Hiking

5 min read

Boston Trails Unveiled: Top 20 Hikes for History Buffs

Ever tread paths where every step whispers tales of the past? Just beyond Boston's bustle lie trails where history and adventure collide. Ready to walk through a storybook of scenery?

Tobi Miles
August 8, 2022

Boston is a city with great character. The history of the city is intertwined with a birth of a nation and is displayed throughout the entire region. It is an epicenter for cultural and social progress, while also being at the forefront of the nation's leading educational and financial institutions.

While Boston is best known as the home of Fenway Park, The Boston Marathon, and the bar from Cheers, the city is also abundant with iconic landscapes and beautiful scenery.

Tucked away in the charming metropolis are miles of hiking trails with stories of yesterday. The history of Boston is written in the trails along the pathway to freedom.

1. Walden Pond Trail

Credit: Tawny042 / Flickr

Directions: From Lexington, head west on Massachusetts Avenue for 1.8 miles and turn right onto MA-2A W and drive for 3.2 miles. Continue for 1.0 miles and merge onto MA-2 W and turn left onto MA-126 S. After 0.2 miles, turn left into the parking area and the trailhead will be on your right.

The Walden Pond Trail is best known as the home to the secluded life of naturalist author Henry David Thoreau. The trail navigates along the beautifully reflective pond as well as the historic cabin home of the famous poet.

The trail is the perfect setting for outdoor living and minimalism. The pond has several excellent fishing beaches and is lush with green fauna. With the abundant resources on the trail, this hike is a prime opportunity for wildlife viewing.

Difficulty: Easy

Distance: 1.9 Miles

Elevation Gain: 72 Feet

2. The Freedom Trail

Credit: H. C. /Flickr

Directions: From downtown Boston, take Cambridge Street and Bowdoin Street to Mount Vernon Street for 0.5 miles and turn left onto Walnut Street. Turn right onto Beacon Street and drive for 0.3 miles before turning left onto Arlington Street.

After 0.3 miles, turn left onto Boylston Street, followed by an immediate left onto Charles Street and the Freedom Trail will begin on your right.

Potentially the most historic trail in the entire United States, the Freedom Trail passes the most iconic and influential milestones where our forefathers shaped our constitution.

Running through the heart of downtown Boston, the trail is marked by a red brick pathway leading you to sixteen different historic buildings, landmarks, cemeteries, and memorials.

The trail takes you to notable locations, including but not limited to - The USS Constitution, Bunker Hill, Old North Church, Park Street Church, and the site of the Boston Massacre outside the Old State House.

Difficulty: Easy

Distance: 3.4 Miles

Elevation Gain: 170 Feet

Related Read: Best Time to Visit New England

3. Breakheart Reservation

Credit: Larisa / Flickr

Directions: From downtown Boston, head north on US-1 N for 9.7 miles and take the Lynn Fells Parkway exit toward Melrose. After 0.3 miles, turn left onto Lynn Fells Parkway and drive for 0.2 miles. Turn right onto Forest Street and continue for 0.3 miles and the parking area for this hike will be on your left.

The Breakheart Reservation Loop is an excellent way to escape into nature without leaving the Boston metro area. This moderate hike leaves the pavement and onto natural dirt walkways, entering lush wooden forests of native Boston.

As you continue to wander, the trail will travel along wooden boardwalks to keep your feet dry through wet meadowlands. The boardwalk will give way to a decent climb up a stone walkway but will lead to the wonderful shores of several peaceful lakes and ponds.

Difficulty: Moderate

Distance: 2.0 Miles

Elevation Gain: 144 Feet

4. Ipswich River Wildlife Sanctuary Trail

Credit: nothingwitheyes / Flickr

Directions: From Ipswich, head west on Linebrook Road for 3.8 miles and turn left onto US-1. Drive for 3.1 miles and turn right onto Howlett Street, followed by an immediate left to stay on Howlett Street.

