Last fall we spent a long weekend in Boston. My best friend, Megan, moved out that about a month before our trip and we enjoyed a weekend of fun, great food, history, and wonderful company.

Italian stromboli, North End, Boston

We arrived on Friday evening and headed right for some chowder. We lucked into two seats at the bar at The Hourly Oyster House in Cambridge for raw oysters and steaming bowls of chowder. Their chowder was our favorite of the weekend and we loved the house-made oyster crackers. After dinner we had drinks at The People’s Republik, a neighborhood bar.

Saturday was our first full day and we were determined to fill it with as much of Boston as possible. We kicked things off with fluffy breakfast sandwiches, coffee, and a very famous sticky bun at Flour Bakery + Cafe. After breakfast we headed over to Fenway Park to take a tour of the Green Monster. It was a really well done tour and we learned a ton about baseball and Boston, I would highly recommend it.

Breakfast sandwiches and sticky bread, Flour Boston

We spent the rest of the early afternoon strolling through some of the public parks and wandering in and out of the shops on Newbury Street. We were a little hungry but didn’t want to ruin our appetites for an early dinner so we stopped at Shake Shake to try some fries and split a shake (Joe had never been!). After refueling we continued our walking tour on foot, taking in some of Boston’s history and landmarks on the Freedom Trail.

Megan knows what she’s doing when it comes to getting a good lobster roll so we got to Neptune Oyster Bar as early as possible to get our names in. The place is tiny, located in the North End – Boston’s Italian neighborhood, and well worth the wait. We put our name on the list, with a party of 4, and the wait was about 2 hours! Luckily there is plenty to do in Little Italy, so we started with dessert – cannoli of course at Bova’s.

Neptune Oyster Bar Lobster Roll Boston

Finally…. we had our lobster rolls! They are sold at market price ($31 the night we ate there) and it was quite the splurge but well well worth it. After dinner we head back to Cambridge and played darts at the People’s Republik before ending the night.

Sunday morning we slept off all of our Saturday walking and I cooked breakfast for everyone at my Megan’s apartment. It was a really nice slower morning. Despite morning rain we headed down to visit the Sunday SoWa Open Market in the Art + Design district.

Megan and I had found our way to SoWa when we first visited Boston during an east coast road trip we took the summer between our freshman and sophomore years of college, it will always be one of my favorite memories. The SoWa market offers locally made and vintage goods, food, food trucks, other local fare. Its a really fun place to visit with several other great shops and galleries near by.

Fenway Park Tour, Boston

We headed downtown for lunch, with the goal of getting more chowder to ward off the rain. Boston Sail Loft serves huge mugs overflowing with thick dill-specked chowder, with a view of the harbor. It was exactly what we needed. The Columbus Day parade made its way by as we ate our chowder and split a cold lobster roll, when in Boston, right?!

Overflowing mug of chowder, Boston Sail Loft

Full and happy, we spent the rest of the day at Octoberfest in Cambridge. It was a huge street festival with beer gardens, music, and tons of people. It was really fun to see so many people out on a sunny Sunday afternoon. I grabbed a freeze from Pressed Juicery because loved it so much when I tried it in California last year.

Monday morning we wrapped up an incredible long weekend with a good diner breakfast before a quick flight back to Cleveland.

I can’t wait to get back for more time with my best friend, and of course more lobster rolls.


4 thoughts on “A Long Weekend in Boston”

    1. So many! I was really glad we made it there. I’m still dreaming about the breakfast sandwich.

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