There's so many breweries in Portland (I went to 10 in one weekend), so there's no way you can go everywhere. Things you definitely need to do:
- Spend at least half a day in the area around Allagash. As of when I visited, there were 5 total breweries there. The previous time I went, there were only 3. It's a hotspot, and there are food trucks at all the breweries, including one with lobster roll flights inside Allagash.
- Go to Bissell Brothers. I think they make the best beer of all the breweries in the city. See below.
- Go to Novare Res. Always great beer options, and cornhole if you can be outside.
Now I'll highlight all the breweries I visited, in my very subjective order of where I think you need to go. Each of the links has more details about the brewery itself.
Bissell Brothers: Just go ahead and get yourself all the New England IPA's they've got. I didn't try the other styles, but I'm sure they don't make anything bad. You can get 6oz pours if you want to maximize the beers you try. Not really near any of the other breweries.
Definitive: This is a relatively new brewery (about a year old), right near Allagash. They do IPA's, sours, and stouts all well.
Battery Steele: My favorite IPA's, there's just not that many of them. Also in the Allagash area.
Allagash: The biggest brewery in Portland for a reason. All kinds of styles, and their tour is pretty enjoyable. I mentioned lobster roll flights earlier, they also have beer flights.
Goodfire: A few different IPA's and pale ales that are all glorious. They'll have a food truck, and are right next to Lone Pine. Feel free to go to both of those, then Oxbow on your way downtown. Speaking of...
Oxbow: They've got a bunch of sour and funky beers, really different from the rest of the places. They also have food from Duck Fat (great, albeit very small, restaurant downtown).
Lone Pine: Next to Goodfire. The IPA's they distribute are incredible, so get some of the other stuff. They had some very good sours while I was there.
Mast Landing: This is a bit further away, in Westbrook, but they make great beer, have a pretty large space, and offer small pours. They have enough options that you could commit some time to it, given it'll take awhile to get there. It also happened that I was staying in Westbrook, so this was a walk for me.
Liquid Riot: Right smack downtown, and open until 1am. They are a distillery in addition to a brewery. Good place to end a night (if you aren't at Novare Res).
Foundation: I didn't go here this time due to time constraints, but it's right by Allagash, and they make a bunch of great beers. I went on my previous visit.
Austin St.: Again, right by Allagash. Really small taproom, but they offer flights and have cornhole outside, as well as a food truck (shared with Battery Steele while I was there).
Other things to do are mostly centered around food. Portland Lobster Company has great beer, live music, and (you guessed it) great lobster. It borders on a must-do. Duck Fat is great and Holy Donut is super popular with their potato donuts. For places to hang out, feel free to give Bubba's a go. It is a really weird place, so I fit right in.