The arrival of fall and winter in Cambridge means moving from spacious outdoor patios to cozy, intimate bars. As the inclination to reach for weather-appropriate wine pairings sets in, we rounded by 5 places to enjoy wine and small dishes.


Inspired by owner Kim Courtney’s time spent in wine bars in the Upper West Side of Manhattan, the emphasis at UpperWest is on always-changing small plates and homemade pastas paired with Old World wines by the glass and bottle as well as wine and amaro flights.

Bisq Restaurant and Wine Bar

While little siblings make get a certain complex, Bisq, the sister restaurant to Inman Square’s Bergamot, shines with a fantastic by-the-glass wine list. Snack on dishes like the legendary fried chicken or the black bass ceviche and splurge on one of the aged madeira options for after dinner sipping.

Puritan & Company

Cozy up to one of the bar seats at Puritan & Company and experience their comprehensive wine list, offered both by the glass and the bottle (including their very special “reserve” list). Pair your wine with small bites like charcuterie or a heartier dish such as the roast chicken with duck fat potatoes or mushroom cavatelli.


The downstairs part of Parsnip offers a carefully curated (and delicious) menu for those looking to enjoy a multi-course meal, while upstairs allows you to sip wine over small plates. Choose from by-the-glass, half bottles, and even large format wines paired with dishes like crab cakes and blistered shisito peppers.


Italian food sings when paired with the right wine, and newcomer Sulmona has a focus on vino with reasonably priced options by the glass and bottle. While there is a heavier focus on Italian red wines, the menu also offers a great selection of Italian whites and sparkling that pair well with traditional small bites like panzerotti and arancini.