When I was growing up, Portland could have been the poster child for gruel, or anything similarly devoid of color and flavor. In the distant past, Portlanders' role model was a straitlaced lumber baron named Simon Benson, who, legend has it, was so determined to keep his loggers out of taverns that in 1912 he had bronze water fountains installed throughout downtown. The Benson Bubblers are still a welcome feature, especially on hot summer days. (It does not always rain here.)

Portland started to pick up some pizzazz the day in 1984 that a tavern keeper named Bud Clark was elected mayor. Simon Benson surely spun in his grave. He must have spun even more after a passion for craft brewing took hold. Portland currently has 53 breweries, more than any other city on Earth. (Take that, Munich!)

Another turning point came in 1990, when three San Francisco transplants opened an acclaimed restaurant called Zefiro. It closed 10 years later, but not before ushering meat-and-potatoes Portland into a brilliant new culinary era with its seasonal, Mediterranean-influenced menu. Now the city is renowned as a foodie haven, attracting an international crowd to Feast Portland, the annual September food festival.

Hip and cool Portland has left boring Portland in its dust. Now there's even a popular TV show, Portlandia, that parodies how hip and cool — and, OK, maybe a little weird — we are.

The ubiquitous “Keep Portland Weird” bumper stickers are a little embarrassing, only because we stole the slogan from Austin, Texas. But the weirdness in our DNA dates to pioneer days, when early Portlanders did eccentric things and then celebrated them. For example, city founders Asa Lovejoy and Francis Pettygrove decided Portland's name in 1845 with a coin toss, making the “Portland Penny” one of our most exalted icons. Lovejoy and Pettygrove were in turn honored by having streets named for them. Portland native Matt Groening, creator of The Simpsons, went further by naming many of his characters after the city's streets — including the TV show's pastor, Reverend Lovejoy.

Portlanders, even those by way of Brooklyn, cherish the independent, entrepreneurial spirit that has made our town a center of creativity and livability. I know a couple of Portland experts who love to discuss this topic: architect and urban designer Paddy Tillett and historian Chet Orloff . We meet at BridgePort Brewing Co., the oldest craft brewery still in operation in Portland, located in a 120-year-old brick warehouse and former rope factory. Tillett, incidentally, was one of only six Portlanders chosen to grace the label of the brewery's Old Knucklehead ale, back in the 1990s.

His crisp British accent betrays his origins, but since moving here in 1982 and joining the firm of Zimmer Gunsul Frasca Architects, Tillett has proved to be an ardent Portland booster. Orloff, who moved to Portland as a teenager in the 1960s, teaches urban studies, planning, and history at Portland State University. He is also director emeritus of the Oregon Historical Society.

Dipping into our plate of house-made hummus and pita bread, Orloff explains that the concept of livability in Portland was introduced in 1972, when a city plan established requirements to make downtown more people-friendly. Today, street-level windows, flexible height standards, and inviting storefronts all make urban exploring in Portland a joy, says Tillett, who walks to work from his Northwest Portland home. Thanks to the city's founders, who built short, 200-foot square blocks, and later generations of Portlanders, who added extensive parks, downtown has always been green and airy. As Tillett noticed when he first set foot in Portland, “From any street in any direction you could see a wooded hillside with evergreens on it. You never forgot you were in the Pacific Northwest.”

You really can't beat Portland's location. Beyond the wooded hillsides lie mountains: the Coast Range and the lofty, snow-capped volcanoes of the Cascades. Eleven bridges cross the Willamette River within city limits, including the Gothic-style St. Johns Bridge, built in 1931. The Willamette bisects the city and flows into the Columbia River, Portland's border to the north, which in turn flows to the Pacific Ocean.

Governor Tom McCall Waterfront Park, on the west bank of the Willamette, hosts events such as the Portland Saturday Market (the nation's largest continuously operating, open-air crafts market) and the Portland Rose Festival. You can extend a stroll there by crossing over the Steel Bridge or the Hawthorne Bridge to the Eastbank Esplanade for a scenic, three-mile loop.

