I think most people enjoy traveling. Of course, I don't have any data to back that up, but there's something exhilarating about seeing new places, taking in novel experiences. I have a knack for writing books largely set in places I've never been (and thank goodness for Google maps and the robust travel journalism industry for getting me out of that bind), but sometimes I ditch the self-sabotage and write about places I've actually visited and thoroughly enjoyed.
I've been lucky enough over the past year to get to know Boston reasonably well. A good friend of mine moved to the area in 2022 and, well, that was all the incentive I needed to fly north.
People tend to rave about Boston, and for good reason. Put simply, it's a really cool place. Sometimes you step foot in a new city and feel like you landed some place special. Special comes in all different forms, and from my experience just about everywhere has a little something special, that spark that makes it unique. But I'm not exaggerating when I claim Boston is on a different level. After New Orleans, it's my favorite city in the United States.
Here's some quick background if you're unfamiliar. Boston is the cultural and financial center of New England. It was incorporated by puritan settlers in 1630, making it one of the oldest cities in America. For reference, the Mayflower landed at Cape Cod in 1620. Boston was an integral part of the American Revolution, and that history is still alive, permanently intermingled with its bohemian heart in a way that seems to contrast and perfectly blend all at once.
Part of why I enjoy Boston so much is because you can walk just about everywhere. And if you're not in the mood, take the T (America's oldest subway system).
I like doing this full-on immersion style, giving a blow by blow of how I spent my time in a new city. But first...
SALEM
Infamous for the 1692 witch trials and all things spooky and haunted. It has a New England fishing town vibe that Boston is way too big and cosmopolitan to pull off. Again, there's history oozing from the studs everywhere you turn, whether it's Nathaniel Hawthorne's childhood home and life's work (I hated The Scarlet Letter but am willing to give House of the Seven Gables a shot) or those fastidious puritans that were just trying to rid their village of witchcraft (not convinced brainwashing is dangerous? Check out the Salem Witch Museum.)
Here it goes:
Arrive in Salem. It's the week after Halloween, so the vibes are still strong. I'm told visiting Salem on Halloween is akin to Mardi Gras in New Orleans - too much. The Airbnb is downtown on Hawthorne Boulevard. We hit some minor museums (there are tons) and eat Italian at Bambolina (delicious).
We walk around after dinner, check out a couple cemeteries and the Salem Common (the nicest houses are in this area), and then see what the nightlife has to offer. It isn't crazy - we're in a relatively small town just after peak tourist season - but it doesn't disappoint.
Here are a handful of places I recommend: Rockafellas, All Soul's Lounge, The Derby, Olde Main Street Pub, and a ritzy place with a club in the basement whose name I can't remember or find anywhere (maybe it closed?). We were partial to a place called Bit Bar that had pinball and old school video games and hosted karaoke the first night we went.
Don't be fooled: there are restaurants and bars everywhere in Salem, along with museums.
The next day, we hit the witch museum and walked around some more. We went down to the House of the Seven Gables on the water(I was disappointed to learn it wasn't haunted) then went back to Bit Bar that night. Salem is a great place to visit in fall. The colors and atmosphere are unbeatable, and it was cold but not unbearable.
But then it was time to leave, which brings us to...
BOSTON
This go around, we stayed at the Revolution Hotel in South End (not Southie, they're two different areas). We were maybe five blocks from Boston Common. The first thing we did that evening was head to Little Italy and have dinner at Cantina Italiano. Some apparently famous little people from TLC showed up and got sat right away (it was Friday night), but trust me, this place is worth a wait. And order the pistachio martini.
Little Italy is nice because it's smack in the heart of North End, pretty close to the historic bars I like (Bell in Hand, Green Dragon, etc.). We kicked it here for a bit and then decided to ride the T over to Fenway. I'd never been before, and honestly wish we hadn't decided to call it a night early (to be fair, it wasn't that early). The best part was this place called Bleacher Bar inside the Green Monster. You could look out this giant gap and see the inside of Fenway Park all lit up. Maybe it's good we left. I would have tried to run onto the field at some point and gotten exiled from Boston.
The next day, we took the T to Harvard so I could have my Rory Gilmore moment and ate lunch in Cambridge. We got back to the city and threw a football on Boston Common (Zack talked to a girl with a dog) and walked through Beacon Hill.
Beacon Hill was my favorite part of the trip. It's incredible, and no wonder houses in the area cost a fortune. We spotted John Kerry's abode and walked up and down hills until the sun went down
Next, we returned to Bell in Hand and eventually two thirds of us made it out to a cool club called Tunnel in the Theatre District. No night is complete without stopping by Chinatown, which ended up being a bust because all the restaurants were packed. I touched the lobsters in a tank while the server wasn't looking and we walked home.
The next day, we shopped at Faneuil Hall and walked over to TD Garden. That whole area was getting ready to pop off for a Bruins game, so we Ubered to Seaport and then ended up at a restaurant in Back Bay called Buttermilk & Bourbon. When in Boston, eat here. First off, Back Bay is awesome. It's almost as cool and upscale as Beacon Hill. Second, this might have been the best Nashville hot chicken and biscuits I've ever had.
Afterward, we headed back to the hotel and got ready to fly south the next morning.
What did we learn? New England is really cool. It's so unlike anything I grew up knowing. The neighborhoods are unique but close enough that you can walk between them. Hell, you can walk across the river to Cambridge if you feel like it.
There's stuff happening at all hours. And the peaceful hamlets like Salem are great when you need to get away for a few days. If it wasn't for this little thing called winter, I might already live there.
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