Heading to Portland in February with 10-15 friends for a bachelor party so I'm looking to make reservations for the 2 nights we're there. Willing to spend $$$ but really just care about great food and drink.
The Best kept secret for parting it up in one location and by far the safest is McMenamins Edgefield. Check it out you won't be sorry. Only a short distance from the airport (taxi) this brewery and estate houses 3 restaurants, a golf course, an amazing spa with outdoor heated pool, private rooms / dorms ($30 a bed!!!) billiards, darts, bands play on the week ends, a movie theatre where you eat and drink, a wine bar and you don't have to drive anywhere, just stubble up to bed in the converted orphanage renovated as a true historical site. Downtown can wait until later...
So if I translate your question correctly it is:
"I got a whole bunch of dudes coming to town, we want somewhere we can grub, maybe get a few adult beverages flowing, have fun and then head out for the night easily."
That is what I am assuming, but please correct me if I am wrong and I can modify my response:
10-15 people in portland is touch since many restaurants are 40-65 seats, but there are still a lot of good options:
Toro Bravo - Spanish tapas. Grab a drink upstairs at The Secret Society and then head down for some awesome food. Lots of things to try, good drink selection and this place is pretty lively. He also owns Tasty N Alder and Tasty N Sons if you want a different vibe but equally good food
Imperial - Same owner as renowned Paley's Place but much more approachable, good atmosphere (more cosmopolitain), a few cocktails on tap and full bar, right downtown and an easy launching pad for the night. Grab beers at Bailey's Taproom after or head straight for Mary's Club (the oldest strip club in portland)
OX Restaurant They take reservations for parties of more than 6. You will 100% need them. Argentina-inspired steakhouse. Next door (owned by same guys) is Whey Bar to drink prior. Ox has great cocktails, food is on point, but will be a slightly more expensive place. It is sort of in a dead zone for other stuff to do however.
Breakside Brewery - Good pub, good beer (won best IPA at the Great American Beer Festival the last 2 years), good vibe. You will probably want to make a reservation as it is not a very big place.
It is possible the 10 Barrel Brewing will have their Portland Pub open. If it is, go. It will be on 14th and between Glisan and Flanders in NW Portland. Great pizzas, other food and the beer is pretty phenomenal.
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One of my favorites is Kells Irish Restaurant & Pub great food, big place, live music and in the heart of down town so you can try out some other fun bars.
I had my bachelorette Departure Restaurant + Lounge - It was a great place to start the night with very good food/drinks, and a rooftop view of the city.
Beast is insanely good--I think the chef even won or at least was nominated for James Beard award. Just make sure you don't have any vegetarians in the group because it's all meat (I don't remember any non-meat dishes). Not cheap, but absolutely worth it.