Boston Solo Trip

With one bag on my back and my skateboard in hand, I balled out in Boston (on a budget) for two days. It was a a really lovely city and I wish I had more time. I hardly travel, so for a first solo trip, I’m glad everything went dandy.


I ran into a fellow longboarder before my 6:00 AM flight. His name was Johaan and he was some sort of travel writer originally from Florida. He was in Kitchener-Waterloo for awhile though and we have two mutual friends. It’s a small world after all.

Plane sunrises


Dunkin’ Donuts coffee at a Washington DC layover to christen my entry into the United States. I noticed the States serve their coffee extra scalding hot.


Arrived in Boston with wonder in my eyes.


I didn’t get to spend as much time by the water as I would have liked. I originally planned to spend time relaxing by the water but I spent too much time skate-sploring the city.

Neptune’s Oyster (63 Salem Street, Boston, MA 02113)

My first meal in Boston. This is what a $27 Lobster roll meal looks like. The total bill (incl. 3 oysters) was $45 and no, it wasn’t worth it. I met a traveller from Tokyo here. His name was Hide.


There is so much cobblestone in Boston! It’s beautiful on the eyes, but annoying on the wheels. However, Boston has really decent bike lanes and wide sidewalks to make up for it. The people I met in Boston were so friendly that I forgot I wasn’t in Canada anymore.

Friend Street Hostel (234 Friend Street, Boston, MA 02114)

I stayed in a 10-person room at a hostel. It was surprisingly okay and super close to everything in the city. I only took brief showers and wore the same clothes for three days straight though. I was pretty gross.

Orchard Skate Shop (156 Harvard Avenue, Allston, MA 02134)

Orchard Skate Shop was the only decent skate shop in/near Boston. They had a mini-ramp inside and I sort of wish I rolled around in it just for the sake of the experience, but the shop owner didn’t seem mega welcoming. I ran into another friendly longboarder outside their second location. He told me “I think that only real longboarders acknowledge other longboarders” Ain’t that the truth?

The Museum of Fine Arts Boston (465 Huntington Avenue, Boston, MA 02115)

The Museum of Fine Arts was free on Wednesday night and the hostel hosted a group outing so I decided to go and make some friends. I realized that I actually don’t enjoy fine art museums too much. I think I prefer more contemporary art. I can “appreciate” this kind of art but I can’t truly appreciate it, ya know? It’s just so hard to comprehend such intricate works of art were created by hand hundreds and thousands of years ago.

All brick everything

There was a small street vendor festival being set up in this alleyway by Suffolk University. They lost a balloon. I didn’t see much graffiti in Boston. (Temple Street)

Massachusetts State House?

This bright white state building was a huge contrast to all the red brick. I honestly didn’t care too much for the rich American History in Boston and didn’t end up seeing a lot of really “touristy” sights unless I came across it skating the city.


Endless old school brick housing and lovely lamps and shops and cobblestone walkways in this narrow Beacon Hill neighbourhood. I wish I had more time to check out all the little shops in this area. This picture just doesn’t do it justice.


Tired selfie. Harvard was oddly underwhelming  but maybe my expectations were too high. I think I liked Boston University and MIT better – but maybe it’s because I passed by those schools first. I went into the student commons in MIT and it was a strange feeling remembering that I’m already graduated. Suckers.


They also had these really odd ugly metal coloured chairs all over their main Harvard Yard. WHY?

YAK Dance Crew (

The street performers/dancers troupe performed both days I was in Boston. They must have been doing a similar routine for years but it was great!

Crock pot of baked beans and corn bread. Durgin Park Restaurant (Faneuil Hall Marketplace, 4 South Market Street, Boston, MA 02109()

Boston is also known for their baked beans.  I feel like I didn’t come across too many people with Boston accents, but one of the chefs in the open kitchen here had a heavy Boston accent.


This is Shaun. He was one of the guys that worked at the hostel. The only way to describe him is that he was super chill and super rad. I sure didn’t think I’d have a skate sesh while I was in Boston…

Head in the clouds city skate sesh (with a selfie stick)

The thing that stood out to me the most in Boston were the pedestrians. I noticed a lot of the times pedestrians would cross the street whenever they felt like it even if there were cars oncoming – but the thing is, the cars would really slow down for them and wait for them to cross. The pedestrians didn’t even speed up! The cars didn’t even honk at them or seem to get mad! it was wild. It made me super confused as to when to cross the street because it also looked like the crossing light was perpetually the “do not walk” hand.


Mid-day skate sesh with Shaun practicing getting off a curb properly. I wish I could city-shred better and pop ollies onto curbs. One day.

Boston Tea Party Ships & Museum (306 Congress Street, Boston, MA 02210)

I checked out the Boston Tea Party Museum (it was on a boat). I hardly went inside any buildings during my two days in Boston. The weather was perfect – sunshine all around and 20’s degree weather.


A public bathroom that costs $0.25 to enter. This was part of the worst part about my Boston trip where I got “lost” in an extremely industrial part of town and wasted a lot of time skating through endless boringness. This bathroom’s door opens up like a spaceship. It was like a spaceship in there. I was a little freaked out.


Obligatory Chinatown photo. I’m so glad I was able to put my Sony ActionCam to use during this trip.

Atlantic Fish Co. (761 Boylston Street, Boston, MA 02116)

Of course I would finally have Boston’s New England Clam Chowder before I left. I loved Campbell’s Clam Chowder when I was a kid. This stuff was good. The total cost of this meal incl. a seafood platter was $42.

South Street Diner (178 Kneeland Street, Boston, MA 02111)

6:00 AM 24-hour diner breakfast on my last morning in BostonIt was about a 10 minute skate through wonderfully empty (and dark) streets across the city to get here.


You sure can cover a lot of ground when all you have is yourself and a skateboard. It’s hard to find people with the same mindset when travelling (I realized food is definitely one of my main priorities), but I think it also would have been nice to have someone to share my trip with. Maybe one day.

September 17-19, 2014
Photos: Sony ActionCam HDR-AS100V

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