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The Couples’ Guide to Boston’s Historic Kenmore Square

Updated: Oct 27, 2019

How couples visiting Boston's iconic Kenmore Square can craft a romantic, enriching + delicious getaway.

Pinterest photo of The Couples’ Guide to Boston’s Historic Kenmore Square

Transformed from swamp land in the 1700s, Boston’s culturally-rich Kenmore Square is now a lively hub thrumming with the energy of Boston University students, offering easy access to Commonwealth Avenue Mall that exudes mega-Boston vibes (especially in Fall when the leaves blaze with color), and featuring a short walk to the iconic Fenway Park and other historic hotspots.

While Boston offers plenty for the entire family to enjoy, Kenmore Square feels especially suited for couples getting away on a babymoon, honeymoon, or “why not” vacation without the kids. This adult time allows space to savor strolls by vine-kissed Georgia and Federal style buildings, an exploration of the eclectic plots in Fenway Victory Gardens, people watching on a park bench with a fresh pastry and cappuccino, or a long gourmet meal at one of the area’s many acclaimed eateries.

To ensure you get the most out of this legendary locale, without feeling overwhelmed with activity to-dos, we’ve pulled together a highly-curated list of where to sleep, eat + explore in and around Kenmore Square.

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When to go: Take in this world-class city in all its splendor by visiting in October when the fire-like colors and crisp Fall are are present… but the layers of snow have yet to arrive.

Airline Tip: If you’ll be flying for over five hours, and really want to treat yourself, consider splurging on a luxury pod in JetBlue’s Mint Cabin. This revamped airline has numerous flights to Boston from other major airports, and has created a first-class experience unsurpassed by any other airline we’ve first-classed it on.


While there are numerous stellar hotels and vacation rentals around Kenmore Square, we only listed one, as this spot is a must if you’re splurging on a full-on Boston immersion.

From its grand lobby dripping in refined elegance, to the large paintings depicting classic events like the Boston Marathon, seats from Fenway Park, and other Boston Red Sox memorabilia, this famous hotel is all-things-Boston wrapped up in one massive, architecturally stunning structure. While many accommodations feel removed from the spirit of the city, as most hotel rooms are pretty generic, the rooms and suites at Hotel Commonwealth allow you to perch in your window seat, or sip champagne on your balcony, as you look down on the constant happenings of Commonwealth Avenue, or gaze on Fenway Park, envisioning the innumerable landmark moments that were birthed on that field.

Beyond the sights, the plush furniture and décor in the rooms are supremely chic, making it easy to envision Boston greats like John and Abigail Adams sitting around making important power-couple decisions in the room. Essentially, you constantly feel that you’re getting the most out of your Boston sojourn when you’re staying in this storied establishment.


As the culinary scene in Boston is world-renowned, and highly competitive, you can be sure any eatery that has lived to celebrate numerous birthdays has something special going. Luckily, many such restaurants reside in Kenmore Square, offering travelers easy access to gourmet nosh.

As soon as you walk through the heavy doors of this brasserie-style restaurant, you’re hit with a wave of old world charm that makes you feel that by simply existing in the restaurant you now possess the poise of the elite from a glamorous bygone era. However, despite the dignified environment, the staff does not put on airs, offering each patron attentive and courteous service. This attentiveness is especially handy as you work to decipher the elaborate cocktail menu, which reads like an ode to the alchemy of mixology.

While you can’t go wrong with any of the drinkable art at Eastern Standard, the Cardini Highball is especially mind blowing with its mix of tequila arette blanco, cocchi rosa, blackberry, lime, soda. And because this restaurant is attached to Hotel Commonwealth, you don’t have to worry about navigating back to your hotel if you go a little wild with cocktail sampling.

And then there’s the food. While menu items might at first seem fairly common, when you take a closer look you discover that the master chefs have come up with creative and delectable twists on favorite dishes. A few favorites include the Crab Imperial, Atlantic Monkfish, Cheesesteak, Sesame Tuna Salad, Mac n’ Cheese, and of course, the bread pudding.

To prep for a full day of cultural wandering, walk across the street from Hotel Commonwealth to this tried-and-true café where you can savor a butter or cream cheese-covered fresh bagel loaded with breakfast favorites like smoked salmon, eggs, bacon, chorizo, and more, then wash it down with a strong cup of coffee. Take your goods to the nearby park for a morning picnic, or snag a spot by the window and relish the fact that you’re not one of the many students rushing to class.

