City Hiking Guides

Top Boston Hiking Trails

POSTED ON January 31, 2023 BY Ralph S.


Introduction

Welcome to America’s Walking City, also known as Boston! While this bustling metropolis is famous for its historic landmarks and vibrant culture, it is also home to some of the most stunning trails. From urban hikes with breathtaking views of Boston’s skyline to secluded paths that lead to hidden waterfalls, there is something for every hiker in this city.

And if you’re feeling adventurous, you can even venture out to the neighboring White Mountains in southern New Hampshire or the Appalachian Trail for some challenging trails.

Whether you are a seasoned hiker or just starting, read on to discover the best hiking trails in Boston that will take your breath away.

Walking City Trail

Boston USA

  • Location: South Boston, Massachusetts
  • Distance: 27 miles (43 km)
  • Duration: 1-2 days
  • Difficulty: Easy to moderate
  • Trail type: Point to point

The Walking City Trail is a perfect choice for those looking for a mix of urban and nature while hiking in Boston. This 27-mile (43-kilometer) trail takes you through the 17 bustling residential neighborhoods of South Boston, starting at the Neponset River Reservation and ending at the iconic Bunker Hill Monument. Along the way, you’ll enjoy stunning views of Boston’s most scenically immersive parks, the Boston skyline, the harbor islands, urban wilds, gardens, and even catch glimpses of historic landmarks like Fenway Park.

The trail is relatively easy with a few moderate inclines, making it suitable for all levels of hikers. You can complete the whole trail in 1-2 days, depending on your pace and how much time you spend exploring each neighborhood.

Neponset River Trail

River In Boston USA

  • Location: Neponset Reservation, Boston
  • Distance: 3.4 miles (5.5 km)
  • Duration: Approximately 1 hour
  • Difficulty: Easy
  • Trail type: Paved and well-marked

The Neponset River Trail is a beautiful and scenic trail that runs through the historic Neponset River Reservation in Boston, about 3 miles (5 km) from Franklin Park and 4 miles (6.5 miles) from Arnold Arboretum, near the southwest corridor of Greenway Park. This 3.4-mile-long (5.5 km) trail is perfect for a leisurely stroll or bike ride, offering picturesque views of the Harvest River bridge and its surrounding marshlands.

Along the way, you will come across several picnic areas, benches, and observation points where you can stop and take in the natural beauty of the area. The trail also passes through parks and gardens, making it an ideal spot for a family outing or a peaceful solo walk.

Freedom Trail

Boston, MA, USA

  • Location: Downtown Boston
  • Distance: 2.5 miles (4.0 km)
  • Duration: Approximately 1.5 hours
  • Difficulty: Easy
  • Trail type: Paved and well-marked

The Freedom Trail is a must-do for anyone visiting or living in Boston. This easy 2.5-mile-long (4.0 km) trail winds through downtown Boston, taking you on a journey through the city’s rich history and significant landmarks. The trail begins at the Old North Church in the North End and ends at the Bunker Hill Monument in Charlestown.

Walking along this iconic trail, you will pass by graveyards, notable churches, and buildings that played a significant role in American history. The trail is marked with simple and special explanatory ground markers, making it easy to follow and learn about the city’s past. You will also get a glimpse of the events that led up to the American Revolutionary War, including the infamous Boston Massacre.

The Innovation Trail

Longfellow Bridge, Boston, United States

  • Location: Downtown Boston to Kendall Square, Cambridge
  • Distance: 5.1 miles (8.2 km)
  • Duration: Approximately 2 hours
  • Difficulty: Moderate
  • Trail type: Paved and well-marked

The Innovation Trail is a unique addition to the walking trails in Boston, combining history and innovation. Starting from downtown Boston and ending at Kendall Square in Cambridge, this 5.1-mile (8.2 km) trail takes you on a journey through history and showcases the city’s innovative spirit.

As you walk along the trail, you will pass by iconic landmarks such as the Longfellow Bridge and the Museum of Science, which have played an essential role in shaping Boston’s innovation scene. You will also get to explore the vibrant culture and diverse neighborhoods along the way, from bustling Cambridge Parkway to the lively Main Street. The trail ends near Kendall Square, known as Boston’s “innovation hub,” where you can grab a bite to eat or continue your exploration of this thriving area.

Here is Google’s direction. But you can download the trail map here.

