Randolph, Massachusetts

Park at the end of Ponkapoag Trail Road to access the trail. Dog friendly, open year round. 

Houghton's Pond Recreation Area is a loop trail that takes you by the lake located near Milton, Massachusetts.

Park in the lot across from Batterymarch Rd off of Willard St. Access the Skyline trail from here, it is marked blue. Follow the signs. The trails in Blue Hills are perfect for training for backpacking because they are so steep and rocky. I would fill up a big pack and take the skyline trail up t...

Park in the lot off of Arborway to access the trail. This place is gorgeous year round. The winter offers a quiet solitude, fall boasts bright colors, spring is the most beautiful as the flowers start to burst and cherry blossoms take over, and summer is overwhelmingly green. There are dozens of ...

Park in the Jamaica Pond parking area. You can go either direction on this loop trail, which is highly trafficked and dog-friendly. Keep a lookout for (and a respectful distance from) the wildlife that live here. The loop around Jamaica Pond itself is 1.5 miles. The best part about running in thi...

Burrage Pond Indian Trail is an out-and-back trail where you may see beautiful wildflowers located near Hanson, Massachusetts.

Fort Revere is an 8-acre (3.2 ha) historic site situated on a small peninsula located in Hull, Massachusetts. It is situated on Telegraph Hill in Hull Village and contains the remains of two seacoast fortifications, one from the American Revolution and one that served 1898-1947. There are also a ...

Choose from multiple trails in Norris that offer beautiful views of the the North river and marshland. Great spot to do some trail running through the woods and see the river too. There is also a pond a short distance from the parking lot that offers a great fishing spot with a picnic table nearb...

Park along the trail and then hop on. The Freedom Trail allows you to not only see the most beautiful parts of Boston (which is an absolutely gorgeous city) but you can learn some history too! Head off the trail a bit to explore the Charles River, the waterfront near the aquarium and picturesque ...

The Charles River Path becomes a center of activity in Boston, especially during the summer, and you can run (or bike) it! It is a paved pathway that travels along both sides of the Charles River from the North End of the city to Allston and beyond. There are several bridges along the way with pe...

Note: The campus is currently closed due to COVID-19 restrictions. This is a lake on Wellesley College Campus.  It is easy to get to from just about any direction. Just park and walk toward the lake, and there are paths that will take you there. The easiest place to park (pinned on the map) is ju...

Park in the parking area near Bellevue Pond. There are multiple entrances to the reservation (some closer to the reservoir itself than others). I have spent days in there hiking around and never seeing the water and there are days when I just hiked right in to the water and sat and enjoyed it. Th...

Lake Rico is a decent sized lake located in East Taunton, MA. You can spend hours out kayaking and exploring. From the parking lot the lake looks pretty small but there is an opening towards the back that leads into three larger sections. There is also an island in the back that is great for sett...

Park in the lot on State Park Road (see map) to access the trail. It's a popular trail that is dog-friendly. Pay attention to the trail as at parts it is not well marked. 

Park in the lot ($8 for MA residents) by Walden Pond to access the trail, and head out either direction on the loop around the pond. Trail is accessible from April-October. 

Hemingway Street Trail is an out-and-back trail that provides a good opportunity to view wildlife located near Marlborough, Massachusetts.