An insider's guide to Portland

Portland, Oregon boasts a real hipster vibe, with edgy bars, a thriving art scene and well-established coffeehouse culture. But the city also offers unprecedented access to the great outdoors, fine dining and some quirky tourist attractions.

With so much to discover, we sought the advice of Portland native Kristian Fleming, 42, who lives in the Piedmont neighborhood of northeast Portland. Here are his four must-visit places in Portland.

Where to Eat
Jake's Famous Crawfish
401 SW 12th Ave., 503-226-1419
“You can’t go wrong with Jake’s if you’re craving fresh seafood,” said Fleming. Open since 1892, this legendary downtown seafood restaurant serves up fresh Northwest fish delivered daily, such as cedar plank-roasted salmon, Oregon Dungeness crab, and razor clams. The setting is casual yet upscale and almost always packed—drawing a mix of after-work locals and tourists alike.

Where to Drink
Clyde Common
1014 S.W. Stark St., 503-228-3333
Located inside the Ace Hotel near the trendy Pearl District, this homey tavern “is a great place to start the evening,” said Fleming. Guests can sit at communal tables and sip unique cocktails, such as the Broken Bike ($8) made with cynar, verdejo and orange zest. A rustic, affordable menu emphasizes local, seasonal ingredients and caters toward a younger crowd. Happy hour lasts from 3-6 p.m. (Mon.-Fri.), when sophisticated signature cocktails cost just five dollars a pop.

What to See
Pittock Mansion 3229 NW Pittock Dr., 503-823-3623, pittockmansion.org
Portland offers terrific mountain landscapes, but visitors don’t need to scale Mt. Hood to take in the scenery. “Mt. Hood, Mt. St. Helens and Multnomah Falls are obvious choices,” said Fleming, “but a lesser-known spot is Pittock Mansion.” This historical estate ($8 entrance fee) offers visitors “a great view of the mountains in the distance and the city below” Fleming said, not to mention a peek into the lives of Portland’s old-school elite. The mansion is lushly decorated, and is situated on Pittock Acres Park, boasting fragrant gardens, miles of hiking trails, and astounding mountain views.

What to Do
Shanghai Tunnels Heritage Tour, 503-622-4898, shanghaitunnels.info
White slavery, prostitution, narcotics — all are part of Portland’s seedy, remarkable “underground” history. Visitors interested in learning about Portland’s sordid side can take a $13 walking tour of the “Shanghai Tunnels” that were created in the late 1800s — a series of trap doors, passageways, and secret spaces located below street level and stretch along the city’s waterfront. “It may be a little bit cheesy,” said Fleming, “but you’ll learn about the history of old Portland and hear some spooky stories along the way—just remember to bring a dust mask.”