My pursuits here would once have gotten me expelled: sipping a fresh-squeezed lemon drop cocktail in the former storage room (now a cigar room and cozy bar); enjoying a frisky movie (The Graduate) in the creaky-floored auditorium; and perusing bottles of pinot noir, whiskey, and other "school supplies" for sale in what was once the principal's office. I feel like I'm back in public school again, only with Jerry Garcia as hall monitor and Ken Kesey as head of the PTA.

The Kennedy School's vice-without-the-vice-principal curriculum plays a big role in luring patrons here night after night. But another big draw is the price: $109 for overnight accommodations for two, plus free admission to the nightly movies, free parking, free use of the heated outdoor soaking pool, and free breakfast at the inn's restaurant. The great deal made my morning meal of scrumptious beer-batter pancakes taste all the sweeter.

Ways to Play in Bargain City Here are two fun itineraries to help you put together a great getaway in Portland that's priceless but not pricey.     By David Sharp  Itinerary #1: Budget Elegance Friday Check-In—MacMaster House Bed & Breakfast Inn. Railroad financier's stately mansion built in 1895. Near upscale Nob Hill shopping district and bucolic Washington Park. 1041 SW Vista Ave. $90-$150; full breakfast included. (503) 223-7362. Kick-Off Spa Treatment—Dosha. 2281 NW Glisan St. Full-body massage $60/60 minutes. (503) 228-8280. Get Your Bearings—Hop the streetcar. Explore the artsy Pearl District and hip Nob Hill without breaking a sweat on the 4.8-mile loop. $1.25 per ticket. (503) 238-RIDE. Friday Dinner—Higgins Restaurant & Bar. Northwest cuisine. The dress code varies from tuxedos to Birkenstocks, and the menu ranges from Columbia River sturgeon to pork tenderloin. 1239 SW Broadway Ave. Entrées $15-$27. (503) 222-9070. Saturday Morning—Portland Classical Chinese Garden. A labyrinth of vest-pocket gardens, keyhole-shaped portals, a hushed teahouse, and more than 500 tons of stonework shipped from Suzhou, China. NW Third Ave. and Everett St. Admission $6. (503) 228-8131. Saturday Lunch—Huber's Café. The Spanish coffee-and the pyrotechnic show that waiters put on when making it-is a Portland institution. 411 SW Third Ave. Lunch entrées $5.95-$8.95. (503) 228-5686. Saturday Afternoon Shopping—Sellwood's Antique Row. Dozens of shops sell a grandpa's attic assortment of antiques, including 19th-century daguerreotypes, Oregon landscape paintings, antique saddles, and '50s-era furniture. SE 13th Ave., from Sherrett to Lambert Sts. Additional shops at nearby SE Bybee Blvd. and Milwaukie Ave. Saturday Dinner—Caprial's Bistro. Best known for their PBS cooking show, chef-owners Caprial and John Pence also run a popular local bistro with an ever-changing menu, recently featuring free-range chicken and panfried ravioli. 7015 SE Milwaukie Ave. Dinner entrées $19-$30. (503) 236-6457. Saturday Night Entertainment—Wilfs Restaurant & Piano Bar. This cozy jazz club inside historic Union Station exudes Orient Express-style romance. 800 NW Sixth Ave. and Irving St. Cover $3 on Friday; free on Saturday. (503) 223-0070. Sunday Great Outdoors—Park Blocks. This blockwide green space runs like a stripe through downtown and is full of coffee shops, historic churches, museums, and eclectic public art, including works by Renoir and Henry Moore (at the Portland Art Museum's free outdoor sculpture mall). Park Avenue, from SW Jackson St. to NW Glisan St.  Itinerary #2: Portland on the Cheap Friday Check-In—McMenamins Kennedy School. A historic inn, brewpub, and entertainment complex housed inside an artfully restored schoolhouse in the northeast Concordia neighborhood. 5736 NE 33rd Ave. Rate $109; includes free breakfast and admission to the hotel theater with overnight stay. (503) 249-3983. Kick-Off Massage—Sassé Salon & Spa. 630 SW Alder St. Fifteen-minute chair massages for $15; foot reflexology $35/30 minutes; full-body massages $65/60 minutes. (503) 228-8266. Get Your Bearings—Pioneer Courthouse Square. Prime people-watching spot loaded with resources: Portland Oregon Visitors Association info counter; Ticket Central, a clearinghouse for half-price, same-day theater and concert tickets (hotline: 800-962-3700 or 503-275-8358); Tri-Met office that sells transit tickets and provides free transit maps and schedules (weekdays, 8:30 a.m.-5:30 p.m.); and Powell's Travel Store, specializing in travel-related books and gadgets. Between SW Sixth and Broadway Aves., at Morrison and Yamhill Sts. Friday Dinner—Jake's Famous Crawfish. 401 SW 12th Ave. From 3 to 6 p.m. weekdays, the huge-portions-low-price happy-hour menu includes chicken-and-crawfish etouffee, Icelandic cod fish and chips, seafood tacos, and cheeseburgers made with Tillamook cheddar. Prices $1.95-$3.95, plus $3.50 minimum beverage purchase. (503) 226-1419. Saturday Morning—Ballet under the elms. From August 19 through September 1, the Oregon Ballet Theatre gives picnickers a sneak peek at the fall season. Dancers rehearse daily on an outdoor stage in picturesque South Park Blocks. SW Park Ave. and Salmon St. 10 a.m.-4 p.m. daily. Free. Saturday Lunch—Pearl Bakery. Anywhere else, a PB&J is just a sandwich. Here, it's made with bread baked by Greg Mistell, the coach of the U.S. baking team that won the 1996 Coupe du Monde (the World Cup of baking). 102 NW Ninth Ave. Sandwiches $2-$5. (503) 827-0910. Saturday Shopping—Powell's City of Books. The world's largest independent bookstore. Before leaving, take a ride on one of the world's only three-door elevators. 1005 W. Burnside St. (503) 228-4651. Saturday Night—Oaks Amusement Park. Coney Island-style park has thrill rides dating to the '50s, the largest roller rink on the West Coast, and a 1912 carousel that's on the National Historic Register. Adjacent to the east bank of the Willamette River, just north of Sellwood Bridge on SE Spokane St. Free admission to the park. Ride prices vary. Skating costs $4 to $5.75, depending on the time and day, and includes skate rental. (503) 233-5777. Sunday Great Outdoors—Walk the river. A 1,200-foot floating walkway-dubbed the Eastbank Esplanade-extends onto the Willamette River, and avid walkers and cyclists swarm here on weekends for the rare thrill of feeling the path beneath them bounce from the wake of passing motorboats. If you're ambitious, turn the Esplanade (between the Hawthorne and Steel Bridges) into a larger loop that includes Governor Tom McCall Waterfront Park and the two spans. Total loop 2.8 miles. Free.

