Why Go
Not to oversell, but Portland is quite simply the coolest city in the Pacific Northwest, and potentially one of the most effortlessly hip places in the entire country. Its inhabitants, besides showing off the latest fashions and tattoos, enjoy artisan beer and cheese, farm-fresh produce, upscale yet affordable places to drink and superior urban planning. It's a city populated by people who, despite the fact that it gets a bit rainy and chilly during the winter, manage to remain absolutely chipper compared to East Coasters who are used to suffering through equal periods of sunlight deprivation.
Enterprising developers have consistently revitalized different parts of the city, whether it's the McMenamins buying up old haunted properties and turning them into exciting hotels and pubs or friends of vintners sprucing up downtown with fancy (yet not pretentious) wine bars. With so many farms nearby and a citywide focus on sustainability, it's possible to eat at the finest restaurants and rest assured that all ingredients came from nearby, including the fruit and mint being muddled in the cocktails.
Equally important are the prices: all of those touches in fancier States cities that people pay out the nose for come standard a lot of the time, meaning that it's simpler to find a pristine bed and breakfast or farmhouse, head out for a three-course romantic dinner, and then hear a fantastic DJ or have drinks at a super-hip speakeasy-style watering hole for a fraction of the cost that the same activities would run in Los Angeles or New York. With plenty of green spaces for exploring, one of the most beautiful public gardens in the world (The International Rose Garden), and public transportation and countless bicycles that lead to people spending their time out and about, it's a city that deserves all of the accolades that it gets. Just consider planning a vacation for spring, summer, or fall, rather than in the chilly months of winter.
Insider Tips
- It's important to learn that everything revolves around the happy hour, with everything from the food and the home-brewed beer to the most high-class cocktails priced in a stunningly affordable manner. The quality at happy hours will always be just as high as actual dinnertime, so it's an incredible way to enjoy a martini and a top-notch entree for a fraction of the cost, but with all of the same ambiance.
- For those who plan on moving outside of downtown, while the public transportation (buses and the green-energy tram) do go where they need to, they might not go where you need do. Don't shy away from using cabs or renting a car, as it's sometimes the quickest method of getting from point A to point B.
- Expect to drink a lot of coffee. Even if it's summertime, Portlanders really like to partake in caffeinated beverage, and in the chillier months, coffee consumption quadruples. To really fit in (or enjoy the ambiance of some of the city's best cafes and coffeehouses), it's best to relax with a coffee-based beverage and perhaps a piece of local artisan chocolate.
- The Pearl District used to be the land of warehouses and industry, but today, houses countless different art galleries and live-work spaces. For a leisurely afternoon strolling from shop to shop, there's no better place to go exploring.
- When packing for Portland, bringing an umbrella is actually a must, no matter the season. While a light rain might not bug locals, it could put a damper on exploring by foot, so it makes sense to come prepared.
- For antiquing and vintage shopping that involves going store to store rather than pile to pile, heading to Hawthorne Street means indulging in the best retail therapy that manages to avoid chain stores. It's a perfect stop for relaxed window shopping and an excellent way to understand the lay of the land.
Where to Stay
Hotel Monaco, right in the heart of downtown Portland is the perfect choice if you want 4-star luxury, complete with a complimentary wine tasting in the evenings (snacks and chocolate included!), spacious rooms and friendly, helpful staff. It's also a very pet-friendly hotel (no extra charge) so great for pet lovers but not for allergy sufferers.
Minutes away from downtown's best shopping and galleries, the McMenamins Kennedy School was once a place of learning and is now home to everything from a movie theater, brewery, and 35 stunning guestrooms that have managed to keep original touches intact (like telephone booths and chalkboards) but provide a truly acceptable level of boutique hotel service. The former classrooms are done up with warm colors and fantastic local art and feature great antique furniture and a true sense of style. For anyone who wants to be in the heart of Portland's thriving downtown scene (and see movies for free, too), it's definitely the place to be. And despite all of the energy happening in the same building, rooms are quiet and cozy enough that it feels like an entirely different world.
