The Boston Road Trip

My friend Dawn’s pal Erin is visiting from Edmonton this week (you may remember her last year when she came on our adventure to Toronto island), and Erin happens to be a HUGE Blue Jays fan. Dawn wanted to take her to a game while she was here, but unfortunately the Jays are not playing in Toronto at all for the duration of Erin’s Ontario trip. They are, however, playing in Boston against the Red Sox at Fenway Park. Boston is a doable drive for us, so when Dawn asked if I would be up for a quick US road trip to Boston I was all over it. I’ve never been! She also lured in our friends Emily and Joanna. So on Sunday, the five of us drove to Boston to see our beloved Toronto Blue Jays.


Joanna, Erin, Dawn, Emily, Moi

We saw the game on Monday evening, so I will get to that…

We left from Dawn’s place in Oshawa at 8:30am on Sunday, and according to our directions Boston was an 8.5 hour drive. But of course we needed to make a few stops, so the trip ended up taking almost 14 hours. That sounds like a ridiculously long time, and even writing that now I am thinking that can’t be right… But it is. We didn’t arrive until just after 10pm. Somehow though, the drive went by very fast. We are VERY good at entertaining ourselves, and I made a hilarious playlist specifically for our trip.

To get to Boston from Ontario, you can either go through the Niagara Falls border on the southwest side of Lake Ontario or the Gananoque/Thousand Islands border on the northeast, both leading into New York. We chose the Thousand Islands border as it was a bit quicker from where we were leaving from.

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Of course beavers and mountie moose are all over the Canadian side of the border. We stopped at duty free and the gift shop and were talking about how funny it is that these are the things that represent our country.

I do enjoy beavers though.

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The Thousand Islands area is incredibly scenic and beautiful, on both sides of the border. After leaving that area we drove through a lot of small towns in upstate New York and it was really surprising to us how deserted some of them were. All I wanted in my life was to eat at a trashy hole in the wall American diner for lunch, but the ones we did see were closed. For a long time everything was closed except for chains and gas stations. Maybe because it was Sunday. I don’t know if that is typical everywhere.

I also noticed how incredibly patriotic Americans seem to be. I could not get over the amount of American flags on porches. They were everywhere.

Anyway, back to eating. We were getting so desperate for lunch that wasn’t McDonalds that I eventually turned my phone data on briefly just to locate a Cracker Barrel. We do not have them in Canada! The closest one I found to us was in Clifton Park, NY. And though it may have been the closest, it was way off the highway so in hindsight maybe not the most convenient. Actually I don’t know if it even required that we get off the highway, I just looked quickly and then shut my data off again so I wouldn’t have to pay a million dollars. Either way, whatever happened there, I would say a good three to four hours of our roadtrip were spent getting to this place and then eating.


It was so exciting to finally find it. It was a little beacon of light. I had Cracker Barrel for the first time last year with Evan in Florida (but only for breakfast!) and I fell in love.

I really wanted southern comfort food, so I ordered the buttermilk fried chicken.


With sweet potato fries, corn, apple barbecue sauce and cornbread muffins and biscuits. And cole slaw but I didn’t really eat that. I very, very rarely order fried chicken and I can’t remember the last time I’ve eaten it. I loved this, but too heavy for every day.

Eventually we arrived at our hotel in Boston. We stayed at the Hotel Buckminster, which I absolutely loved. Apparently it is one of the first Boston hotels, and it definitely had a historical feel to it. It was clearly old, but in a charming way that we all really enjoyed. Also, the front desk staff were all extremely efficient, nice, and really went out of their way to help us. They were so great. I have nothing but good to say about the Hotel Buckminster.


And it is located in Fenway Square, basically right beside the park. Perfect location. Right where we needed to be.


We checked in and got all settled in for our one night stay (that’s right, just one, we drove home the following night after the game). I wish we could have stayed longer, our room was awesome. We had two bedrooms.



And three beds! We weren’t expecting that and we were ready to bring up a rollaway bed, so it was perfect for us.

We didn’t get to the hotel until about 10pm, but we got changed and had a few drinks while we got ready, and then we headed out for a night on the town.


Boston, we’re comin’ for ya.

It was so late by the time we got out, and it was Sunday night so not exactly party night… Most of the bars around were pretty dead. We ended up walking to the Bleacher Bar on the Fenway strip, and while it wasn’t busy there were enough people around who enjoyed our antics. It was a pretty low key night and nothing big happened, but it was still hilarious. And upon getting back to our hotel we ordered the best pizza from Domino’s.


We have Domino’s here but it is absolutely NOT as good as this! Maybe it’s because I was drinking, but I couldn’t get enough of this pizza. So, so good.

Monday was the most fun day ever and we packed in as many Boston activities as we could possibly fit in, so more to come on that. I loved the city and am already thinking about my next adventure there!


One response to “The Boston Road Trip

  1. I totally did want to comment yesterday but was DENIED! haha! When I went to Boston, it was an accident. We were on a fabulous road trip and then I saw a sign for something and all of a sudden i was like “how far are we from Boston?” So we changed plans and speed-dated Boston for a day. Because I had done zero research, everything was a surprise. We parked the car for a million dollars and then just ran for a tour. As soon as I saw Cheers, I had to get off. So cool! I rarely buy t-shirts but I bought two in Boston that day. Cheers and a $5 Boston t at the harbour out of a cardboard box. 🙂 Great day.

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