Continue for 0.7 miles and turn left onto Perkins Row. Drive for 0.3 miles and make a left into the parking area for this hike.

The Ipswich River Wildlife Sanctuary Trail is a family-friendly hike with wonderful opportunities to appreciate the elements of nature. Living up to its namesake, this trail is abundant with natural wildlife.

This sanctuary is a safe and healthy habitat for deer and turtles, but the highlight of the trail is the chickadees.

These curious birds are known for their absence of timidness. For a memorable experience, bring a handful of sunflower seeds – the chickadees are known to gently eat these treats right from your hands!

Difficulty: Easy

Distance: 3.5 Miles

Elevation Gain: 187 Feet

5. Long Trail Loop

Credit: Jeffrey Guyette / AllTrails

Directions: From Worchester, head east on MA-9 for 12.0 miles and merge onto MA-85 S. Continue on MA-85 S for 2.1 miles and turn left onto Forest Lane into Hopkinton State Park. Follow the signs for Long Loop and park in Parking Lot C.

The Long Trail Loop is a beautiful hike that follows along the shores of Hopkinton Reservoir. This shady trail is perfect for a hot afternoon. The reservoir has several swimming holes, a refreshing way to recover from the warmest of days.

Thanks to the abundant water source, this trail is an excellent place to see wildlife – including deer and toads. For a unique experience, visit during the evening hours and watch the fireflies as they light up the night sky.

Difficulty: Moderate

Distance: 3.1 Miles

Elevation Gain: 262 Feet

Related Read: 20 Best Hiking Trails in Massachusetts

6. Halibut Point Trail

Credit: goodharbor / Flickr

Directions: From Gloucester, head north on MA-127 N/Eastern Avenue and drive for 3.3 miles. Make a left turn onto MA-127 N/Railroad Avenue and continue for 2.5 miles and turn right onto Gott Avenue. Continue for 0.1 miles and the parking area for this trail will be on your right.

The Halibut Point Trail is a unique hike that follows the edge of a retired quarry. The quarry is filled with water and is very deep. The trail takes you into the surrounding woods before it returns you to the quarry.

The trail is interpretive and tells the history of the quarry as you go. Once reaching the wavy shores of Halibut Point, you can see as far as the Maine mountains and the New Hampshire Islands on a cloudless day.

Difficulty: Easy

Distance: 1.6 Miles

Elevation Gain: 121 Feet

7. Hedge Drive Loop in Maudslay State Park

Credit: Peter Zafris / Flickr

Directions: From downtown Boston, head north on I-93 N for 10.4 miles and take exit 28A to merge onto I-95 N. Stay on I-95 N for 8.4 miles and keep right at the fork to stay on I-95 N and follow the signs for Portsmouth NH. Take exit 86 for MA-113 toward Newburyport and after 0.6 miles, make a sharp right onto MA-113 W.

Drive for 0.4 miles and turn right onto Daniel Lucy Way. Continue for 0.6 miles and turn left onto Curzon Mill Road and after 0.1 miles, turn left into Maudslay State Park. Follow the signs to the parking area for this hike.

The Hedge Drive Loop is a beautifully secluded hike in Maudslay State Park. Leaving the city limits offers excellent opportunities to appreciate the open pastures and the riverside gardens along this short hike.

With the beautifully lush landscape, this trail is abundant in vibrant wildflowers for as far as the eye can see. With a backdrop of large oak and pine trees, the area is a popular area for weddings and other glamorous gatherings.

Difficulty: Easy

Distance: 1.7 Miles

Elevation Gain: 82 Feet

8. Mount Auburn Cemetery Trail

Credit: Miriam Morse / AllTrails

Directions: From downtown Boston, head west on MA-28 S/Storrow Drive W for 4.6 miles and take the exit toward MA-2. Merge onto Eliot Bridge and use any lane to turn slightly right toward Gerrys Landing Road.

