Just about every Bostonian—even non-sporty types—has fought some battles in and around Fenway Park, but now, more than ever, a plethora of notable hangouts have popped up within a long fly ball of America’s most beloved ballpark. A mix of sudents, young professionals, and out-of-towners come together every night to eat and drink the night away, even if the local nine is out of town. Once you’ve had your fill of the Fens, check out our guides to the best restaurants in Boston, best live music in Boston, and best museums in Boston.
RECOMMENDED: Full guide to the best things to do in Boston
The best of the city under one roof
Time Out Market Boston features 15 curated food offerings—including one of our Fenway faves, Hojoko—plus two top-notch bars and lots more. There is plenty of seating (both indoor and outside) and some of the biggest culinary names in Boston are on hand crafting a varied assortment of delicious dishes and killer bites. The market is housed in the 401 Park Drive building, an Art Deco masterpiece built in 1929 as a Sears, Roebuck and Company warehouse.
Things to do in the Fenway neighborhood
Seeing a game at Fenway Park has been a rite of passage among most locals since it opened in 1912. The catch? As the oldest ballpark in the majors, it’s one the smallest, with a capacity of around 38,000, meaning tickets can be hard to come by for most games. (A smattering of big-name concerts and other sporting events provide additional access to the venue.) Fortunately, public tours are offered year-round, wowing even non-baseball types by detailing the park’s colorful history and intricate details. If you get the chance, take a seat atop the stadium’s most distinctive feature, the 37-foot-high left-field wall known as the Green Monster.
A legendary Fenway hangout, the Cask is housed on a busy corner in the shadow of the Green Monster. Multi-generational groups of Sox fans pack the sprawling interior alongside fair-weather college kids and eager out-of-towners. Upscale bar snacks share table space with classic fried treats, and a lengthy beer list ensures there’s something for every taste. During the warmer-weather months, the sidewalk patio is a must for people-watching before or after a game.
The House of Blues is one of New England's busiest and most popular music clubs; you can’t beat the big name acts that parade through the cavernous expanses. Veteran concertgoers know not to get stuck too many rows back in the balcony, while also being wary of busy Landsdowne Street when the Sox are in town.
This pretty park is a reminder of the very thing that gave the Fenway its name: wetlands. It’s hard to believe that this was once tidal saltwater marshland connected to the Atlantic Ocean. But, as part of the massive landfill operation that created the Back Bay, it was cut off from the sea. As part of the Emerald Necklace development, Frederick Law Olmsted created a fresh water lagoon amongst the park’s shrubbery and trees. The Fens actually houses many interesting memorials, several sports fields, and space to wander and feel free of urban cares. Highlights include the Kelleher Rose Garden, where spring blooms bring color and fragrance, the Westland Gate, Duck House, Fire Alarm Office, and Japanese Temple Bell.
A tour of Fenway Park isn’t complete without a stop at Bleacher Bar. Featuring a full-on view from underneath the field, this annex of the oldest ballpark in the country offers an unparalleled environment for die-hard sports fans. Beer is the order of the day here — there’s an extensive menu of bottles and drafts. A varied menu of accessible bar snacks helps to fuel the crowds.
One of the classier joints near Fenway Park, Citizen Public House offers a strong bar program whose main draw is 100+ whiskeys. (Try them all and you’ll get your own bottle of single barrel bourbon and an engraved whiskey glass.) If you're looking to consume some solids, the eponymous oyster bar is a great option, with local options including Wellfleets and Island Creeks shucked to order. Pop in on weekends to brunch on huevos rancheros or buttermilk ricotta pancakes.
Compared to the busy, sporty bars near Fenway Park, this great neighborhood spot — brought to you by the owners of Somerville gem Trina’s Starlite Lounge — provides a sleek, adult alternative. The curated beer list includes highbrow and lowbrow choices, and the creative cocktails feature house-made syrups and unlikely combinations. There’s also an inventive food menu, served from lunchtime until late. During the summer, head out back for one of the best (and semi-secret) patios in the city.
This self-styled upscale bowling lounge is located within earshot of Fenway Park. As if bowling weren’t entertainment enough, there’s also a wall-to-wall video screen showing the day’s must-see sporting events. Fan-friendly bites keep the masses satiated.
Game On! is unabashedly unironic, an arcade of a sports bar that’s connected to Fenway Park and popular with pre- and post-game crowds. Max and Leo’s artisan thin-crust pizzas, plus a wide assortment of apps, beers and burgers, keep the crowds satiated. If you tire of the always-rowdy scene upstairs, head downstairs for ping pong, batting cages, and more big screens.
This younger sibling of haley.henry, a popular wine bar near Downtown Crossing, offers a similarly stylish, diminutive space for sampling interesting wines. The small space, filled with black tile and exposed lightbulbs, includes a counter, bar, and tables. Most notably, all of the by-the-glass wines are from female wine producers, and the staff will open any bottle of wine if diners commit to at least two glasses. An assortment of fancified nibbles (corn nuts, olives, foie gras) pair nicely with the wine-focused environs.
Tiffani Faison’s “adult snack bar” resides steps away from her other two Fenway restaurants, Sweet Cheeks and Tiger Mama. Fool’s Errand is inspired by European tapas bars; the standing-room-only space contains crystal chandeliers and French wallpaper. When the interior, which can only hold a couple dozen, get packed, the crowds can spill out onto the outdoor patio. An assortment of creative small bites emanate from a small open kitchen at the center of the wood bar.
With its perfectly positioned location across the street from Fenway Park, the city's O.G. brewpub is often overrun with baseball fans between April and September. But it’s worth popping in here at any time of year to stretch out in the big space adn enjoy the beers, made on the premises, including the crisp Fenway Pale Ale and the hearty Boston Red. There’s also a menu of burgers and bar snacks.
No one would call Boston a country music hub, but that doesn’t mean the city lacks hardcore fans. Loretta’s fills the void between the occasional big-name shows at Gillette Stadium, hosting regular acts out of Nashville as well as some local up-and-comers. For those needing a further primer on the country music scene, there’s also weekly line-dancing, a bluegrass brunch, and even the occasional “Countryoke” night (aka Country Karaoke). A menu lineup of country classics, including hot chicken and chicken fried steak, completes your hat-to-spurs transformation, at least for one night.