Portland has no shortage of nicknames. Between the City of Roses, Bridge City, and Stumptown, it’s no wonder that Portland is as famous for its nicknames as it is for its attractions.
Portland has epic scenery, fantastic gastropubs, and the Pacific Ocean. But the nightlife is where this city shines. Portland is home to fabulous restaurants, bars, breweries, and pubs. If you go for happy hour, you have an astonishing number of places to choose from for your discount drinks and appetizers. Check out this list of my favorite spots for the best happy hour in Portland below!
3632 N Williams Ave, Portland, OR 97227
We start our journey at one of Portland’s premier pizza spots. Wood-fired pizza is a treat no matter what time of day it is, but it’s best during happy hour. At Life of Pie pizza, you’re right between two incredible venues: Mississippi Studios and Wonder Ballroom. So whether you’re waiting to catch a live show or head for a ballroom dancing lesson, you can start with happy hour. Happy hour runs every day from 11 in the morning until 6 P.M. I tried the Margherita pizza and the house beer and thoroughly enjoyed every moment of both.
2075 NW Glisan St, Portland, OR 97209
On the west side of the Willamette River in the infamous Northwest District of Portland, Pope House Bourbon Lounge sits ready and waiting to serve you the best happy hour you’ve ever had. Pope House is open daily, and they host a happy hour from 4 P.M. to 7 P.M. You can get a dollar off a pint of beer, an affordable whiskey, or a cheap cocktail. I went for the cocktails, and I wasn’t disappointed. Their version of Pimms is exquisite, mixing Pimms with cucumbers, lemon, and soda. I enjoyed it so much that I added the Kurt Russell entree to stay longer.
8115 SE Stark St, Portland, OR 97215
The Observatory is a very stylish, very American classic-style neighborhood restaurant with a great craft cocktail menu and an interesting take on all the original styles that we’re so used to these days. Situated in Montavilla on Southeast Stark Street, just a couple of blocks from Monticello Antique Marketplace, the Observatory is a trendy spot to enjoy happy hour in Portland with your friends. Happy hour runs from three to five daily, and no reservations are needed. I went for another cocktail here and wasn’t disappointed by the Guava-Ginger Mimosa. It paired perfectly with the Sesame-Sweet Chili Glazed Chicken Wings. After the experience, I wanted to go back the next day!
4205 N Mississippi Ave, Portland, OR 97217
If you’re looking for something more closely resembling a tavern, you’ll find yourself at home at the Rambler. Located in the Boise neighborhood on the east side of the Willamette River, the Rambler’s is just a few blocks from Denorval Unthank City Park. The Rambler hosts happy hour until six, Tuesday through Friday, and all day long on Monday. They offer $1 off all beers and wines on tap, well spirits, and signature cocktails. I loved the house beer and affordable Chicken Strips featuring tornado potatoes and ranch dip. But I recommend checking out all their menu specials, especially the Rambler Poutine and the Smoked Brisket Chili.
3356 SE Belmont St, Portland, OR 97214
Down in Belmont, on Belmont Street, next to the H Mart Belmont, you’ll find an elegant wine and cocktail bar with a hip, trendy vibe. The patio seating makes this place a popular attraction, and the nightly D.J. is another big bonus. You can enjoy happy hour every day from 5 to 7 P.M. The $4 menu makes this one of the best comfortable hour spots, especially for customers ready to tip generously. When I enjoyed happy hour at the Aalto Lounge, I had The Belmont Jewel, which featured bourbon, lemon, pomegranate juice, and orange blossom water. It was the most refreshing cocktail I’ve ever consumed. The Oven-Baked Pretzel followed it up with an exceptional burst of flavor.
2733 NE Broadway, Portland, OR 97232
A tiki bar in Portland is just what the doctor ordered to get rid of your Monday blues. The tropical experience that you’ll have on Northeast Broadway is simply unbeatable. Enjoy the Beverly Cleary Sculpture Garden before or after your happy hour adventure here, and be sure to check out the Case of Bass art gallery that’s only a two-minute drive away! There’s no shortage of fun things to do in the area before you enjoy your happy hour experience. I always enjoy a good Mai Tai, and their take on it didn’t disappoint. It was a little strong, but that’s preferable to too weak. The slight fruitiness made it perfectly balanced.
611 SW 10th Ave, Portland, OR 97205
In Downtown Portland, you’ll find an old-school place to enjoy classic American fare and a great whiskey selection. There’s a surf & turf element that you’ll thoroughly enjoy, and the happy hour is what Jake’s Grill is all about. Enjoy the famous happy hour at Jake’s. You’ll have access to affordable spirits, including an excellent bourbon collection. You can also get cheap hand-crafted cocktails, like Jake’s Iced Tea, or grab a local craft beer, like the smooth Ecliptic Capella Porter. Cheap appetizers like the Raw Oyster Shooters made this happy hour stand out. Jake’s offers a lot of variety for really great prices. It’s not an experience that you’ll want to miss.
