Hiking In Massachusetts: 15 Best MA Hikes Near Boston

Massachusetts is home to innumerable gorgeous hiking trails, each offering breathtaking vistas of the state’s stunning natural landscape. From the rugged cliffs of Cape Cod to the sprawling forests of the Berkshires, hikers of all experience levels can find a trail that suits their needs. And with so many scenic routes to choose from, it’s easy to spend an entire day exploring the great outdoors.

Whether you’re looking for a challenging hike or a leisurely stroll, Massachusetts has a trail that’s perfect for you.

What Makes Hiking in Massachusetts Uniquely Interesting?

• Massachusetts has a variety of landscapes to offer hikers, from the mountains of the Berkshires to the beaches of Cape Cod.
• There are over 200 state parks and forests in Massachusetts, providing hikers with plenty of places to explore.
• The state is home to some of the most popular hiking trails in the country, including the World’s End Trail and the Cape Cod National Seashore.
• Hikers in Massachusetts have access to a variety of amenities, including camping sites, cabins, and lodges.
• The state also has a number of organizations that offer guided hikes and other resources for hikers.

15 Best MA Hikes Near Boston

Here are 10 of the best hikes near Boston, all within a couple hours’ drive of the city. So lace up your shoes and get ready to explore some of the most beautiful scenery in the Bay State!

1. Ipswich River Wildlife Sanctuary

The Ipswich River Wildlife Sanctuary is located at 87 Perkins Row, Topsfield. The sanctuary offers 12 miles of trails for visitors to explore. The visitor center is open from Tuesday to Sunday, 9:00 am-4:30 pm, and the trails are open Tuesday through Sunday, from dawn to dusk, and are closed on Mondays (except holidays).

The sanctuary is home to a variety of wildlife, including deer, foxes, turkeys, and migratory birds. The trails wind through forests, meadows, and wetlands, providing hikers with a chance to see a variety of plant and animal life. The Ipswich River Wildlife Sanctuary is also a popular spot for picnicking, fishing, and canoeing. So if you’re looking for a great place to get away from the city and enjoy the outdoors, the Ipswich River Wildlife Sanctuary is definitely worth checking out.

2. World’s End Trail

Located just 11.7 miles from Boston, this 2.5-mile trail is one of the best hikes near Boston that offers stunning views of the city skyline and the surrounding harbor. Olmsted designed the park as a residential community, but it was eventually transformed into a national park. Today, this moderate 3.5-mile trail loops around World’s End, a peninsula in the Boston Harbor Islands National Park, and an oasis of tranquility and natural beauty. The trail offers panoramic views of the harbor, the city skyline, and the nearby islands. Along the way, hikers can also enjoy a variety of landscapes, including woods, meadows, and rocky beaches.

The trail winds through rugged cliffs and coastal forests, and it includes a number of lookout points where hikers can stop to enjoy the view. There are also plenty of opportunities for picnicking, birdwatching, and fishing along the way. The World’s End Trail is also a great choice for hikers of all abilities, as it is relatively flat and well-maintained.

3. Walden Pond State Reservation

Walden Pond State Reservation is a hiking destination located in Concord, MA, about 30 minutes outside of Boston. The property includes a replica of Thoreau’s single-room cabin as well as hiking trails that wind through woods and meadows. The pond itself was created by retreating glaciers 10,000 to 12,000 years ago and is now a popular spot for swimming, fishing, and picnicking. The reservation is open year-round and offers a variety of activities for visitors to enjoy. Walden Pond State Reservation is also a great place for birdwatching, picnicking, fishing, and swimming.

4. Mount Norwottuck, Mount Holyoke State Park

Mount Norwottuck is the highest peak of the Holyoke Range of traprock mountains and is located in the Mount Holyoke State Park in Amherst, Massachusetts. The Mount Holyoke State Park is a state-owned public recreation area that covers the eastern half of the Holyoke Range in the Pioneer Valley region of western Massachusetts. It is adjacent to J. A. Skinner State Park and its facilities include hiking trails, a scenic overlook, and picnic areas. The mountain is popular with hikers and features a variety of hiking trails. The summit of Mount Norwottuck offers views of the Connecticut River Valley and the Berkshires.

5. The Skyline Trail Loop, Middlesex Fells Reservation

The Skyline Trail Loop is a hiking trail located in Middlesex Fells Reservation, a public recreation area in Malden, Medford, Melrose, Stoneham, and Winchester, Massachusetts. The trail covers more than 2,200 acres in size and offers scenic views of the Boston skyline. The Skyline Trail Loop is one of the premier destinations of hiking in Massachusetts. Hikers of all skill levels can find a challenge on the trail, as there are several difficult sections. However, the rewards are well worth it, as the trail provides stunning views of the Boston skyline and the surrounding area.

6. The Freedom Trail, Boston

The Freedom Trail is a 2.5-mile-long path through Boston, Massachusetts that passes through 16 key U.S. historical sites. The trail is a great way to explore the city and learn about its rich history. The trail begins at the Boston Common, the country’s oldest public park, and ends at the site of the Battle of Bunker Hill. Along the way, visitors will see such landmarks as the Old State House, Faneuil Hall, and the USS Constitution Museum. The Freedom Trail is one of the best hikes in Massachusetts and is a great way to experience the city of Boston.