Another spot to score oh-my-wow cocktails, this elegant, yet unpretentious, establishment allows you to try the best of the seafood dishes New England is known for, such as lobster rolls, crab cakes, clam chowder, and fish n’ chips. All catch is incredibly fresh, and adorned with sumptuous favorites like premium butter, herbs, vegetables and other goodies, but the oysters are really where it’s at. The center of Island Creek Oyster Bar, an icy-world behind the glass of this extensive bar, features a smorgasbord that would make any oyster lover swoon. And the sensual, candlelit environment of this establishment makes it a utopia for romantic dinners.


Because Boston was the birthplace of many of the most significant moments in American history, it’s overflowing with amazing cultural attractions. To prevent your itinerary from exploding, like ours did the first time we said yes to Boston, we’ve narrowed down the list below to must-see landmarks within walking distance of Kenmore Square. If your trip will be longer than two or three days, you can hop in a rideshare and venture out into the wide world of Bostonian museums, monuments, and more.

While we only had two hours to explore this palace of creation, founded in 1876, we wish we would have had two days. As it’s home to almost 450,000 works of art from almost every corner of the world, and seemingly endless eras, the Museum of Fine Arts Boston is a visual feast for those that appreciate 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. In addition to the permanent collections, the museum is almost constantly introducing traveling exhibits.


* If you’ll be visiting on the weekend, skip the line by purchasing tickets here.

* To fully immerse yourself in the history of the museum’s treasures, utilize a mobile MFA Guide, or hop on one of the free one-hour guided tours.

* If you’ll have limited time, make a plan of attack before setting forth, making sure you don’t run out of time to see the exhibits you’re most keen on.

Little girl planting seeds at Fenway Victory Gardens

Almost the backyard of Hotel Commonwealth, the 7.5-acres that make up Fenway Victory Gardens house over 500 vibrant plots tended by Boston community members dedicated to infusing city life with the back-to-nature goodness of nurturing soil, covering plants when the freezes settle in, and pruning their plant babies. Beyond the vegetables, flowers and other foliage in the gardens are the eclectic collections of gnomes, mosaics, plastic figurines and other peculiar objects that make the plots double as mini-curio-museums.

While we didn’t see many people during our garden stroll, there were gaggles of geese that followed, and sometimes gently herded, us as we explored. One woman we spoke to, who has been gardening at Fenway Victory Gardens for over 50 years (!), said there’s a goose (who she’s named Zaly) that has learned her schedule and is waiting for her at the gate of her plot every morning.

Female empowerment abounds at this library and church that are the result of a woman who blew past bull sh*t convention in the name of pursuing her dream and bettering the world. The library chronicles the story of this wonder woman of yore, Mary Baker Eddy, who founded the Church of Christ, Scientist, during a time when women weren’t even allowed to vote. This story is revealed with letters, videos and other in-depth articles that will leave you awed. And then there’s the stunning church, adjacent to the museum, that’s the physical manifestation of what a purposeful vision and dogged passion can produce.

An additional draw of the library is the one-of-a-kind Mapparium, a three-story, stained-glass globe you can walk inside, immersing you in a surreal and thought-provoking experience.

Fenway Park baseball diamond

Even if you’re not a baseball fan, touring this famed stadium, which has been home to the Boston Red Sox since 1912 and backdrop to famous scenes in movies like Field of Dreams, Good Will Hunting and Fever Pitch, is a bucket-list-worthy stop. The one-hour tour fills you in on all the greatest historic moments that have taken place within the stadium’s hallowed walls, and gives you a chance to sit on the Green Monster, the legendary wall that stands over 37-feet high and overlooks leftfield.

Lansdowne Street

Beer being poured from tap at Lansdowne Street in Boston

The spot to go to join in on Boston nightlife, Lansdowne Street is filled with bars and clubs providing laid back environments to eat, drink, sing, dance and get silly. Favorite spots include Bill’s Bar, a five decade old haunt, Cask’n Flagon, the place for understanding how fiercely Bostonians love their Red Sox, House of Blues, The Landsdownes, a classic Irish Pub, and Jillian’s and Lucky Strike Lanes, a three story, 70,000-square-foot paradise for big kids wanting to revel in bowling, pool, arcade games, drinks and comfort food with contemporary twists.


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