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Urban Suburban Kids
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stroller Friendly Outdoors

Outside Stroller Friendly Options

One of the toughest things I discovered after becoming a mom of two was trying to figure out what to do with my very active 2 year old while still trying to stick to nap routines with a newborn. The stroller is a great option but where do we go when walking the neighborhood requires a change of scenery.


  • Wakefield: Lake Quannapowitt - if the parking lot by the church is full, you can always park near the baseball field. The entire lake is a really long walk, but the whole trail can be done on paved surfaces.
  • North Reading: Ipswich River Park- lots of parking, paved trails and a playground (not fenced) but plenty of places to sit and entertain. 
  • East Boston: Deer Island - This is one of our newer favorites. This paved trail is mostly flat or has very small moderate hills if you stick to the outer loop (interior is paved, but hilly). You get views of the City, the boats coming in/out of the harbor and planes landing. Yes, there are also the wastewater treatment tanks,  but with the city as a backdrop and most of the trails on the water it's a great distraction.
  • Minutemen Bike Path: You can pick this trail up in a number of locations, but from Cambridge Bedford you can follow the rail trail through the woods.Spy Pond Park and Field has parking and a playground and might be the closest location to us. You have miles and miles of trail to explore all offering a slightly different setting http://minutemanbikeway.org/wp-content/uploads/2021/10/BikewayBrochure2021.pdf
  • Lincoln: Drumlin Farm- This place offers a lot of options, the train is either hard packed or paved, but almost all are stroller friendly. There are some hills, especially at the end leading back to the parking lot. You can explore the space at your own pace and visit the animals along the way, picnic in the woods or visit the nature play area. https://www.massaudubon.org/get-outdoors/wildlife-sanctuaries/drumlin-farm/about/trails
  • Wakefield: Breakheart Reservation - you can enter either side (Saugus or Wakefield) and have paved trails that wind throughout. The Wakefield side has gentle hills and leads to the lower pond and play space. The sand along the beach is pretty hard packed so you could get a stroller on it you wanted. 
  • Burlington: Mary Cummings Park - The Pollinator Trail is a .8-mile loop that is wheelchair accessible. It can be accessed from both The Trustees and Burlington Soccer Field parking lots on Blanchard Road.
  • Lincoln Decordova Sculpture: Most of the Sculpture Park grounds are grass or paved path/drive. There is one accessible pathway through the property. 
  • Boston: The Charles River Esplanade-  If you start near the Beacon Hill side of the river you'll be able to do a large loop following Storrow Drive, over the Mass Ave bridge, down the MIT side to the Salt and Pepper Bridge. There are foot bridges that are accessible in Beacon Hill and near BU. 
  • Boston: Charlestown Navy Yard -  If you park in the Navy Yard you can wind your way along the waterfront from the USS Constitution to Menino Park near Spaulding. There is also a fenced in park with small splash pad (Charlestown Naval Shipyard Park on 8th Street). A great place to watch the planes and the boat action on the Harbor. Menino playground is new and right on the water.
  • Boston: Castle Island and Pleasure Bay- This loop is just over a mile, but you can certainly add onto it by following Day Boulevard into South Boston towards Dorchester. While the area is paved and there are parks and playgrounds along the way (and beach to play at). The loop around the fort at Castle Island is great for watching the birds, planes, boats and fishing.  Sullivan's is open seasonally for ice cream and snacks.
  • Stoneham: The Stone Zoo -  We ended up getting a family membership here and it was very worth it! The entire zoo is stroller friendly and it's really easy for new walkers to navigate. Besides the zoo animals, there is a small barn with goats and chickens (sometimes you can pet) and a nice fenced in playground. We also love the Dino dig. 
  • Middlesex Fells: The Spot Pond Loop while most of the Fells are not stroller friendly, the Spot Pond loop is paved. You can enter near the boating access and head towards Medford. It's less than .5 one way and runs along the pond and Woodland Road.
  • Winchester/Stoneham:The Tri Community Greenway links the towns of Winchester/Woburn and Stoneham. You can take it all the way from Winchester to Stoneham (7mi) or take the route to Horn Pond. There is parking at each end. The whole trail is paved.  http://www.tricommunitygreenway.org/maps
  • Danvers:  Danvers Rail Trail -This trail is mostly flat and not entirely paved (some sections of stone dust), but is good for strollers that have bigger wheels. There are some urban areas, some wooded areas and a marshier area. https://www.danversrailtrail.org/contact
  • Chelmsford: The Bruce Freeman Trail - A 25 mile  rail trail through the communities of Lowell, Chelmsford, Westford, Carlisle, Acton, Concord, Sudbury, and Framingham.   A guide to parking and access points, some of the sections in Sudbury/Acton are not complete yet so view the map: https://brucefreemanrailtrail.org/visit-bruce-freeman-trail/visiting-trail/
  • Newburyport: Parker River Wildlife Sanctuary- The Hellcat Boardwalk loop is 1.3 miles and runs through marshes, dunes and the woods. There are other trails at the Sanctuary that are a little tougher to navigate (mowed grass, packed sand, gravel) so plan accordingly to your level of comfort.https://www.fws.gov/media/parker-river-accessibility-guidepdf
  • Belmont: Beaver Brook -  This loop is fairly short, less than a mile and leads from the parking lot through the conservation woods. Beaver Brook also has a great splash pad and playground. Ample parking.
  • Somerville: Somerville Community Path - a paved and well lit path with funky artwork that cuts through the heart of Somerville. There are many entry points: somervillehub.com
  • North Andover: Harold Parker State Forest The Berry Pond trail is just over a mile through the woods and on a hard packed surface. https://www.mass.gov/locations/harold-parker-state-forest
  • East Boston: Belle Isle Marsh this marshy trail is one I hesitate to put on. It's short (less than 15 min loop), it's under the flight path so can get noisy and it also is known to be buggy. I added it because it's relatively close, easy to park and has lots of bird watching. 
  • Revere: Revere Beach Boulevard: This isn't a trail, just the boardwalk that runs along the beach. All paved and offers ocean views and facilities. On street parking.
  • Nahant/Lynn: Nahant Beach Promenade Trail - Similar to above, the trail is a boardwalk that runs along the ocean. If you go all the way to Swampscott,  there is also a playground on the ocean in Lynn
  • Chelsea: Mary O'Malley Park: This park overlooks the Mystic River in Chelsea with views of Boston and the Tobin Bridge. There's a playground, open fields and the trail is all paved.
  • Acton: Discovery Museum - this space is great for kids of all ages, they offer everything from an 550 SF outdoor treehouse to inside soft climbing play, STEM experiments, exhibits, workshops and guest speakers. 
  • Jamaica Plain: The Emerald Necklace Trail, JP Pond and the Arnold Arboretum are all beautiful green/urban places to explore. You won't even realize you're in Boston inside the Arboretum. The trails are all paved and there is lots to explore, check their website for events and food trucks. 
  • Brookline: Larz Anderson Park. This is a great play area for kids, lots of hills to run up and down, a walking trail that is both paved and packed dirt. At the top there are skyline views of Boston. 

