Travel

Where to Stay, Eat and Explore In and Around Boston’s Legendary Kenmore Square

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Photo Credit: Hotel Commonwealth

Boston’s vibrant hub of Kenmore Square is an area rich with history that serves as a favorite hangout for Boston University students, and sits on the doorstep of Fenway Park.

I recently had the opportunity to explore this area on a solo trip to Boston. This solitude allowed the city to be my companion and show me the nuances that make it so special: vine covered facades of Georgia and Federal style buildings, the creatively decorated plots of Fenway Victory Gardens, and the changing leaves that were like bright flames of Fall.

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Because exploring a city can easily make one feel hurried and drained, the following guide will help to ensure you absorb the historic adventure the area around Boston’s Kenmore Square has to offer, while tapping into comfort and creativity along the way:

Stay

Hotel Commonwealth

I splurged on a room at the iconic Hotel Commonwealth because I wanted all aspects of my trip to be drenched in Boston vibes. While many hotels feel separate from the heart of the city, because of the often-generic ambiance of the rooms, I felt that I was actually staying inside the heart as I perched in the window seat of my room overlooking Commonwealth Avenue. This cozy space above the chilly and bustling street allowed me to take in the big picture of Kenmore Square at all hours of the day.

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The rest of the hotel was filled with adornments that reminded me I was in Boston: large paintings depicting classic events like the Boston Marathon, seats from Fenway Park, and other Boston Red Sox memorabilia.

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Fenway Executive Suite Terrace at Hotel Commonwealth

Eat

Eastern Standard

I was hit with old school charm when I first walked into this large brasserie-style restaurant. The waiters were friendly and eager to discuss the elaborate cocktail menu that read like an ode to the alchemy of mixology. I didn’t understand half of what I was reading, but trusted my waitress to guide me down a yummy path.

The drinkable art, called a Southside Royale, that arrived woke up every one of my taste buds – and they had a raging party. Best. Drink. Ever. I did not have just one.

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Main dining area of Eastern Standard. Photo Credit: Flickr- Nathan Forget

The food that quickly followed was equally unique and delicious: A Turkey and Bacon Cobb salad that had uncommon Cobb salad accompaniments like roasted squash and cranberries that elevated the dish in all the right ways.

Bruegger’s Bagels

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Photo Credit: Lara604

For easy, hearty and mega-tasty breakfasts I would wander over to this New York- style bagel shop that stuff their fresh-baked-goods with generous helpings of classic breakfast ingredients, and serve up coffee strong enough to get me through a full day of city strolling.

Island Creek Oyster Bar

This elegant, yet unpretentious, establishment offered similar creative and OMG-delicious cocktails to the ones found at Eastern Standard, and seafood selections so good the noise of the patrons was drowned out by my happy tummy howling “Oh yeah!”

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Photo Credit: Marco Varisco

Explore

Fenway Victory Gardens

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While making my way to a museum I stumbled on these 7.5 acres that house over 500 gardens tended by Boston community members. Each garden featured eclectic décor, vegetables, flowers and more. Curious geese roamed the gardens alongside members who were busy caring for their colorful fares. One woman I talked with has been gardening there for over 50 years in rain, snow and sun.

Museum of Fine Arts, Boston

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I had two hours to explore this palace of masterpieces, but I should have allotted two days. This museum is home to almost 500,000 works of art: paintings by masters like Monet, Renoir and Van Gogh, jewelry from ancient Egypt, Buddhist sculptures, thought-provoking pieces by contemporary artists and so much more you could spend years visiting this museum and see something new on each trip.

Mary Baker Eddy Library and Mother Church

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If you want a dose of female empowerment do not miss these stops: the library tells the story of Mary Baker Eddy, who founded the Church of Christ, Scientist, during a time when women weren’t even allowed to vote, and the awe-inspiring adjacent church shows what a purpose-full vision and dogged passion can produce.

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The library also features the Mapparium, a three-story, stained-glass globe you can walk inside, offering a surreal and poignant experience.

To take in this landmark city in all its glory I recommend visiting in October when the vivid colors and crisp air of Fall are present, but the layers of snow have yet to appear.

And don’t forget to take an obligatory selfie in front of Fenway Park!

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