1. Hopkinton State Park—Hopkinton  

Why it’s good for kids: This park is not only home to the start of the Boston Marathon but also boasts 1,500 acres of forest filled with trails for all levels of hiking. Download a map before heading out and then start at Split Rock which will connect you to tons of trail options. There's also a reservoir with two swimming beaches to reward yourself with a swim after you finish your hike.
Bonus: Dogs are welcome on leash so bring the whole fam! If you're feeling really adventurous, you can also rent a canoe or kayak when you hit the water. 
Parking and restrooms: There is parking for 100 cars at Split Rock, which can fill up quickly on a busy day. Restrooms are located by the beach areas. 
Fee: Small parking fee

2. Breakheart Reservation—Saugus, Wakefield 

Why it’s good for kids: This state park features more than two dozen trails for hiking and biking on its 700-plus acres. For the little guys, Eagle Rock Trail is the way to go. Cool off with a dip at Pearce Lake and try your hand at fishing or go bird watching along the Saugus River. There's also a 3-mile paved loop around the park for a more casual stroll with a stroller, or to cruise on bikes. 
Bonus: Your four-legged family members are welcome on leash on the hiking trails, but there's also a dog park inside the reservation where they can roam and play freely. 
Parking and restrooms: Free parking is available on site. There are portable toilets at both the visitors center and Pearce Lake. 
Fee: Small parking fee

Moms and babies bond with nature in Middlesex Fells. Photo courtesy of the author

3. Middlesex Fells Reservation—Malden, Melrose, Stoneham, Winchester

Why it’s good for kids: Located just north of Boston right off I-93, it's one of the most convenient spots to tromp through the woods. The Middlesex Fells is massive, so pick up a map at the Botume Visitor Center or download one before you go. The Pine Hill hike to Wright's Tower is a short, fun destination hike. Long Pond Nature Trail and Spot Pond Brook Archeological District Self-Guided Trail are both about one mile of easy hiking, so they’re also perfect for the whole family—and they're totally stroller friendly.
Bonus: Take advantage of Babes in the Woods and Hide 'n Seek guided hikes for families with babies and young children, offered by the Friends of the Fells.
Parking and restrooms: There are several parking lots around the perimeter of the Fells. There are no restrooms, so go before you arrive (or duck behind a tree if need be).
Fee: Free

Walden Pond is a four-seasons destination. Photo courtesy of Massachusetts Office of Travel & Tourism

4. Walden Pond State Reservation—Concord and Lincoln

Why it’s good for kids: Walden Pond has it all—recreation and history in one beautiful place. I’m partial to the trail that runs along the perimeter of the pond, which is 1.7 miles of easy walking in the woods with little walking companions or a stroller, and with plenty of spots to stop for a break, including the site of Henry David Thoreau’s original cabin where he wrote Walden.
Bonus: Bring a picnic lunch and take a dip in the pond in the summer, see a replica of Thoreau’s cabin and check out the visitor center, which features a gift shop, exhibit space, and large deck.
Parking and restrooms: In the lot on Route 126, which fills quickly in the summer. Call 978-369-3254 to see whether there are spots available before you arrive. Bathrooms are located at the visitor center and near the pond along the trail.
Fee: Small parking fee

5. Drumlin Farm Wildlife Sanctuary—Lincoln

Why it’s good for kids: If your children love animals, Drumlin Farm is the place to go hiking. There are four miles of trails for your family to explore while encountering farm animals and wildlife along the way. Try the Farmyard Loop Trail (½ mile) and combine it with the Forest Discovery Trail (additional ⅓ mile) for a great overview of the farm. This farm is perfect for all ages, including walking toddlers and babies in strollers. 
Bonus: Visit the animal barns, take in wildlife exhibits, stop by the learning garden, go on a hayride, visit the farm stand, or participate in a kid-friendly drop-in activity.
Parking and restrooms: Plenty of free parking. Bathrooms are located throughout the facility, including at the Nature Center, picnic area, and Red Barn.
Fee: Free for Mass Audubon members 

Whoooooo knows what animals you'll encounter at the Habitat Wildlife Sanctuary. Photo courtesy of Mass Audubon

6. Habitat Wildlife Sanctuary—Belmont 

Why it’s good for kids: Only seven miles from Boston, Habitat is a great place to go hiking with kids if you don’t want to spend a lot of time in the car. There are four miles of trails that wind through forests, meadows, and around ponds, providing a quiet escape from the city. Don’t miss the half-mile Turtle Pond Loop where you can glimpse turtles and frogs plopping into the water in the summer.
Bonus: Habitat offers year-round programs and events for children and adults. You can even host a birthday party there!
Parking and restrooms: Plenty of free parking. Bathrooms are located in the visitor center.
Fee: Free for Mass Audubon members 