Am I missing any?

Open to suggestions and I'm happy to add to this list, let me know!

Send me a message

Stroller Friendly INSIDE

Inclement weather? Need to get indoors?

I wish this list was a bit longer - but these are the creative solutions I've come up with for indoor play when you have a stroller.


  • Boston's Childrens Museum. The only tricky thing about this is the parking. You have multiple lots nearby and a garage, but getting from the parking to the museum can be a bit of a struggle, especially if it's just snowed and Boston has not done the best job fully clearing the sidewalks.That said, once you're inside there is lots to do and all is accessible. Tip: Discounted access from the local library
  • Boston: New England Aquarium - Parking is much easier, it's just a little bit of a sprint from the parking garage to the front doors. Once inside, assuming it's not a super hectic day you can easily navigate all the floors of the Aquarium. There are ramps and elevators. Tip: Discounted access from your library, timed entry and you can use google to see what times are most busy.
  • Boston Science Museum - So much to see and do and play with. This has been a great place for us to explore, the parking is attached and easy to get to. There are wide open spaces for littles to walk around and it is easy to navigate with a stroller.
  • Target or the Mall.  Not at all creative, but an easy way  to get out and explore.
  • Acton: Discovery Museum - this space is great for kids of all ages, they offer everything from an 550 SF outdoor treehouse to inside soft climbing play, STEM experiments, exhibits, workshops and guest speakers. 
  • Reading: Beanstalks/Sprouts Ropes Course - this is one you definitely need to plan ahead for. Be prepared to wait in line, you get 30 min inside the course. They also have tables for watching and ice cream and a water feature that sprays to music.  
  • Beverly: Room to Bloom -Room to Bloom is a drop-in  indoor playground for children ages 0-6, with play equipment,  slides, swings, nooks and crannies to explore, and decks to spy from for year-round indoor active play. They have four themed rooms including a quiet room for infants & crawlers, train table room, a reading nook and lending library. Socks are required. www.RoomtoBloomBeverly.com
  • Peabody: The Children's Piaza - "Our space is especially designed for young children, from infancy through kindergarten, to learn through unstructured play". Reservations strongly recommended in inclement weather, Walk-in play subject only to availability. Socks are required. Nut Free facility.www.thechildrenspiazza.com
  • Burlington: Camp Experience. CAMP Burlington has themed exhibits (PAW Patrol Currently), activities and retail store. I have not been but I'm told it is fun for all ages. Worth looking into.https://camp.com/locations/boston
  • Also see my section on indoor play spaces for more.

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