The Greater Boston area is filled with reservations and parks with trails suitable for all levels of hikers. However, you don’t need to sacrifice scenery just because you aren’t up for a steep climb. Whether you’re short on time or have folks with little legs in tow, these seven trails are some of the best hikes in Boston that are also easy enough for everyone to enjoy.
- Deer Island (Winthrop)
Images by Lane Deer Island offers two miles of mostly flat hiking trails that are easy to traverse. While the view to one side includes a wastewater treatment facility, in the other direction, water views stretch towards the horizon. The Boston skyline seems to be a mirage, rising in the distance. Tufts Avenue, Tufts Ave, Everett, MA 02149, USA
- Beaver Brook North Reservation (Waltham)
Flickr/DiscourseMarker This reservation flies under the radar, but those in the know appreciate the peaceful, wooded scenery found here. Make a short loop around Rock Meadow Conservation Area or extend your walk into the rest of the reservation. Although the trails around the water are limited, check out the ponds and waterfall off Mill Street. Beaver Brook North Reservation, Waltham, MA 02452, USA
- Webb Memorial State Park (Weymouth)
Tripadvisor/Jeff P Small enough that you won’t run out of steam, this overlooked state park is a must-see. Enjoy views of the skyline, ocean, and harbor. The terrain is gently sloping and easy to navigate, plus it’s dog-friendly! Webb Memorial State Park, 371 River St, North Weymouth, MA 02191, USA
- Hemlock Gorge Reservation (Newton/Needham)
Flickr/Josh Wardell This lush oasis feels far more wild and remote than you’d expect from its suburban location. Follow the Charles River, admire Echo Bridge - which really does echo - and let the sight of the abundant foliage relax you. The reservation consists of a mere 23 acres, which limits the length of hikes; the only difficulty comes from changes in elevation and the steps surrounding Echo Bridge. Hemlock Gorge Reservation, 21 Bridge St, Needham, MA 02494, USA
- Wilson Mountain Reservation (Dedham)
Wikimedia Commons/John Phelan Wilson Mountain Reservation Trail forms a short 1.6-mile loop through a forest. The trail is simple to follow and, in addition to lush greenery, there are some hulking boulders along the way. This spot is popular with dog owners. Wilson Mountain Reservation, 384 Common St, Dedham, MA 02026, USA
- Chestnut Hill Reservation (Brighton)
Tripadvisor/A TripAdvisor China Member Strolling around the 1.5-mile-long, paved trail that rings the Chesnut Hill Reservation is an ideal way to unwind. Chestnut Hill Reservation, Beacon Street, Brighton, MA 02135, USA
- The Southwest Corridor Park
Flickr/Ed Lyons Cover any of the 4.7 miles that make up this park, which connects Back Bay to Forest Hills, for a convenient and pleasant hike. Southwest Corridor Park, 38 New Heath St, Boston, MA 02130, USA
Do you agree that that these are some of the best hikes in Boston? Did we leave any good ones off the list?
Images by Lane
Deer Island offers two miles of mostly flat hiking trails that are easy to traverse. While the view to one side includes a wastewater treatment facility, in the other direction, water views stretch towards the horizon. The Boston skyline seems to be a mirage, rising in the distance.
Tufts Avenue, Tufts Ave, Everett, MA 02149, USA
Flickr/DiscourseMarker
This reservation flies under the radar, but those in the know appreciate the peaceful, wooded scenery found here. Make a short loop around Rock Meadow Conservation Area or extend your walk into the rest of the reservation. Although the trails around the water are limited, check out the ponds and waterfall off Mill Street.
Beaver Brook North Reservation, Waltham, MA 02452, USA
Tripadvisor/Jeff P
Small enough that you won’t run out of steam, this overlooked state park is a must-see. Enjoy views of the skyline, ocean, and harbor. The terrain is gently sloping and easy to navigate, plus it’s dog-friendly!
Webb Memorial State Park, 371 River St, North Weymouth, MA 02191, USA
Flickr/Josh Wardell
This lush oasis feels far more wild and remote than you’d expect from its suburban location. Follow the Charles River, admire Echo Bridge - which really does echo - and let the sight of the abundant foliage relax you. The reservation consists of a mere 23 acres, which limits the length of hikes; the only difficulty comes from changes in elevation and the steps surrounding Echo Bridge.
Hemlock Gorge Reservation, 21 Bridge St, Needham, MA 02494, USA
Wikimedia Commons/John Phelan
Wilson Mountain Reservation Trail forms a short 1.6-mile loop through a forest. The trail is simple to follow and, in addition to lush greenery, there are some hulking boulders along the way. This spot is popular with dog owners.
Wilson Mountain Reservation, 384 Common St, Dedham, MA 02026, USA
Tripadvisor/A TripAdvisor China Member
Strolling around the 1.5-mile-long, paved trail that rings the Chesnut Hill Reservation is an ideal way to unwind.
Chestnut Hill Reservation, Beacon Street, Brighton, MA 02135, USA
Flickr/Ed Lyons
Cover any of the 4.7 miles that make up this park, which connects Back Bay to Forest Hills, for a convenient and pleasant hike.
Southwest Corridor Park, 38 New Heath St, Boston, MA 02130, USA
For more fun hiking ideas, check out these trails that lead to extraordinary ruins.
If you’re a fan of exploring the beautiful natural areas found across the state, check out our Massachusetts Nature Lovers group on Facebook to see more fantastic photos snapped by fellow Massachusettsans and feel free to add your own!
OnlyInYourState may earn compensation through affiliate links in this article.
