Best Things to Do in the Fenway: 13 Cool Hangouts and More (2024)

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 ona 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 eagerout-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 throughthe 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.Feeling a little VIP? Grab a one-night pass to The Foundation Room for your own club entrance and co*cktails one hour prior to doors.

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.

Built inside the Green Monster, this sports bar overlooks the outfield and is actually a part of Fenway (pro tip: it’s the best place to watch a game for free, with a full-on view from underneath the field). 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 400-plus whiskeys. If you're looking to consume some solids, the eponymous oyster bar is a great option, with local bivalves from locales such as Wellfleet and Island Creek shucked to order. The 10-person pig roast is just perfect for a summer celebration.

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 co*cktails feature house-made syrups and unlikely combinations. There’s also an inventive food menu, daily specials (hello, Taco Tuesdays and Wednesday poké), and a semi-secret bamboo patio out back.

This self-styled two-story upscale bowling lounge is located within earshot of Fenway Park. As if bowling weren’t entertainment enough, there’s also a wall-to-wall LED video wall, classic parlor games, billiards, and a state-of-the-art arcade. 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 forping 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.

This “adult snack bar” inspired by European tapas bars offers a tight standing-room-only space adorned with 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.

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.For your sweet teeth, indulge at the pop-up of Back Door Donuts open nightly from 7pm to 2am on the side of the restaurant.

This playful pizza spot is an homage to the ‘80s, complete with a rollerskate-adorned wall and a soundtrack that hits every note. The pizza is piping hot and cheesy, with classic toppings along with inventive combos including Ono Grinds (fontina, pork belly, roasted pineapple, and jalapeno goo) and Greek Out (kalamatas, roasted cherry tomatoes, marinated artichokes, lemon, and feta). Turn up the music and frolic through the co*cktail list, packed with fun drinks names like Flutter Pony, Little Bunny Foo Foo, and Ghost Monsters.