Hiking in Boston: 20 Best Hiking Trails Near Boston for the Perfect Adventure! 


Cobblestoned streets, quaint shops, historic neighbourhoods, and museums are just one side of Boston! The city is laced with parks and trails which draws flocks of locals and tourists alike. If you have a day off or want to get away from city life, there are beautiful parks, hills, and evergreen forests to hike in Boston. Boston's gentle topography makes for easy hikes and offers magical views of spring blooms, lush summer forests, and colourful fall foliage. So don’t restrict your Boston visit to just the city; explore the ‘great outdoors’ and spend a day immersed in nature with this curated list of the best hiking trails in and around Boston! 

20 Best Hiking Trails In Boston 

1. Emerald Necklace

Emerald Necklace
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The Emerald Necklace is a collection of parks, trails, and waterways in Boston that offer stunning hiking, biking, and running trails in Boston. Designed by Olmsted, the Emerald Necklace consists of  Boston Common

Public Garden, Commonwealth Avenue Mall, Forsyth Park, The Riverway, Jamaica Pond, and Arnold Arboretum. The best time to visit the park is between April to October with over one million visitors each year. Located at the heart of Boston and a local favourite, the Emerald Necklace also has various other recreational activities like sailing, golfing, softball, and a zoo. Spend some quiet time on the bench or explore any parks and enjoy the green urban landscape! 
Distance: 32.5 miles entire loop; but has various mini-trials between 1.6 to 4.2 miles. 
Difficulty Level: Easy to Moderate
Address: Shattuck Visitor Center, 125 The Fenway, Boston, Massachusetts

2. Battle Road Trail

Battle Road Trail
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Famous for the colourful fall leaves, wildlife, and flowers, the Battle Road Trail located in the Minute Man National Historical Park is an easy and interesting trail for history buffs of all ages. The trail passes through the countryside with scenic views of farms, fields, and changing trees. Check out the annual Patriot's Day celebration and explore the Lexington-Concord battle and the lead up to the revolutionary war throughout the trail. History breathes and lives in this part of Boston, so take your time and enjoy with friends and family! 
Distance: 7.4 km point to point. 
Difficulty Level: Easy to Moderate
Address: Concord, Massachusetts, USA

3. Blue Hills Reservation

Blue Hills Reservation
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Blue Hills Reservation is only a few minutes from downtown Boston, making it the perfect getaway for a quick weekend hike! Swamps, meadows, marshes, forests, and several endangered wildlife dot the reservation, and the trails are best explored in Spring. Hancock Hill, Great Blue Hill, Ponkapoag Pond, Skyline Loop, and the Buck Hill Loop offer panoramic views and the stunning Boston skyline. With flat roads to rocky hilltops, Blue Hills Reservation has trails for everyone! After an exciting day of Hiking in Boston, check out other activities such as Mountain biking, Camping, Swimming, Canoeing, kayaking, and Golfing!
Distance: 125 miles entire loop
Difficulty Level: Moderate to Difficult 
Address: Milton, Massachusetts, USA 

4. The Atlantic Path and Halibut Point

The Atlantic Path and Halibut Point
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Trek to Halibut point through the Atlantic Path in Rockport, Massachusetts, cross the quarry dotted with wildflowers and fauna, and loop back to the visitors centre! The 60 foot deep, 19th-century granite quarry is filled with water and is a beautiful sight to behold. Hike alongside the quarry and reach the ocean with its rolling tides and a magnificent view of the Atlantic! You can also set up picnic spots on the way or go fishing. The Halibut point is a short trail ideal for family hikes and is accessible throughout the year.
Distance: 1.7 km loop
Difficulty Level: easy 
Address: Gott Avenue, Rockport, MA 01966

5. World's End

World's End
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World's End is one of the most popular trails for hiking in Boston. It is a conservatory located on a peninsula bordering the Weir river and the Hingham harbour. On a foggy, pleasant morning, the park looks straight out of a Victorian novel with evergreen trees and vast green fields. The waterside trails offer spectacular views of the Boston skyline. The entry fee is USD 8 per person and free for children. Go birdwatching or hiking in World’s End and revel in nature’s magnificence. 
Distance: 6.1 km loop
Difficulty Level: Easy
Address: Martins Ln, Hingham, MA 02043, United States

6.Charles River Reservation

Charles River Reservation
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Charles River Reservation is the perfect place for a hike if you do not want to stray too far from the city. It offers plenty of activities, from picnics and hiking to sports such as Baseball, Basketball, Tennis, and outdoor adventure activities like Boating, Canoeing, Kayaking, and Fishing. Hike in the short loop for a leisure stroll along the historic Charles river waterway or walk the southwest corridor trail for a more challenging hike. 
Distance: 20-mile reservation with various trails from 1.4 km to 5.6 km. 
Difficulty Level: Easy to Moderate
Address: 1175A Soldiers Field Road, Boston, MA 02116

