Best pedaling: According to the U.S. Census, Portland ranks as the top large American city for the number of commuters biking to work, in part because of its myriad bike lanes and paths. A favorite is the Waterfront Bike Loop (503-823-7529), an almost three-mile route that runs through Tom McCall Waterfront Park and the Eastbank Esplanade. The path, friendly to bikes and pedestrians, traverses a 1,200-foot floating walkway on the water and offers great views of the city. Daily bike rentals are available via Fat Tire Farm (503-222-3276).
Best snow fix: Mount Hood is just one and a half hours east and home to four ski resorts. The highest runs are at Timberline Lodge (503-622-0717), which is open for skiing an average of 345 days a year-the longest season in North America. The 11,249-foot, glacier-covered dormant volcano is also popular with climbers; about 10,000 mountaineering enthusiasts climb Mount Hood annually. Reaching the peak can be perilous; hire an experienced guide from Timberline Mountain Guides (541-312-9242).
Best hiking: Some cities have a big park in their center, but with 10,510 acres of parkland within the city limits, Portland feels like it's in the center of one big park. The best in-city hiking can be found in Forest Park (503-823-7529); covering more than 5,000 acres with almost 70 miles of serene forested trails, it's the largest wooded city park in the country. Sign up for half-day naturalist-guided hikes with the Friends of Forest Park organization (503-223-5449) to learn about everything from wild thimbleberries (similar to a raspberry) to the ecology of the park's old-growth forest.
Quick tip: Buses are free in the downtown area called the "fareless square," including the Pearl District, home to Powell's City of Books and some of the best galleries in the city. Look for maps at TriMet bus stops; they indicate the fareless area with a grey dotted line.
Best spot to take in the wild side: The Columbia Gorge National Scenic Area (541-308-1700), just 40 minutes east, features some of the most breathtaking waterfalls in the nation, where glacier-fed rivers tumble from basalt bluffs into the river gorge below. Bask in the fine mist coming from 620 feet of falling water at the popular Multnomah Falls, or hike to less-frequented spots like Ponytail Falls, where you'll seldom see another soul.
Best place for urban tranquillity: Thousands of Japanese immigrants made Portland home in the 1880s and were instrumental in bringing economic prosperity to the region. The cultural connection is proudly displayed at the Japanese Garden (503-223-1321), a five-and-a-half-acre wooded park with five distinct garden styles, including a Zen-inspired sand and stone display and a teahouse garden.
Best way to spend a rainy afternoon: Escape the occasional downpour at Powell's City of Books (503-228-4651), an independent bookstore with more than a million titles in a building that occupies an entire block; browsers use color-coded maps to navigate it. Find further guidance from the witty handwritten cards pointing to staff favorites with observations like, "I stayed up until 3 A.M. reading this book, and you should, too..."
Best ecofriendly stay: The Ace Hotel (from $95; 503-228-2277) is a great place to absorb Portland's artful vibe and green sensibility. Recently refurbished, the Ace features artwork painted directly on the walls and a fleet of bicycles so guests can traverse the city like natives.
Best stay for art lovers: The Heathman Hotel (from $189; 503-241-4100) features superior service, a renowned restaurant, and an opulent eucalyptus-paneled lounge. Each room contains original artwork, including the Andy Warhol Suite, which boasts colorful prints by the king of pop art.
Best active stay: Located 42 miles east in the beautiful Columbia River Gorge, Skamania Lodge (from $101; 509-427-7700) features a golf course, spa, and stunning views of the river. The concierge and U.S. Forest Service office in the lobby help guests fill their days with the hiking, windsurfing, and fishing for which the area is known.
Best Wine Country accommodations: The Abbey Road Farm Bed and Breakfast (from $175; 503-852-6278), 32 miles southwest of Portland, offers stays on a working farm in the heart of Willamette Valley wine country. The rooms are fashioned from three former grain silos; yet with heated floors, spa tubs, and divinely soft beds, they feel more like Park Avenue than Green Acres. You'll also enjoy hearty breakfasts including fresh eggs and goat cheese made on-site.