Those who don't mind a commute to the city might consider staying at Edgefield a different McMenamins property located a 20-minute drive from Portland's city center. Once the country's poor farm, Edgefield is now 74 acres of upscale dining, wine tasting, organic spa treatments, and golf. The lack of technological distractions in rooms (telephones and televisions aren't present but phenomenal upscale country decor is) makes it even easier to really get away. There really is nothing quite like it, and while the word “quirky” doesn't really fit, it's safe to say that this is the kind of repurposed use of space that could only happen in Portland. Plus, how often do you get to stay that you spent the night at a National Historic Landmark?
What to Eat
For a romantic French dinner for two, look no further than Le Pigeon. If your sweetheart and you are foodies, try to reserve the Chef’s Counter to get an up close view of Chef Gabriel Rucker as he orchestrates his masterful creations, from duck meatballs with truffles to beef cheek bourguignon to foie gras profiteroles with caramel sauce.
Not to worry, if upscale French cuisine isn’t your style Portland has many lower key, quirky cafes, bars and multi-purpose spaces. One of these, the Doug Fir Lounge, manages to combine a restaurant with a swank outdoor patio, complete with fireplaces and bamboo décor, and a downstairs bar with live music. It channels the feeling of an old hunting lodge (wear flannel and you won’t feel out of place) and has a floor reminiscent of the Hudson Hotel's original bar. It's an appropriate venue for grabbing breakfast, lunch, or dinner (stay with simple classics such as the burger for dinner or eggs benedict for breakfast), as well as for enjoying truly stellar and shockingly affordable cocktails. The stylish, vaguely arty people enjoying blackberry mojitos next to you might be local scenesters…or they might be touring DJs and bands performing downstairs. Another example of impeccable Portland style, which combines friendly service with a cosmopolitan atmosphere.
Stumptown Coffee has managed to make its way from Portland all over the country, but heading to one of the original spots means getting to taste the best brews at their very source while snacking on organic pastry treats. A fantastic start to a day of sight-seeing, those who pick the Stumptown located in the Ace Hotel can also relax on one of the comfortable lobby sofas, poach the Wi-Fi without incident, and figure out what to do with the rest of the day.
A true Portland institution, Jake's Famous Crawfish has managed to hold onto its original flair, despite 100 years of changes and a shifting of ownership. Look for the unmistakable neon sign and head indoors, where things are likely to be busy but not overly packed or loud. Grabbing a table that's tucked away is a breeze, and the staff is kind but not overly attentive, meaning the chance to enjoy seafood staples such as pristinely fresh oysters and halibut cheeks. Jake's is also a great place to enjoy more of Portland's signature affordable yet stellar cocktails, which make use of fresh juices and local ingredients. There's also a fantastic selection of craft beers and local wine from the Willamette Valley. Save room for luscious desserts such as chocolate truffle cake and three berry cobbler. Happy hour specials, available 3-6pm with a $3.50 minimum beverage order, include garlic steamed mussels ($4.95), salmon cakes ($3.95) and oyster shooters ($1.95 each).
What to See
The International Rose Test Garden is known for its stunning collection of roses from around the world, as well as a large number of varieties that it developed itself. For those who care about gardening, it's an incredible and inspiring resource for checking out the future of flowers. For anyone who appreciates natural beauty, it's a great chance to take a break from the city, though Portland's pace of life is everything but frenetic. Especially great on sunny days in springtime and summer, when it's packed with locals and tourists alike.
For dancing while a band plays (or learning to dance via lessons), the Crystal Ballroom is the ideal destination. For history buffs, it's well worth a visit, considering that the Crystal Ballroom first opened its doors in 1914 and has since then seen rock and roll legends, Depression-era revivals, and contemporary legends from all musical genres. With a nationally-famous dance floor (it moves while you do), there's no better place to take that special someone who is in the mood for a truly unique night on the town.
The Lan Su Chinese Garden in Portland might not be particularly huge, but what it lacks in size it makes up for in stunning charm. A walkway designed for visitors to see the various different spaces at exactly the right angle, it's a great place to explore any day, though it does get more packed during special activities at the Chinese New Year and when the weather is particularly nice.
For a ballet, theater performance, or lecture on the arts, the Portland Center for the Performing Arts is an excellent place to head for truly well-rounded cultural experience. Visually compelling interiors and a fantastic central location make it easy to get to, and with the caliber of entertainment scheduled throughout the year, it's a reliable bet even if what's on happens to be unfamiliar.
