On Visiting Boston, Massachusetts

Sunset over Charles River

During the last week of December 2014, my wife Shannon and I went to Boston, Massachusetts on a brief 5-day trip. It was my first trip to a major US city outside of my Atlanta home since my City Stereotypes post went viral last summer.

Boston is a big city for tourists, and you can find generic tourist information all over the Internet. You’ll find no shortage of people who have been to Boston who’ll tell you where to go.

I read all that information, talked to friends who had been there, and friends who live there before the trip. But here’s 11 things in no real order that still stood out to me once I got there, and makes Boston a really worthwhile visit (or home).

Quick Aside: I get paid to mention CityPASS in this post. Before we visited Boston, we bought the Boston CityPASS where you get tickets to the 5 main tourist attractions for 1/2 the price of buying each one separately. It’s worth looking into if you’re going to visit the main attractions (check out CityPASS Boston details here).

The Museum of Fine Arts

In my home of Atlanta, we’re really proud of The High Museum of Art. It has a really amazing and diverse permanent exhibition, along with multiple world-reknown visiting exhibitions throughout the year. Even though it’s not in the same class (or even category) as somewhere like the Met or Lourve – it can hold it’s own among major world cities.

Since the Boston Metro area is roughly the same size as Atlanta, I expected the Museum of Fine Art (‘MFA’) to be roughly the same size/scope of The High.

It’s not.

The Museum of Fine Arts
The Museum of Fine Arts

The MFA is in a different class than most art museums. It’s the part of the Met that took a wrong turn in New Jersey and ended up a few hours north. It’s big, diverse, and has a permanent exhibition that puts The High to shame (and again, The High is really amazing).

We spent about 3 hours in the MFA and didn’t see it all. One thing that gives the MFA a big boost is its long-standing relationship with Harvard University. Even back in the 1800s, the MFA was co-sponsoring Egyptian archaeology trips with Harvard (and have a very respectable collection to show). The same partnership has helped them collect a large and interesting Asian exhibition, which is well-curated and presented (they house one collection of Buddhist carvings inside a replica Japanese temple).

Since Boston is one of America’s oldest cities, it has also had an opportunity to inherit large collections of American art – especially art from the colonial era.

If you’re planning a visit, you can go ahead and build high expectations for the MFA since it will live up to the hype.


Before visiting Boston, I was under the impression that Harvard and MIT were across the Charles River, but otherwise Boston was just a normal city student-wise.

It’s actually just a big University town. Big Universities are everywhere. The catch is that most all of them don’t have famous football teams, so you don’t often hear about them..even though they are huge.

Northeastern University has a large campus near the MFA with 21,000+ students. Boston College has 14,000+ students. There’s a Boston University (different from Boston College) that has 33,000+ students. All totaled – there are over 60 universities in the Boston area.

We went over Winter Break, so large portions of the city felt empty. But I’m sure that during the school year, the population inside the city surges.

Intellectual Air

Paul Graham, a Silicon Valley venture capitalist & essayist, wrote a fascinating article in 2008 about Cities and Ambition. In that essay, he argues that cities have a certain “air” about them.

It’s that ambitious pressure telling you to be more [fill in the blank]. For example, New York City’s air is that you should be more wealthy. Washington DC’s air is that you should know more people. Los Angeles’ air is that you should be more famous.

He argues that Boston’s air is that you should be smarter and more intellectual. You should finish that book you’ve started. You should have better ideas. You should have smart conversation.

I found it to be absolutely true. I have no idea what it is. Maybe it’s the 60 universities. Maybe it’s sitting next to Harvard grad students on the subway. Maybe it’s seeing a random middle aged person waiting at a bus stop reading Moby Dick. Maybe it’s walking by Victorian row houses and seeing stacks of books through the bay window.

But ideas are certainly in the air. It’s really interesting to be around, and makes visiting Boston a really cool city to simply be in.

Dunkin’ Donuts

Starbucks is the poster child of globalization. It’s the chain that is everywhere, and the third place you can find on every corner of every major city. Starbucks is supposed to rule the world.

