The Best Weekend in Portland Ever

Wanna get weird for a weekend? Head to Portland for three outlandish days of bikes, brews, and quirky clubs in the Pacific Northwest.

How to Spend 3 Days in Portland

In addition to its weirdness, Portland also boasts natural beauty and one of the best food scenes in the country. If you’ve only got a couple of days to get away, follow these tips for the best weekend in Portland ever.

Day 1

Fight off any jet lag by renting a bicycle and getting some exercise. Cycle Portland offers bike tours or bike rentals so you can explore on your own. Alternatively, you can try out Portland’s bike share program, Biketown. Pay as you go plans are available for as little as 8 cents per minute.

Take the scenic trail along the shore of the Willamette River where you’ll be free from car traffic and can enjoy the ride in a peaceful environment. Another great place to cycle is in the 5000-plus acres of Portland’s Forest Park. If you’re not inclined to ride on two wheels, this is also a great place for an urban hike just a few miles from downtown Portland.

After resting back at your hotel, it’s time to check out some unusual nightlife. The Funhouse Lounge is a fringe theater that has everything from comedy, burlesque, and bingo, to musicals, karaoke, and a clown room.  A clown room, you ask? If the thought of such a room doesn’t give you nightmares, lounge among the clown covered walls and rotating clown head coffee tables.

Day 2

Start your day off with a brunch at La Luna Cafe with a menu that includes a unique salmon pastrami benedict, crepes, and fresh juices. After you’ve satisfied your taste buds, head over to Powell’s City of Books to browse through approximately one million new, used, and rare books. It’s five stories covering an entire city block make this the largest independent bookstore in the world.

Just a block away from Powell’s, you’ll stumble across Deschutes, one of Portland’s most famous micro-breweries. Sample a wide variety of brews or take one of the daily brewery tours to get an up-close look at the brewing process. Make sure to try one of the seasonal brews or the selection of beers that you can only find in its tap room.

If you’re into the food truck scene, Portland will not disappoint. There are over 500 food carts to choose from, which usually congregate together in lots around the city. In the center of downtown, at the corner of SW 9th and Alder, you’ll find the largest concentration of street food in America. This is a great place to go if you want Mexican food and your friends are craving something else like Chinese, Egyptian, or Greek cuisine. Food cart tours are available if you’d like to be guided through some of the best pop-up eateries around Portland.

Every Sunday night in Portland, you can experience Zoobomb, which is one of the strangest organized bike rides you’ll come across. Bicycle enthusiasts convene near the Oregon Zoo and ride unusual bicycles down the city’s west hills. Many come in costume and you’ll usually find young adults riding miniature bicycles. There’s even a “Zoobomb Pyle” of spare bikes for those who don’t have their own.

Don’t like biking? Why not go sing some karaoke. Stripparaoke starts at 9pm every Sunday night at Devil’s Point, where you can sing your favorite song and have a dancer back you up with some impressive moves around the pole. If you’re looking for a low-key dive bar, try the Slingshot Lounge for hand-crafted cocktails, and watering hole classics like a pool table, pinball, and a jukebox.

Day 3

Seattle often gets mentioned as the coffee capital of the U.S., but some will argue that there are better roasters in the Pacific Northwest’s other major capital, Portland. Stumptown Coffee’s flagship cafe in Portland is a great way to wake up with a fresh brew and enjoy some people watching. For a quick and sweet breakfast, grab one of the more than 50 varieties of doughnuts from Voodoo Doughnuts before you head out for a day of sightseeing. The menu includes original creations such as a Bacon Maple Bar or a “PB&J” doughnut.

You won’t want to miss out on the natural beauty that surrounds Portland. Take a trip down to the Columbia River Gorge and the impressive Multnomah Falls. Taking in the power of the falls from the pedestrian bridge is a breathtaking experience in any season. Within the city of Portland itself, you can find tranquility at the Portland Japanese Garden.

Of course, there are plenty of other attractions in the city of Portland. For a quick weekend trip, I’d recommend picking one or two things to see for each day and leaving yourself some free time to explore anything else you may come across during your stay.

Cheap Weekend Flights to Portland

If you’re looking for a cheap flight to Portland for the weekend, try out our new Weekender search tool, where we find the best prices for upcoming weekends departing from your local airport. It searches for flight deals departing on Thursdays or Fridays, and returning on Sundays or Mondays, so you can take advantage of a cheap flight without taking a lot of time off from work. The Weekender also has the option to add a recommended hotel for your trip so you can quickly and easily book your next weekend getaway.

Featured image by Joshua Rainey Photography / Shutterstock.com

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