Portland State University's campus houses the Portland Farmers Market — a festival of fruits and veggies with live entertainment, food carts, and photogenic produce displays. Several blocks north is the Cultural District, which includes the Oregon Historical Society, the Portland Art Museum, and the Arlene Schnitzer Concert Hall, built in 1928 as a Rococo Revival movie palace.

Next door to the Schnitz, as Portlanders call it, you'll find the elegant 1927 Heathman Hotel, a Historic Hotels of America member. The Heathman is renowned for its restaurant, tea court, and library of more than 2,500 books signed by their authors, many of whom have lodged there while appearing at the Schnitz's Portland Arts & Lectures series. The Nines, another top-rated hotel, occupies the upper floors of the former Meier & Frank department store. Departure, its rooftop restaurant, offers one of the best views in Portland.

The Nines' glazed terracotta building was the first major commission of architect A.E. Doyle, whose works, including the beloved Georgian-style Central Library (1913), dot the city. Don't miss the library's exquisite black granite stairway, with words of inspiration such as “Hope,” “Seek,” and “Explore” half-hidden among etchings of flora and fauna.

Another downtown building given new life is the 1883 Ladd Carriage House, a once-neglected English Stick structure transformed by a major restoration into the Raven & Rose restaurant. Owner Lisa Mygrant has modeled it after a British Isles–type gastropub, while honoring the building's past. I make a trip there to soak up the beauty of the place, as well as my favorite Campari-based cocktail, the Souracher. As I sit and sip under a huge framed portrait of William S. Ladd, one of Portland's founding fathers, Mygrant tells me her customers can't get enough of history. “We include the building's history on the menu. People keep taking the menus, but that's OK.”

Back at the brewpub, Tillett surprises me by passing over the Old Knucklehead and ordering a Kingpin, a double red ale. We're hoisting our pints (IPA for me, thank you) at the northern reaches of the Pearl District, a former rail yard and industrial area that now boasts exclusive condominium buildings, upscale boutiques, and restaurants. Turns out we three are all partial to Northwest 13th Avenue, which runs along one side of BridgePort Brewing Co. This is the part of the Pearl that most resembles the gritty warehouse district it once was. Next to cobblestone side streets, the old brick buildings and loading docks are still there, just scrubbed and polished.

As we empty our glasses, Orloff mentions Portland's nearly 100 distinct neighborhoods. “This sense of self-identity has allowed Portland to become the city it is today,” he says. “I still look at Portland as a city of 100 villages. A sense of neighborliness is really the essence of what makes this city livable.”

And you never know which neighborhood will suddenly blossom into the hottest, most desirable place to hang out, shop, and eat. The juxtaposition of new and old, highbrow and populist, is what makes each one so vibrant. Mississippi Avenue and Alberta Street, in the northern reaches of the city, are good examples of this eclectic mix. On Mississippi Avenue you can shop for used construction materials at the ReBuilding Center, and for gourmet salts and chocolates at The Meadow. Alberta Street boasts unique art galleries, as well as the Grilled Cheese Grill, a sandwich shop in an old school bus.

Most recently, funky Southeast Division Street, with its modest homes and secondhand stores, has turned into restaurant row. Practically every local restaurant worth its salt (or Salt & Straw, in the case of the artisanal ice-cream shop) is opening a branch there.

In fact, two of the first restaurateurs to put down roots on Division Street, Duane Sorenson and Andy Ricker, have since expanded all the way to New York. Sorenson founded Stumptown Coff ee, which now has several locations, including two in Manhattan. He also counts Ava Gene's, named in 2013 as one of Bon Appetit's best new restaurants in America, among his four establishments on Division Street. Ricker started his Thai street-food restaurant, Pok Pok, in a Division Street shack in 2005. Now he has three bustling restaurants on Division, one elsewhere in Portland, and three more in New York — including two in, yes, Brooklyn.

Ricker, who was named Best Chef in the Northwest for 2011 by the James Beard Foundation, told me he chose to open restaurants on Division Street because he lived there. “I loved the 'hood already.”

I can relate. I’m pretty fond of my own 'hood, charming Multnomah Village, and as a native, my roots run deep. I suspect I’ll never leave. My son, also a native, moved to Philadelphia a few years ago for a change of scenery. When he told people he had left Portland, they always asked, “Why?” Why, indeed.