The Skyline Trail Loop is one of the Middlesex Fells’ (or just the Fells as Bostonians call it) most popular paths, and for good reason. This 7.6mi (12.2km) route offers a decent amount of elevation gain (935ft/285m), accompanied by views of the trail’s namesake – the Boston skyline. If you’re just here for the panoramas, you don’t have to walk the entire loop trail as there are plenty of shorter sections leading to the summit.
The Arnold Arboretum is a peaceful oasis within Boston. Managed by Harvard University, this 281-acre (114ha) park is free and open to the public from sunrise to sunset every day. See everything that the arboretum has to offer on this easy, level trail that loops around the entire park – but make sure you leave time to read the signs along the way that identify the different types of plant life.
If you want solitude along the Charles River Greenway, come for a sunrise walk or jog. At all other times of day, this shared-use path is bustling with walkers, runners, cyclists and rollerbladers. With more than 20mi (32km), this trail is the longest off-street path in the city (which explains its popularity) and runs along the Charles River, offering sweeping Boston views around every bend.
As its name indicates, the Minuteman Commuter Bikeway is a popular cyclist commuting path from Bedford to Cambridge. However, the trail is shared use, and its paved, level surface is great for walkers and joggers as well. The 10mi (16km) route can be made even longer by connecting to the Somerville Community Path at the end by Alewife T-station. Hungry or thirsty? There are a few towns along the way to break up your walk for some refreshments.
Located 10.5mi (16.9km) outside Boston, the Blue Hills Reservation encompasses over 7,000 acres (2,833ha) of green, rolling hills. For a real challenge, opt to summit Great Blue Hill (the highest of the 22 hills in the park). You’ll climb 635ft (194m) and be rewarded with incredible views of the Boston skyline. If that’s not enough of a workout for you, there are 125mi (201km) of other trails to explore here, with a wide range of difficulty.