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bukowski back bay
A great Back Bay bar
Bukowski Tavern/Facebook

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Take a Four-Stop Booze Crawl Through Back Bay

A little bit fancy, a little bit divey

Welcome back to Food Crawls (or in this case, Booze Crawls), a series in which Eater Boston staffers guide you (virtually) on various food and booze crawls in the Boston area.

When we go out, we often find ourselves wanting to try more than one restaurant (or bar) at a time — a drink and a snack here, another drink and perhaps a dessert there — and want to share our favorite multi-stop combinations with you. These crawls are meant to be relatively walkable, and the amount of food and drink is meant to correspond roughly to a couple of average appetites (so bring a friend), although your mileage may vary. Email us if there’s a particular theme, specific dish or drink, or neighborhood you’d like to see covered in a future installment.

While throwing a few back in Back Bay, it’s compulsory to stop off at the Fairmont Copley Plaza Hotel for a twee cocktail at Oak Long Bar & Kitchen. From there, be sure to head to Bukowski’s for one or several cheap-ish beers and then to the Pour House for more of the same. Finally, finish the night in the moody red light of Lolita.

  • Total stops: 4
  • Drinks imbibed: Depends on whether or not it’s a work night

A Peachy Keen at Oak Long Bar & Kitchen

138 St. James Ave., Boston, MA 02116

oak long bar and kitchen
Oak Long Bar & Kitchen oozes swank
Oak Long Bar & Kitchen/Facebook

The space is gorgeous, and it sure feels good to be there and to drink there. Get a Peachy Keen, which is an Old Fashioned made with peach-infused Maker’s Mark bourbon, demerara, and peach bitters.

A Beer or Two at Bukowski Tavern

50 Dalton St., Boston, MA 02115

bukowski tavern
Good ole Chucky B
Bukowski Tavern/Facebook

Bukowski Tavern isn’t exactly a dive bar, but it’s not not a dive bar, either. And it’s especially not the Oak Long Bar & Kitchen, either in appearance or patronage. There are 20 beers on draft, and then many, many more in bottles and cans. Start off with something local — the hazy, fruity, slightly funky Fiddlehead IPA is an exemplar of the American IPA variety — and then move onto the rare bird that is draft PBR.

Another Beer — and a Burger — at Pour House

907 Boylston St. #21, Boston, MA 02115

pour house
A good Boylston Street dive bar
Pour House/Facebook

If it’s local craft beer you’re after, the Pour House isn’t your joint. If it’s cheap domestic lager you’re after, the Pour House is very much your joint. Grab a Budweiser, and eat a surprisingly good — and quite cheap — burger too. If you happen to be there on a Saturday between 6 p.m. and 10 p.m., that burger will be half price.

A Nightcap at Lolita

271 Dartmouth St., Boston, MA 02116

Lolita Cocina
Sexy lighting at Lolita

End the night with the Oaxacan Old Fashioned, which is made with Altos Reposado tequila, Del Maguey, agave nectar, and chocolate mole bitters. It’s as much dessert as it is night cap.

Pour House Bar & Grill

907 Boylston St, Boston, MA 02115 (617) 236-1767 Visit Website

Lolita (Back Bay)

271 Dartmouth Street, , MA 02116 (617) 369-5609 Visit Website

OAK Long Bar + Kitchen

138 Saint James Avenue, , MA 02116 (617) 585-7222 Visit Website

Bukowski Tavern (Back Bay)

50 Dalton Street, Boston, MA 02115 617 437 9999