7. Black Heritage Trail

Black Heritage Trail
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The Black Heritage Trail is a historic trail through Boston’s beacon hill neighbourhood. It explores the history of Boston’s 19th century African American community who primarily lived on the north slope of Beacon Hill. It covers everything from the Abolition Movement, the Underground Railroad, and the Civil War. Visit the museum and take a guided tour through the Massachusetts park rangers for a complete lesson in history as well as a fun and informative hike. 
Distance: 1.6 miles 
Difficulty Level:  Easy 
Address: 14 Beacon St, Boston, MA 02108, United States

8. Boston Freedom Trail 

Boston Freedom Trail
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The Boston Freedom Trail can be paired with the Black Heritage Trail. Hiking in Boston does not get more interesting than this! The Freedom Trail compressed 250 years of rich history in a 2.5-mile hike covering nearly 16 historic sights in Boston. Follow the iconic red line on the sidewalk for a self-guided tour from Boston Common to Bunker Hill Monument. Walkthrough museums, churches, burying grounds, and huge parks and check out some cosplays for a history education! 
Distance: 2.5 miles
Difficulty Level: Easy to Moderate
Address: 139 Tremont St, Boston, MA 02111 

9. Boston Harbour and Castle Island 

Boston Harbour and Castle Island
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Boston Harbor and Castle Island is a peninsula in south Boston with beautiful nature views and other outdoor activities like bird watching and biking. The trail is very family-friendly with paved pathways and huge lawns for picnics. Check out the Boston sunset and planes flying low overhead from Logan airport! 
Distance: 2.2 miles loop 
Difficulty Level: Moderate 
Address: 2010 William J Day Blvd, Boston, MA 02127, United States

10. Middlesex Fells Reservation 

Middlesex Fells Reservation
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Middlesex Fells Reservation is home to many hiking trails routes, most notably the Skyline trail loop which is a challenge even for the most experienced trekker. This reservation makes Hiking in Boston fun and adventurous! From wooden landscapes, steep rocky ascents, and flat terrain next to lakes, the Middlesex Fells Reservation has something for everyone. Check out the Rock Circuit, Reservoir Trail, Virginia Wood Trail, Willow Spring Path, and North Dam road. You can go biking, fishing, or kayaking and even take your dog to the dog park! 
Distance: Between 1 mile to 8 miles depending on the trail 
Difficulty Level: Moderate to Difficult 
Address: 4 Woodland Road, Stoneham, MA 02180

11. Crane Beach Loop

Crane Beach Loop
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Hike through dunes, forest paths, and marshy Crane Wildlife Refuge for stunning views of the Crane Beach Ocean. You can sunbathe on the beach and even bring your dogs between October and March. Avoid the summer and explore this hidden gem in the cooler months to enjoy solitude and escape the crowds. 
Distance: 3.9-mile loop 
Difficulty: Moderate 
Address:5 miles east of Ipswich, MA 

12. Dogtown Loop

Dogtown Loop
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This eerie abandoned settlement has remnants of Boston’s ancient history. For those interested in the road less travelled, Hiking in Boston does not get more spooky! Legacies of ghost towns, witches, and eccentric elite are scattered across the trail! Head over to Dogtown for the adventure of a lifetime! 
Distance: 6.1-mile loop  
Difficulty: Moderate 
Address: 1.8 miles north of Gloucester, MA

13. Wachusett Mountain State Reservation

Wachusett Mountain State Reservation
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At 2000 feet, Wachusett Mountain is the tallest mountain near Boston and is a popular winter hiking and skiing location. Accessible throughout the year, this State Reservation has many trails like Old Indian, Bicentennial Trail, Mountain House trail, and Harrington trail spread over 3000 acres of forests. Enjoy scenic views, hiking, and a mountainside barbecue at Wachusett
Distance: 2.6 miles point to point 
Difficulty: Easy to Moderate
Address: 345 Mountain Road, Princeton, Massachusetts

14. Breakheart Reservation

Breakheart Reservation
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Breakheart Reservation is a park in Massachusetts covering more than 600 acres. With hardwood forests, freshwater lakes, and the Saugus River, the reservation offers magnificent views of Boston and the New England countryside. Some trails worth exploring are- Pierce Lake and Upper Pond, Ridge Ash and Fern Loop, Yellow Blaze loop, and Ridge Trail Loop. You can also go to birdwatching and swimming in the summer! 
Distance: 2 miles to 4.1 miles 
Difficulty: Easy to Difficult 
Address: 177 Forest Street, Saugus, Massachusetts

