Groton, 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...

The White Dot Trail is the shortest, steepest ascent to the summit, while White Cross has a slightly easier grade down with very little difference in distance.  Therefore, per the park's rangers, the best way to conquer this loop is White Dot up, White Cross down.The White Dot Trail begins at Mon...

Monadnock State Park is located in and around the 3,165-ft. Mount Monadnock. Mount Monadnock is crisscrossed by many miles of well-maintained hiking trails. The popular White Dot Trail (2.2 miles) is the shortest but steepest ascent to the summit, accessible from the Monadnock State Park headquar...

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 ...

Arriving at the Old Toll Road/Halfway House Trail head you will have $5 entrance fee. Starting on the Old Toll road you'll find yourself walking on a gradual incline into the beautiful New Hampshire wilderness. Everything you see and smell is fresh and vibrant. Following the road for 1.1 miles yo...

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 ...

Start at the Marlboro Trailhead (you can enter this in Google maps) off Shaker Road. There's parking and porta-potty bathrooms. The trail is well-marked with white dashes/M marks all the way up. Once on trail, the initial 800 ft climb is through forested terrain with a few brooks and streams alon...

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.

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 parking area off of Refuge Rd. Take the Dunes Trail, a boardwalk path for the ~1-mile loop. Enjoy the views from an observation deck on three-story-high dunes. This trail is accessible from April-October.

Located just north of Boston, Parker River National Wildlife Refuge was established in 1941 to provide feeding, resting, and nesting habitat for migratory birds. The refuge lands are both scenic and diverse, with approximately 4700 acres of habitats including sandy beach and dune, cranberry bog, ...

Park at the lot at the corner of Staples Lane and County Street. From here you can access the Blackstone Gorge Trail. Dogs are allowed on leash, and you can enjoy various paths along the river or through the forest. At multiple points you can find yourself looking down at the Blackstone River fro...

Douglas State Forest is located off of Rte 16 in south central Massachusetts. To access trails and the lake, head to the parking area on Wallum Lake Park Road. From the parking lot, you can access the Coffeehouse Loop Trail, as well as a few other shorter trails by the lake. The Coffeehouse Loop ...

Rattlesnake Loop to Red Trail is a loop trail that provides a good opportunity to view wildlife located near Erving, Massachusetts.