Boston Harbor and Castle Island

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 Beacon Hill. If you have a nice day and want an easy way to see the best parts of Boston, this is de...

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 pedestrian walkways so you can access both sides. The path often parallels green space, including the ...

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 this area is that it links up to so many other running trails. It is a part of the Emerald Necklace whi...

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 water tower with an observation deck, a military history museum and picnic facilities. The fort itse...

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 spots around the arboretum where you can just nestle under some trees and have a private picnic or m...

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 to the gorgeous views at the top. It is forested and leads past a couple of bodies of water. A perfec...