Posted October 3rd, 2017, 03:20 AM
^+1 to the above, and aside from specifying that you definitely want to visit Vista House as one of the scenic stops along the gorge I really don't have a thing to add to that I82-Maryhill-US97 loop, it definitely incorporates the top views and the oddest of Great American Roadtrip roadside attractions. I'll even tolerate McMenamins beers - which in almost any other state of the union would be very good, but suffer poorly in comparison to the truly ridonkulous number of great Oregon brews - because they do do a superb job with their building renovation & repurposings (consider staying in one of their hotels - e.g. the Kennedy School in Portland - for a night).
On the Portland itself front, which breweries/restos/donuteries to visit definitely needs more info about your tastes, budget, and tolerance for queuing up. The donut angle is the only one I'm confident in summarizing - tourists go to Voodoo because they are gloriously weird, but actually making a quality donut was never their game plan; it's all about ridiculous toppings which sometimes work and sometimes don't on top of middle-of-the-road donuts. Tim Hortons up here makes better actual donuts than Voodoo...
Blue Star is the bees knees of modern donuts - and if you prefer old-school then Pips or waiting until you get to Seattle to eat Top Pot. For me, as a broad-spectrum donut lover, Blue Star spanks literally everything else out there - I only eat them once a year as a birthday treat these days (diabetes), and I have returned to Blue Star for my donut fix every year since they opened. Their Old Fashioned base is pretty much as good as anyone's but their brioche dough version is, pardon the pun, the real bread & butter of their rep. If in doubt, start with the Blueberry Bourbon Basil.
Resto-wise, you have to hit a Food Truck pod for a casual meal - but there's so many that again without knowing what would be the best kind of food for you impossible to say which to hit - and at least one locavore PNW resto. But depending how high/low brow you like your food, it's seriously challenging to say which to visit. Kachka definitely deserves all the praise heaped upon it, and how often do you find good Russian food in the US?
Happy Hour in the Portland City Grill is a safe bet - be prompt if you want a window seat, it's all about the views! The regular menu is a fairly typical big city steakhouse affair, but there's a few quirkier items available too (kung pao calamari is reliably good) and it's very keenly price during Happy Hour (worth a buck or two extra per beer compared to Bailey's close by for the view). I could go on for hours about the food scene - but instead I'll point you to Eater, where the PDX site is very active and should give you a very solid start on new & interesting as well as tried & true eateries.
Baileys is the pub to go if you want a single spot to sample as many beers as possible - while there are a couple of other beer halls with even more choices on tap, they are pricier and less convenient for downtown core tourism. If you have the time to actually visit multiple breweries, then you need to do more research or give examples of particular beer styles and other breweries you enjoy to tease out the likeliest candidates for you - personally I'd try comparing different takes on the same kind of beer all the way up the coast. I think at last count Portland alone was approaching 70 breweries inside the city limits, more than anywhere else on the planet (they overtook Cologne last century IIRC) so it's simply not even feasible for most to sample even one product from each brewery!!!
Other stuff to do - Tripadvisor is a great starting point, but there are some things that are way down the list due to their obscurity that might really make for a definitively Portlandian experience. Try googling 'weirdest things to do in Portland' and you'll find lots of travel blogs with big lists of stuff. The single best thing we've done was the bridge tour we went on - with PDX Bridge Tours
. While there are some cities that have more bridges, apparently there's nowhere else you can actually see every type
of bridge simultaneously - and you get to join an operator inside their 'control tower' as well as actually standing inside the guts of a bridge while it's opened & closed.
Princess: Emerald, Golden x3, Island, Star x2
NCL: Gem, Pearl
Edumacational kiddie cruises: SS Uganda