Continue for 0.2 miles and make a slight left onto Mount Auburn Street and drive for 0.3 miles. Make a left onto Central Avenue followed by an immediate right into the parking area for this trail.

The Mount Auburn Cemetery Trail is a scenically beautiful, but eerily mysterious hike through the historic burial grounds of figures in early American.

The trail wanders through these hallowed grounds, but also passes through a stunning arboretum with an exquisite array of floral beauty.

As you continue along the trail, you will reach a lookout tower that looks upon these carefully crafted headstones. This is an active burial ground, please try to be as respectful as possible in honoring those that lie here.

Difficulty: Easy

Distance: 3.3 Miles

Elevation Gain: 177 Feet

9. Great Blue Hill Loop via Skyline Trail

Credit: Charles Van Rosenburg / AllTrails

Directions: From South Weymouth, head west onto MA-3 N for 4.6 miles and take exit 43B for I-93 N. Continue for 1.0 miles and take exit 8 toward Furnace Brook Parkway. Continue along Willard Street for 0.4 miles and merge onto Furnace Brook Parkway.

Drive for 1.3 miles and make a slight right onto Chickatawbut Road. Continue for 2.8 miles and merge onto Hillside Street. After 0.4 miles, the parking area will be on your right.

The Great Blue Hill Loop is historic not only for the city of Boston but for the entire state. Native Americans originally discovered this exposed granite hill, they named it “Massachuesett,” where Massachusetts gets its name.

The trail climbs upwards along the Blue Hills Skyline Trail for a knee-buckling 800 feet in just a short distance. The summit is highlighted by Eliot Tower, a fire tower that rises above the tree line, rewarding your efforts with spectacular overlooking views of downtown Boston.

Difficulty: Moderate

Distance: 3.0 Miles

Elevation Gain: 813 Feet

10. Vetter Trail and Ward Trail Loop

Credit: Kelly Smith / AllTrails

Directions: From Andover, head east on Summer Street for 0.9 miles and turn left onto Highland Road. Make an immediate left to stay on Hillside Road and continue for 0.2 miles.

Make a sharp right onto MA-125 S and drive for 1.4 miles. Turn left onto Prospect Road and after 0.4 miles, the parking area will be on your right.

Ward Reservation is north of Boston and is home to a series of trails that while incredible, are curiously less traveled. The Vetter Trail and Ward Trail Loop circumvents the reservation and provide nearly four miles of dense Massachusetts woodlands.

With the relatively quiet foot traffic, this peaceful trail offers great opportunities to see wildlife in their natural habitat. The hike leads you to Holt Hill and Boston Hill, excellent vantage points of the swamps and marshes below.

Difficulty: Moderate

Distance: 3.6 Miles

Elevation Gain: 380 Feet

11. Harold Parker Loop Trail

Credit: Malini Rao / Flickr

Directions: From Andover, head east on Summer Street for 0.9 miles and turn left onto Highland Road. Make an immediate left to stay on Hillside Road and continue for 0.2 miles. Make a sharp right onto MA-125 S and drive for 1.9 miles.

Turn left onto Salem Street and drive for 0.5 miles and turn right to stay on Salem Street. Continue for 1.0 miles and turn right onto Jenkins Road. After 0.7 miles, turn left onto Harold Parker Road and the parking area will be on your left.

If you have all day and are in adventure mode, then the Harold Parker Loop Trail is for you! The Harold Parker State Forest is a diverse landscape that takes you along rolling hills, croaking swamps, picturesque lakes, and unique rock formations.

Follow along glaciers through historic remnants of farming and milling operations from the 1800s. This trail is truly a journey that takes you back to a time before Boston transformed into the metropolis you see today.

Difficulty: Moderate

Distance: 16.6 Miles

Elevation Gain: 810 Feet

12. Lynn Woods Reservation Loop

Credit: Thea Prum / Flickr

Directions: From Lynn, head west on Washington Street for 0.6 miles and turn right onto Boston Street. Drive for 0.7 miles and turn left onto Broadway.

