Cocktail Bar, Restaurant, and Venue Lollipop Shoppe Opens in Portland | Eater Portland

"Housed in the former home of Dig a Pony, this New Orleans–inspired cocktail bar and independent live-music venue feels like the bar your out-of-town friends expect to find in Portland: think hurricanes, house shrimp po’ boys, hardcore sandwiches, and live bands on the edge of breaking out. Founded by Tyler and Devon Treadwell (of Tulip Shop Tavern) alongside Elizabeth Elder and Bryan Wollen (of Lose Yr Mind Fest), Lollipop Shoppe pairs a venue-focused vibe with a menu rooted in Cajun-Creole tradition thanks to Mississippi‑raised chef Nick Seabergh, who traveled New Orleans to help develop the food. The menu features po’ boys topped with everything from catfish to beef debris (a saucy roast beef), a rotating vegan option, gumbo with chicken and andouille, and a permanent take on red beans and rice; crinkle-cut fries smothered with beef debris, house cheese sauce, green onions, and pickled Fresno chiles have become an early favorite. Cocktails lean on Louisiana classics — Vieux Carrés, hurricanes, Sazeracs — alongside daiquiris, low-proof spritzes, a Brandy Crusta made with Brandy Sainte Louise, Combier Orange, Maraska maraschino, and bitters, and a polarizing absinthe frappé featuring absinthe and Meletti Dry Anisette. Shows don’t run every night, but the space has already hosted local acts (Reptaliens, Bijoux Cone, Buddy Wynkoop) and upcoming bills include Pearl & The Oysters (Nov 10), Oh, Rose (Nov 12), and Forty Feet Tall (Nov 17); tickets generally run $10–$20. It’s minor‑friendly until 7 p.m., the kitchen serves until 1 a.m. on weeknights and 2 a.m. on weekends, and a takeout window is expected by February." - Brooke Jackson-Glidden