7. Blue Hills Reservation—Milton, Quincy, Braintree, Canton, Dedham, Randolph

Why it’s good for kids: Much like the Middlesex Fells, Blue Hills Reservation is a quick jaunt south of the city, making it an easy place to escape without a long car ride. The best views are up Big Blue, straight up from the Trailhead Museum. Houghton’s Pond has a nice, easy loop trail that’s suitable for all ages. Or for kids who don’t mind a little rock scrambling, take the path up to the Chickatawbut Overlook for stunning views of the city skyline. If you're going to be pushing a stroller, opt for Bugbee Path and check out our full list of easy Blue Hills Hikes to take with little ones.
Bonus: Bring a picnic and take a dip in Houghton’s Pond after your hike to make a day of your adventure.
Parking and restrooms: There are several parking lots around the perimeter of the Blue Hills (see trail map for details). Bathrooms, which are open seasonally, can be found at the visitor center, Houghton’s Pond, the Trailside Museum.
Fee: Free

World's End trails were formed along what used to be carriage roads. Photo by R.Cheek courtesy of the Trustees

8. World’s End—Hingham

Why it’s good for kids: World’s End used to be an island at high tide, but colonial farmers reshaped the landscape by damming the salt marsh to grow hay. Frederick Law Olmsted was commissioned to design a subdivision on the property and though it was never built, the carriage paths from that time remain. There are 4.5 miles of easy to moderate trails to explore, many with views of Boston, which is only 15 miles away.
Bonus: Bring your dog for a leashed walk the whole family can enjoy or bring a picnic to make a day of your trip.
Parking and restrooms: Parking is limited and fills quickly on weekends, so it’s recommended that you check the World’s End Twitter account for availability. There is a bathroom at the main entrance.
Fee: Free for Trustees members 

9. Maudslay State Park—Newburyport

Why it’s good for kids: A former estate, Maudslay is about as picturesque as it gets. And while you can go anytime, spring might just be the perfect season for a visit. That’s because Maudslay has one of the best and biggest displays of azaleas and rhododendrons around. Take them in on the Introductory Walk, which is an easy one- to two-mile hike depending on which trails you decide to take. Either way, if you have a stroller that can handle bumps, the trails are wide enough for all ages!
Bonus: Dogs are allowed, so this can truly be an outing for the whole family. It’s also a lovely place to bring a picnic. And the estate offers educational programs in the summer.
Parking and restrooms: Ample parking and bathrooms are available at the main entrance.
Fee: Small parking fee

Ward Reservation offers spectacular views. Photo courtesy of the Trustees

10. Ward Reservation—Andover and North Andover

Why it’s good for kids: Ward Reservation is another great spot to take in views of the Boston skyline from afar. It’s also home to a few very unique natural features. On top of Holt Hill, you’ll find the Solstice Stones, large stones embedded in the earth marking various compass and solstice points. With kids, don’t miss the boardwalk that takes you to Pine Hole Pond, where you’ll encounter the rare quaking bog.
Bonus: Holt Hill is the highest point in Essex County. You can bring dogs and picnics to the reservation.
Parking and restrooms: Parking is available at the main entrance. There are no restrooms.
Fee: Free for Trustees members 

11. Broadmoor Wildlife Sanctuary—Natick

Why it’s good for kids: If your children love seeing wildlife in its natural habitat, Broadmoor Wildlife Sanctuary is the place to go. The property’s nine miles of trails are teeming with dragonflies, turtles, otters, and many species of birds. Most of the trails at Broadmoor are short and suitable for kids of all ages, so you really can’t go wrong no matter which path you choose. The boardwalk path is deemed an All Person Trail, meaning strollers, wheelchairs, and walkers are all welcome.
Bonus: The accessible boardwalk means that all visitors can enjoy the beauty of the sanctuary. Picnic in designated areas and check the schedule for kid-specific programming.
Parking and restrooms: Parking and bathrooms are available at the main entrance.
Fee: Free for Mass Audubon members

Walk in the dunes at the Crane Estate. Photo by Goodharbor/CC BY 2.0

12. Crane Beach Dunes—Ipswich

Why it’s good for kids: Crane Beach is a popular summer destination for families who love the sand, sea, and sun. It’s one of our favorite beaches and even when it’s not beach weather, we go to Crane to hike the dunes. This is a super unique experience that you can’t have in many places. It’s best for people who are babywearing or with slightly older children as some of the dunes are a bit tricky to navigate for small legs. But kids will love scrambling around in the sand.
Bonus: If it’s warm out, sit on the beach after your hike or even take a dip in the ocean. This is a great spot for picnics. And you can even visit Castle Hill while you’re there. 
Parking and restrooms: Parking is available on a first-come, first-serve basis. It often closes during busy summer weekends, so check the Crane Beach Twitter for availability. Bathrooms are available at the main entrance.
Fee: Small parking fee

Top photo courtesy of August Muench via Flickr/2.0