The Alphabet District is one of Portland’s busiest, most happening neighborhoods, popular with out-of-towners, local residents, and visitors from the suburbs. It’s named for its streets which run alphabetically, from Ankeny and Burnside through Couch, Davis, Everett, all the way to York and Reed (which was never renamed with a Z). Simpsons fans will recognize names like Flanders and Quimby, and it’s no coincidence: Matt Groening grew up in Portland and named many characters after these streets.

 

Crossing north and south through the alphabet are 21st and 23rd, affectionately referred to as “Trendy-First and Trendy-Third”. Shops, restaurants, bars, and movie theaters line them, and there are dozens of happy hours available. We’ve narrowed it down to five of our favorite bar spots. Let us know if we missed yours on our Facebook or Twitter.

 

This bar in an old Victorian house is one of our favorite whiskey bars in the city. It offers a wide variety of whiskeys, excellent cocktails, and a bourbon class. Happy hour runs from 4 to 7 PM and offers many options. Well drinks, wine, and beer are each $1 off, a set of cocktails including a Brown Derby (pictured at top), Hot Toddy, and whiskey sour are $5 each, and a list of whiskeys are discounted down to just $4. The food menu ranges from $4–$7 and features snacks such as deviled eggs, frito pie, and sliders. On Sundays, happy hour goes all day.

Rather than the newer craft scene many other Portland bars are known for, Bartini focuses on a long list of martini variations. This fun menu has over 100 drinks in every color of the rainbow, ranging from the classic dry martinis to fruit infused vodka drinks, herbal concoctions, and dessert drinks. Categories include “Spicy”, “Bold”, “Decadent”, and “Fresh & Fruity”, among others. During happy hour, all of these are only $4, while the shorter list of “craft cocktails” is just $6. Discounted food items are also available, such as tacos, sliders, flatbread, and, of course, fondue from the connected Urban Fondue.
 

The Fireside is a beautiful, cozy wooden bar with numerous fireplaces throughout and a patio for summer dining. The approach is northwestern, evoking campfires and backyard picnics. Happy hour offers a list of excellent cocktails, all $6. The menu features classics like the Vesper cocktail, with vodka, gin, and Cocchi Americano, and the Airmail, with rum, honey, lemon, and sparkling wine, as well as original drinks such as the Mexican Firing Squad, with tequila, lime, grenadine, and Angostura bitters. $6 red or white wine is also available, along with some snacks, including a $7 corndog and $6 s’mores.

 

 

North 45 is small, lovely spot from the same folk as Circa 33 and Paddy’s, and shares their aesthetic with a tall, mirrored, ladder-reached back bar. North 45 features an excellent whiskey list and Belgian beer menu. The happy hour here is simple: Trumer Pilsner and well drinks are $4, house wine is $5, and the Pompeii Punch, a mixture of whiskey, lemon, nutmeg, simple syrup, and a seasonal stone-fruit syrup, is $6. There are some healthier options for happy hour snacks here, including Arugula Salad ($5) and Sambal Green Beans ($4.50) as well as more classic bar foods like Honey Garlic Wings ($6.50) and Mac n Cheese ($4.50). Mondays are happy hour all day.

 

 

It’s definitely a lounge, but Rae’s has a view of no lake. Indeed, there isn’t even a lake anywhere nearby this part of town. But Rae’s, separate from the other bars up on NW 27th, is a great, fun, neighborhood spot with good food and solid drinks. Its distance from the hubbub of Trendy-Third and First make it easier to find a seat. Rae’s dubs itself “the Gold Standard of Day Drinking in Northwest Portland”, and it’s no wonder: happy hour runs from 2 to 6 PM, with $4 wells, $3 glasses and $9 carafes of house wine, and, best of all, $1 Miller High Lifes. You can’t be blamed for day drinking if it’s champagne, even if it is just the champagne of beers.