My Top 3 Things To Do When Exploring Boston

Boston - Bunker Hill Monument
294 Steps.. running them hurts. I tried.

Winter is coming, and Boston is cold, really cold, it’s also really wet (no wonder it’s located in ‘New England’ it’s always bloody raining). It’s not quite snowing yet and the only cold that comes close to this in Australia is found in the self-serve freezer at your local bottle shop or in the icy stare of the Perth Airport security staff so make sure you rug up. There has to be something about the cold that inspires innovation with the capital of Massachusetts producing some of the most forward thinking political leaders in US history over the years, as the Kennedy family, Malcolm X and Benjamin Franklin among others all hail from this chilly city.

Boston Common
The picaresque Boston Common

With Boston being one of Americas oldest cities, you’re pretty much surrounded by more important historical landmarks than you’ll have time to see. Although I’d recommend trying as there really are some good ones, especially given the major role Boston played in orchestrating America’s middle finger to the British Empire (the American Revolution).

Here‘re my top 3 to do’s when visiting Boston on any long term travel adventure.

1.       Vive la Revolution

Tip your hat, polish your musket, tighten your draws and let’s start with the obvious one, The Freedom Trail; a renowned walking tour that starts at Boston Common and ends in style with the beautiful Bunker Hill Monument. The trail takes a meandering gander, through Boston’s history and the birth of the American Revolution including the site of the Boston Massacre, the USS Constitution (the world’s oldest commissioned warship) and the Bunker Hill Monument, located on the site of the first battle. You can literally stroll through America’s revolutionary history at the same time as some of the most picturesque areas of Boston. If you time it right you can conclude the walk as the sun is setting for some spectacular views over the city from the top of the Bunker Hill monument (294 steps.. if you have the stones to climb it).

Downloading one of the many available ‘Freedom Trail Podcasts’, which describe each of the 16 destinations on the trail was really handy as I found it really added greater depth to each stop. As an alternative take one of the tours which leave from Boston Common that come fully equipped with colonial dressed local volunteers to guide you on your way.

Boston State Street
A Statue of Benjamin Franklin on State Street

2.       Get Educated

Both Harvard and MIT are a short train ride out of Boston. Spend some time in Harvard Square which is jammed full of shops, cafes, bookstores and caffeine fueled students. I loved the look and feel of the Harvard campus with it’s beautiful old red brick buildings, wrought iron gates, ivy covered walls and the many deciduous trees that litter the grounds with naked branches that look more like giant skeletal fingers. Explore the grounds and follow in the footsteps of multiple presidents, world renowned authors, philanthropists and scientists, feeling all illuminated and what-not, or visit Harvard’s fantastic natural history or art museum, both located on campus.

Boston - Granary Burial Ground
Amazing old headstones at the Granary Burial Ground

In the spirit of education, here’s a random bit of information to keep in mind while you’re in the US. Americans are very polite, so never ask for a toilet, it’s only ever called the ‘restroom’. Saying ‘toilet’ gets you a funny look, ‘dunny’ or ‘loo’ are answered with blank confusion and ‘shitter’ will generally offend people.

3.       Sports ‘Bahs’

You can’t throw a stone in this great city without hitting one of it’s numerous ‘Sports Bahs’. Quick lesson in Boston English (the letter ‘r’ is pronounced ‘ah’ or not at all) so…

‘Ahnt’ = Your uncles wife

‘Cah’ = Car

‘Hahvuhd’ = Harvard

‘B’daydas’ = Potatoes

You get the idea. Anyway have a Samuel Adams (locally brewed Boston beer) as you catch an NFL game in a local ‘bah’. Soak up the atmosphere and the alcohol, just note that some of these places can kick on pretty late and often get pumping after about 10 o’clock so if you’re in the mood to hurt your liver then why not stick around past your bedtime and mingle with the friendly locals over a bourbon or three…


The Boston Streets

About Author


Hi, I'm Pete, an ex-cubical slave and corporate love monkey currently writing my way around the world. My background is in branding, digital marketing, media and I'm probably about a level 10 at moustaches.


  1. I spent some time in Boston earlier this year. Although parts of it are a bit touristy, I definitely enjoyed the Freedom Trail. It was cool to see so many different aspects of American history in a small area. I liked the university areas as well.

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