Since moving to Boston, I’ve loved when visitors have made their way to this historic New England city. Upon arrival, I immediately go in to tour guide mode. And while I’ve only lived here for a few months, I’ve been able to log in dozens of mile, bringing family and friends around my new home.
Because I live in Charlestown, you would think that it makes the most sense to follow the Freedom Trail through downtown Boston. While that’s fun and all, I can only walk through Faneuil Hall so many times before I go cray.
Instead, I suggest an alternative route (it’s about 5 miles). If you’re starting in my ‘hood (Charlestown), I recommend starting at the Bunker Hill Monument. You can actually walk up all 294 steps to the top (plus, it’s free). From there, if you follow part of the Freedom Trail across the Charlestown Bridge, rather than going through the North End, I recommend banging a right and heading towards Beacon Hill.
At this point, you’ll see TD Garden on the right and then Mass General Hospital. Just keep walking… you’ll get there!
After about 10 minutes, the architecture starts to change and once you cross over Cambridge St, you’ll officially enter Beacon Hill. From here, there’s really no right or wrong direction. Every single street and alley has something new to discover… from ivy covered buildings to cobblestone streets to beautiful window boxes. I recommend strolling by Louisburg Square and taking a peak at Acorn Street (usually it’s pretty crowded though).
Need a coffee break at this point? Stop by Tatte Bakery on Charles St. for a pick-me-up.
Once finished, continue down Charles St., take a right on Chestnut St. and you’ll spot the walking bridge that leads you to the Charles River Esplanade.
From there, you’ve entered the domain of cyclists, runners, geese, ducks & energetic dogs let off their leashes. Thankfully, if you don’t mind any of those, you also get an amazing view of the river, beautiful sailboats included. My favorite part? A public dock with adirondack chairs, perfect for a relaxing pitstop on your tour through Boston.
Two and a half miles in and you might be getting tired, but there’s still much to see.
As you continue walking along the Charles River Esplanade path (heading towards the CitGo sign), you’ll stumble across the next walking bridge that brings you to Boston’s Back Bay neighborhood.
Once you’ve crossed, go one block past Beacon St., another block past Marlborough St, and then one more block until you find yourself on Commonwealth Ave. A major street that runs through Boston’s Back Bay, it’s also home to a beautiful park that runs through the center, perfect for viewing the historic architecture on both sides of the street.
Looking to do some window shopping? Just one more block over (I know, I keep saying one more block, but really, it is), you’ll stumble across Newbury Street…. essentially the 5th Ave of Boston. If you’re like me, you’ll soon veer off, as it’s definitely one of the more crowded areas of Boston.
At this point, you’re oh-so-close to one of my favorite Boston landmarks, the Boston Public Library. Even if you don’t like reading, I highly recommend stopping here for a peak inside. But shhhh… the library is actually used by, you know, real students 🙂 therefore, while climbing the marble stairs and walking through the Bates Hall, you gotta keep your voices down.
Once finished up with your self guided tour of the library, I typically like to finish up by exploring the Boston Public Garden. While just as beautiful as Central Park, I absolutely love how non-crowded it is. No offense to NYC, but you won’t be trampled by tourists when walking under the weeping willow trees or trying to cross the historic bridge across the garden’s pond.
By now, I’m sure you’ll have some hangry friends in tow so I suggest ending your tour at this point for a bite to eat. The best part? You’ve just walked over 5 miles, so it’s time to treat yo’ self 🙂
