In case you haven't noticed, I like a good deal. Portland has so many restaurants, trying them all for full evenings out would be a financial undertaking akin to a downpayment on our first house. So I have become a self-proclaimed expert on Portland's abundant happy hour scene, a scene that has allowed us to sample restaurants that would otherwise be outside our normal dining budget. After 18 months of exploration, here are my six favorites, from the casual to the upscale:
Dig a Pony: This is where the 20-something hipsters come to play like it's 1899. Huge windows fill this lovely open space with natural light; the artisanal lightbulbs and plentiful candles means attractive lighting for all once the sun sets. Exposed brick walls, an old-fashioned horseshoe bar, and a smattering of old books class up the joint, while the thumping (but always hip) music keeps it young, and the moody bartenders with their suspenders and bowties keeps it attitudinal. Happy hour runs until 7, with local beers, well drinks, and plates of food all $3. Best bet: the Cubano. The fries are good, too.
Hubers (411 SW Third): For something completely different - think 1890s without the irony - get to Huber's early to snag a booth in its dark-wood bar before it fills up with happy hour regulars. The menu is not particularly noteworthy other than its incredible cheapness: a long list of meal-sized dishes for $3 or $4. Since the food's such a deal, splurge on a Spanish coffee, the making of which Huber's has turned into performance art.
Clyde Common (1014 SW Stark): A new classic on the Portland scene, Clyde Common combines the woodsy/light industrial look with well-executed dishes that typify Portland's trendiest food trends (e.g., nettles, terrines, obscure pasta shapes, various forms of pig). The happy hour food menu is limited - you're here primarily for the $5 cocktail specials, most of which involve bourbon. Sitting around the communal table as the open kitchen behind you gets on with dinner prep, you will feel jazzed and maybe even a little hip; you might even feel inspired to stay for dinner, but be forewarned that the dinner menus aren't even printed until happy hour ends at 6.
Heathman (1001 SW Broadway): On the other side of downtown, and at the other end of the new school/old school spectrum, is the Heathman Hotel. Portland doesn't go for grand or ostentatious; it likes understated and comfortable elegance, which pretty much sums up this traditional lodging and dining establishment. The Heathman's reliably excellent restaurant is a popular lunch spot for lawyers and business types, and its bar is a classy choice for an afterwork drink. A cheaper food menu is available all night long in the bar and in the tea court lounge, where you can sip with sophistication on chaise lounges and love seats underneath the grand chandelier. Even better, the tea court lounge hosts live jazz Wednesday through Saturday.
ClarkLewis (1001 SE Water Ave.): For a classy but modern ambiance, head over the Hawthorne Bridge to the cluster of trendy establishments in the inner east side's warehouse district. ClarkLewis was a hot restaurant five or seven years ago; the buzz has died off, which just translates to "same great space, more chill vibe." I love that their happy hour drinks include real martinis and gimlets - and more-than-just-house wines - for $5. As for the food, expect a scaled-down version of their regular fare, not as good or as intricate but a decent value: a deliciously fatty burger is $6, a plate of house-made spaghetti bolognese (properly cooked al dente and not overladen with sauce) is $4, and a large green salad with seasonal toppings is $3. They also keep a dessert option on the happy hour menu (usually around $3, too), so you could have a full three-course meal for $12-$15 per person. Particularly on a nice day, with the garage-door windows rolled up, this lovely space feels positively date-like, or at least more New York than new Portland. Happy hour runs daily until 6:30 (6:00 on Fridays).
Lincoln (3808 N. Williams): Like Clyde Common, Lincoln focuses on what I think of as new Portland cuisine - house-made mousses and terrines; perfectly prepared local vegetables; well-seasoned game ragus. Like comfort food, but cooked with the precision of a French-trained chef (and speaking of chefs, chef-owner Jenn Louis is one of the best in town). Even the space feels like an upscale pub, with big windows and comfortable booths and a small bar flooded with light as the sun sets. Service is friendly and attentive; the happy hour menu is ample and constantly changing to keep pace with seasonal ingredients. This is a perfect end to the day: mellowing over plate after plate of perfectly executed fare while watching the bike commuters on N. Williams whizz by. Happy hour runs until 7 on weekdays.