I left my heart in Boston.

Boston blends almost 400 years of rich history seamlessly with the staples of a vibrant, modern city. Cobblestone streets with colonial style houses turn into rows of nineteenth century brownstones in the blink of an eye, with the shadows of impressive skyscrapers looming off in the distance. Boston is an eclectic mix of architecture, food, culture, and people. Yet the city inspires a love and dedication within its inhabitants that makes them all such proud Bostonians. While walking the streets of Beacon Hill and the North End on a humid summer day, I could feel deep within my soul the excitement and electricity that makes Boston special. Simply put, I was in love. So today I want to share my top five Boston experiences.

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Brownstones on Beacon Street.

1. Relax in the shade at Boston Common during the summertime. Better yet, relax in the shade with a cone of soft serve ice cream and good company. Although I’d lived on the East Coast for a few years when I was younger, I forgot what a truly humid day felt like and I found the park to be the perfect place to spend a few calm, cool moments before continuing my adventure around the city. Boston Common is the oldest city park in the United States, and is a breath of fresh air in the city. In the summer the park is a vivid shade of green, and is bustling with happy tourists and locals alike. Its also happens to be the natural starting point of Boston’s Freedom Trail.

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My brother and I surrounded by the greenery at Boston Common.

2. Follow the Freedom Trail and brush up on Boston’s revolutionary past. As much as I love to leave the map at home and explore a new city on my own terms, sometimes its nice to not get lost. Starting at Boston Common and ending at Bunker Hill, the two and a half mile Freedom Trail leads visitors to historic locations like Paul Revere’s house, the site of the Boston Massacre, and the old, as well as the new, Massachusetts State Houses. While there are guided tours availible, I opted follow the red brick line through the city at my own pace, which allowed for an unplanned stop for lobster rolls for my mom and brother.

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The Old Statehouse and some much newer looking buildings.

3. Catch a game under the lights at Fenway Park. You haven’t seen Boston until you’ve experienced a baseball game at Fenway Park. Built in 1912, Fenway is the oldest ballpark and one of the smallest. However, the small size makes the game feel much more intimate than those at large stadiums. The streets around the park become one big party before home games, and interacting with the animated and energetic Red Sox fans is half of the fun. Fenway Park is magic, and while I was there I couldn’t help but feel that something extraordinary could happen at any moment. There’s a small chance I might be a bit biased; I am a Red Sox fan myself after all.

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The infamous Green Monster at Fenway Park.

4. Indulge in Cannoli in the North End during Saint Anthony’s Feast. I’d tried cannoli on a few different occasions before and I was never very impressed. I’ll confidently go as far as saying that my life changed when I had my first real cannoli in Boston’s North End, the historically Italian American neighborhood. While looking for a place to eat one night, I accidentally stumbled upon the annual Saint Anthony’s Feast. The Italian American festival takes over the streets of the North End every August. Local vendors sell pizza, pasta, and gelato, among other Italian inspired treats, but the real prize of the night were the cannoli. The fresh fried dough shells were filled with ricotta and dipped in chocolate chips right before our eyes. If I hadn’t just polished of a bowl of giant ravioli, I probably would’ve went back for seconds. Luckily, for those who aren’t visiting during the last week of August, delicious cannoli are availible year round in Boston.

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This baby is easily one of my top favorite travel treats.

5. Escape the heat inside the stunning John F. Kennedy Presidential Library. Kennedy was a Massachusetts native, who loved sailing the state’s beautiful coastline. Accordingly, his presidential library is located next to the Boston Harbor and boasts a panoramic view of the city skyline. Its easy to feel engulfed by revolutionary history in Boston- you really can’t avoid it. The JFK library informs visitors about Kennedy’s life and legacy, as well as the tumultuous 20th century. The museum’s message about Kennedy and his mission for peace is powerfully presented, and by the end I had tears in my eyes.

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The JFK library was designed by the imaginative architect I. M. Pei.

Well, those are my five favorite moments from my time in Boston. Although each activity was an experience within itself, my adventures in New England were made all the better by the people I was traveling with, and by the lively locals I encountered along the way. Almost a year later, Boston remains my favorite American city, and I’m looking forward to finding myself lost amongst the chaotic maze of streets that make up the City on the Hill.



Tiff Dawg


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  1. This captures the magic of the city beautifuly. Now I want cannoli.

    Liked by 1 person

  2. Having grown up a New Englander, (and a Red Sox fan too) I find myself sitting here in California totally taken back to my youth by your expressions.

    This blog absolutely made my day!!!

    Liked by 1 person

  3. Must agree with your Dad about growing up in New England, you took me right back there. Your Mom and brother have the right idea about the lobstah rolls, too.


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