Much like New York, Philadelphia, and other historic cities along the East Coast, Boston has no shortage of old restaurants and bars with tons of character, and yes, many of them are hugely popular with tourists, such as the Union Oyster House, Durgin-Park, and the Chart House. But what about dining and drinking spots with a lot of history behind them that tend to be favored more by the locals? Plenty of them can be found as well, with Doyle’s Cafe in Jamaica Plain, Marliave in downtown Boston, and Jeveli’s in Eastie coming to mind, along with a classic old Italian-American restaurant called the Pleasant Cafe that is a bit farther out (near the Roslindale/West Roxbury line) but well worth seeking out for its old-school charm, laid-back vibe, and excellent food and drink.
The Pleasant Cafe basically sits on the east “slope” of Boston’s highest point (Bellevue Hill) on a stretch of Washington Street that drops steeply down into Roslindale Village, which is just under a mile to the northeast. The dining spot is tough to miss at night with its bright neon sign out front—and yes, neon signs are a real rarity in the Boston area for some reason—and the vintage feel continues inside with the almost obligatory wood paneling, hissing radiators, narrow diner-like restaurant section, and old-fashioned bar area complete with a wood-paneled partition that separates the actual bar from another narrow dining area. The staff at the Pleasant Cafe is exceptionally friendly, with servers seeming to know many of the customers by name while also welcoming newcomers to the place. By the way, the Pleasant Cafe has something that not too many restaurants within the Boston city limits have—a lot with free parking. And if the parking lot is full, plenty of spaces can be found along the street, so for those who drive, it is generally a pretty stress-free situation once you get here.
There seems to be a common thread among many of the old-school restaurants and bars in the Boston area—they tend to focus at least in part on Italian-American food, with such places as NewBridge Cafe in Chelsea, Gregg’s in Watertown, Pearl Street Station in Malden, and Kelley Square Pub in East Boston being a few of the better examples of this. The Pleasant Cafe is certainly in this category as well, offering classic Italian-American comfort food dishes that tend to be simple and unpretentious, while portions are mostly substantial enough that bringing leftovers home for a second meal the following day is not an uncommon occurrence. The restaurant’s menu has a good number of highlights, with some of the best of the best including a wonderfully old-fashioned chicken and eggplant parmigiana combo plate with plenty of house-made red sauce; a hearty lasagna with lots of cheese and sauce, and dense and delicious meatballs that pretty much make this dish; a large and reasonably priced roast prime rib of beef that is offered on Saturday nights; a ravioli plate that can be ordered with sweet Italian sausage; and some of the best thin-crust pizza in all of Boston, with the eggplant and meatball toppings being two faves here. The drink menu at the Pleasant Cafe is something to behold if you’re a fan of old-fashioned cocktails, with good takes on such options as a ward 8, tom collins, brandy alexander, harvey wallbanger, sidecar, old fashioned, and so many more. For those not in the mood for a mixed drink, more than 30 beers and more than 40 wines are available as well, along with the usual soft drinks, coffee, and tea.
The Pleasant Cafe is one of those places that is so “Boston” that it really would be tough to imagine the city without it. Here’s hoping that this 80-year-old restaurant and bar keeps going for at least another 80-plus years, as it is a neighborhood icon that is truly a destination spot for those who like a little history with their food and drink.
PLEASANT CAFE. 4515 WASHINGTON ST., ROSLINDALE. PLEASANTCAFE.COM
Marc is the founder of @hiddenboston, a textbook editor, a hike leader for @AppMtnClub, and a food and travel writer and commenter for DigBoston, NBC/NECN, WBZ, WMFO and indie617.