I’ve watched enough glamourized, Hollywood-produced films in my lifetime to know that summer road trips need to be undeniably epic. I mean, sure, it’s great to get away to Banff for a weekend or to head out to the West Coast, but sometimes you’ve got to wonder: “If I stick it out in this car — packed with friends, luggage and no A/C — could it take us somewhere really cool?”

The answer is yes. It can take you to Portland, OR.

Prior to planning this road trip with my friends, my main exposure to Portland “culture” centered on the popular skit series, Portlandia. If you’re not familiar the show, I would suggest Googling “Put a Bird on It.” In reality it’s nothing like that. Okay, maybe a little bit....

The drive from Calgary is about three hours longer than trekking to Vancouver. There are a few routes to get to Portland, but the one that takes you down through Fernie, out of B.C., into Idaho, Washington and, finally, Oregon — U.S. 95 via Crowsnest Pass Highway — boasts spectacular scenery. (We enjoyed Idaho’s scenery more so for the right-wing Republican propaganda signs and massive American flags....)

Checking into the Ace Hotel will place you right in the heart of downtown Portland, near the historic Pearl District. You can snag a (surprisingly not teeny) room in this boutique hotel with three beds for just $125. Between the three of us sharing the room, it came to just under $45 per night. Eat your heart out Holiday Inn.

Also: the Ace is so cool, you almost don’t want to leave the premises. From the lobby, you can turn right to grab a great cup of coffee from Stumptown Coffee Roasters, which now has seven locations in Portland and one in New York City. Having a fresh brew here was the only way I could start each morning.

Also accessible from the lobby is the slick Clyde Common, which puts other hotel lounges to shame — you can go for a handcrafted cocktail or a cold microbrew and have a bite to eat from an organic, locally driven menu. Although our dinner was pretty solid, the real winner here, food-wise, is their late night “happy hour” menu — with dishes running anywhere from $3 to $6, it’s one hell of a deal.

Walk a couple blocks down from the hotel to the gigantic Powell Books, a Portland institution which features equally large new and used selections. Close by, you’ll find a handful of cool vintage shops — Ray’s Ragtime, for instance — that have everything from clothing to records to antiques that would make your grandma jealous.

A good thing to know, once you’re ready to step out of the Pearl District, is that the city uses quadrants much like Calgary — it’s very easy to navigate and has extremely accessible public transit. It’s also very bike friendly, which is great — although, oddly, and perhaps because of the high-use of transit and cycling, we had trouble locating cabs, a problem that we had repeatedly during our stay in Portland.

If you’re going to make a point of eating at one specific place in this city, I’d pick (hands down) Pok Pok on Southeast Division Street. James Beard-award-winning chef Andy Ricker creates a menu here inspired by Thai street food. The prices won’t blow your budget, but the flavour will blow your mind — I would venture a claim that this is better than anything you’ll find in similar restaurants in Western Canada. A must try is the Pok Pok Papaya, a spicy salad made with unripened papaya, tomatoes, long beans and a mix of intense Thai spices. Wash it down with their signature Tamarind Whiskey Sour — bourbon at its best with some Asian flare.

It’s rare that I’d recommend going to a place of education during a weekend getaway, but I’ll make an exception for The Kennedy School. Owned by an Oregon-wide restaurant group, the McMenamins, this heritage school has been converted into a hotel, pub, movie theatre and more. Here, the old boiler room becomes a two level pub, and the gymnasium is now a concert hall. Perhaps best of all, the “detention room” is now a cigar and whiskey bar. If you overindulge in liquids while roaming the halls (which can happen easily), the upper levels of the school have been turned into a small hotel — feel free to stay the night.

When your own long weekend road trip comes to a close (three days go by way too fast in a city like this), I’d make sure your last stop in Portland is the famous Voodoo Doughnut. Head there early, though, as the lines can get up to several blocks long. With choices like “Cock-N-Balls,” “Gay Bar” and the original “Voodoo Doll,” it’s no surprise this place is a hotspot, and the massive sugar rush will help energize you for the long ride back to Canada.