At the breezy Fireside, with its wide windows and sprawling sidewalk patio seating, the Cold Gold Chain is like a caffeinated old fashioned. This bourbon drink doubles down on the caffeinated side of things with both coffee liqueur—from Portland’s own New Deal Distillery—as well as cold brew. Chipotle-cacao bitters emphasize the chocolate notes in the coffee and give the drink some nuance and complexity without any overt spice. It’s best enjoyed on the sidewalk seating with a view of the passersby and their dogs on the bustling NW 23rd Avenue.

This Pearl District Mexican restaurant, owned by coffee roaster Angel Medina, serves a take on an Old Fashioned that nods to its neighboring cafe, La Perlita. When You Are Old pairs a Reforma Roasters coffee tincture with bourbon and a syrup used to make La Perlita’s cafe de olla, sweet and gently spiced. Smooth and silken, this is the ideal coffee cocktail for those who hate coffee cocktails.

While the history is disputed, the team at Huber’s reportedly invented the Spanish coffee sometime in the 1970s; regardless, Huber’s version is a Portland icon, arguably the city’s most famous drink. At the dark and old-school restaurant, waiters and bartenders still make the drink table-side, igniting the overproof rum in the sugar-rimmed glass before dusting it with nutmeg, sending up sparks. After snuffing out the flames with coffee liqueur, they top it with coffee, whipped cream, and more nutmeg. Beyond the spectacle, it’s a potent, sweet, caffeinated part of Portland’s drink history.

While Either/Or’s full slate of coffee cocktails hasn’t returned entirely, customers can still find a takeout version of the Salty Russian, a chocolate-salt-topped, oat-milk-layered coffee mocktail meant to mimic a White Russian. But in the evenings, when the cafe shifts into a bar, Either/Or serves a slushy version of the drink, available with or without booze. It’s best served swirled with a shot of vodka.

One of the city’s older pubs, Produce Row is going strong with its elegant dining room and spacious and enclosed back patio. While many bars avoid drinks that are “too” sweet, the team at Produce Row is ready to satisfy those with a sweet tooth—enter the Canadian Iced Coffee, a brunch drink for those who prefer the sweeter things in life. Made with Skrewball peanut butter whiskey, Caffe Umbria cold brew, and topped with whip cream and peanut butter cups, it’s the perfect pairing for some french toast or breakfast sandwich.

Though we lost the chic seafood bistro Jacqueline due to the pandemic—at least for the time being—the space is currently home to its alternate concept, Fair Weather. If that sticks around permanently the trade-off will be worth it, as Fair Weather brings an excellent brunch program to Clinton Street. That means caffeinated cocktails, of course: the Crooked Rain is an intriguing highball that pairs dark rum with coffee and tonic. The bitterness of the tonic and richness of the rum balance those opposing aspects in the coffee, making for a refreshing and bubbly drink that pairs excellently with the playful and indulgent food. Plus, the coffee in question is made by Push X Pull, one of the city’s finest roasters.

One of the newest members of Portland’s micro-distillery scene, Aimsir specializes in gin and bourbon, including a coffee-cut bourbon. Instead of the usual water used to bring the barrel-proof spirit down to a bottle-proof, the distillers here use cold brew from Junior’s Coffee. That bourbon goes into a number of cocktails on the menu: The Coffee Maine is a caffeine-infused Remember the Maine—botanical, lush, and layered, it’s best enjoyed slowly as the ice gradually mellows the flavors. La Rouge is a rich, silky smooth drink that tastes like a coffee-infused Boulevardier. And any of the regular whiskey drinks, like the Old Fashioned and Manhattan, can be made with the coffee whiskey.

Newly opened Mexican restaurant Nightingale sees its dark, narrow interior and enclosed front patio filled with diners nightly. Along with the stellar Mexican cuisine, Nightingale offers a killer cocktail menu that includes the My Cherry Amore. It’s reminiscent of a cherry coke and a sherry cobbler with rum, sherry, Good Coffee cold brew, soda, and spiced cherry bitters. It’s on the lighter side for the cocktail menu thanks to the soda, but still lush and vibrant. Plus the chocolate-covered cherry makes for a delicious edible garnish.

Tucked in an unassuming little strip mall on 82nd Avenue, the dive bar Buddy’s Lounge may not be the most obvious destination for cocktails, but the recent legislature to allow takeout drinks meant the bar could start serving boozy bubble tea to-go. Most of them are made with tea, but Buddy’s also serves a whiskey and boba take on ca phe sua da, the classic Vietnamese coffee drink. It’s rich, creamy, and sweet, and diners can also order a $3 plate of nachos to qualify for the required food purchase.