60 Hours in Boston | Travel Vlog

If you want to take weekend trips during the semester, you have to time them to match up with your workload. Take a look at all of your syllabi, and if you have a lot of big assignments due one week, that’s the perfect weekend to go: after you turn in those assignments, but before you get another load of work to do. Or, you can plan your trip for one of the first weekends of the semester, before too much work has piled on, which is what I did when I went back to Boston! Check out a recap of my trip below.


I took an early morning flight out of BWI and landed at Boston Logan by 9am. I quickly hit the streets and met up with my friend Lydia (who is now a published author!!) for brunch at The Friendly Toast, a Kendall Square staple tucked away in a shady plaza.

Then, I stopped by the American Repertory Theater to say hi to all of my old co-workers (including Guthrie, our beloved office pup). It was wonderful to be welcomed back, catch up with everyone, and see the good old Loeb Drama Center again.

loeb drama center cambridge
Love the Loeb.

Afterwards, I walked down the block and met my friend Tae at Tatte, an adorable, two-story coffee shop in the heart of Harvard Square. This was where we used to always meet up to chat when I used to live in Cambridge!

tatte bakery harvard dream everyday floor
Cool floor tiles at Tatte!

Then, we grabbed a scoop at J.P. Licks and headed down to the banks of the Charles River–my absolute favorite spot in the city. It’s a serene escape from the Harvard Square hustle and bustle, and a great place to watch the sunset.

charles river john weeks bridge cambridge
The banks of the Charles

I had to do a little bit of reading for my political science seminar, but then met up with my friends Amy and Tony for dinner at the Five Horses Tavern (spoiler: we all got pizza) and a show at the Huntington Theatre Company (spoiler: we all cried).

It was Merrily We Roll Along‘s first preview, and I loved every second. Merrily is an infamous Broadway flop with a score by Stephen Sondheim and a book by George Furth. (OBC member Lonny Price made a documentary about it if you want to learn more!) But because of that, it is seldom produced, so I jumped at the chance to see this production.

I knew and loved the Encores! 2012 cast recording, and I worked with Lonny Price this summer, but I’d never seen the show. It was thrilling to finally find out what happened between songs, see the stakes get raised, and learn how all the puzzle pieces fit together.

The story follows three old friends, Frank, Charley, and Mary backwards in time, from a party honoring Frank’s latest Hollywood hit, all the way to the night they first met on a Manhattan rooftop as wide-eyed twenty-somethings. It’s a cautionary tale about friendship and achieving your dreams. The Huntington production is a transfer of Maria Friedman’s West End production that Sondheim himself called “the best” production of Merrily that he’d ever seen, and I think that’s all I need to say about that.

After the show, Amy, Tony, and I attended the Under35 after party and mingled with the cast, enjoyed live music, and ate one too many marshmallows at the chocolate fondue station.


I was on my way to breakfast when I ran into two friends from a Harvard student organization I am a part of, so we all decided to grab a quick bite together. On our way to the restaurant, we ran into even more friends! What serendipity.

Then, I took the T into Boston and met up with my friend Lindsay! We hung out in her dorm room, grabbed some snacks from The Thinking Cup, and sat out on the esplanade, enjoying the perfect, breezy weather.

Lindsay is a dog walker, so later, we took an adorable pup, Rookie, on a walk around the Boston Common. Rookie is the most loving (and most easily distracted) dog I’ve ever met.

After saying bye to Lindsay, I went into Central Square and dined al fresco with my friend Monica at Veggie Galaxy, an entirely vegan and vegetarian diner. Oh, and we also got ice cream at Toscanini’s because I have the world’s largest sweet tooth.

Then, I met up with Amy and we went to the invited dress rehearsal of WARHOLCAPOTE at the A.R.T. One of the actresses I worked with this summer was also in attendance–what a small world!

WARHOLCAPOTE American Repertory Theater
Are you more of a Warhol or more of a Capote?

A world premiere play by Rob Roth, WARHOLCAPOTE weaves together the words of Andy Warhol and Truman Capote from hours of old tape recordings, when they spoke of wanting to write a Broadway play together. The play is an insight into the personal lives of two American icons, offering a look at the sides you never get to see.

After the play finished, Amy and I stopped by L.A. Burdick across the street for a late-night hot chocolate fix because hot chocolate is always a good idea.


I got breakfast at Zinneken’s, where Belgian waffles are made by actual Belgians! I sat in a window seat and indulged in a waffle covered with Speculoos, chocolate, and whipped cream. Then, I spent the rest of my morning walking up and down the Charles River, from Harvard to Kendall, where there is the perfect view of the Boston skyline. After that, I browsed the stacks at the Harvard Book Store for a while…and ended up buying three used books.

For lunch, Amy and I got Sicilian cheese pizza slices at Pinnochio’s and cannoli from Mike’s Pastry and sat on a bench by the Charles for an impromptu picnic! We talked and pet dogs and enjoyed the view.

Then, I went to 5pm mass at my church in Harvard Square and attended a spaghetti supper, where I caught up with so many dear friends I’d made when I lived in Cambridge.

After countless goodbyes, I got a ride over to Boston Logan airport for my flight home!

I loved being back in Boston. The city has stolen my heart. It’s charming, welcoming, and well-loved, and I’m so blessed to have lived there, even if only for a few months.


Merrily We Roll Along is playing at the Huntington Theatre Company through October 15. For more information and to purchase tickets, visit their website here.

WARHOLCAPOTE is playing at the American Repertory Theater through October 13. For more information and to purchase tickets, visit their website here.

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More about Kelly

Hi, I’m Kelly! I’m here to give busy college students a guide to navigating the modern theatre world. I’m passionate about spreading my love of theatre, traveling, and trying new things.

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