Walking into Lollipop Shoppe, the new bar within the former home of Dig a Pony, it may seem like little has changed — until the night really begins. Portlanders sip hurricanes and house shrimp po’ boys before bands like Spoon Benders and Rip Room take to the bar’s small stage. From the teams behind one of Portland’s cult favorite cocktail lounges and an independent music festival, Lollipop Shoppe feels like the bar your out-of-town friends expect to find here, with hardcore sandwiches and live music from bands right on the edge of blowing up. Below, we’ve compiled the crucial details you’ll need before you visit, including what to eat, what you’ll hear, and what’s coming next.
What is Lollipop Shoppe, and why should I care?
A new New Orleans-inspired cocktail bar and independent live music venue, Lollipop Shoppe comes from Tyler and Devon Treadwell of Tulip Shop Tavern and Elizabeth Elder and Bryan Wollen of Lose Yr Mind Fest. The former is a North Portland cocktail bar known for its stellar tavern burger and sharp cocktails; the Treadwells both spent time at local favorite Rum Club before opening Tulip Shop. The latter is a Portland-based music festival with a focus on rock subgenres; Willamette Week once called it “one of the best places to find your favorite new local and national bands.” As a result, Lollipop Shoppe is well-positioned to succeed both as a venue and as a bar.
What’s the food situation?
The Treadwells have enlisted the guidance and prowess of Tulip Shop chef Nick Seabergh, who has been adding a Southern bent to some of the dishes at Tulip Shop. At Lollipop Shoppe, the Mississippi-raised chef goes deeper into the Cajun-Creole canon. He and the Treadwells traveled around New Orleans’s bars and po’ boy spots to help develop a menu, and Lollipop Shoppe now serves a selection of po’ boys topped with everything from catfish to beef debris — essentially a saucy roast beef — as well as a rotating vegan option. Lollipop Shoppe’s gumbo comes with chicken and andouille, and the menu will always have some version of red beans and rice. Lollipop Shoppe also smothers crinkle-cut fries with beef debris, house cheese sauce, green onions, and pickled Fresno chiles, which has become a popular order in the bar’s first few weeks.
What to drink?
Like the food menu, the cocktails here lean heavily on New Orleans standards; turns out, many quintessential American cocktails have Louisiana roots. Here, you’ll find Vieux Carrés, hurricanes, and Sazeracs, as well as a broader spectrum of drinks like daiquiris and low-proof spritzes. Tyler Treadwell is particularly happy with his Brandy Crusta, “a precursor to the sidecar” made with Brandy Sainte Louise, Combier Orange, Maraska maraschino, and bitters. For something a little bolder, Lollipop serves an absinthe frappé, a “warming and soothing” cocktail with both absinthe and Meletti Dry Anisette. “It’s definitely a polarizing cocktail,” he says. “Some people love it, some people hate it.”
What will I hear?
Lollipop Shoppe doesn’t have shows every night, but some of its upcoming acts are ones to watch. Some hew a little more art-punk-esque; others live somewhere closer to synth pop. On its first night open, October 28, Portland’s own Reptaliens played alongside Bijoux Cone and Buddy Wynkoop. Upcoming shows include psychedelic synth duo Pearl & The Oysters on November 10, Olympia’s Oh, Rose on November 12, and Portland’s Forty Feet Tall on November 17. Ticket prices vary, but generally live in the $10 to $20 range.
What else should I know?
Parents craving gumbo and a strong drink, good news: Lollipop Shoppe is minor-friendly until 7 p.m. On the other side of the token, those desperately seeking some good late-night dining in Portland will be able to find it here, with the kitchen churning out food until 1 a.m. on weeknights and 2 a.m. on weekends. The kitchen’s takeout window should be up-and-running by February, for those just seeking a beef debris po’ boy to go.
Where is it?
736 SE Grand Avenue