1233 N Killingsworth St, Portland, OR 97217
Up around Humboldt is an excellent little eatery and bar that offers a wide selection of spirits, cocktails, wines, and craft beers. Committed to local brewers and distillers first, you can get the best that Portland has to offer at Haymaker Bar. They have a great happy hour atmosphere that’s laid back and relaxed; it’s everything you would want from a night out in Portland. I loved their cocktails. I started with the Bees Knees, a gin drink featuring fresh lemon and honey syrup, and followed it up with a Kentucky Mule with fresh lime and ginger beer. Both were mixed to perfection and highly refreshing.
716 NW 21st Ave, Portland, OR 97209
R&R Bar is a newer spot in Northwest Portland that’s not too far from the Freakybuttrue Peculiarium and Museum in Slabtown. If you head to Arlington Heights, you’ll enjoy the Portland Japanese Garden. With happy hour right in between, what could be better? You’ve got two chances for happy hour at R&R Bar, from five to six. They also offer specials from 11 until they close every day. You’ll want to try the Coconut Shrimp Tacos, regardless of when you go. You could pair that with a draft of the day or enjoy the Golden Hour cocktail with pineapple rum and coconut liquor. The fresh lime tops it off perfectly. Overall, my experience cemented this spot as one of the best happy hours in Portland.
720 SE Sandy Blvd, Portland, OR 97214
When you visit Buckman on the east side of the Willamette River, you’ll want to enjoy your happy hour drinks at the Rum Club. The cozy cocktail bar has a tropical trend you don’t want to miss. You can enjoy happy hour Sunday through Thursday at the Rum Club, from 3 until 5 P.M. The first thing you should do is ask about the drink of the week. They’re always coming up with something interesting for the clientele. The other option is to try the Coco Cafe, a delicious cold brew coffee drink with cream of coconut and pineapple topped with cinnamon and nutmeg. It’s refreshing, energizing, and delicious.
232 NW 12th Ave, Portland, OR 97209
The Pink Rabbit sits close to the Pearl District. It’s an exciting place dedicated to geometric shapes, lofty cocktail recipes, and Asian pub fare. It’s just a short walk from the Oregon Jewish Museum and the McMenamins Crystal Ballroom. You can get in for happy hour from three in the afternoon until six in the evening. During this time, you can access an incredible menu that includes things like Dirty Edamame, Wonton Nachos, and Fried Chicken with Kimchi Ranch. The drink I tried was the Strawberry Gimlet. It’s a gin drink that they combine with strawberry, lime leaf, lime, and anise. The flavors are incredible, and the atmosphere makes it all the more enjoyable.
111 SW 5th Ave 30th Floor, Portland, OR 97204
Downtown Portland is a great place to spend the day. You can access parks, museums, interesting buildings, and unique markets, all within walking distance. There are playhouses and theaters, as well as ballrooms and lovely greenspaces. One of the more upscale places to spend happy hour in Downtown Portland is the Portland City Grill. You’ll enjoy the American fare and the fantastic views of the city and the Willamette River. You can get into the lounge for happy hour Monday through Friday, from four until six. I suggest the Truffle and Rosemary French Fries paired with a signature Cucumber-Elderflower Mash. It’s hard to describe, but it’s easily one of the most interesting botanical drinks I’ve enjoyed.
920 E Burnside St, Portland, OR 97214
Hop back over the river for this all-day coffee shop experience as a restaurant and bar: the tropical-themed interior features local art and international fare. You’re right next to the Portland Rock Gym and not too far from Revolution Hall, where you can catch a live show if you’re interested. While you wait for the show to start, you can enjoy the happy hour at Hey Love. They have exciting cocktails and delicious appetizers, and they’ll help you remember that you’re on vacation. If it’s available, I suggest trying the house Gin and Tonic. Their unique take on the classic features star anise and grapefruit peel.
2337 NE Glisan St, Portland, OR 97232
Another great Caribbean-style and Latin American-inspired drink spot in Portland is Tropicale in the Kerns neighborhood. You’ll find a bouldering gym just down the street if you’re interested in that sort of thing. Once you get a good workout in, head to the Tropicale for happy hour. You’ll want to try all the cocktails, but your priority should be the Negrete. The mezcal mixed with sweet vermouth and cacao nibs is simply stunning. Their food is just as delicious as their drinks, so grab a plate or two. You won’t regret it!
801 NW 23rd Ave, Portland, OR 97210
The Fireside is one of those Portland gastropubs you’ve likely heard so much about over the years. I was pleasantly surprised by the bright atmosphere and comfortable bar when I went. It’s over in the Northwest District, so definitely a place to check out if you’re staying downtown. Stop by between three and five for happy hour options, including the House Margarita. I thoroughly enjoyed their take on the classic cocktail with an epic Cheese & Charcuterie Board. Whether catching up with friends or having drinks with colleagues after work, you’ll love The Fireside’s ambiance and charm.