The best running trails around The Pinehills
4.0
(2)
145
runners
26
runs
If you've ever tried to plan jogging around The Pinehills, you know how quickly the options can feel overwhelming. With so many trails, it's tough to tell which ones are genuinely worth your time and effort, and which are just filler. That's where we come in. Our komoot community has mapped, run, and reviewed these routes, sifting through the noise to bring you a curated shortlist of the best jogging routes The Pinehills has to offer. Consider this your shortcut to finding the most popular jogging trails in The Pinehills, Plymouth MA, without the guesswork.
Jogging around The Pinehills is a unique experience, defined by its rolling hills and depressions, a result of the region's glacial topography. You'll find yourself running through extensive old-growth forests and woodlands, offering a serene natural backdrop. The trail network here thoughtfully connects to various ponds and integrates with conservation areas like Myles Standish State Forest, providing a diverse range of terrain. Whether you're looking for easy jogging routes or something more challenging, there are options for every ability level.
If you only do one, we'd start with the Bentley Loop Trail – Myles Standish State Forest, a moderate 3.7 miles (5.9 km) route that’s a local favorite for its natural contours. For a slightly longer, scenic run, the Long Island Pond Loop – Myles Standish State Forest covers 4.8 miles (7.8 km) and offers beautiful pond views. With more than 120 runners having already explored these paths with komoot, you can trust you're in good company. Dive in and discover your next favorite run!
Last updated: June 1, 2026
5.0
(1)
3
runners
5.89km
00:43
50m
50m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
2
runners
7.76km
00:54
50m
50m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
Sign up for free
4.86km
00:33
40m
40m
Easy run. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
13
runners
6.53km
00:41
40m
40m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
3.0
(1)
12
runners
22.0km
02:20
100m
100m
This extensive College Pond – Charge Pond loop takes you deep into the full forest of pine and oak trees within Myles Standish State Forest. You'll experience varied terrain, including easily accessible paths and some unpaved roads, all while being immersed in the natural beauty of the area. The route passes by the serene Charge Pond, a 23-acre kettlehole pond with undeveloped shorelines, offering a tranquil natural feature.
Starting from College Pond, a convenient day-use area, this difficult jogging route covers 13.7 miles (22.0 km) with 332 feet (101 metres) of elevation gain, typically taking around 2 hours and 20 minutes. Parking is available at College Pond, making it an accessible trailhead. For the best experience, plan your visit during the cooler, drier months to enjoy the forest without excessive heat.
Myles Standish State Forest is renowned for its globally rare pine barrens habitats and coastal plain kettle ponds, providing a unique ecological backdrop for your run. Keep an eye out for diverse flora and fauna, including various bird species. This long loop is ideal for experienced joggers seeking a challenging and immersive natural escape.
Get access to more routes and recommendations from other explorers.
Sign up for free
Already have an account?
Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
Start today with a free account
Your next adventure awaits.
Login or Signup
Tips from the Community
There are plenty of great seafood bar & grills along the wharf like The Shanty Rose, Lobster Hut, and Wood's Seafood. This is a great place to grab a bite and browse the whale watching companies along the wharf.
1
0
The place to eat lobster in Plymouth: several restaurants to choose from and the fishery haven as well! Fresher than fresh.
0
0
The Mayflower is one of the United States' national treasures. The ship is a reminder of the many ships that crossed the Atlantic in the 17th century. Since 1957, a scale replica, the Mayflower II, has been moored in the port of Plymouth in Massachusetts. Today, the Mayflower II is a floating training and work ship. The ship was restored in 2020 and added to the National Register of Historic Places. https://plimoth.org/plan-your-visit/explore-our-sites/mayflower-ii
1
0
‘Plymouth Rock’ is the historic site where the Mayflower settlers landed and founded the Plymouth Colony in December 1620. https://en.m.wikipedia.org/wiki/Plymouth_Rock
1
0
A faithful replica of the Mayflower on which the first settlers arrived in Plymouth in 1620. In 1957 it sailed from Plymouth in Great Britain to Plymouth Massachusetts.