Spectacle Island Trail

Lighthouse, Nature, Boston

  • Location: Boston Harbor Islands
  • Distance: 3 miles (4.8 km) loop
  • Duration: Approximately 2 hours
  • Difficulty: Moderate
  • Trail type: Out and back

For a unique hiking experience, head to Spectacle Island in the Boston Harbor Islands. This remote island is only accessible by ferry but offers spectacular views of the city skyline and harbor. The island has a 3-mile (4.8 km) loop trail that takes you through forests, meadows, and open fields with stunning views at every turn.

The trail is moderately challenging, with some rocky terrain, but the views and experience are worth it. Along the way, you can also learn about the island’s history and its transformation into a beautiful recreational area from an old landfill. Pro tip: Plan your visit during low tide to explore the tidal pools and see some marine life up close.

You can check out the island image here.

The Boston Harborwalk

  • Location: Boston Waterfront, MA
  • Distance: 47 miles (76 km)
  • Duration: Varies depending on the route
  • Difficulty: Easy to moderate
  • Trail type: Point to point

For those who prefer a more urban hiking experience, the Boston Harborwalk is the perfect trail for you. Stretching over 47 miles (76 km) along the city’s waterfront, this public walkway takes you through some of Boston’s most vibrant neighborhoods and iconic landmarks.

Along the way, you can catch breathtaking views of the harbor and explore various parks, beaches, and public art installations. The trail also offers access to some of the city’s best seafood restaurants and cafes, making it a perfect combination of nature and culture.

It also connects with many other trails, such as the Freedom Trail, the Lower Neponset River Trail, and the Millers River Trail in Middlesex County.

Stony Brook Reservation Public Park

  • Location: Hyde Park, Boston, central Massachusetts
  • Distance: There are plenty of trail loops that vary in length
  • Duration: Approximately 2 hours
  • Difficulty: Easy-moderate
  • Trail type: Loop

Located just a short drive from downtown Boston, the Stony Brook Reservation Public Park is a hidden gem waiting to be explored. This 475-acre (0.7 square mile) park offers plenty of trail loops, making it a great place for a half-day hike with friends or family.

As you make your way through the park, you will be greeted by stunning views of Turtle Pond Parkway north to Bellevue Hill and south to Kelley Playground at Mother Brook, providing serene moments to relax and take in nature’s beauty. The trails are well-maintained and perfect for walking or mountain biking, and leashed dogs are also welcome.

The park is a great place to escape the hustle and bustle of the city and immerse yourself in nature without having to travel too far.

With its paved paths, Stony Brook Reservation Public Park is easily accessible for all hiking levels, making it a great spot for beginners or those looking for a leisurely walk. And with its proximity to the city, it is a convenient outdoor escape for Bostonians.

Nearby Hiking Trails

Boston, Massachusetts,

Just outside of Boston, there are even more trails waiting to be explored. From coastal walks to mountain hikes, these nearby trails offer different terrain and scenery for hikers of all levels.

So, here are the best spots for what Boston’s great outdoors offers.

Middlesex Fells Reservation State Park

Boston, MA, USA

  • Location: Medford, Stoneham, Winchester, and Melrose
  • Distance: Over 100 miles (160 km) of trails with varying lengths
  • Duration: Varies depending on trail length
  • Difficulty: Easy to challenging
  • Trail types: Point to point and out and back

Located just a short drive, about 9 miles (14 km) from downtown Boston, Middlesex Fells Reservation offers over 100 miles (160 km) of trails through beautiful forests, wetlands, and hills. With trails varying in length and difficulty, this reservation is perfect for all levels of hikers.

One popular trail within the reservation is the Skyline Trail, which takes you to some of the highest points in Middlesex County with stunning views of downtown Boston. For a more challenging hike, check out the Rock Circuit Trail, a 3.1-mile (5 km) loop that takes you through rocky terrain and up to the summit of Wright’s Tower.

Middlesex Fells Reservation is also a great spot for activities such as biking, horseback riding, and bird-watching. It’s a must-visit for anyone looking to escape the city and immerse themselves in nature.

Battle Road Trail

  • Location: Minute Man National Historical Park, Lexington and Concord, MA
  • Distance: 5.5 miles (8.8 km)
  • Duration: Approximately 2 hours
  • Difficulty: Easy to moderate
  • Trail type: Point to point

For a historically significant hiking experience, head to the Battle Road Trail in the Minute Man National Historical Park, 23 miles (37 km) from Boston. This 5.5-mile (8.8 km) trail follows the path where the first battle of the American Revolution took place in 1775.