Continue for 0.4 miles and use the left two lanes to turn left onto Lynnfield Street. Drive for 0.7 miles and turn left onto Great Woods Road, and after 0.3 miles, the parking area will be on your left.

The Lynn Woods Reservation Loop is a nice trail for the novice adventurer, but especially so for geology enthusiasts. The loop will take you along three different bodies of water that make up the reservation, one of which is Walden Pond.

The hike leaves the dirt path and begins climbing onto unique massive boulders emerging from the surface. With these unique formations, there are distinctive features for hikers to keep an eye out for – including Stone Tower, Pirate Boulder, and the underground Dungeon Rock tunnel.

Difficulty: Moderate

Distance: 5.0 Miles

Elevation Gain: 328 Feet

13. Wachusett Summit Loop

Credit: Alan Bradley

Directions: From Princeton, head north on Mountain Road for 3.3 miles. Make a left into the Wachusett Mountain State Reservation and follow the signs for the Bicentennial Trail and make a left into the parking area of this hike.

The Wachusett Summit Loop is a network of trails that lead up steep ridges before reaching the summit of this mountain. There is not one definitive trail, but several forks from which you can choose. Naturally, the steeper the fork, the shorter your hike will be.

This beautiful woodland hike takes you into the dense wilderness, passing gravity-defying Balance Rock. As you approach the peak, you will be rewarded with stunning panoramic views, overlooking the reflective Echo Lake.

Difficulty: Moderate

Distance: 6.1 Miles

Elevation Gain: 1,847 Feet

14. Noanet Peak Loop Trail

Credit: Kevin Ung / Flickr

Directions: From Dover, head southeast on Springdale Avenue for 0.2 miles and merge onto Walpole Street. Drive for 1.9 miles and turn left onto Powisset Street. After 0.7 miles, the parking area will be on your left.

The Noanet Peak Loop Trail is home to some of the best views in New England. This family-friendly hike is a moderate climb to the summit of Noanet Mountain and its stunning expansive views of downtown Boston.

The hike is easy to follow, with colorful trail blazes around every corner and carefully crafted rock cairns pointing you up the rock. Get out the leash for this hike, this is one of the few pet-friendly hikes in New England.

Difficulty: Moderate

Distance: 3.2 Miles

Elevation Gain: 492 Feet

Related Read: Boston to New York City: New England Road Trip!

15. Mount Monadnock via White Dot Trail

Credit: Zimu Zhou / AllTrails

Directions: From Winchendon, head north on US-202 N for 5.9 miles and turn left onto Charlonne Street. Drive for 0.3 miles and turn left onto NH-124 W and continue for 1.9 miles.

Make a right onto Dublin Road and drive for 1.3 miles and turn left onto Poole Road. After 0.8 miles, the parking area for this hike will be on your right.

The Monadnock Lollipop Loop is a challenging hike that leads to the peak of Massachusetts’s favorite mountain. This mountain is heavily trafficked – and for good reason.

Mount Monadnock stands tall above any other peak in the panoramic landscape. This peak has been an inspiration for the works of some of our world’s most famous poets.

“Monadnock is mountain strong, Tall and good my kind among; But well I know, no mountain can, Zion or Meru, measure with man.” – Ralph Waldo Emerson.

Difficulty: Strenuous

Distance: 3.6 Miles

Elevation Gain: 1,742 Feet

16. Boston Harbor and Castle Island Loop

Credit: Ellen F / Flickr

Directions: From downtown Boston, head south on Congress Street for 0.8 miles and turn right onto Dorchester Avenue. Make an immediate left onto Summer Street and drive for 1.4 miles before turning left onto E 1st Street.

Continue for 0.5 miles and turn right onto Farragut Road and drive for another 0.2 miles. Turn left onto Broadway and make an immediate left onto William J. Day Boulevard. After 0.6 miles, the parking area will be on your left.