I’ve been in 2 cities that haven’t gotten that memo. First, Athens, GA is refreshingly dominated by Jittery Joe’s coffee. Second, Boston has a simply absurd number of Dunkin Donuts.

I mean seriously – they are everywhere. Sure, there are Starbucks. But I overwhelmingly saw soft pink, orange, and brown across the city.

Dunkin Donuts Boston
Dunkin Donuts Everywhere!

Kudos to Boston for being different.

Although, I will say that Dunkin’ Donuts still can’t go head to head against the South’s Krispy Kreme.

The Neighborhoods

You probably know the city you live in not as 1 single place – but as a collection of smaller, much more distinct places. For example, many tourists think of “Atlanta” as a single monolithic, place. Or even after they visit, they might just think if it as Centennial Park, Peachtree Street, and the Georgia Aquarium.

But as an Atlanta resident, I know Atlanta as a super-spread out metro area, and as the city of Atlanta. Even in the City of Atlanta, it’s really a collection of very different neighborhoods. Peachtree Hills is very different than Reynoldstown or the West End. Downtown has a very different feel than Buckhead.

Maybe it’s because Boston’s neighborhoods aren’t as famous as New York’s (ie, SoHo, Williamsburg, or Midtown) or even as San Francisco’s (Russian Hill, South of Market), but I had a conception of Boston as sort of a single place.

It’s not. In fact, it’s neighborhoods are just as diverse, and just as interesting as any other city – if not more. In fact, one of my favorite things about visiting Boston was simply going for long runs through the different neighborhoods.

Each was completely unique with different architecture, different history, and a unique neighborhood feel. I was able to visit only a few of them during our stay. Here’s 3 of my favorites.

The Back Bay is full of beautiful Victorian brick townhouses along gridded streets fronted by Boston Common.

The South End is an agglomeration of a range of architecture applied to Brooklyn-esque walkups. The stretch along Tremont Street was once home to a thriving post-American Civil War African American culture. It’s a neighborhood that went through a period of decline, but looks up can coming again. It’s also pocketed with several beautiful Episcopal churches.

Church in the South End
Church in the South End

The North End is Boston’s original town. Walking through the North End is like being transported to the 1770s (Paul Revere’s house is still standing – along with the Old North Church). It has narrow streets, colonial architecture, quaint Italian restaurants (a legacy of early 20th century immigration).

Street on the North End of Boston
Street on the North End of Boston

And there are dozens more within the city of Boston – and more in the metro area to explore. If you are able to visit, be sure to venture outside of the tourist belt Downtown. Even if there’s no specific destination – checking out the neighborhoods is worthwhile.

The Museum of Science

Science museums are really tough to do well. Unlike art museums, which always have unique content to that museum, science museums pretty much all have the same stuff.

As a rule, once you’ve seen a replica Tyrannosaurus  – you’ve seen them all. Ditto with the optical illusion exhibits and rock exhibits.

To stand-out for tourists (who often have at least a basic science museum in their city), you’ve got to excel on presentation. You’ve especially have to strike that really tough balance between being interactive for kids while also having thoughtful, interesting exhibits for adults.

Boston’s Museum of Science is the best science museum I’ve ever visited (also on the CityPASS). If you have kids traveling with you, it has more interactive stations than you could do in a day. But even if you’re traveling sans-children, the Museum also has dozens of well-put together, interesting exhibits that are worth the visit. The Hall of Life and the Global Food exhibits presented information in ways that no book or even documentary could present.

The Cold

The rumors are true. It’s cold in Boston.

Visiting Boston

It’s also probably in my head, but I think that 20F in Boston feels colder than 20F in Atlanta.It’s probably for the same reason that people say 90F in Atlanta feels hotter than 100F in Phoenix.

Either way – winters are cold in Boston.

The Transit System

One of our first experiences with the Boston subway system was a transfer to the Green Line at Government Center Station.