Along the way, you can stop at various historic sites and monuments, including the Hartwell Tavern and Meriam’s Corner. The trail is mostly flat with some gentle inclines, making it suitable for all ages and skill levels.

This trail also connects with the 11-mile (17.7 km)-long Minuteman Bikeway, which runs from Cambridge to Bedford, making it a great option for those who want to combine hiking and biking in their outdoor adventure.

Blue Hills Reservation State Park

  • Location: Milton, Quincy, Braintree, Canton, Dedham and Randolph
  • Distance: Over 125 miles (201 km) of trails with varying lengths
  • Duration: Varies depending on trail length
  • Difficulty: Easy to challenging
  • Trail type: Mostly natural surface, some paved sections

Just a short drive south of Boston lies the Blue Hills Reservation. A perfect place for hiking and outdoor adventure. With over 7,000 acres of green space, hills, forests, and over 125 miles (201 km) of trails.

For a challenging hike, check out the Blue Hills-Skyline Trail, which takes you to the summit of Great Blue Hill for breathtaking views of Boston and beyond. The reservation also offers family-friendly trails such as the Quarry Loop, perfect for a leisurely stroll or picnic.

Aside from hiking, Blue Hills Reservation offers a variety of activities, such as mountain biking, boating, and camping. With its close proximity to the city and stunning natural beauty, this reservation is a must-visit for outdoor enthusiasts.

The Skyline Trail, a 4.5-mile loop, is a popular hike that rewards hikers with panoramic views of the Boston skyline.

Wachusett Mountain State Reservation

  • Location: Princeton, MA
  • Distance: Over 17 miles (27 km) of trails with varying lengths
  • Duration: Varies depending on trail length and chosen route
  • Difficulty: Easy to challenging
  • Trail type: Loop, point to point, out and back

Located 55 miles (88 km) from Boston, Wachusett Mountain State Reservation offers a variety of trails for hikers to explore. With over 17 miles (27 km) of trails, this reservation is perfect for both beginners and experienced hikers.

One popular trail within the reservation is the Wachusett Mountain Summit Loop Trail, a challenging 3-mile (4.8 km) loop that takes hikers through forests and rocky terrain up to the 2,006-foot (611 meters) summit of Wachusett Mountain, the tallest mountain near Boston, for breathtaking views. For a more moderate hike, try the Stage Coach Trail, a 2-mile (3.2 km) loop that takes you through ponds and wetlands filled with diverse wildlife.

Breakheart Reservation

Breakheart Reservation, Forest Street, Saugus, MA, USA

  • Location: Saugus, MA
  • Distance: Over 10 miles (16 km) of trails with varying lengths
  • Duration: Varies depending on trail length and chosen route
  • Difficulty: Easy to moderate
  • Trail type: Loop, out and back

Breakheart Reservation is a popular hiking spot located just 11 miles (18 km) from downtown Boston in Saugus, central Massachusetts. This reservation offers over 7 miles (11 km) of trails through forests and along two lakes for hikers to enjoy.

One of the best hikes within Breakheart Reservation is the Turtle Pond Trail, an easy 1.5-mile (2.4 km) loop that offers scenic views of Breakheart Hill and Grass Pond. For a longer hike, check out the 3-mile (4.8 km) Crystal Lake Trail, which takes you through forests and along two lakes.

Aside from hiking, visitors can also enjoy swimming, fishing, and picnic areas within the reservation.

Conclusion

Whether you’re a seasoned hiker or just starting out, Boston has something for everyone. From the challenging mountain hikes of Wachusett Mountain to the peaceful trails of Harold Parker State Forest, the diversity of hiking options around Boston is incredible. These trails offer stunning views of the surrounding area, provide a peaceful escape from the city, and are perfect for a day hike or a weekend backpacking trip.

So, grab your hiking boots, pack a backpack, and head out to explore the amazing trails that Boston has to offer.

Don’t forget to check out our Hikes and Trails page to see other exciting locations in America and beyond.


RALPH S.

Ralph S. is the founder of Silverlight, an avid hiker and trail runner he enjoys spending time outdoors, riding his motorcycle and swimming at the beach when he's not busy replying to customers or developing new Silverlight gear.

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