The Best Food and Drink of Harvard Square

Cambridge, Massachusetts, with an impressive history as a lasting academic center in United States higher education, has long attracted intellectuals and artists from around the world. As English America’s first planned village, founded in 1630, and home to America’s oldest University (Harvard), the area deserves a visit for anyone interested in American history or fantastic bookstores (shout-out to Harvard Bookstore!).

Fortunately, Harvard Square, the area of Cambridge that surrounds Harvard University, has an appeal that far surpasses a typical college town. After living within the bounty of New York City for several years, I still think fondly of the 6 years I lived in Cambridge. Balancing both its fascinating history and now, a quality food scene, Harvard Square is an enriching place to spend a few days.

Below find my absolute favorite Harvard Square spots for quality food and drink:

Alden & Harlow - Best Fancy Dinner

I end up in Boston at least once a year for either work or pleasure, and have chosen Alden & Harlow the past three visits for a nice or romantic dinner stop. Using local farms and fisheries, Alden & Harlow has a really fresh and delicious take on preparing local ingredients. I recommend trying the three-onion dip and Berkshire crispy pork belly.

40 Brattle St, Cambridge, MA 02138

Alden & Harlow restaurant in Harvard Square

Border Cafe - Best Casual Dinner

While this is not the place to go for traditional Mexican fare, you are guaranteed a fun tex-mex meal, surrounded by a diverse cross-section of the Cambridge social scene. I especially enjoy the free chips and salsa, and always choose the frozen margarita!

32 Church St, Cambridge, MA 02138

Pinocchio's Pizza & Subs - Best Slice

You may find yourself just hungry enough to indulge in a slice of pizza on the go. If this occurs during your stay in Cambridge, you should absolutely head to Pinocchio’s. You’ll be met by hilarious painted wall murals and an eclectic selection of old photographs. Local celebrities Mark Wahlberg, Ben Affleck, and Matt Damon apparently stop here, so if that convinces you to try it, then cool! For the rest of you, you’ll just have to trust me.

74 Winthrop St, Cambridge, MA 02138

Darwin’s, Ltd. - Best Lunch Sandwich

A good sandwich can make a magical meal. And unlike some good dinners, I never seem to forget a good sandwich! Darwin’s was my regular stop for 6 years and never got old. You may encounter a line at lunchtime, but any wait is well worth it. Sandwich options are many, and bread choices are fresh baked! Also take note of the case of local cookies or shelves of excellent wines.

148 Mt Auburn St, Cambridge, MA 02138

Tatte Bakery & Café - Best Pastry

I didn’t want to include Tatte on this list, as they started opening in the Boston area after I moved away, but after just a couple visits, I was won over. Stepping into their Harvard Square cafe, you will notice a buzz that can only come from serving up the very best. Just try walking past their cases full of fresh-baked pastries and pies — you won’t make it out of here the same weight as you walked in.

1288 Massachusetts Ave, Cambridge, MA 02138

Flour Bakery - Famous Sticky Buns

Selecting between the excellent local bakery options is difficult. This is why you’ll find a few on this list! But Flour, founded by a Harvard grad, serves up some of the best sweets in the square, especially the famous sticky bun. This place is also popular if you need a spot to sit and study, as there are several tables.

114 Mt Auburn St, Cambridge, MA 02138

Hi-Rise Bread Company - Best Cup of Coffee

Hi-Rise does a lot of things right. Interior decor is adorable. Breads, sandwiches, and pastries are top-notch (like the apricot-filled brioche). But this place is also a favorite for a cup of joe from their high-quality coffee bar, using beans from Counter Culture Coffee.

1663 Massachusetts Ave, Cambridge, MA 02138

Hi-RIse Cafe next to the Harvard Law School, Cambridge

L.A. Burdick Chocolates - Best Chocolate Treats

Sometimes you find yourself chilled by the New England winds and just need a hot cup of thick hot chocolate. It’s nothing like the hot chocolate you’ve had from a dry mix. This stylish Brattle Street shop also sells chocolate mice, which are a wonderfully unique gift.

52 Brattle St, Cambridge, MA 02138

The Sinclair - Hippest Bar

Sometimes you grow tired of a traditional tavern or pub, so ubiquitous to the Boston area. The Sinclair is a wonderful alternative if you want an good selection of quality cocktails and the very best of local brews. Attached to a lively music venue, you can’t help but feel energized by the cool space and quality drinks.

52 Church St, Cambridge, MA 02138

The Sinclair Bar and Event Venue in Harvard Square

Shay's Pub & Wine Bar - Best Pub

Finally, a classic Cambridge pub! You should plop yourself down at Shay’s and enjoy a cool glass of beer and maybe even one of their delicious burgers. Located in the basement level on JFK Street, you’ll feel at ease here. So do as the Harvard students do, stay and keep the drinks coming.

58 John F. Kennedy St, Cambridge, MA 02138