This mix of quirkiness and affordability is hardly unique to the Kennedy School. In this city of sustainability-minded, proudly eccentric individualists, Portlanders have taken the things that most other cities bulldoze, pave over, or throw away and turned them into the coolest attractions in town—all the while turning Portland into one of the hottest cities in America.

Mention Portland to savvy urban planners, cyclists, hikers, shoppers, avid readers, gourmets, or music fans anywhere and they're likely to let loose with a tsunami of accolades. Among the things they'll crow about: nearly 250 miles of bike routes and more than 200 parks and public gardens, including 5,000-acre Forest Park, the largest U.S. wilderness park within any city's boundaries. Portland also offers a vast array of offbeat shops like Hippo Hardware, a 30,000-square-foot trove of new and used house parts so vast and unusual that grade-schoolers come here on field trips, and Powell's City of Books, the world's largest independent bookstore. There are also dozens of music clubs showcasing genres from bluegrass to reggae and every flavor of jazz imaginable, and splendid yet affordable restaurants that trumpet such Northwest delicacies as Columbia River sturgeon, Willapa Bay oysters, and locally crafted cheeses, wines, and beers.

Indeed, Portland is so routinely celebrated as one of the nation's top places to live by magazines ranging from Money to Outside and so frequently lauded as kid friendly, disability friendly, pet friendly, and most wired (electronically, that is) that locals sometimes take such kudos for granted.

Yet for all the praise heaped on it, Portland seldom gets any recognition for what may be its greatest accomplishment: making its cosmopolitan riches available to locals and travelers alike at bargain prices. I've lived in Portland for a decade, and its affordability still catches me by surprise. One recent weekend, I took a stroll through 97-year-old Oaks Park, the nation's oldest continuously operated amusement park, which boasts a National Historic Register carousel, the largest roller rink on the West Coast, and no admission charge. Later that day, I enjoyed a gospel concert at Billy Reed's, a club that never hit me up for a cover. That night, I paid less than $100 for a room at the Mallory, a grande dame-style hotel known for its power broker clientele, its uptown location, and a tempting restaurant menu that's easy on the wallet.

