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Time Out Market Boston, 401 Park
Photograph: Eric Grossman Time Out Market Boston, 401 Park

The best things to do in the Fenway

Sure, the Fenway’s best known for its namesake ballpark, but there are plenty of other cool things to do around the Fens

By Eric Grossman and Time Out Boston Staff

Just about every Bostonian—even non-sporty types—has spent some time 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 Bostonbest live music in Boston, and best museums in Boston.

RECOMMENDED: Full guide to the best things to do in Boston

Things to do in the Fenway neighborhood

Fenway Park, Sights and attractions, Boston
Photograph: Elan Fleisher

1. Fenway Park

Things to do Sport events Fenway/Kenmore

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.

Cask 'n Flagon
Photograph: Courtesy Cask 'n Flagon

2. Cask ’n Flagon

Bars Sports Bars Fenway/Kenmore

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.

House of Blues, Music and nightlife, Boston
Photograph: Michael Young

3. House of Blues

Things to do Concerts Fenway/Kenmore

The House of Blues is one of New England's busiest and most popular music clubs; you cant 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.

Back Bay Fens
Photograph: Time Out Boston

4. Back Bay Fens

Attractions Parks and gardens Fenway/Kenmore

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.

Bleacher Bar, Bars, Boston
Photograph: Courtesy Bleacher Bar

5. Bleacher Bar

Bars Sports Bars Fenway/Kenmore

A tour of Fenway Park isnt 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.

Citizen Public House & Oyster Bar, Bars, Boston
Photograph: Courtesy Citizen Public House & Oyster Bar

6. Citizen Public House & Oyster Bar

Bars Gastropubs Fenway/Kenmore

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. 

Audubon Boston
Photograph: Courtesy Audubon Boston

7. Audubon Boston

Bars Café bars Fenway/Kenmore

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.

Lucky Strike
Courtesy Yelp/Lucky Strike

8. Lucky Strike Social Boston

Bars Sports Bars Fenway/Kenmore

This self-styled upscale bowling lounge is located within earshot of Fenway Park. As if bowling werent entertainment enough, theres also a wall-to-wall video screen showing the days must-see sporting events. Fan-friendly bites keep the masses satiated.

Game On!
Photograph: Courtesy Yelp/Brian S.

9. Game On!

Bars Sports Bars Fenway/Kenmore

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.

Photograph: Courtesy Yelp/Jack E.

10. Nathálie

Bars Wine bars Fenway/Kenmore

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.

Fool's Errand
Photograph: Courtesy Yelp/Colt V.

11. Fool’s Errand

Bars Cocktail bars Fenway/Kenmore

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.

Boston Beer Works, Bars, Boston
Photograph: Chris Bourn

12. Boston Beer Works

Bars Beer bars Fenway/Kenmore

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 its 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. Theres also a menu of burgers and bar snacks.

Loretta's Last Call
Photograph: Loretta's Last Call

13. Loretta’s Last Call

Music Music venues Fenway/Kenmore

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.


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