Behemoth SODO wine emporium Esquin offers free wine tastings every Thursday and Saturday, with themes like "92 Points and Above," "Viva Argentina," and "Under $10 Specials." Sometimes winemakers join in, and snacks are not unheard of. Check their website to find out which wines they're uncorking. Free.
Every Thursday and Saturday, Vino Verite hosts a casual wine tasting that will not part you from any of your money. Free.
Bottomless anything is good, especially if it involves champagne. Just order brunch at the Coterie Room or Ma'ono (both pretty damn great) and your mimosa ($10 at the former, $12 at the latter) will have no bottom.
Champion owner Emile Ninaud possesses Seattle's very first wine license: He opened in 1969 and works there to this day. Champion's wine tastings—from the more than 1,500 bottles in stock, with tons from France—are all about "obscure wines from obscure regions," he says. Though he's French by birth, he's made Champion a snobbery-free zone, with wine novices welcome and an emphasis on good value for whatever your budget may be. FREE.
McCarthy & Schiering claims to be the oldest wine shop in Seattle; it is not. But they were recognized as retailer of the year by Food & Wine in 1998 and as one of the "top 10 small specialty shops featuring wines from Piedmont and Tuscany” by GQ in 2004. They offer free wine tastings at both their Ravenna and Queen Anne stores every Saturday, with winemakers often there for discussion purposes. Free.
Adrian Ryan says Sylvia O’Stayformore’s drag brunch “features entertainment not only from her own fine self but also a rotating handful of very talented performers. And it is surely the most adventurous of them all—as it features a train ride (magical!), and it happens at the glamorous Royal Room.” $8.
The great DeLaurenti Specialty Food & Wine in Pike Place Market offers free wine tastings upstairs in their wine department every Saturday, and—bonus!—the nice people there pair the selections with some of their more than 250 kinds of cheese, samples from their wall of olive oils, and other assorted tastinesses. Past tastings have included ports paired with Stilton cheese and (separately) Veuve Cliquot champagne (!). Check their website to find out which wines they'll be uncorking. Free.
Civilized but not-too-schmancy wine shop Portalis offers free tastings on Saturday and Sunday. A lot of regulars show up, particularly Ballard-farmers-market shoppers on Sundays. Those people sound smart. Free.
Geeks Who Drink is a company that hosts trivia quizzes at different bars every damn day of the week, here in Seattle and all over creation, usually free (except for bar owners, who pay a "reasonable" rate). Starred for geeks who drink who like pub trivia.
Literally millions of happy hours are taking place around Seattle RIGHT NOW. One is highly likely right under your all-too-sober nose: Find out where it is here (for iPhone users) or here (for Luddites). Food! Drinks! Cheapness! Yes! CHEAP!.
The goal of Biscuit Bitch is "to bring fresh, homemade food with attitude to the partying masses of Downtown Seattle" on Friday and Saturday nights. They do this with biscuits and gravy/jam/etc. served in various bitchy incarnations for prices ranging between $5 and $13.