A rocker takes a stroll down memory lane.

Singer-songwriter Chris Trapper, frontman of local pop-rock trio the Push Stars, bounced through odd jobs for years before the band’s late-1990s breakout album, Meet Me at the Fair, earned it favorable comparisons to the Replacements. The 38-year-old Westwood resident has since recorded half a dozen albums, toured the country, and landed songs in TV shows and films including the upcoming Jonathan Rhys Meyers project August Rush. When not performing—or answering the demands of new fatherhood—Trapper spends precious free nights visiting old friends in the hangouts where he cut his teeth.

>>8 P.M. Setting out solo for a bite, Trapper fuels up at the Other Side Café (407 Newbury St., 617-536-8437), where he worked for tips before his band’s 1999 Capitol Records deal. Looking the part of the prodigal rock-and-roll son in a fitted, vintage black velvet jacket, he sips a Hoegaarden and noshes on vegetarian chili. “This is a return to my comfort zone,” he says, laughing, as he fights the urge to clear the table himself.

>>9:30 P.M. Passing through the gold lions that grace the entrance to the Fairmont Copley Plaza, Trapper heads to the Oak Bar (138 St. James Ave., 617-267-5300) to see a few familiar faces from his days as the hotel’s food and wine inspector in the mid-1990s. (His 2002 wedding to wife Hania also happened here.) He catches up with friends over a glass of 10-year-old Laphroaig and a celebratory raspberry Romanoff champagne cocktail before his sentimental side surfaces: “I love this property. It’s ‘old Boston,’” he says. “Sometimes, when you’re here, you can feel the ghosts.”

>>11 P.M. Trapper ends the evening with live music and a nightcap at the South End club Wally’s Café (427 Massachusetts Ave., 617-424-1408), where a budding horn-and-string trio is set to take the stage. A longtime jazz devotee, Trapper took a departure from his rock roots to record his 2005 solo album Gone Again with the local Wolverine Jazz Band. Relaxing with a Red Stripe beer, he perks up as the band begins to play. “I’m inundated with pop and rock on tour,” he says. “To see good jazz and have a night out is a great escape from my world.”