We were initially quite underwhelmed by the streetcar that just goes underground. It turns out that the line is actually part of the oldest subway system in America.

After a day or so, we realized just how awesome Boston’s subway system (aka the T) is. Sure, Bostonians may complain about it. Sure, it’s nowhere near as extensive as New York’s. However, for an American metro of Boston’s size – the transit system is really useful.

It’s frequent, understandable, extensive, cheap, and pretty fast. Plus, it has several connections with frequent commuter rail and Amtrak service to the rest of the metro area and beyond. It makes visiting as a tourist doable and fun (something that most of American metro areas can’t say).

The History

Boston was one of America’s first cities. It’s certainly not old global standards, but it’s absolutely ancient by modern American standards (Boston had been around for 200+ years before Atlanta was even founded).

It’s also a place where a disproportionate amount of early American history happened.

The Old State House Downtown Boston
The Old State House Downtown Boston – The crowd is on the site of the Boston Massacre

And the city has thankfully done a fair job in preserving the most important parts of that history. The Old State House still stands in Downtown Boston. It has a really amazing staff giving tours and telling stories about how/where/what everything that Americans learned in grade school happened.

Paul Revere's House
Paul Revere’s House

The spot of the Boston Massacre is marked. The Old North Church and Paul Revere’s house still exists, which is really, really odd to see in person after 20+ years of knowing the “2 if by day, 1 if by night” saying.

Old North Church In Boston
Old North Church Alerted Paul Revere

Even though I knew all this before visiting Boston, actually seeing it was still a pleasant surprise. If you’re into history or are a fan of HBO’s John Adams, Boston would be a good visit.


As I mentioned in the Neighborhoods section, I was really surprised by the range of architecture in Boston. I knew it was an old city with lots of immigrants – but that never translated into an expectation of interesting architecture.

I will say that I didn’t find the Boston skyline (while beautiful) to be very interesting, but I did find the range of architecture all around the neighborhoods and Downtown to be really interesting.

The range spans all the architectural styles that I know – including the Soviet-esque Brutalist City Hall Downtown (what were people thinking in the late ’70s? Atlanta’s Central Library came from the same era). The New England clapboard houses surround the harbor, along with Victorian brownstones in the Back Bay, and the random agglomeration of walkups in the South End.

Boston's City Hall
Boston’s City Hall – Photo Credit to Daniel Schwen

The Restaurants

Good restaurants tend to exist in large, prosperous cities with a history of immigration. Boston is no exception, even though I was pleasantly surprised by how good all the restaurants went to were. A particular shout out goes to Marliave and Back Bay Social Club.

City Stereotypes

In July 2013, I catalogued all the Google Suggest stereotypes for America’s 50 largest cities. Here’s Boston’s stereotypes and how I thought they played out to a first time visitor.


I think this might still be left over from the Boston Fire Department controversy. I found Boston to be incredibly diverse, and generally open and tolerant. That said, this still might be true in city politics or in some other area not apparent to a visitor.


Boston is expensive. That’s not a stereotype – it’s simply true, especially for housing costs. I learned while I was there that it’s partly due to outdated zoning and historic preservation. Boston has the infrastructure to add more housing and become denser – but it having a tough time finding the right balance in city politics.

Until they get more housing, more people will continue to want to live & visit, which will just keep pushing prices up.

On the upside – there is a reason so many people continue to live/visit Boston despite the high prices – it’s that awesome.


Boston has a deep Irish history. Their basketball team is even nicknamed the Celtics, and they have a very famous St. Patrick’s Day party. That said, I found the city to be incredibly diverse and certainly not defined by a single ethnicity.

expensive to live

Yup. It’s so expensive that it gets “expensive” twice. We saved a bit of money by renting an apartment and cooking a couple meals ourselves instead of staying in a Downtown hotel.

If you are exploring the idea of visiting Boston – you should definitely check out their CityPASS for discounted admission to all the tourist attractions – but don’t just stick to the tourist stuff. Get out and explore. It’s an amazing city to walk around in.

Let me know you experience/ideas in the comments!

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