I've witnessed out-of-towners look almost dazed, as if they'd wandered into a fiscal time warp, after discovering the deals to be had here. "You mean, if the tag says $19.80, the price is really $19.80?" asked my 15-year-old nephew, visiting from Indianapolis, incredulous that stores and restaurants in Oregon charge no sales tax. He seemed just as flabbergasted when we then boarded a city bus without paying. (Public transit is free throughout downtown and parts of the east side—a sizable swath of territory dubbed "Fareless Square.") In other cities, a cab ride from the airport to downtown can cost $40 or more. Here, you can skip the cab by hopping the recently opened light-rail line for $1.55.

Peter Reader, a former advertising manager and native New Yorker, was so bowled over by Portland's low-cost livability when he visited in 1998 that he actually packed up and moved here. "Portland is big enough to sustain everything I like in a city," he says. "But it's also affordable, spectacularly beautiful, and small enough that I can walk, bike, or take public transportation everyplace. It's to the human scale."

Why is Portland such a steal? Partly, simple economics: Incomes in Portland are lower than in many other big cities, so the cost of living—and playing—is cheaper here, too. Since businesses cater mainly to locals, prices can't creep too high without prompting Portlanders to label them "spendy," a regional pejorative that's more effective than a fire alarm at making customers race out the door. "In Portland, you're rarely going to find a main course that's over the mid-$20s, and for most part, you're going to get tremendous dishes for under $20, with generous portions, too," says Greg Higgins, chef-owner of Higgins restaurant.

What also helps to hold down prices is the city's unique personality—an odd mix of funkiness, contrariness, and outdoorsiness reminiscent of a beloved aunt who clomps around in hiking boots and a nose ring. To catch the local mind-set in all its glory, I often drop by Pioneer Courthouse Square. Known as "Portland's living room," this downtown brick plaza regularly looks like some skewed version of a Where's Waldo? puzzle, with ethnic festivals, gay pride rallies, hacky sack players, anarchists, shoppers, sidewalk preachers, and picnicking office workers all thrown together and loving every minute of it.

Portlanders can thank their own enlightened cussedness for ensuring that many of the city's greatest treasures are still around. Decades ago, when other metropolitan areas couldn't pour pavement fast enough, Portland was canceling highway projects and limiting urban sprawl to safeguard the character of its downtown and close-in neighborhoods. The city even jack-hammered a downtown expressway that bordered the Willamette River to make way for Governor Tom McCall Waterfront Park, which now reverberates all summer with joggers, cyclists, impromptu drum circles, and outdoor festivals. "We're now bearing the fruits of truly forward-thinking decisions that were made in the 1970s," says Catherine Ciarlo, executive director of the Bicycle Transportation Alliance, a statewide bicycle-advocacy organization.

If you're going ... All phone numbers are area code 503 unless noted. Pick up AAA's Portland map and Oregon & Washington TourBook. For general information and "cool summer deals" on hotels, contact the Portland Oregon Visitors Association, 275-9750, (877) 678-5263, www.travelportland.com. Sleeps Benson Hotel, 309 SW Broadway Ave. $145-$255. 228-2000, (888) 523-6766. Doubletree Hotel Downtown, 310 SW Lincoln St. $79-$350. 221-0450. Heathman Hotel, 1001 SW Broadway Ave. $149-$650. (800) 551-0011. MacMaster House Bed & Breakfast Inn, 1041 SW Vista Ave. $90-$150. 223-7362. Mallory Hotel, 729 SW 15th Ave. $95-$165. (800) 228-8657. McMenamins Kennedy School, 5736 NE 33rd Ave. $109. 249-3983. Eats Bluehour, 250 NW 13th Ave., 226-3394. Caprial's, 7015 SE Milwaukie Ave., 236-6457. Heathman, 1001 SW Broadway Ave., 241-4100. Higgins, 1239 SW Broadway Ave., 222-9070. Huber's, 411 SW Third Ave., 228-5686. Jake's Famous Crawfish, 401 SW 12th Ave., 226-1419. Pearl Bakery, 102 NW Ninth Ave., 827-0910. Rivers, 0470 SW Hamilton Ct., 802-5850. Wildwood, 1221 NW 21st Ave., 248-9663. Things to See and Do Billy Reed's, 2808 NE Martin Luther King Jr. Blvd., 493-8127. Forest Park, between NW Skyline Blvd. and St. Helens Rd., 823-2223. Governor Tom McCall Waterfront Park, along Naito Pkwy., 823-2223. Hippo Hardware, 1040 E. Burnside St., 231-1444. Jimmy Mak's, 300 NW 10th Ave., 295-6542. Kidd's Toy Museum, 1300, 1301, and 1327 SE Grand Ave., 233-7807. Oaks Amusement Park, SE Spokane St., 233-5777. Periodicals and Books Paradise, 3315 SE Hawthorne Blvd., 234-6003. Pioneer Courthouse Square, SW Broadway Ave. and Yamhill St. Portlandia, 1120 SW Fifth Ave. Powell's City of Books, 1005 W. Burnside St., 228-4651. Urban Wineworks, 407 NW 16th Ave., 226-9797. Wilfs Restaurant & Piano Bar, 800 NW Sixth Ave., 223-0070.

