A great family hike…What other outdoor activity allows physical exercise, fresh air, and the ability to have conversations with your family, while also being surrounded by the complete serenity of nature? If you and your family haven’t delved into family hikes around Massachusetts, there are quite a few great hiking trails and areas to check out.
How to hike Massachusetts with kids to see breathtaking views
There are a ton of family-friendly hiking trails near Boston that are available for you and your family to enjoy for a day of adventure together, or even just a short hike to pass a bit of time.
One thing to remember is to pack accordingly for your hiking adventure because many hiking trails don’t have any type of water sources or restrooms available. Pack reusable water bottles full of refreshing water for your family members, as well as cooled rags and sunscreen.
Plan for your hiking adventures as if they may take longer than expected, just to be on the safe side. Once you are planned and packed accordingly, have fun researching trails in the state that are the best fit for you and your family. There are a ton of amazing hiking trails available, so plan, pack and have fun!
Discover breathtaking hikes here in Massachusetts kids will love
Breakheart Reservation in Saugus, MA.
Address: 177 Forest St, Saugus, MA 01906
GPS Location: 42.4799773° N, -71.0258374° W
Difficulty: Easy and moderate options (They even have a paved path)
Notes: There is a swimming option about 0.75 miles in from the Saugus side.
Especially in the summer months, we love to visit Breakheart to go swimming, but is still a wonderful place to explore year-round. With events like Maple Sugarin’ it’s more than just hikes that make this place special. Plus, because of the paves path, you can even try out cross-country skiing in the winter. Venture off the paved path and you’ll find berries and all sorts of wildlife, making it a great close-to-the-city destination. (We’ve even seen deer on our walks!)
Blue Hills Reservation in Milton, MA.
Address: 695 Hillside Street Milton, Ma. 2186
GPS Location: 42.2142° N, 71.0933° W
Difficulty: Easy, Moderate, and Challenge options
Notes: The average hike requires 1.5 hours.
You’ll find no shortage of trails at the Blue Hills Reservation. With over 125 miles of different types of trails, there are many family-friendly options for your family to enjoy a beautiful day hiking in nature. For a shorter, family-friendly hike that may be a bit easier for the little ones, consider the Chickatawbut trail. It’s short and offers some of the best views around. And if a view is what you are after, make certain to add the Skyline Loop Blue Blazes trail to your bucket list while you are there. It offers panoramic views that you won’t be able to see anywhere else.
Monument Mountain in Great Barrington, MA.
Address: 545 Stockbridge Rd, Great Barrington, MA 01230
GPS Location: 42.205744° N, -73.3468619° W
Difficulty: Easy, Moderate, and Challenge options
Notes: Parking lot does not get plowed in the winter
Why not combine your family-friendly hiking experience with a bit of a history lesson as well? Monument Mountain offers different types of trails for different ages, but do your research on what trail is most appropriate for you and your children.
If you have younger children, this may not be the best trail for you to consider due to the fact that the majority of the trails are climbing up a mountain, so there are drop-offs and cliffs that can be sudden and appear. If Monument Mountain is a trail that you feel is good for your family hiking experience, then have fun exploring and learning about the history of how the famous “Moby Dick” was inspired by the mountains found within this area.
World’s End in Hingham, MA.
Address: 250 Martins Ln Hingham, MA 02018
GPS Location: 42.2584° N, -70.8734° W
Notes: Set aside 4 hours to do the whole loop
Did I mention that there are so many trails throughout the state that are just riddled with amazing history as well? World’s End actually used to be an island, that was then dammed off to create cropland, which was then changed to become a subdivision that never developed.
Whew…follow all that?
With 4.5 miles of trails and carriage paths to explore, your family will have a blast hiking the day away on this awesome island, turned farmland, turned subdivision that never was, turned beautiful trails.
Middlesex Fells Reservation in Stoneham, MA.
Address: 4 Woodland Rd, Stoneham, MA 02180
GPS Location: 42.4550078° N, -71.09099349° W
Difficulty: Easy, moderate, and difficult options
Notes: While a difficult hike, Skyline trail offers views of the city or an easier option is to go to the Medford side of the park and hike up to Wright’s tower for a great skyline view of Boston. The sheepfold is also a great place to go if you have a dog as it’s a large off-leash park.
Probably the closest to Boston center and parts easily accessible via the T (Orange Line, Oak Grove) , this is a family favorite.
For a short and easy quick hike that is less than a mile in length, consider taking your family on the Long Pond Nature Hike. You can even grab a nature pamphlet that’s offered and learn about nature, insects, and plants along the way. If you have little ones in your family, they’ll be certain to love learning while hiking! For an even easier hike that takes even less time, consider the Bear Hill Trail which actually leads you to the base of the Bear Hill Tower. And while you’re there? You guessed it! Let your family hike to the top to get some totally awesome views.
More resources for exploring the greater Boston Area as a family