7. Purgatory Chasm State Reservation

Purgatory Chasm State Reservation is best known for its hiking trails, which wind through a series of rocky formations, including The Corn Crib, The Coffin and Lovers’ Leap. The park is located at 198 Purgatory Rd in Sutton and is managed by the Massachusetts Department of Conservation and Recreation. Purgatory Chasm is a protected state park and one of the best hikes near Boston. The park offers views of the surrounding countryside, as well as geological features such as cliffs, caves and porphyry rock outcroppings. Purgatory Chasm is also home to a variety of plant and animal life, making it a beautiful place to hike year-round.

8. The Cape Cod Rail Trail

The trail runs for 22 miles, from South Yarmouth to Wellfleet, and includes a section that runs along the scenic Cape Cod Canal. Along the way, hikers can enjoy views of Cape Cod Bay, the Atlantic Ocean, and the Massachusetts coastline. The Cape Cod Rail Trail is also a popular destination for bird watching, as it is home to a variety of species, including ospreys, herons, and eagles. The trail is also an important part of Cape Cod’s history. The trail follows the path of an old railroad line that was built in the 1800s to transport goods between Cape Cod and Boston. Today, the trail is open to hikers, cyclists, and horseback riders, and is a popular destination for both locals and visitors to Cape Cod.

9. Bish Bash Falls State Park

No matter what time of year it is, there’s always something to see at Bish Bash Falls State Park. The park is home to Bash Bish Falls, the highest single-drop waterfall in Massachusetts. Swimmers, picnickers, and hikers enjoy the area around the 80-foot falls and emerald plunge pool.

The Bish Bash Falls Trail is one of the best hikes near Boston, and it offers stunning views of the falls and the surrounding mountains. The trail is located in the town of Mount Washington, and it is named after Bash Bish Falls.

10. Wachusett Mountain via Harrington Trail

Wachusett Mountain via Harrington Trail is one of the best hikes near Boston. The 4.8-km out-and-back trail takes an average of 1 hour and 43 minutes to complete. Dogs are welcome on the trail, and the best times to visit are March through October. The trailhead is located in Princeton, and the trail winds through woods and meadows with stunning views of the surrounding mountains. There are several rocky sections, but overall the trail is well-maintained and suitable for all experience levels.

At the summit, hikers can enjoy panoramic views of Boston and the surrounding area. After taking in the views, hikers can head back down the trail and relax knowing they’ve completed one of the best hikes near Boston.

11. Mount Greylock State Reservation

Mount Greylock is a popular destination for hikers and nature lovers alike. Located in the Mount Greylock State Reservation, the mountain offers 12,000 acres of public recreation and nature preserve area. It is home to the highest point in Massachusetts, making it a popular spot for hikers and outdoor enthusiasts.

The reservation offers a variety of trails of different lengths and difficulty levels, making it a great place to explore whether you’re a casual hiker or an experienced climber. The Mount Greylock State Reservation also offers camping, fishing, picnicking, and bird watching.

12. Robert Frost Trail

This 47-mile long footpath located in Eastern Hampshire County and Franklin County is named after the renowned poet Robert Frost, who lived in the area for many years. The trail passes through the eastern Connecticut River Valley of Massachusetts. It is one of the five longest hiking trails in Massachusetts, and it offers stunning views of the river valley and the surrounding countryside.

The trailhead is located just outside of Boston, making it a great option for hikers who want to escape the city for a day or two. The Robert Frost Trail is well-marked and well-maintained, and it provides a great opportunity to get away from the hustle and bustle of daily life.

13. Salem Heritage Trail

The Salem Heritage Trail is one of the best hikes near Boston. Created in the 1980, the trail was designed as a self-guided walking trail to help visitors explore Salem’s historic sites. The trail runs for nearly three miles through Salem, MA and passes by some of the city’s most iconic landmarks. These include the witch trial sites, Salem Maritime National Historic Site, and the House of Seven Gables. The trail is well marked and easy to follow, making it a great option for both experienced hikers and those new to the sport.

14. Blue Hills Skyline Trail

Blue Hills Skyline Trail offers spectacular views of Eliot Tower and the Boston skyline as well as varied terrain. The trail is about 10 miles south of downtown Boston and features more than 125 miles of trails, making it one of the largest undeveloped conservation lands in the Boston metropolitan area. Blue Hills Skyline Trail is a great hike for all levels, from beginner to expert. It is a great way to get outside and enjoy the fresh air while getting some exercise.

15. Mount Everett State Reservation

Situated in Mount Washington and Sheffield, Mount Everett State Reservation is one of the MA hikes that offer panoramic views of Massachusetts, Connecticut, and New York. A total of 530 acres (210 ha) of old-growth forest can be found on Mount Everett’s east side, most of it on the east side of the mountain. The hike to the summit of Mount Everett is moderate to difficult, but it’s well worth it for the stunning views. On a clear day, you can see all the way to Vermont and New Hampshire.

Wrapping Up

So whether you’re looking for a challenging hike or a peaceful place to enjoy nature, our list of best MA hikes is sure to provide a challenge and an unforgettable experience for you. With so many options available, there’s no excuse not to get out and enjoy the best hiking that Massachusetts has to offer. And if you’re thinking about purchasing a property near one of these great trails, or any other property in Massachusetts, consult our team of property experts. We would be happy to help you find the perfect home for your needs.

Steph Wilkinson

In her 25-year career, Steph Wilkinson has been involved in the acquisition, marketing and sales of over $3 Billion dollars of residential real estate. A number of years ago, Steph transitioned into Brokerage Leadership for National real estate brands and tech start-ups. She has served as a Business Strategist for real estate agents and brokerages alike and is also a real estate coach and trainer. In her new role with the Iconic Team, Steph will be responsible for the growth of the team and will be working with all of our agents to increase their productivity and bottom line.