Starting Tuesday, Feb 17, Portland's beloved annual jazz festival kicks off at venues across the city. We dig the following five shows in particular, because each hits (at least) three perfect notes: quality act, a spot-on venue—and proximity to a primo pre-show drinking hole.

Vijay Iyer Trio
Feb 20, Winningstad Theatre
Tickets 

THE MUSIC The 43-year-old pianist is modern jazz’s consummate renaissance man. He holds a PhD in music cognition, composes both chamber and electronic music, produces multidisciplinary performance pieces, regularly publishes in various journals, and is on the faculty at Harvard. Basically, he’s a genius, and his trio has been blowing minds live and in the studio for over a decade. This month’s critically adored Break Stuff is no exception.

THE PLACE The Winningstad's courtyard-style space inside Antoinette Hatfield Hall feels surprisingly intimate for its size. Procure seating along the side balcony seating for interesting views of the performers and a game of “spot the people you know” (pretty easy in Portland's small jazz scene). 

THE TOAST A 20-year downtown institution, Higgins Restaurant and Bar is a block away from the Winningstad, and has maintained its status as a top dining destination in Portland's ever-evolving foodie scene. The bar is a cozy spot to savor a pre-show cocktail or a glass of wine or beer from Higgin’s impressively curated lists.

BLUE CRANES
Feb 21, Alberta St. Pub 
Cover: $10 

THE MUSIC This quintet are one of Portland many acts (across many genres) that remain inexplicably just under the national radar. Their brand of jazz—if you want to call it that—is simultaneously accessible and progressive. As evidenced by 2010’s fantastic Observatories and 2013’s even more accomplished Swim, the group manages to meld the dynamism and drama of post-rock, folk's lyrical pacing, and the raw energy of Portland’s underground indie scene into a truly special sound.

THE PLACE Renovated nearly two years ago, the Alberta St. Pub—a one-time dive bar—is arguably now the best-sounding small venue in Portland. The elevated pub menu (think meatloaf with truffled potatoes) and solid bar program are no slouches either.

THE TOAST On a street filled with precociously hip bars, the Knock Back could take top prize. Yet tonight, we think the off-kilter-yet-comforting vibe—with boozy marshmallows, beer cocktails, and Manhattans on tap—plays a cool accompaniment to the show you’re out to see.

HAL GALPER TRIO
Feb 27, Old Church
Tickets 

THE MUSIC Pianist Hal Galper has played with a generation of jazz luminaries including Cannonball Adderley, Phil Woods, and John Scofield. Now playing together for over 25 years, his impressive trio—which includes bassist Jeff Johnson—is known for onstage chemistry, playing almost with one mind.

THE PLACE The sonically pristine Old Church in downtown Portland is a nonprofit venue housed in exactly that: a historic church built in 1882. The lovely natural reverb and beautiful architecture just about make up for the uncomfortable (vintage!) pews.

THE TOAST Continue with the history-buff theme by taking your evening to the Raven and Rose, housed in the nearby 132-year-old newly-renovated Ladd Carriage House. The cozy upstairs Rookery Bar is the perfect spot to hide from the February weather; the uniformly spot-on libations from Bar Director David Shenaut, like single barrel Manhattans or hot buttered rum, also don't hurt.

Hailey Niswanger
Feb 27, Jimmy Mak's 
Tickets 

THE MUSIC A Portland born-and-bred saxophonist makes something of a triumphant homecoming; Hailey Niswanger, who now lives in New York, returns to her hometown as a festival headliner. The Berklee grad, who toured with local hero Esperanza Spalding’s Radio Music Society, will be accompanied by 17 Portland-based musicians for a performance that doubles as the release party for her newest album PDX Soul (recorded entirely here in P-town).

THE PLACE Right in the heart of the Pearl District, Jimmy Mak's has long been Portland’s premiere place to see live jazz, and with good reason. A plushy intimate hub for international touring greats and weekly local residencies in equal measure, there’s really not a bad night to be here.

THE TOAST Sazeracs and champagne cocktails abound on Jimmy Mak’s menu, so why not swing for something different beforehand? A few blocks south, Bailey’s Taproom boasts a tap list so esoteric that even beer skeptics should be intrigued. Should the pub's street level be crowded, head upstairs; beer options are sparser but the vibe is relaxed and cozy. 

CYRILLE AMIEE
Feb 28, Evans Auditorium at Lewis and Clark College
Tickets 

THE MUSIC After receiving first prize in the Montreux Jazz Festival Vocal Competition, this French singer released her debut on Mack Avenue Records, It’s A Good Day, last year to critical acclaim. Her performance at the Jazz Festival will feature the interplay of two guitarists: electric guitarist Michael Valeanu and gypsy-style steel-string guitar player Adrien Moignard. Continuing the six-string display, local alt-jazz favorites Trio Subtonic open the show with a special guest, Portland guitar titan (and Lewis and Clark instructor) Dan Balmer.

THE PLACE Show up early and take a walk around this liberal arts school’s gorgeous campus, built on the old M. Lloyd Frank Estate, listed on the National Register of Historic Places. Or, if you’re feeling even more adventurous, arrive early and explore nearby Tryon Creek State Park.

THE TOAST There’s not exactly an excess of great bars—or mediocre bars, for that matter—near the Lewis and Clark Campus. So do what the (of-age) students do: go to Tryon Creek Bar and Grill, get a commendably strong Long Island iced tea, drink it hastily and with gusto, and get on with your night.