A Family Guide to Boston in the Fall: Things to Do, See & Eat with Kids

A Bit of Wanderlust Heads to Boston 🍂

We packed up the kids and headed to Boston to see a Dartmouth Rugby game at Harvard, and what an experience and beautiful time of year to pack up the kids for a family trip to Boston in the fall! If you’re like us, and this is your first family adventure to Boston, it will not disappoint. I will share all that we did so you can have a copy and paste itinerary. Save this for later, and pin it to your board.

Key notes

  • Boston Commons
  • Tadpole Playground
  • Salty Girl
  • Fenway Park

Where to Go: Family-Friendly Boston Attractions for Kids

I can recommend staying at The Row Hotel at Assembly Row 

and we drove into the city and parked at a conveniently located parking garage very close to The Old Meeting House. There a few to pick from on your drive while passing by pick the one that works best for you, or Uber! More on that later… 

Then by foot we took our adventures, I think it is important to note we did not bring a stroller this trip and that was a first for me! I think I would have rather had my stroller for when the young five year old got tired of walking through Newburgh street after the Boston Gardens on our way to Fenway Park. But hey, it was a totally walk-able city with so much to see that was free, including our steps along the Freedom Walk! 

  • Boston Common was the perfect spot to let the kids run and soak in the sun. It was unseasonably warm when we went, but now it’s changing and I’m sure the park is just as beautiful with all the trees.
  • Tadpole Playground, a nice gated playground, easy to let your kids have a little bit of running around freedom while you stand by.  In the summer, they have a tiny section of water you could splash around in for hot days.
  • From there, we started the Freedom Trail right at the Massachusetts State House, following the red brick path that winds through history. The kids loved spotting the trail markers and learning a bit about Boston’s past without it ever feeling too “museum-like.” 
  • Our walk took us past the historic Granary Burying Ground, where you get a quiet, shaded moment among the city’s oldest landmarks — there were tour groups we could easily navigate around and the kids had fun taking photos along the way with leaves on the cobblestones. 
  • We continued through the park, crossing over to Newbury Street, where the city’s energy really picks up. It’s the perfect stretch for a family stroll — tree-lined, full of charm, and easy to navigate with kids in tow. We stopped for lunch at Salty Girl, which was absolutely amazing and surprisingly welcoming to families during the day. It’s one of those Boston moments where you feel like a local, even with little ones tagging along. The line was long for outdoor seating but we were advised to put our name in for inside seating and we got a table in under 10 min.  Note there is a fun, but pricey K-Pop store nearby off of Newbury street in a neighboring store for a fun look-see while you wait. 
  • After a beautiful lunch, including caviar dip, we continued the family adventure by walking to Fenway Park.  I might recommend getting in an Uber at this point, since we had to walk the entire way back and my cell phone died, but live and learn; learn from my mistakes! Even if you’re not a huge baseball fan, Fenway is such a classic Boston stop — the kids loved seeing the ballpark up close, and it made the day feel like the perfect mix of local Boston culture and family adventure. We bought Boston Red Sox baseball cards from a woman that had some items on a table outside the Bleacher Bar the backside of The Green Monster. 

For me, those were the best family-friendly attractions in Boston and very easy on the pocket-book.