Because of those decisions, many historic buildings and pre-World War II business districts that would have become victims of the wrecker's ball have been preserved—and now bustle with restaurants, theaters, and shops offering a one-of-a-kind ambience and an oddball assortment of merchandise that no suburban entertainment complex could hope to duplicate.

Sellwood, a southeast neighborhood that's the closest thing Portland has to a grandpa's attic, routinely draws hordes of scroungers to its dozens of antique stores stuffed with back-in-vogue '50s furniture, vintage fishing tackle, 19th-century daguerreotypes, and other dusty treasures. The Pearl District, immediately north of downtown, is packed with such a profusion of art galleries that a simple stroll through the neighborhood turns into a crash course in contemporary painting, sculpture, and photography. The chic westside Nob Hill, known for its hot restaurant scene and funky boutiques, spills over with half-century-old Japanese kimonos, Ecuadoran sweaters, and other global goods. The bohemian Hawthorne District on Portland's east side attracts Gen Xers and nostalgia buffs alike to its classic theaters and retro shops, such as Periodicals and Books Paradise, which carries a quarter million vintage and newer magazines, including such defunct favorites as Look and Life dating to the 1930s, usually for $8 or less a piece.

What you won't find—by design—is the standard tourist district riddled with souvenir shops and locals-wouldn't-be-caught-dead-there, overpriced theme restaurants and bars. Instead, Portland is full of excellent yet reasonably priced establishments serving superb Northwest fare. Top spots include Caprial's, Heathman, Higgins, Rivers, and Wildwood. "This region has the best salmon in the world, great seafood—razor clams, prawns, oysters, sole, and cod—and probably 50 varieties of mushrooms, gathered in the wild and brought in at different times of the year," says chef Higgins.

Lying within the fertile Willamette Valley, known both for its vineyards and for its hops, Portland is also awash in award-winning, locally produced wines and beers. At the Heathman Restaurant, for example, the wine list goes for 20 pages and includes many of the Pacific Northwest's best vintages. And at Urban Wineworks, a combination tasting room and art gallery that features Oregon wines for as little as $7 a bottle, the staff will even hand you a beaker so you can combine different straight-from-the-barrel wines into your own custom blend.

The city's reputation for affordability sometimes serves as a self-fulfilling prophecy. Case in point: Leading jazz musicians have moved here in such droves in recent years to escape the out-of-sight rents in other, pricier places like New York City and San Francisco that Portland has quietly become a jazz powerhouse. The city now blossoms with clubs that offer top-caliber music for low cover charges (from zero to $6, typically). "Per capita, there are way more jazz musicians and venues in Portland than in New York," says Thara Memory, a local jazz trumpeter and orchestra conductor. "Portland has the scene that New York had 30 years ago."

On a recent Saturday night at Jimmy Mak's, named one of the 100 best jazz clubs in the world by Down Beat magazine, I heard a nine-piece band all but peel the paint off the walls with a sizzling, evening-long tribute to great African American jazz musicians dating as far back as 19th-century savant "Blind Tom" Bethune. The following week, I trekked over to 106-year-old Union Station—the nation's oldest continuously operated passenger train station—to hear cool jazz in what's easily the most atmospheric jazz room anywhere: Wilfs, filled with wing-backed chairs, brass chandeliers, and other elegant accoutrements.

Since Portland tends not to festoon its greatest assets in neon and blinking lights, you have to stay alert when exploring the city or you might overlook some of its most intriguing attractions. Blink as you go by and you might miss discovering that Portlandia, the second largest hammered copper statue in the United States (the Statue of Liberty is the largest), lurks on the ledge of the postmodern Portland Building, above a canopy of trees. Or that Kidd's Toy Museum, home to 10,000 mostly vintage toys, including mechanical banks, lead soldiers, and model trains, resides in three innocuous eastside buildings, two of which double as auto parts stores. Or that dancers with the Oregon Ballet Theatre rehearse outdoors in the South Park Blocks daily during late summer and invite the public to bring a picnic lunch and watch.

Or that all the sights I just named are absolutely free.