Weston, Massachusetts

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. 

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 small parking area right before the trailhead. *Notice this parking area is small and only fits about 3-4 cars so prepare to find street parking on a busy day. You can punch in the coordinates to a GPS if you need help finding it: 42.4545482, -71.4358192.  The loop is very diverse wit...

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 ...

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

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...

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 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 ...

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

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

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 on Tank Road to access the Nashua River Trail. Keep your eyes peeled for turtles, chipmunks, birds, and other wildlife! This trail is open from April to October.  The trail can become flooded and muddy after a rain/ snow, so for a shorter alternative to the 9.5 miles, you can take...

Haggetts Rail Trail to Haggetts Pond is an out-and-back trail that takes you through a nice forest located near Lawrence, Massachusetts.

From Rt. I-495 Exit 31, Gibbert Hill has one of the greatest sunsets around Groton, MA area. You will see a lot of cows and even a castle. This is a very easy hike and a not so easy place to park, you have to leave you car on the side of the road, which is totally fine, I guess, it is easy.The wa...

Deer Jump Reservation Loop is a loop trail that takes you by a river located near Andover, Massachusetts.

For this 1-mile hike, you can park at the Purgatory Chasm Visitor Center. From there hit the trail and explore the unusual gap between the tall granite walls, which might be adorned with climbers. Great for all ages and dogs are welcome too. The trail is open March-November.