Four Great Stroller Runs South of Boston

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stroller run - Boston Moms Blog

Before my babies were born, I was a slow but enthusiastic distance runner. It was easy to schedule an hour or more to head out alone for a long run. Bumpy sidewalks? Roots on a trail run? No problem — I just hopped right over. Now, time by myself is more difficult to come by. And with a stroller to push, evenly paved surfaces make everyone a lot happier. Here are four places I have found joy running with my little ones. So pull out your jogging stroller and try one of these stroller runs! 

Castle Island :: South Boston 

My toddler’s favorite part about being in the stroller at Castle Island is watching the airplanes fly overhead. My favorite part is being near the water. Call it a win-win. Best suited for warmer months, one great feature of the out-and-back run up Carson Beach and around Castle Island is the ease of changing the length of your run by changing your parking spot. There is a playground if you want a spot for the kids to get the wiggles out after your run. 

Parking: McCormack Bath House on Day Blvd. (165 Harborwalk, Boston)

Columbia Point :: Dorchester

From the same parking area on Day Boulevard, head southeast toward Columbia Point. Sights for your little(s) to see on this run just keep coming: people fishing, airplanes flying, flags waving, and the seemingly endless construction at UMass Boston. There is no automotive traffic for most of this run, which helps everyone relax a little bit. The wind can play a role here, though, so make sure everyone is dressed warmly! 

Parking: McCormack Bath House on Day Blvd. (165 Harborwalk, Boston) 

Pond Meadow Park :: Braintree/Weymouth 

Stroller runs in Pond Meadow Park are lovely. There is a hilly 1.5-mile loop with plenty to see! Traffic moves in one direction around the pond. Along our runs, we love to count squirrels. This is a popular spot for (on-leash) dog walking, so if that doesn’t work for your family, it might be best to skip this one. There are picnic tables near the Braintree parking lot. If you’re feeling adventurous, go for two loops! 

Parking: Lots available at 470 Liberty St. in Braintree or off Summer St. in Weymouth 

Wompatuck State Park :: Hingham 

Wompatuck State Park is a great place for a stroller run. The trails are wide, the options for crafting the perfect route feel endless, and parking is plentiful. This is the best option on the list if you are hoping to run with another mom friend, as keeping strollers side-by-side at Wompatuck has worked pretty well for me. While perhaps the easiest location on the list for mom, there isn’t as much variety in what your little one might be looking at. If you’re heading to Wompatuck, it might be worth packing a book or a toy for your sidekick. 

Parking: 204 Union St. in Hingham 


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Katie McKiernan
Katie grew up on the South Shore before spending four years apiece in Indiana and Louisiana. She returned to the Boston area in 2012. She and her husband have two red-headed children: a son (2016) and a daughter (2018). Katie spends her days teaching middle school math and French and her evenings trying to get dinner on the table. She recently traded in her beloved Corolla for a minivan. Yes, please: camping, palindromes, and drinking coffee on the back porch. No, thanks: science fiction, pickles, and disorganized drawers.