There are so many, but here are my faves: Cambridge:
Grendel's Den - Right in Harvard Square. It's been there for 50+ years and the vibe is it's a bar that has been there for 50+ years. Something about that is very charming to me. A plus is that Pinocchio's Pizza is pretty much across the street, so you can get a late night slice or three after drinks.
Plough & Stars - A favorite of many. A very cozy vibe and great live music.
State Park - 70s basement vibes. Wood paneling, a bunch of cool/weird neon signs and vintage lamps, and great food. Also pool and I think shuffleboard
Daedalus - Maybe more of a restaurant, but I love it. Also in Harvard Square Somerville:
Highland Kitchen - Incredible food and a small bar. Mostly a sit-down place, but they have good drinks too.
The Burren - One of the best places in the Boston area and maybe my favorite. The best live music around. There are usually some Irish/folk/instrumental bands playing in the front room and some larger acts in the back room.
Saloon - A speakeasy, so to speak. Great drinks.
Olde Magoun's Saloon - Great spot for food/drink if you're near Magoun Square
Bronwyn - German bierhall with great food
Pub in Jamaica Plain where I was a trivia regular for 2017-2020 and would stop by on a occasion after I moved to Cambridge. They don't have trivia anymore but its a nice place to have a couple beers with some friends in a down to earth environment. They had cheap PBR/'Gansett/Yuengling and a good selection of new england craft beers like Proclamation/Maine Beer Company/Fiddlehead (before it was widely distributed). It is dark, has a homey wood interior and a slow to warm but sweet bartender named Jess. They play good music like classic soul and the Smiths. One time a barback that looked like Billy Joe Armstrong played Beach House for like an hour. Overall, everything you want out of a neighborhood bar.
tomorrow PI.FYI launches to the public this project is the result of thousands of hours spent coding everything from scratch after I got laid off six months ago no thiel-bucks or weirdo outsider money, just a pure desire to make something fun and true to Perfectly Imperfect’s day one goal of helping people find new things from real human beings, not algorithms or AI a pure labor of love that I’ve been quietly plotting for two years and it’s completely self-funded from my (rapidly) dwindling savings account so thank you for coming along for this weird ride 🫶 let's see where it goes