The OIYS Visitor Center
Best Hikes In Boston April 22, 2022 Sara Dager Can I hike to historical sites in Boston? Of course you can! Probably the best known and most can’t miss historical hike in Boston is along the Freedom trail. The trail crosses through sixteen different spots that are integral to the history and settlement of the United States. You can walk this trail on your own (there are audio tours you can download,) or take a guided tour with actors playing different historical characters who will give you a detailed history of each stop on the trail. At 2.5 miles long and entirely paved, this is a great jaunt for the whole family and will show you so much of what makes Boston so important. If you’d like to learn more about the Freedom Trail and other free outdoor activities in Boston you can check out our article. What are the most family friendly hikes to go on in Boston? Hiking with the whole family is an absolute delight, but also there is a lot more to think about than when you lace up your boots for a solo hike. You have to consider the ages of everyone involved and what capacity they have for hiking, there may be a need to bring along a stroller and/or some snacks or a meal to keep you all going, and you want to make sure that everyone is prepared for the weather. Boston has some great family friendly hikes that will be perfect for every member. The Broadmoor wildlife sanctuary is a great choice as there’s a few trails of different lengths to choose from, as well as lots of wildlife like birds and turtles for the kids to look out for, and even an exciting audio tour for one of the shorter trails. If you are looking to get a little bit out of the city, we have also compiled a list of some of the best family-friendly hikes in Massachusetts that will keep you busy for a while. What parks should I visit in Boston? If you’re feeling a little overwhelmed with all of the hustle and bustle that is Boston, you may be looking for the perfect park to spend the day in getting some fresh air and admiring the greenery. The Esplanade is one great choice, laying alongside the Charles River. It can be reached by way of multiple footbridges and even features a band shell where the Boston pops play in the warm months. Another great choice from the tree hugger in all of us is the Arnold Arboretum, full of charming pathways and ponds, while this space does feature a wide variety of flora, it is designed to be more casually enjoyed than the traditional botanical center.
The OIYS Visitor Center
Best Hikes In Boston
April 22, 2022
Sara Dager
Can I hike to historical sites in Boston? Of course you can! Probably the best known and most can’t miss historical hike in Boston is along the Freedom trail. The trail crosses through sixteen different spots that are integral to the history and settlement of the United States. You can walk this trail on your own (there are audio tours you can download,) or take a guided tour with actors playing different historical characters who will give you a detailed history of each stop on the trail. At 2.5 miles long and entirely paved, this is a great jaunt for the whole family and will show you so much of what makes Boston so important. If you’d like to learn more about the Freedom Trail and other free outdoor activities in Boston you can check out our article. What are the most family friendly hikes to go on in Boston? Hiking with the whole family is an absolute delight, but also there is a lot more to think about than when you lace up your boots for a solo hike. You have to consider the ages of everyone involved and what capacity they have for hiking, there may be a need to bring along a stroller and/or some snacks or a meal to keep you all going, and you want to make sure that everyone is prepared for the weather. Boston has some great family friendly hikes that will be perfect for every member. The Broadmoor wildlife sanctuary is a great choice as there’s a few trails of different lengths to choose from, as well as lots of wildlife like birds and turtles for the kids to look out for, and even an exciting audio tour for one of the shorter trails. If you are looking to get a little bit out of the city, we have also compiled a list of some of the best family-friendly hikes in Massachusetts that will keep you busy for a while. What parks should I visit in Boston? If you’re feeling a little overwhelmed with all of the hustle and bustle that is Boston, you may be looking for the perfect park to spend the day in getting some fresh air and admiring the greenery. The Esplanade is one great choice, laying alongside the Charles River. It can be reached by way of multiple footbridges and even features a band shell where the Boston pops play in the warm months. Another great choice from the tree hugger in all of us is the Arnold Arboretum, full of charming pathways and ponds, while this space does feature a wide variety of flora, it is designed to be more casually enjoyed than the traditional botanical center.
The OIYS Visitor Center
The OIYS Visitor Center
Of course you can! Probably the best known and most can’t miss historical hike in Boston is along the Freedom trail. The trail crosses through sixteen different spots that are integral to the history and settlement of the United States. You can walk this trail on your own (there are audio tours you can download,) or take a guided tour with actors playing different historical characters who will give you a detailed history of each stop on the trail. At 2.5 miles long and entirely paved, this is a great jaunt for the whole family and will show you so much of what makes Boston so important. If you’d like to learn more about the Freedom Trail and other free outdoor activities in Boston you can check out our article.
What are the most family friendly hikes to go on in Boston?
Hiking with the whole family is an absolute delight, but also there is a lot more to think about than when you lace up your boots for a solo hike. You have to consider the ages of everyone involved and what capacity they have for hiking, there may be a need to bring along a stroller and/or some snacks or a meal to keep you all going, and you want to make sure that everyone is prepared for the weather. Boston has some great family friendly hikes that will be perfect for every member. The Broadmoor wildlife sanctuary is a great choice as there’s a few trails of different lengths to choose from, as well as lots of wildlife like birds and turtles for the kids to look out for, and even an exciting audio tour for one of the shorter trails. If you are looking to get a little bit out of the city, we have also compiled a list of some of the best family-friendly hikes in Massachusetts that will keep you busy for a while.
What parks should I visit in Boston?
If you’re feeling a little overwhelmed with all of the hustle and bustle that is Boston, you may be looking for the perfect park to spend the day in getting some fresh air and admiring the greenery. The Esplanade is one great choice, laying alongside the Charles River. It can be reached by way of multiple footbridges and even features a band shell where the Boston pops play in the warm months. Another great choice from the tree hugger in all of us is the Arnold Arboretum, full of charming pathways and ponds, while this space does feature a wide variety of flora, it is designed to be more casually enjoyed than the traditional botanical center.
