A loyal local following pours into Brian Boru Public House (57 Center St., 207/780-1506, www.brianboruportland.com ) for its cheap pints of Guinness, views of Casco Bay, and free live Irish music.
Come Sunday afternoons for a traditional Irish session Big-deal, national musicians take the stage at Port City Music Hall (504 Congress St., 207/899-4990, www.portcitymusichall.com ), from rap and soul artists to blues and alterna-jazz artists.
With such a deluge of art venues, it’s no surprise that Portland  offers a slew of art performances, concerts, openings, and other events over the course of every year. One of the most regular—and festive—is First Friday Art Walk (www.firstfridayartwalk.com , 5–8 p.m. on the first Friday of every month). All Portland turns out to stroll the city’s streets for free self-guided tours of its art galleries, performance art, and sidewalk concerts.
Come holiday time, a sure bet is the month-long Light Up Your Holidays festival (207/772-6828, www.portlandmaine.com ). Kicked off by a tree-lighting ceremony in early November, the celebration continues with free horse and wagon rides, late shopping hours, and Santa visits.