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Best and worst places in Boston for families with strollers

Lisa Daley of Weymouth and son Luke enjoyed an outing at Pleasure Bay in South Boston.
Lisa Daley of Weymouth and son Luke enjoyed an outing at Pleasure Bay in South Boston.

Boston is full of history and idiosyncratic charm, with its architectural treasures, narrow streets, drivers who view motor-vehicle laws as more akin to suggestions, and miles of red-brick, cobblestone, and cracked and broken sidewalks. It can also be a trial for moms, dads, or nannies pushing strollers. We quizzed a number of families about some of the most and least stroller-friendly destinations in and around the city. Here’s what they had to say:

Castle Island

The recreation area in South Boston was named as a favorite of many families, because there are lots of paved paths and walkways, plenty of green space for frolicking and picnicking, a couple of small beaches, and even an inexpensive eatery for those who are either too tired or forget to bring lunch. Tasha Brown, who lives in Dorchester with her three children, Daniella, 24 months, Tristan, 8, and Tahja, 11, likes Castle Island because it’s all encompassing. “Well, the walking paths are smooth, and that’s a must with a stroller,” Brown says. “And you have just about everything any young kid would want in a warm weather spot — there’s beach, fun food, playgrounds. And they really are all easy to get around. Even if I wasn’t here with my two older kids to help, if it was just me and the baby, she and I could still get around this park easily.” If there are downsides to Castle Island, it’s the long parking lot that can make lugging accessories like diaper bags and beach bags from car to play areas a major, exhausting chore. And it’s not easy to reach the island on public transportation.

Beacon Hill

This small, historic neighborhood exudes charm. But if you’re a mom or a nanny with a stroller, it can be a nightmare. Many tell us that while Beacon Hill is home to a couple of nice parks and playgrounds, getting to them with a stroller can be about as easy as climbing a rugged wilderness path. The downsides first: narrow sidewalks, extreme uphill walks, and a lack of parking. Haley Gerber, a nanny, demonstrated that difficulty, when we encountered her powering a stroller carrying 15-month-old Lyla DiPietro up a 45-degree slope to get to a playground. “It’s a great neighborhood in a sense,” Gerber said. “But the cobblestone? The tiny sidewalks? If you’re not in great condition, this neighborhood can either get you in shape, walking around with a stroller, or it can break you!” The most common complaint we heard? The area’s narrow sidewalks sometimes force those with wider strollers into the street, because they just won’t fit — a dangerous proposition, what with vehicle traffic. On the upside, our moms loved the play areas, Myrtle Street Playground chief among them. Its equipment is toddler friendly. The fence separating it from the sidewalk and street is sturdy, well-painted, and not at all rusty or jagged.

Faneuil Hall Marketplace


Most families agree that Faneuil Hall Marketplace — which includes North and South markets, Quincy Market, and Faneuil Hall — is a mixed bag. All love the many and varied shopping options — dads and moms can take turns breaking away to browse. Noel Porter and Mohammed Jawado of Hyde Park say taking turns is the main reason they take their infant son, Tyree, there. “I feel better leaving him with the baby for a few minutes at a time and knowing that he’s not going to struggle to get around,” Porter said. Another draw is the range of dining options, from actual restaurants (including that old Boston favorite Durgin Park) to the eclectic food court. Kids of all ages love the street musicians, jugglers, and acrobats who perform throughout the day. But for families with strollers there are issues. The area is paved with a mix of stone and brick, which are fine for sturdier or jogging strollers, but it can be a hassle for those with lightweight umbrella strollers. Also note that in warm weather the marketplace gets quite crowded so you’ll need to keep a close eye on wandering toddlers. Jawado said, “Sometimes the people can make or break it. And here, if it’s too crowded it can be miserable.” Street parking around the marketplace is limited and very expensive, but there is plenty of public transportation nearby.

Drumlin Farm

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About 20 miles outside of the city, Drumlin Farm feels like it was designed with kids in mind — and that’s because it was. The Mass. Audubon farm, located in Lincoln, features a collection of accessible farm animals for petting, feeding, and educational lessons. There are also paths through the forest around the farm, bird-watching, and rescued wildlife. Drumlin is a favorite of this reporter’s wife and her friends for its smooth walking paths and easy access to barns, stables, and the like. Even the dirt paths through the woods around the farm are smooth, easy to walk and push a stroller on, and not bumpy or rocky. Take note: Admission is free for Mass. Audubon members, but it is $7 for adult nonmembers, $5 for nonmember children ages 2-12, free for those under 2.

Arnold Arboretum

Families who want a little nature in the city flock here. Part of the Frederick Law Olmsted-designed Emerald Necklace, the 265-acre arboretum is owned by Harvard University and is free and open to the public. Crisscrossed with wide, wide paths that wend around the facility’s collection of trees, shrubs, and vines, this is a fabulous place to enjoy the seasons. For the most part, the paths are flat and easy but note that there are some steeper inclines as you go farther in. And, dads and moms will tell you, that while there aren’t any playgrounds here on sunny days it won’t be hard for kids to meet new friends to run around with. The arboretum is accessible by public transportation, and there is a fair amount of street parking. However, traffic on the Arborway can be heavy, and it tends to move very fast so it can be tricky when loading and unloading cars and vans.

Boston Common and Public Garden

Without a doubt, this is a favorite of many families. Easily accessible and easy to get around with generous walkways and flat terrain. There are plenty of grassy areas to run around and while the Common and Public Garden are tourist favorites the paths seldom seem cramped. Besides the history and natural beauty there, moms and nannies love that there is so much to do. Rose Machado of Taunton agrees. Machado, who makes the trip regularly with her 10-month-old daughter, Aubee, said, “There are so many different things to do, you can keep a baby busy just with the sights and sounds for a couple of hours.’’ On the Common, parents and kids head to Frog Pond where there is ice skating in winter and a spray pool — which just closed for the season — in the summer. Nearby there is a carousel and the Tadpole Playground, which is scaled for younger children. At the Public Garden, kids can ride swan boats and on the corner of Beacon and Charles streets sits a series of bronze ducklings inspired by Robert McCloskey’s “Make Way for Ducklings.’’ Before you go read the book; and when you’re there be sure to snap some pictures. Getting here by public transportation is easy. There’s not much in the way of street parking, but there are a number of public lots around, including one underneath Boston Common.

James H. Burnett III can be reached at
Follow him on Twitter @James