15. Neponset

Neponset
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Just a stone throw from Boston, Neponset rail trail is a beautiful hike by the river trail near Dorchester. Enjoy a tranquil day of hiking, picnicking, and nature with friends and family. Paved paths make it easier for biking or strollers for kids! 
Distance: 5.1 km out and back 
Difficulty: Easy 
Address: Hallet Street, Boston, MA 02124

16. Jamaica Pond

Jamaica Pond
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The Jamaica Pond is perfect for a quiet, pleasant morning walk. With flat roads and beautiful views of the lake, Jamaica Pond is accessible to all skill levels and can be used throughout the year. Located in Emerald Necklace Conservatory, Jamaica Pond provides facilities for rowing, sailing, and fishing. Do not miss out on the Annual Lantern Festival in October! 
Distance: 2.4 km 
Difficulty: Easy 
Address: 507 Jamaicaway, Jamaica Plain, MA

17. Spectacle Island Perimeter Trail 

Spectacle Island Perimeter Trail
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Just four miles from Boston, and accessible by ferry, the Spectacle Island Perimeter Trail is a 114-acre island with outdoor activities like hiking, swimming, and boating. Listen to jazz music and relax by the beach or take in the Boston skyline's panoramic views from North Drumlin's top.
Distance: 3.1 km loop 
Difficulty; Easy to Moderate 
Address: 15 State St, Boston, MA

18. Harold Parker State Forest

 Harold Parker State Forest
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Located in Andover and merely an hour away from Boston, Harold Parker State Forest is popular among hikers, equestrians, fishers, and bikers. With numerous trails crisscrossing around the forest and scenic ponds to relax and camp at, this forest also has a rich historical past. Explore the beautiful forestland home to numerous flora and fauna at under USD 10 a day! 
Distance: 56 miles of trails 
Difficulty: Moderate to Difficult 
Address:133 Jenkins Rd, Andover, MA 01810, United States

19. Belle Isle Marsh 

Belle Isle Marsh
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The Belle Isle marsh trail is a short hike but with scenic views. Famous for bird watching and strolls, this marsh is best explored in the spring and summer. Picturesque landscapes and coastal wetlands make for breathtaking sunset views. 
Distance: 1 km loop
Difficulty: Easy 
Address: 1399 Bennington St, Boston, MA 02128, United States

20. East Boston Greenway 

East Boston Greenway
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Mary Ellen Welch Greenway is a shared path and park in East Boston connecting all the major parks including  Piers Park, Memorial Stadium, Bremen Street Park, Wood Island Bay Marsh, and Belle Isle Marsh. Easily accessible by public transit, the Greenway has wide paths for biking, walking, and skating. It is the perfect place for a hike if you want a quick break. 
Distance: 3.3 miles 
Difficulty; easy 
Address: East Boston, MA, USA 

Best Time to go Hiking in Boston

Hiking in Boston is an all year round activity you can do! Spring and Summer are the best time to hike if you are still new to the sport or are hiking with kids and pets. The lush green trees and sunny weather make for the best hiking experience! Fall is equally inviting! New England is breathtaking during the fall season and hiking through yellow-orange foliage is a fantastic experience! Hiking in Winter is slightly tricky if you haven’t done it before. The snow makes the trail slippery and without the right gear and experience it can get dangerous., However, if you are up for an adventure, World’s End on Boston’s South Shore is one of the best winter hiking trails 

Tips for Hiking in Boston 

  • Check the weather before heading out. You don’t want to get stuck in heavy rains midway through your hike. Checking the weather also gives you an idea of the trail conditions and if you need extra gear. 
  • Dress Appropriately- Wear hiking boots, comfortable pants, and polyester or nylon shirts. Avoid cotton, jeans, and other restrictive clothing.  
  • Pack essential items like enough food and water, a torch, a map of the trail sunscreen, and your mobile phone. 
  • Make a trip plan and inform a few people where you are going and when you expect o to be back. In case you get lost, your loved ones will know where you are and can send for help. 
  • Hike with other people- Friends, family, or a hiking group. It’s safer and more fun!
  • Know your limits and medical conditions- Avoid difficult hikes if you have weak knees and ankles or pre-existing medical conditions like asthma or diabetes. 
  • Check out local regulations regarding bringing pets, purchase of trail passes, and other relevant information before starting your trek. 
Hiking in Boston is an easy and no-cost way to spend the day! Explore Boston’s hidden wealth of trails and foliage, take some Instagram-worthy pictures, and make some unforgettable memories along the way!

This post was published by Anupama Manjunath

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