Dining Playbook: Where To Grab An After-Work Cocktail

There are countless bars and restaurants around the city to grab a drink. Are you looking to shake things up, and venture to a new spot for brunch, an after-work drink, or just a place that’s not your couch? Read on for a few recommendations on where Dining Playbook suggests you go.

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Legal Harborside

There are so many great restaurants with a view in Boston, but our favorite has to be Legal Harborside. With a great selection of local beers, craft cocktails and fresh seafood, you can’t go wrong. There are three different levels of Legal Harborside, and each floor has a different concept. If you’re looking for the iconic, picnic table atmosphere, dine on the first floor. If you’re looking to celebrate, or have a business meeting, the second floor is for you. And if you’re looking for a more relaxed, laid back atmosphere, head to the roof deck, with gorgeous views of the Boston Fish Pier to accompany your libations.

Legal Harborside: 270 Northern Ave, Boston, MA 02210

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Lord Hobo

Yes, it’s an interesting name for a brewery, but haven’t you heard of the phrase “don’t judge a book by its cover?” Maybe we should change that to “don’t judge a beer by its name” because Lord Hobo is the bee’s knees. Go for brunch and pair your Boom Sauce with a plate of the Steak and Eggs, and their delicious Cheddar Grits. With locations in both Woburn and Cambridge, it’s easy enough for any city dweller to get there. Try one of the 40 beers on tap in Cambridge, or head to the tap room in Woburn and sample some of the year-round, seasonals, and limited release beers.

Lord Hobo Brewing: 5 Draper St, Woburn, MA
Lord Hobo Beer Hall: 92 Hampshire St., Cambridge, MA 02139

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Green Street

Green Street is home of the city’s longest standing liquor license. Since they’ve been around so long, it’s no surprise that they have an award-winning cocktail menu. Take a seat at the bar and treat yourself to a burger and a craft beer, or sit down in the dining room upstairs and have a glass of wine with your dinner. Any drink you get here will be a good one, we promise.

Green Street: 280 Green St, Cambridge, MA 02139

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Highball Lounge

Enjoy gorgeous craft cocktails whilst playing a game of Jenga with your friends. Grab the DuckieRosé, a glass of rosé garnished with a rubber duckie, or order one of their unique cocktails like the Chin UP!, made with Citadelle Gin, Dry Vermouth, Cynar, Cucumber.
Highball Lounge: 90 Tremont St, Boston, MA 02108

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Drink

This spot is dedicated entirely to the art of cocktails. They don’t have a drink menu, but fear not, if you’re not sure which cocktail you’d like, tell your bartender a few of your likes and dislikes, and they’ll whip up something just for you. In addition to their inventive cocktails, they have a small beer list as well as an incredible wine menu.

Drink: 348 Congress St, Boston, MA 02210