City Guide for a Weekend in Boston

It was Friday morning, I had just woken up from pretty much a 24-hour post night shift sleep fest knowing I had 6 days off ahead of me, but really no big plans. Brad was a day behind so I went to pick him up from the hospital after he finished his night shift. We got home, Brad hopped in the shower and next thing I know I hear is: “Rozz, come here for a second…I know this sounds crazy but I found an amazing deal on Patriots tickets…so we should go to Boston this weekend!”. Now normally our trips are fairly planned, we book things in advance, and have some idea of things we want to do while we are there. This kind of spontaneity was new for us but was totally fun and exciting.

We immediately went on Airbnb to see what would still available for the weekend and stumbled across this cute 1800s Victorian style apartment in the Allston area of Boston. We packed our suitcases as quickly as we could, grabbed our passports, and jumped in the car shortly after. Besides the Patriots game we made no other big plans and just decided to hit the road and see where the weekend took us. Brad hadn’t slept yet, so he nestled up in the front seat with a pillow and blanket while I drove the 7 hours to Boston.

Our GPS took us through Montreal (*not my favourite city to drive through, let me tell you), then we crossed the border in Vermont. We drove through the winding hills of Vermont and New Hampshire and finally arrived in Massachusetts and soon after, in Boston.

We met up with our Airbnb hosts who were super friendly born and raised Bostonians (yes, accents and all) and they settled us in to our place.

We were starving by this point so we hopped on Yelp to see what restaurants were near us. We found a bar called Deep Ellum IMG-2331which seemed right up our alley for some craft beer and local eats. A cool vibe for a Friday night in Boston and it definitely hit the spot after a long day’s drive.

Day 1 – City Exploring and Patriots Game

We woke up the next morning and besides our Patriots game that evening, we really had no other plans so we ventured out to see where the day took us. We found a local donut shop (that was nut free for Brad) called Blackbird Donuts, so we each got a gourmet donut and shared a cold brew to start the day off right.

We grabbed a lyft downtown to check out the Saturday markets and were thoroughly impressed with all the food options there were. We wandered through the Boston Public Market, to the Quincy Market and Faneuil Hall which sold local produce, cheeses, meats, seafood, pastries, beer + wine, clothes – you name it, you could find it at these markets.

From the markets we took a stroll along the Freedom Trail and checked out some of the historical buildings as well as the Boston Harbour (crazy to think we only drove 7 hours and we were on the Atlantic Ocean). There is so much history in the city of Boston and the Freedom Trail gives a neat (and free) way to learn about the English explorers and the history of America.

For lunch we found the oldest tavern in the U.S. called The Bell in Hand Tavern which opened in 1795 (…CRAZY) for some local beers and pub grub. It was pouring rain by this point and we were a little soaked from walking by the harbour, so we were glad to take a break from walking and warm up in this cozy bar.

The pub got us in a beer mood so we then went on a hunt for some local craft beer. We stumbled on Democracy Brewing, another cozy spot to hide from the rain. We each tried some of their made-in-house beers – very impressed. Their nitro stout was delicious and unique.IMG-2351

Once we were plenty warmed up from the beer we ventured out back into the rain to check out the Boston Common and from there we walked to the beautiful Beacon Hill neighbourhood. With beautiful red brick row houses, mature trees, and cobble stone streets this area was picture perfect Boston and made for some pretty cute insta pictures. Apparently Acorn Street is one of the most picturesque and it did not disappoint.

It was getting later and we needed to grab a bite before the game. We started at Rumba for drinks in the beautiful intercontinental hotel right on the harbour then headed to Taste to try some local wines. Tatte was our last stop before the game because we needed some coffee fuel before at 8:15 game. Yes, if you were wondering…we certainly indulged in our food a little on this trip, but that’s one of our favourite parts of traveling.

After dinner it was time to head to South Station to catch the Gillette train to Foxborough for the Patriots game. We thought this would be an easier way to get to the game, which would definitely be the case if you wanted to drink at the game, but man this train took forever. When we arrived in Foxborough so did 80,000 other fans…the atmosphere was like nothing we had ever experienced before. So many people all in one place with one common goal to cheer on their team.


It was pretty incredible – and I’m not even really much of a sports fan. Our seats were amazing – 11 rows from the field, even close enough to see Brady’s and Edelman’s muscles (sorry Brad). The vibe was awesome everyone cheering their hearts out. Unfortunately the Pats did not win – but we were still so grateful for the bucket list experience.

Day 2 – Breakfast, Beer, and Seafood

Waking up after a late night at the game we decided to take our second full day a little slower. We grabbed breakfast at the local Allston diner down the street. We also checked out Kohi Coffee Co. for a latte which we discovered was right near the New Balance training facility area. IMG-2362

We booked a beer tour at the Sam Adams Boston Brewery – not exactly the kind of place you’d expect to have craft beer but we were thoroughly impressed. We opted for the bier kellar tour– which encompassed three samples of some of their one of a kind barrel aged beers paired with local cheeses. They took us down in their barrel cellar which made for a nice atmosphere for the tour. Our tour guide told us about how Sam Adams brewery started making barrel aged beers and where they get supply their barrels from – a mix of wine, whiskey, tequila, and even aquavit barrels.

We then checked out their tap room for a flight of some of their other unique craft beers. We really enjoyed each one, which is something to be said about an otherwise mainstream brewery.

From the beer we worked up an appetite and knew we had to check out some local seafood while we were in New England. Walking around the day before we had found the Union Oyster House in downtown, the oldest restaurant. Kind of a tourist trap, to be honest, but the clam chowder was incredible. The seafood however, was mediocre but still a fun experience.

We were both totally wiped from the day before so we opted to head back to the Airbnb and have a quiet night in, which ultimately ended up in us falling asleep at 8PM.

Last Day

With another full day of driving ahead of us we asked our Airbnb host for a breakfast recommendation and we ended up at a diner called The Breakfast Club for a nice hearty meal before we hit the road back to Ottawa.

We really enjoyed our weekend in Boston! This seems to be a theme for us – doing a weekend city trip in January (check out my other city guides). This is our favourite kind of travel as a couple as we love checking out local food, drinks, and coffee as well as walking around cities. Boston is a great city with so much history as well as a great spot for a couple of foodies. We’d definitely recommend the trip to those living in Ottawa – quite a reasonable road trip for a long weekend!

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