Caffe Vittoria on Hanover Street has poured espresso and grappa in Boston's North End since 1929. Four floors, three liquor bars, a cigar room; the city's first Italian cafe-bar.
Food program: Italian pastry
Tip: Basement liquor bar after 21:00 is the under-toured seat. Grappa and espresso is the canonical close.
Address: 290-296 Hanover St, Boston, MA 02113
Trillium on Thomson Place is the Fort Point three-storey taproom and brewpub in Boston since 2018. The third-floor roof terrace is the marquee seat; hazy IPAs, lagers, kitchen runs to 22:00.
Signature drink: Trillium IPA
Food: Brewpub menu
Tip: Third-floor roof seats fill by 17:00 in summer. Online order ahead for can release lineups.
Harpoon Brewery's Beer Hall on Northern Avenue in Boston's Seaport has poured pints since 1986. New England's first craft brewery, Massachusetts brewing licence number 001, daily tours.
Signature drink: Harpoon IPA
Food: Beer hall pretzel and brats
Tip: Saturday tour at 13:00 includes the full brewery and four pours. The hot pretzel is the kitchen signature.
The Wig Shop has run a speakeasy-style cocktail bar behind a fake wig-shop storefront on Temple Place in Downtown Boston since 2019. 1940s magazine-ad decor, craft cocktails, absinthe service.
Signature drink: Absinthe Sazerac
Food: Snacks and bar bites
Tip: Find the unmarked door inside the wig storefront. Reservations on Resy 5 to 7pm, walk-in after.
Backbar in Union Square Somerville has poured artful cocktails behind an unmarked door in Boston since 2011. Sam Treadway founder; Field and Vine team bought it in 2025; obscure-spirits programme.
Signature drink: Greek mastiha milk punch
Food: Snacks
Tip: Walk-in only, no reservations. Last call 23:15. Order from the staff-pick chalkboard for the best off-menu drink.
Bleacher Bar on Lansdowne Street sits beneath the centre-field bleachers at Fenway Park in Boston's Kenmore Square since 2008. Live view of the field through a one-way window, sports-bar food.
Signature drink: Pint of Sam Adams Boston Lager
Food: Pub food and burgers
Tip: Reservations on the website during Sox games; arrive 2 hours before first pitch. The garage-door window opens onto the field on rainouts.
Julio de Haro's Estragon on Harrison Avenue has poured Spanish gin-tonics and tapas in Boston's South End since 2008. Boston Magazine Best of Boston 2023; all-Spanish wine list.
Signature drink: Spanish gin and tonic with juniper
Food: Spanish tapas
Tip: Happy hour 17:00 to 19:00 weekdays runs half-price tapas. The lounge is the walk-in seat; book the dining room for parties.
