If you like it weird, Portland is the place for you. This offbeat Oregon city is getting more than its fair share of limelight lately, and with good reason. Gorgeous gardens, hip foodie hot spots, ample indie entertainment and trendy, tax-free shopping (yes, that's right) make Portland more than worthy of both its newfound pop culture presence and its selection as your next weekend getaway destination.
9AM TASTY N SONS
Brunching is practically a sport in Portland, so be prepared to line up with the locals. Kick off your weekend of weird with a unique breakfast experience at Tasty n Sons, a popular spot featuring an "industrial-chic" aesthetic and eclectic international menu. Options ranging from a full English breakfast to the popular Burmese Red Pork Stew will make sure your meal is a memorable one. Because omelets are just too mainstream.
11AM INTERNATIONAL ROSE TEST GARDEN
After you've had your fill of international fare, frolic through the flora at one of the many gorgeous gardens in the city. Featuring more than 10,000 roses, the Portland International Rose Test Garden is a popular travel destination for visitors from around the world and the primary reason Portland is known as the "City of Roses." Take in the sights, scents and sensational views, as the garden offers one of the best vantage points of downtown as well as Mount Hood, a dormant but potentially active volcano in the Cascade Volcanic Arc of northern Oregon. (Did we mention admission is free?)
1PM ALDER STREET FOOD CART POD
With Portland being known as a food cart capital, it would be a crime not to check out the city's legendary street food scene, featuring more than 600 (and counting) of these mini kitchens. Luckily, the carts are organized into "pods" located in different areas of the city, so you can pick a pod and sample a smattering of food cart fare. If you're having trouble narrowing it down, try the Alder pod, which is one of the largest in Portland and includes Nong’s Khao Man Gai, a popular Thai stand that keeps it simple by offering only one menu item—their savory signature chicken and rice wrapped in butcher block paper.
2PM PORTLAND SATURDAY MARKET
2 SW NAITO PARKWAY PORTLAND, OR 97204
In order to pack as much Portland as possible into your short stay, hit the Portland Saturday Market next for a taste of everything that makes the city the cultural hub that it is. This massive outdoor arts-and-crafts fair is a fixture of the Portland scene, running every Saturday and Sunday from March through December (making it the largest continuously operated outdoor market in the U.S.). Feel the local love as you enjoy live music performances ranging from bluegrass to jazz and observe the handiwork of a variety of art vendors.
5PM DESCHUTES BREWERY & PUBLIC HOUSE
After all that walking around, you will have more than earned a stop for pre-dinner drinks at Deschutes Brewery’s Portland Public House. Just one of 53 breweries and counting located in Portland (making Portland the brewery capital of the world), Deschutes opened its Portland Public House in 2008, bringing its Northwest Oregon flavor into the heart of the Pearl District. Kick back and enjoy 18 taps worth of Deshutes staples, seasonal selections and experimental brews in a relaxed atmosphere.
7PM CLYDE COMMON
1014 SW STARK ST. PORTLAND, OR 97204
Portland is famous for its farm-to-fork foodie philosophy, and proximity to bountiful local resources means you can find the freshest ingredients almost everywhere, including hip Ace Hotel nosh spot Clyde Common. After going ultra low-key for lunch with your food cart tour, it's time to get gussied up and go all out for dinner at this European-style dining establishment featuring ingredients from the ample Northwest Oregon farmlands. Savor dishes that are fresh and trendy without being unrecognizable and some of the best cocktails in the city alongside in-the-know locals around long communal tables.
Don't lose steam yet! Portland has a thriving arts and music scene to say the least, and you can get a healthy dose of both at popular indie-infused venue Holocene. A nightclub, event space, and music and arts venue rolled into one, Holocene offers everything from epic dance parties to live bands to artsy multimedia events on any given night, transforming the old 5,000-square-foot auto parts warehouse that accommodates it into an industrial-chic hipster haven where you can dance the night away in your beat up Chucks.
10AM VOODOO DOUGHNUT
You simply can't leave Portland without experiencing the devilishly decadent pastries at Voodoo Doughnut; it's a rite of passage. The creepy confections at this cultish culinary destination feature unique toppings ranging from bacon to cookies to sugary cereals. Grab yourself a classic Voodoo Doll Doughnut (each one a sugary snowflake of a pastry, uniquely decorated and unlike any other before it) and envision all your most odious spurned lovers as you bite off the deliciously frosted head.
11AM POWELL’S CITY OF BOOKS
After overdosing on doughnuts, embrace your inner bookworm at Powell's City of Books, a local landmark and literature lover's dream encompassing an entire city block. Grab a map; you're gonna need it to navigate the nine color-coded rooms housing more than 1.5 million new and used books organized among 3,500 different sections.
1205 SW WASHINGTON ST. PORTLAND, OR 97205
In further celebration of the food-cart culture of Portland, check out former-food-cart turned stationary sandwich shop Lardo. Carnivores will delight in the meaty menu items (even the fries are smothered in pork scraps), which range from more traditional options to unique hybrid creations such as the Pork Meatball Banh Mi and Pork Belly Gyro. But don't worry, veggies; there are green options as well, such as the Roasted Asparagus Sandwich and Kale Salad, and both carnivores and herbivores can agree on the tasty cocktail menu and craft beer selection.
3PM PORTLAND JAPANESE GARDEN
After lunch, get your zen on at the Portland Japanese Garden, lauded as one of the most authentic outside of Japan. Leave your worries and the outside world behind as you weave your way through five separate but harmonious styles, from the Tea Garden to the Sand and Stone Garden, immersing yourself in a lush world of serene streams, tranquil walkways and rich greenery.
3PM HOLLYWOOD THEATRE
If there are two things Portland has plenty of, it's craft beer and film fests. Kill two birds with one stone by bringing happy hour into the theater at one of the many "brew 'n' view" spots in the city. A non-profit Portland mainstay since 1926, the historic Hollywood Theatre, with its authentic old-school marquee and newly renovated sound system, is the perfect spot to catch an indie flick, art film or old Hollywood classic while enjoying some pizza and a pint.
8PM DOUG FIR LOUNGE
It wouldn't be a trip to Portland without some ultra-obscure music, right?Doug Fir Lounge is your best bet for a cool, modestly priced live show that is not so indie as to be unrecognizable, but indie enough that you can catch a buzz-worthy new band in an intimate setting before they hit stadium-level stardom. You're likely to get a good blend of some nationally recognized acts opened by as-yet-unknown local artists in a log cabin-esque lounge setting that makes for some high quality acoustics and a hip atmosphere.
WHERE TO STAY: HOTEL VINTAGE PLAZA
422 SW BROADWAY PORTLAND, OR 97205
You're on vacation—might as well treat yourself! A four-diamond boutique hotel in the heart of downtown Portland, Hotel Vintage Plaza was named one of the "Top 500 Hotels in the World" in 2009 by Travel + Leisure Magazine. Each room is themed after a local winery or vineyard to honor Oregon's world-class wine industry.