First of all, let me be clear, free just means there’s no entry fee. You would still need to spend money on transportation to get there (unless you walk ALL of it…Boston as a city is fairly small and pretty walkable), you might want to buy food or have to pay for parking. Please note, if you can walk fairly well, 1-6 could be done in one whole day. It will be tiring but that way you can cover pretty much everything the city of Boston has to offer.
1: Take a self-guided tour around Freedom Trail, start at the State House, here’s a map
2. Fanueil Hall, A marketplace and meeting hall since 1700s, still is an iconic and popular (collection of) buildings in Boston. Walk the busy alleys, try the clam chowder, grab a community style table, then walk over to the very “happening” outside for open street art/ literature in the summer and musical twinkling lights in the winter.
4. Spend half a day strolling and picnicking at the Boston Common Park, let the kids splash in the Frog Pond and then boat in the swan boats at the Garden. Now is the time to take out those cannolis you got from Little Italy and sit by the willow trees near the water and watch the geese. Didn’t do #3? Walk to Fig, grab yourself some awesome pizza and enjoy.
5. Like to window shop and people watch? Walk over to Newbury Street and the world is your oyster. We love tasting espresso (free!!) at the Nespresso boutique next to Taj, trying L.A.Burdick’s signature hot chocolates and/or dipping into Georgetown cupcakes, as if the coffee and chocolate wasn’t enough.
6. Walk along the Backbay Fens and Emerald Necklace Conservatory, exploring the lush greenery that Boston hides in it’s bosom.
7. Chinatown: Eat your heart out in Chinatown, tasting dim sum in every little hole in the wall.
8. Deer Island– 15 minutes from downtown Boston and a stone’s throw from the airport to Winthrop. Enjoy panoramic views of the Massachusetts Bay and Atlantic Ocean and a beautiful view of the Boston skyline; there’s also a small beach. Walk or run around the entire island 2.5-3 miles. Dog and stroller friendly. Carry water!
9: Memorial Drive– Enjoy a ride along the Charles, marveling at Boston’s homey skyline and then park in the designated spots and walk over Mass Ave bridge to enjoy even better views with sail boats in the foreground and bridges near the horizon.
10. Head over to the Esplanade and enjoy some time in the calm greens of the city. Visiting over the 4th of July? This is where the action is! Here during spring? You’ll love the cherry blossoms, magnolias and daffodils. Here at Fall? No better place to watch the golden, orange and red foliage reflect on water.
16. Hang out in Harvard Square and rub shoulders with the brainiest of the world. Bask in the sun on the grassy yard and enjoy a fro-yo. Wednesday evenings, come and dance off in the open-air Zumba class and then treat yourself at one the food trucks. If you thought, Harvard Square was all snooty brains, think again…there are more community festivals, funky stores, wonderful street music, lavish farm-to-table dinner at one of the hidden restaurants like Harvest or Henrietta’s, interesting people watching here than almost anywhere else in Massachusetts, but then this is my neighborhood and I’m biased.
17. Plan your trip so you can score a free/low-cost museum day here in Boston.
18. Walk the peaceful Mount Auburn Cemetery in Cambridge in the fall and spring (only a couple miles from Harvard Square)
19. Walk around Fresh Pond Reservation in Cambridge and discover hundreds of different wildflowers (only a couple miles from Harvard Square)
20. Check out old churches from 1600-1700s from this previous post
This is not an exhaustive list of course, for example, if you have more time on hand and would like to space things out, hop on over to my self-guided tours in the Boston areas post, to find more walking tours you can take. Enjoy your time in Boston, drive safe (or don’t drive at all! please?) and don’t mind the Bostonian rudeness (I wish I could say they mean well, they don’t).