It's Always Happy Hour in Portland

By Anna Moss


Anna Moss
Join Bartender Anna Moss for the ultimate, all-day happy hour hop through Portland.
Join Bartender Anna Moss for the ultimate, all-day happy hour hop through Portland.

Food, cocktails, wine, beer, coffee—we’re spoiled in Portland, and our happy hours are no exception. If timed right, you can spend an entire day bouncing from one to the next. So, that’s exactly what I set out to do. Monday is the day of choice for many of us industry folk, and since it’s traditionally a slower day for bars and restaurants, it also has the highest frequency of extended happy hours. Be prepared to drink a lot of water and coffee along the way, snack constantly, tip well, and don’t even think about driving.

11am-noon: Devil’s Point
For those of you thinking, “This is how I like to end my day,” think again. You’re embarking on a 12-plus hour day of drinking, so giddyup at Portland’s rock ’n roll strip club and home of stripparaoke.
Happy hours: 11am-7pm daily; $1 off draft beer, $2.50 well drinks, 50 cents off other drinks, half off food menu

12:30pm-2pm: Ecliptic Brewing
All-day happy hour on Mondays with a beautiful patio. The A.L.F. Stout and $3 deviled eggs with boquerones are surprise standouts.
Happy hours: All day Mon.; 3pm-6pm Tues.-Fri.

2:15pm-3:15pm: Little Bird Bistro
House cocktails are $3 off, which kind of feels like stealing, but no complaints here.
Happy hours: 2:30pm-6pm Mon.-Fri.; 5pm-midnight Sun.; 10pm-midnight daily

3:30pm-4:15pm: Headwaters
Dollar oysters from 4pm to 5pm daily and plenty of other lovely options. Also, it’s a good time to have a Water Avenue Coffee espresso and enjoy the afternoon light.
Happy hours: 2pm-6pm Mon.-Fri.; 3pm-6pm Sat.-Sun.; late night varies

4:30pm-5:30pm: Shift Drinks
Happy hour all day, every day! $7 orange wine and iced Irish coffee were almost enough to make me toss out the whole day and stay.
Happy hours: Always! 4pm-2:30am Mon.-Fri.; 5pm-2:30am Sat.-Sun.

5:45pm-7pm: Cooper’s Hall
Discounted bottles of to-go wine and the best $7 Brussels sprouts in town. Grab a bottle of skin contact Chardonnay for later and treat yourself to a glass of something special, like the Texier Grenache/Cinsault while you’re there because it’s so rare to find it on tap.
Happy hours: 4pm-6pm daily

7:15pm-8pm: Star Bar
This is an excellent time to sip slowly on a $2.50 PBR as you contemplate how late it feels but how early it actually is.
Happy hours: 4pm-8pm daily

8:15pm-9pm: Crush
Home of Bi Bar—the bi/pan/fluid/queer dance party—and burlescape/boylesque, this is the most eclectic and welcoming neighborhood/LGBT bar in Portland that just so happens to be directly across the street from your next destination.
Happy hours: 3pm-midnight Monday (first Monday Bingo, benefitting Dykes on Bikes on the night I stopped by), 3pm-7pm daily; $5 martinis, discounted well drinks and food

9pm-10pm: Nostrana
$5 charcuterie, insalata nostrana (the radicchio salad we’ve all tried to make at home without success) and pizza marinara. Need I say more? Do yourself a favor and grab a double Spella Caffè espresso before ordering more wine or a Negroni of the month.
Happy hours: from 9pm daily

10:15pm-11pm: Kachka
They’re not on the happy hour menu, but $4 cookies and $3 tea are all you need to keep going.
Happy hours: 4pm-6pm & 10pm-midnight daily; $5 Moscow mules and discounted vodka infusions

11:15-midnight: La Moule
I’m biased, but I do believe in saving the best for last. Sazeracs and Daiquiris ($7) in a dark, sexy space are the perfect nightcap.
Happy hours: 5pm-6pm & 10pm-midnight daily

Continue on if you must, but the happy hours have all ended. Get home safe and get your drunk butts in bed.

Anna Moss has worked in hospitality since she was a teen and has tended bar in Portland since 2009. She is currently behind the stick at La Moule where she makes a mean gin martini dirtied with cornichon brine and a peppery Cognac Old Fashioned.   


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