25 Boston Area Hikes & Trails for Your Family

Tracy Snyder Molina said:  This 640-acre forest has many unpaved trails to explore as well as a 3-mile paved loop that is perfect for strollers, bikes and tiny legs. The extensive trail system guides visitors to the different woodland areas and two fresh water lakes. In addition, seven different rocky hills provide lovely views of Boston, southern New Hampshire and central Massachusetts. There are bathrooms and vending machines available near the Forest Street entrance as well as a playground and a swimming beach in the summer months.

Amanda Banta said:  When I was a kid my best friend lived near a small entrance to Wompatuck State Park and we would spend hours exploring the trails, usually making our way to the reservoir within the park. Now that I'm a parent, I love sharing this park with my adventurous kids. My boys love to explore the wooded trails and there are plenty that are easy for their little feet to maneuver.

There are plenty of paved paths if you have a stroller or little ones who want to walk by themselves but aren't ready for the uneven terrain of the park. See here for a list of highlighted hikes and bike rides.

Amanda Banta said:  Hike through World's End Reservation and you will be rewarded with a stunning view of the Boston skyline just 15 miles across the water. When you're within the tree-lined trails and hills it's easy to forget how close you are to the city, Throughout the year walkers, joggers, cross-country skiers and others stay active on the property, part of the Trustees of Reservations. If going with little ones, bring an all-terrain stroller for navigating uneven paths. There are public bathrooms and a water fountain. Parking is limited.

Tracy Snyder Molina said:  Visit Great Misery Island and explore more than 2 miles of moderate hiking trails around the island. You'll pass the remains of an early 20th-century resort on your way through forest, meadow and rocky shores that lead to gorgeous views of the North Shore and Salem Sound. At very low tide, you can wade across to Little Misery Island and view the remains of the steamship, "The City of Rockland," which wrecked off the coast of Maine and settled there many years ago.

NOTE: The Misery Islands can be accessed by dinghy, canoe, or kayak. (The Trustees does not offer any boat excursions.)

Tracy Snyder Molina said:  Mass Audubon's largest sanctuary offers 12 miles of interconnecting trails for exploring through forest, meadows and wetlands with plenty of wildlife viewing. The trails lead to a vernal pool and observation tower, along boardwalks and a rockery which consists of several narrow passages and caves. There is also a nature play area for the kids to enjoy.

Tracy Snyder Molina said:  Established in 1638, Appleton Farms has six miles of footpaths, bridle paths, and farm roads (which are great for easy walking and jogging strollers) across the property. In addition, you can also walk at the adjacent Appleton Farms Grass Rides which offers more than five miles of wide carriage paths bordered by woods with plenty of opportunities for wildlife viewing. The trails are part of the Bay Circuit and Discover Hamilton trail systems. Bring a picnic lunch to enjoy at the stone paddock and say hi to the friendly farm animals.

Tracy Snyder Molina said:   Situated on the Merrimack River, this park features 19th century gardens and plantings, as well as one of the largest naturally-occurring stands of mountain laurel in Massachusetts. Along your hike, you'll walk through meadows, towering pines and an exquisite rhododendron forest. During May and June, the azaleas and rhododendron are in full bloom.

Tracy Snyder Molina said:  Formerly known as Agassiz Rock, the Monoliths are examples of giant boulders that were picked up from bedrock and carried far away by the last glacier. A 1-mile moderate loop trail leads you up Beaverdam Hill where Little Rock emerges as a giant granite silhouette. A short distance away, other boulders lie perched on the edge of the landscape left steep and jagged as the glacier broke off chunks of rock as it passed. Below rests the 30-foot-tall Big Rock. No one knows how far below the ground it is buried.

Tracy Snyder Molina said:   Hiking through the refuge offers many opportunities to view wildlife in a variety of habitats including salt marsh, dune, and maritime forest. The Hellcat Interpretive Trail boardwalk includes both a marsh and dune loop. There are also two observation towers for magnificent views, the handicap accessible Pine Trail, the Bill Forward Bird Blind, and a number of other wildlife viewing areas to entertain the whole family.

Tracy Snyder Molina said:  Ravenswood is comprised of 10 miles of former carriage paths and trails that wander through a tranquil setting of hemlock groves, a magnolia swamp, and other trees' species where you’ll find remnants of Colonial habitation. The Ledge Hill Trail is a 2-mile round-trip walk among whimsical looking, fern-covered boulders that children will love or you can hike to the overlook to Gloucester Harbor. The carriage roads are covered with dense crushed stone and should be fairly suitable for strollers.