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A restaurant interior features red leather stools at a bar. Neon signage over a mirror in the background advertises Charlie’s double cheeseburger special.
You’re going to end your night here
Katie Chudy for Eater

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Harvard Square Booze Crawl: Rock and Roll, Jazz, and One Damn Fine Jukebox

Pad the stomach with a slice or two at Pinocchio’s, then drink some cheap beer and fancy cocktails

Welcome back to Food 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.

Aesthetically speaking, Harvard Square is peak New England. Centuries-old brick buildings and colonial-era homes? Check. The manicured yards of a world-renowned institution of higher learning? Check. A Dunkin’ Donuts on a street named for John F. Kennedy? You bet.

Because Harvard Square is home to thousands of professors and students — and host to untold numbers of tourists — there’s plenty to eat and drink in the neighborhood. From cheap burgers (Shake Shack and Tasty Burger) to cafés (Crema) and bars, an eater/drinker has much to choose from.

Because it’s the holidays — and just because — this trip to Harvard Square is drinking-heavy. Padding the stomach with a little grub before imbibing is important, though, and so the first stop on this crawl will serve those purposes.

Stats for this food/booze crawl:

  • Total stops: 5
  • Total mileage: A quarter mile, ish
  • Total square slices eaten: One or two, depending on how much booze we plan on swilling
  • Total drunk people at the end of the crawl: Again, this depends. How many people are participating? Take that number, multiply it by two, then divide it by two.

A Square Slice (Or Two) at Pinocchio’s Pizza

74 Winthrop St., Cambridge, MA 02138

Pinocchio’s Pizza
The square slice at Pinocchio’s is a Harvard Square icon
Terrence B. Doyle for Eater

Pinocchio’s is a Harvard Square institution. Tucked away from the main drag on Winthrop Street, this shop has been slinging square slices to hungry students since 1966. The classics are good: cheese or pepperoni. They’re heavy, so one or two should do the trick.

A Quick Pop at Shay’s

58 JFK St., Cambridge, MA 02138

Shay’s Harvard Square
The patio at Shay’s is the best patio
Terrence B. Doyle for Eater

Take a left out of Pinocchio’s and another left onto JFK Street, and walk about 73 feet to Shay’s. Shay’s is perhaps best enjoyed in the summer when patrons can get the most out of the patio, but it’s not so bad inside either. Grab a cheap beer — Miller High Life, anyone? — luxuriate in that cheap beer, tip your bartender, and head back into the cold and toward the next watering hole.

The Old Glory at Beat Brasserie

13 Brattle St., Cambridge, MA 02138

Beat Brasserie Cocktail
A good, festive drink

Beat Brasserie is the Beehive’s sibling bar and restaurant. Like at the Beehive, eaters and drinkers can enjoy live music at Beat Brasserie — everything from soul to blues to jazz and hip hop — most nights. Grab the Old Glory, a cocktail made with apple brandy, triple sec, maraschino and cinnamon.

Smoking the Hive at The Sinclair

52 Church St., Cambridge, MA 02138

The Sinclair
A great venue for music and drinking
Terrence B. Doyle for Eater

One does not have to be taking in a show to enjoy a drink at the Sinclair (but by all means go there and take in a show because the acoustics are pitch perfect). My favorite cocktail is called Smoking the Hive — Bulleit bourbon, Sombra mezcal, smoked honey, lemon, and a scotch rinse. It’s heady, but we’ve only got one drink left after this, so who cares?

Another Cheap Beer, This Time at Charlie’s Kitchen

10 Eliot St., Cambridge, MA 02138

Charlie’s Kitchen
The appropriate last call spot
Terrence B. Doyle for Eater

The double cheeseburger king is also the king of jukeboxes and cheap beer and, occasionally, punk shows. Also, there’s karaoke every Tuesday night. Fire up some old soul or some punk on the jukebox, snag a PBR tallboy, and settle into what should by this point in the night be a decent drunk.

Beat Hotel

13 Brattle St, Cambridge, MA 617 449 0001 Visit Website

Pinocchio's Pizza & Subs

74 Winthrop Street, , MA 02138 (617) 876-4897 Visit Website

Charlie's Kitchen

10 Eliot Street, , MA 02138 (617) 492-9646 Visit Website

The Sinclair

52 Church Street, , MA 02138 (617) 547-5200 Visit Website