The Best Hiking And Walking Trails Near Boston Massachusetts

You don’t have to drive all the way to the White Mountains to find good walking and hiking trails – there are plenty of scenic routes in and around Boston. The city itself is home to many off-street trails, from historic paths past locations such as the Old South Meeting House, Faneuil Hall and Paul Revere’s House; to steep slopes through Blue Hills Reservation that feel miles away from the urban bustle.

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The Freedom Trail

Get a side of history with your exercise on Boston’s famous Freedom Trail. This 2.5mi (4km) trail is a must-do for any tourist and is marked by a red line (either paint or brick) that runs through 16 historic sites. The path will take you past the Old South Meeting House (where the Boston Tea Party began), Faneuil Hall, Paul Revere’s House and more. The trail starts at the Boston Common and ends at the Bunker Hill Monument.

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.

Arnold Arboretum Trail

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.

Charles River Greenway

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.

Minuteman Commuter Bikeway

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.

Skyline Trail, Blue Hills

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.

Since you are here, we would like to share our vision for the future of travel - and the direction Culture Trip is moving in.

Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.

Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.

We know that many of you worry about the environmental impact of travel and are looking for ways of expanding horizons in ways that do minimal harm - and may even bring benefits. We are committed to go as far as possible in curating our trips with care for the planet. That is why all of our trips are flightless in destination, fully carbon offset - and we have ambitious plans to be net zero in the very near future.