail Trail. About the Route The eastern point of the trail starts at Depot Road, in the center of Chatham, across from the fire station and adjacent to Veterans Field, home of the Chatham Anglers baseball team of the Cape Cod Baseball League. Here you will find ample parking in the elementary school lot across the street, a large playground, and rest rooms just a short walk down the hill at the Chatham Community Center. The route, in general, is flat, family-friendly, and easily managed. The first 1.5 miles of the trail is mostly on quiet quaint streets with slight vehicular activity. The reminder of the trail is on an off-road dedicated child-safe bike path. Inexperienced cyclists should face few difficulties. Should you wish to bi-pass the first 1.2 miles share-the-road portion of the trail, you can park at the Chatham Airport on George Ryder Road or the parking lot at the corner of Meetinghouse Road (Route 137) and Main Street (Route 28). If you start at Depot Road, begin by proceeding down Hitching Post Road for 0.2 mile, then turn left onto Tip Cart Drive. At the bottom of the hill, cross over Crowell Road to join the first segment of the off-road trail. The trail passes tennis and pickle ball courts, basketball court and parking lot through a short wooded area emerging to cross Stepping Stones Road. At the bottom of Stepping Stones Road continue straight across the intersection and onto Wilfred Road. This on -street portion of the trail is only 0.6 mile and Wildred Road is a quiet neighborhood street with scarcely any vehicle traffic. The off-street trail continues at the end of Wilfred Road. Here the trail begins its loop around the Chatham Airport before pausing at George Ryder Road where signage directs you to turn right to continue on the Old Colony Rail Trail or left for the short ride to West Chatham. This section of the Old Colony Rail Trail offers a unique view of this small airport used primarily for personal small aircraft. Lunch can be obtained at the airport restaurant or a short ride to West Chatham and rest rooms and water bottle fill are available at the police station located across from the airport hanger on George Ryder Road. After crossing George Ryder Road, and passing a rest area with picnic table, the remaining 5.4 miles of the trail remain off-road. While there are several cross streets along the way, the trail, in general, is peaceful, enjoyable and extremely well maintained. Here you can enjoy the solitude of nature, for the next few miles, interrupted only by other trail users. You will pass a granite post border marker announcing your entry into the town of Harwich from Chatham. Approximately three (3) miles from George Ryder Road is a half-round-about and then crossing over Route 39. While this can be a busy crossing, warning signs alert drivers to slow down and visibility for both trail users and drivers is good. Once crossed, the trail continues past Brooks Park in Harwich Center where there are restrooms and water bottle fill available (in season). Approximately 1.2 miles from this point, the trail reaches its western end at the next roundabout where it connects with the Cape Cod Rail Trail from the north and west.
I love this trail, but right now part of it is closed for utilities repair. It will not be open until March 2025. You can still go for a ride, but you will have to take a detour on the street.
Enjoyed my ride on this trail. One sees the "shining sea" for maybe a mile and a half or so the rest being village, woods, and wetland views. There are some pretty big bumps in some areas due to tree roots. One in particular nearly bounced me off and they are not marked well. So, keep hands tight on handlebars and pay attention. Sandwich shop/bakery in Woods Hole is awesome!
I would want to return due to the diversity of trail. From sea to shining sea, says it all.
Not as scenic as I was hoping for but still a nice ride through the trees. Nice to be on a paved trail too. Many options to pull off the trail for a bite to eat.
Great for walking most intersections are low traffic areas. Peace and quiet in the middle of town.
Easily the most beautiful trail I’ve ridden on. E-bike made it easy. Not crowded.
I have been using this bike/run trail for 13 years. You can zip around the island on a beautiful, private trail. There are some spots in towns that put you on the road- or places that you need to cross a road. from our house, I can jump on the trail and happily head all over the place. I used to put my kids in a bike trailer and ride them all over the island. Certain years for barrack obama and his family have been on the trail with their secret service agents. I was engaged on this trail after a 10 mile round trip ride into edgartown to dine at seafood shanty. please don’t let bad review discourage you from testing out the trail!
Trail starts just outside downtown Chatham near Veterans Field. There are lots of road crossings but traffic stopped in all cases to let us go. Also some places to grab a bite on the trail of you need a break.
Nice trail beautiful scenery nice trail to do if you got a couple hours to spend and you're on the cape on vacation
Very nice trail a lot of wonderful scenery plan on spending the whole day or a good part of it must do if you're ever on the cape
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