The Boston Harbor and Castle Island Loop is a historic walk along a peninsula that leads to Fort Independence. This historic landmark was an active military stronghold in both WWI and WWII. Along the beach, there is a powerful memorial to those who died in WWII.

The hike to Castle Island is incredible. What once was a solitary island is now a natural sandbar, allowing you to reach the fort via a boardwalk that is surrounded by water.

Difficulty: Easy

Distance: 2.2 Miles

Elevation Gain: 36 Feet

17. Deer Island Trail

Credit: Mario Casal / Flickr

Directions: From Winthrop, head east on Washington Avenue for 1.0 miles and turn right onto Shirley Street. Drive for 1.0 miles and turn left onto Elliot Street followed by an immediate left onto Otis Street. Make a quick right onto Tafts Avenue and drive for 0.3 miles and turn left into the parking area for this hike.

The short loop of Deer Island is an incredibly scenic walk around this beautiful area. Surrounded by the Merrimack River, this trail leads you through conservation lands abundant with coastal wildlife.

As you continue your hike, you will encounter sandy beaches and interesting coastal rocky outcroppings. To extend your adventure, head off-trail into the woods and explore a unique area rarely discovered.

Difficulty: Easy

Distance: 2.7 Miles

Elevation Gain: 59 Feet

18. Jamaica Pond Trail

Credit: Jack Parrott / Flickr

Directions: From Forest Hills, head north on Walk Hill Street for 0.4 miles and turn right onto Hyde Park Avenue. Drive for 0.1 miles and turn left onto Ukraine Way, followed by an immediate right onto Washington Street.

Continue for 0.2 miles and turn left onto New Washington Street and follow the shores of Jamaica Pond until you reach the parking area on your right.

Jamaica Pond is a calm and relaxing body of water in the heart of Boston’s wealthiest communities. The loop trail around the pond is popular with travelers looking for an effortless walk within a beautiful environment.

There is a short climb that leads to an excellent view of the lake from the Pinebank Promontory. With open grasslands and great overlooking views, this area is a peaceful place for a picnic or just relax in this tranquil atmosphere.

Difficulty: Easy

Distance: 1.5 Miles

Elevation Gain: 45 Feet

Related Read: 10 Best Places for Snowtubing in New England

19. Commonwealth Avenue Monument Tour

Credit: Adam Hoyt / AllTrails

Directions: From downtown Boston, head west on MA-28 S/Storrow Drive for 1.4 miles and use the left lane to take the exit toward Kenmore Square. Drive for 0.1 miles and turn left onto Commonwealth Avenue followed by an immediate left onto Charlesgate E and the parking area will be on your right.

The Commonwealth Avenue Monument Tour is a city walk along a historic path honoring our forefathers. The hike takes you through Victorian Boston in the heart of Boston. Lined with beautiful wildflowers, this trail is an incredibly scenic tour of the grandest part of Boston.

The Commonwealth Avenue Mall leads past statues and sculptures in memoriam of Alexander Hamilton, John Glover, and the Boston Women’s Memorial. Take a moment to honor these prominent figures in our history.

Difficulty: Easy

Distance: 2.2 Miles

Elevation Gain: 13 Feet

20. Millennium Park Trail

Credit: David Forsyth / Flickr

Directions: From Dedham, head north on Boston Providence Highway for 2.3 miles and turn left onto Charles Park Road. Drive for 0.4 miles and turn left into Millennium Park and the parking area will be on your left.

The Millennium Park Trail is an open-air park with miles of comfortably paved trails in the center of Boston. The hike walks around an expansive field that is popular with fetching pups, playful children, or even a pick-up soccer match.

The trail is busy, but with the surrounding woodlands and the abundance of water sources, this hike is an excellent hike for birdwatching.

Difficulty: Easy

Distance: 3.7 Miles|

Elevation Gain: 173 Feet

Article updated:
January 5, 2024

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