1
0
Mayflower II is a reproduction of the 17th-century ship Mayflower that brought the pilgrims over to the New World. It is a living history museum that you can visit and explore. The Mayflower II was built in Plymouth, England and on April 20, 1957 set sail for Massachusetts, just like the original Mayflower. You can purchase tickets to board the Mayflower II at the Plimouth Patuxet Museums site. plimothpatuxet.centeredgeonline.com/retail/items
1
0
Nelson Street Park is a park located at the north end of Water Street and is open daily from dawn until dusk. The park has a playground and a "splash pad" for kids to cool off on hot summer days, a boat ramp, an overlook with beautiful harbor views, and a small beach.
1
0
Frequently Asked Questions
How many running routes are available in The Pinehills?
The Pinehills offers a wide selection of running routes, with over 25 trails available for exploration. These routes cater to various preferences, from easy strolls to more challenging runs.
What makes The Pinehills a unique place for jogging?
The Pinehills is characterized by its unique glacial topography, featuring rolling hills and depressions that provide varied terrain. Runners can enjoy extensive old-growth forests and woodlands, a serene natural setting, and a network of trails that connect to various ponds and conservation areas like Myles Standish State Forest. A significant portion of the land is preserved as open space, enhancing the outdoor experience.
Are there running routes suitable for beginners or families?
Yes, The Pinehills offers several easy running routes perfect for beginners or families. For example, the Cherry Pond Loop – Myles Standish State Forest is an easy 3.0-mile (4.9 km) trail that leads through woodlands and past Cherry Pond, offering a pleasant and accessible experience.
What do other runners enjoy most about the trails in The Pinehills?
The running routes in The Pinehills are highly rated by the komoot community, with an average score of 4.0 stars. Runners often praise the varied terrain, the serene natural settings through forests and past ponds, and the well-maintained network of trails that integrate with state parks.
Are there any loop running routes in the area?
Absolutely. Many of the running routes in The Pinehills are loops, providing a convenient way to explore without retracing your steps. Popular options include the Bentley Loop Trail – Myles Standish State Forest and the Long Island Pond Loop – Myles Standish State Forest, both offering scenic circular paths.
Can I find running trails with scenic views in The Pinehills?
Yes, The Pinehills offers several running routes with picturesque views. You can enjoy ocean and woodland vistas from certain ridgelines, and paths that traverse through beautiful forests and past ponds. The Long Island Pond Loop – Myles Standish State Forest, for instance, provides lovely views around the pond.
Are the running trails in The Pinehills dog-friendly?
Many trails in The Pinehills and connecting conservation areas are dog-friendly, but it's always recommended to check specific regulations for each trail or park, especially within Myles Standish State Forest. Generally, dogs should be kept on a leash to protect wildlife and ensure a pleasant experience for all users.
What kind of terrain can I expect on the running routes?
The terrain in The Pinehills is diverse due to its glacial topography. You'll find a mix of rolling hills, gentle slopes, and some more challenging inclines. The trail network includes both well-maintained paved and unpaved paths, winding through old-growth forests and alongside ponds, catering to different preferences and fitness levels.
Are there any longer, more challenging running routes for experienced runners?
For experienced runners seeking a challenge, The Pinehills offers several difficult routes. The College Pond – Charge Pond loop from College Pond is a notable option, spanning over 13 miles (22.4 km) with significant elevation changes, providing a demanding and rewarding run.
What attractions or landmarks can I see near the running routes?
While running in The Pinehills, you can explore various natural and historical attractions. Many routes integrate with Myles Standish State Forest, and you might pass by ponds like Charge Pond or College Pond. The area is also close to historical sites like Mayflower II and Plymouth Rock, though these are typically found on routes closer to Plymouth's waterfront.
Are there any less crowded running routes in The Pinehills?
While popular routes like those in Myles Standish State Forest can see moderate traffic, the extensive network of trails and preserved open spaces in The Pinehills means you can often find quieter paths. Exploring some of the less-trafficked unpaved trails or visiting during off-peak hours can lead to a more solitary running experience.
Most popular routes around The Pinehills
Most popular attractions around The Pinehills
Get inspired with the komoot mobile app
Explore more
Browse the best Running Trails & Routes in other regions.
