family hikes in Boston

My love of hiking emerged organically, as my parents were avid hikers and often took me and my brother for hikes on weekends and vacations. As we grew older, the types of trails we tried became more adventurous, more beautiful, and more fun! I knew hiking was an activity I wanted to encourage my children to try as well because of the vast confidence, peace, and appreciation of nature it gave me growing up.

Now, we hike often as a family. Family hikes are a fabulous way to communicate with our kids about important things in an emotionally safe way. But most importantly, hiking has been a way for us to bond and have fun and be physically active together in the midst of the daily distractions and chaos and carpools.

Below you’ll find some of our favorite family-friendly hiking spots in and around the Boston area. What are your favorite family hikes?

Cutler Park

Where? Needham

What makes it special? Cutler Park is an even-terrained 1.5-mile loop with options to do more extensive hikes. It has enough pit-stops during the loop to keep the little ones engaged, challenged, and happy, like the little alcove near Kendrick Pond where you can have a little picnic and skip rocks. Or the bevy of benches overlooking the water at various points along the route.

My kids especially love: Skipping rocks in Kendrick Pond.

Blue Hills Reservation

Where? Milton

What makes it special? There is so much to do at the Blue Hills besides hiking. With a mini zoo, marine life, science center, museum, swimming, mountains, and a ton more, this could easily be a half-day or full-day activity for the family.

My kids especially love: The Skyline Trail, with its sprawling views of the Boston skyline and an observatory tower at the summit.

Needham Town Forest

Where? Needham

What makes it special? I lived in Needham for eight years before I knew this gem existed! But it’s easy to access and has a super fun geocaching route, which is so great to do with the kids. It’s like a forest scavenger hunt!

My kids especially love: Discovering the hidden working railroad.

Elm Bank Reservation

Where? Wellesley

What makes it special? In addition to beautiful meandering hiking trails, Elm Bank Reservation also boasts beautifully kept gardens and incredible landscaping.

My kids especially love: The nearby horticultural center.

Hale Reservation

Where? Westwood

What makes it special? In addition to the numerous hiking trails for all levels and abilities, Hale Reservation also has a summer camp, fishing, and biking opportunities and outdoor water sports and even horseback riding.

My kids especially love: The family trail.

Broodmoor Wildlife Sanctuary

Where is it? Natick

What makes it special? Broadmoor Wildlife Sanctuary boasts more than 150 species of birds, plus beaver dams, nesting wood ducks, and basking turtles. There are nine miles of easy-to-moderate well-groomed trails that lead you through woodlands, into open fields, and along the edges of streams, ponds, and marshland.

My kids especially love: Ponding at the marsh after a family hike! They find tons of sea critters, including mini lobsters.

Looking for even more family hikes in the Boston area? Check out this guide of kid-friendly hiking trails!

Jenny is a crass and pushy (read = sweet) native New Yorker who has always had a penchant for New England, after attending Brandeis for 4 years, but especially so after meeting her husband Barry, who also happened to live in Boston. After marrying, and creating 3 awesome daughters - ages, 11, 8 and 6 - she and her husband moved to Needham and love it there! Jenny is a Certified Eating Psychology Coach, Mindful Eating Instructor and Wellness blogger. She loves writing about how Mom's can navigate and prioritize their health and positive body image after having children. When she's not trying to figure out how the heck to parent a tween, She can be found blogging at the Huffington Post, (healthy living section) and on her site Heck yes! - mindfulness, kettlebells, body acceptance, yoga, traveling the word and eating decadent and unctuous (vegetarian) food. No way, man! - arthritis at 40, allergies to anything, animal cruelty, waiting in line.