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Winter nights may be long and dark, but if you think about it, those are ideal concertgoing conditions.
Sure, braving the rain and cold takes a certain level of fortitude, but there’s no better reward for your efforts than enjoying live music in a small venue that is either cozy and intimate or raucous and sweaty. Lucky for us, the Rose City has everything from quiet listening rooms to full-on rock-’n’-roll parties and a rather busy wintertime concert calendar to boot.
Unlike the grand spectacle of larger productions, small shows are all about passion and the connection between performer and audience. Passion and connection—what more do you need for a big night out at one of these exceptional smaller spaces?
Laurelthirst Public House
There may be no other place bearing the torch for Old Portland’s hippie past more than this Glisan Street institution. Fortunately, The Thirst, as it’s known to regulars, was saved from redevelopment in 2016 after musician Lewi Longmire stepped in along with a few employees to buy the joint. Longmire can frequently be found onstage sitting in with various bands or playing with his own groovy country-rock outfit The Left Coast Roasters. Free happy hour shows are especially popular, as bands like Jack Straw and Portland Country Underground throw down everything from boogie-woogie and country rock to bluegrass and freak folk. Portland soul legend Ural Thomas and the Pain even stopped by recently. On weekends, the Laurelthirst hosts matinee shows, which is one of the best ways you can burn your way through a gray and rainy afternoon. While die-hard regulars like to fill up the dance floor, they are generally welcoming to newcomers looking to mix it up.
2958 NE Glisan St. (laurelthirst.com)
Landmark Saloon
Despite its frequent cryptic social media posts practically threatening to close if it doesn’t get more business, this Division Street bar is a staple at this point. Within the old house turned saloon—which seemed to emulate Austin’s famed Rainey Street (when it was cool) upon opening in 2010—is one of Portland’s most intimate venues. Shiner Bock and margaritas flow as the touring and local bands that grace the corner (there isn’t really a stage per se) tend to lean toward honky-tonk, outlaw country, and folk. Yet, you still never know what you might find with local legends like Mike Coykendall as well as a range of more experimental fare occasionally popping up on the bill. This setting gives the Landmark a rowdy house party vibe. Live music at the Landmark is always free, so tip well and often.
4847 SE Division St. (landmarksaloon.com)
Al’s Den
Tucked into the basement of McMenamins Crystal Hotel, this tiny, triangular-shaped room takes its name from the 1940s gambling boss Al Winter. These days, you won’t find any illicit activities happening at the Den, but it still feels like a speakeasy. Once you grab a drink and descend into the red-lit room, find a table and get comfortable as you take in a performance by an artist or comedian you’ve never heard of. It’s easy to forget the world outside and the passage of time and simply bask in the moment. Many shows here are free or have an enticingly low cover, making it a great spot to discover your next favorite act. This is an especially good room to catch singer-songwriters.
303 SW 12th Ave. (mcmenamins.com/crystal-hotel/als-den)
Turn! Turn! Turn!
Is it a record store? Is it a DIY performance space? A place to score some cheap grub? Turn! Turn! Turn! is all those things and more. The Killingsworth space is sort of a bohemian living room–meets–cool record store, and it plays host to some of the strangest, coolest and most obscure artists to play Portland, both local and touring. Compared to other venues around town, Turn! Turn! Turn! feels like a true community gathering space with its mix of normal shows, open mics, karaoke, art shows, poetry readings, movie screenings, and more. It even hosts all-ages daytime shows, so you can bring the kiddos along.
8 NE Killingsworth St. (turnturnturnpdx.com)
White Eagle Saloon
Supposedly, ghosts haunt this little gem of a spot on quiet North Russell Street a stone’s throw from Widmer Brewing. This writer can’t attest to having experienced any spectral visits in either the bar or the hotel upstairs, but I have seen more than a few excellent shows here. The stage takes up the back corner while the front is a welcoming pub, all of which has sort of a psychedelic vaudeville feel. The setup means that every show feels up close and personal, whether you are dancing the night away to a jam band, hanging on every lyric by legendary troubadours, or rocking out with a heavy metal band. White Eagle doesn’t discriminate when it comes to the acts it books, making it one of the more eclectic rooms in town. If you’re visiting Portland, why not book a room right upstairs? Who knows, you might bump into the artist you came to see or maybe even a ghost.
836 N Russell St. (mcmenamins.com/white-eagle-saloon-hotel)
The Showdown
Stepping into this bar on Powell is like going through a portal and landing in a saloon somewhere in the Texas Hill Country. The stage is particularly unique for its semicircular shape that juts right into the crowd, and depending on the act, this is as much a listening room as it is a place to get your two-step on. These days, The Showdown is booked by the talented team behind Pickathon, and for the most part, the music skews toward genres that fit the vibe of the room. That means country, folk rock, bluegrass, even the occasional zydeco band.
1195 SE Powell Blvd. (showdownpdx.com)
Alberta Street Pub
No other club in Portland embraces the something-for-everyone approach like the Alberta Street Pub. Besides a food menu that skews toward Southern staples like fried chicken and fish, this local institution maintains a packed schedule of music and events in the cozy listening lounge tucked beside the bar and dining area. Here you can forget about the wet and dreary weather outside and soak up tunes ranging from roots music and Americana to gospel, hip-hop, soul and blues. Shows are often free or low cost, and on weekends The Showdown often hosts three separate shows—lunch, happy hour, evening—throughout the day. There isn’t anything particularly unique or special about the actual venue portion, but it’s a straightforward space with good sound and few distractions. In other words, good clean fun.
1036 NE Alberta St. (albertastreetpub.com)
Oregon Winter is Willamette Week’s annual winter activity magazine. It is free and can be found all over Portland beginning Friday, November 21, 2025. Find your free copy at one of the locations noted here, before they all get picked up.
