Little Black Book

Pre-Gaming: The New Kenmore Square

by Devorah Klein Lev-Tov
Sunny day out in Kenmore Square. Photo: Soe Lin / Flickr

Fathom contributor Devorah Klein Lev-Tov gives us plenty of reasons, both old and new, to explore Boston's Fenway Park neighborhood.

BOSTON – For decades, Kenmore Square has served as a crossroads for people going to and from the Back Bay. But despite being the site of major trolley and subway lines, it has never really been a destination. Unless you count the punk scene it attracted in the 1980s, or the methadone hub it became in the '90s.

When Fenway Park opened nearby in 1912, Kenmore Square became a way station for players, with visiting teams staying in the Square's numerous hotels. While most of those have long since closed, the opening of Hotel Commonwealth a little more than a decade ago seeded a renaissance in the area. And while some old-schoolers are nostalgic for clubs and famous and now closed late-night greasy spoon Deli Haus, most people would agree that Kenmore has changed for the better.

Island Creek Oyster Bar

Photo: Courtesy of Island Creek Oyster Bar


Eastern Standard, located inside Hotel Commonwealth, has become a Boston institution. The neighborhood brasserie's specialties include steak tartare and pan-fried pollock with leek remoulade, celeriac, and fingerling potatoes.

Top Chef contestant Tiffani Faison opened Sweet Cheeks Q in 2011 and has gained major praise for her top-notch barbecue (especially short ribs and brisket), as well as her mile-high fluffy biscuits.

For traditional New England seafood, chef Jeremy Seawall's Island Creek Oyster Bar will more than satisfy. The oysters are fantastic. The fried fish sandwich is the dish to order for brunch or lunch. The full effect of the shell wall is quite a sight to behold.

Fenmore American Bistro opened inside Hotel Buckminster last year, filling the niche in the local dining scene for bistro food that's softer on the wallet. Fish and chips or a burger will tide you over before a game.

lower depths boston

Photos: Courtesy of The Lower Depths


If you need a few beers before a game, head to The Lower Depths for quality craft brews like Heavy Seas' Peg Leg from Maryland and Left Hand brews from Colorado. They also serve delicious hot dogs with outrageous toppings like the Boston Strangler, which has sautéed onions and Mackin' Cheese.

For a classier feel, speakeasy-like The Hawthorne has a venerable book of cocktails on offer. Of note: Attention, an absinthe-spiked number that goes down smooth and has a nice fennel and lemon finish.

Cornwall's is a classic British pub where you can actually hear yourself speak. They have dozens of beers on tap, like Wachusett Country Ale, Young's Double Chocolate Stout, and Fuller's London Porter.

museum of fine arts boston

Photo: Courtesy of Museum of Fine Arts


Game day or not, a visit to the Museum of Fine Arts is in order. Built in 1909 and expanded in the mid-2000s, the museum's collection includes Egyptian artifacts and Impressionist works by Gaugin, van Gogh, and Monet.

If you like your art more out-of-the-box, the Isabella Stewart Gardiner Museum is a must-see, housed in a building designed to emulate a 15th-century Venetian palace. If your name is Isabella, you get in for free. 

Boston Symphony Orchestra also makes its home in Kenmore Square, and hearing music in Symphony Hall is truly enchanting.

While legendary punk haven Rathskeller is no longer, there's still a great music scene around the Square. Check out The Church for reggae and funk on Wednesdays and shows from such bands as  Nashville's Cheap Time and Boston locals Strange Machines.

hotel commonwealth

Photo: Courtesy of Hotel Commonwealth


Hotel Commonwealth is an instant classic, and you'll be treated like Boston Brahmins throughout your stay. Rooms are timeless and traditional, with four-poster beds and handsome desks. Boston-themed books, pillow chocolates, Frette robes, and Malin & Goetz bath products are the little details that linger after you check out. 

Hotel Buckminster is one of the hotels that survived the not-so-great-years: It was built in 1897 and has withstood the test of time, offering 116 elegantly furnished rooms and suites. An historical landmark, this is where bookie Joseph "Sport" Sullivan and White Sox first baseman Arnold "Chick" Gandil fixed the 1919 World Series.

Citgo sign

The famous Citgo sign. Photo: ADupnik / Flickr

Much has changed in Kenmore Square, but one landmark remains: The famous 60-by-60-foot neon Citgo sign atop 660 Beacon that went up in 1965 still illuminates Fenway and Kenmore Square. It may not be the most glamorous attraction, but it reminds you that this is Boston, after all — simultaneously gritty and classy.


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