Lollipop Shoppe was a music venue, bar, and restaurant in Portland, Oregon, United States. It opened in October 2022, in the space that had previously housed Dig a Pony, in southeast Portland's Buckman neighborhood. The venue hosted concerts and served Cajun and Creole cuisine, including po'boys, popcorn shrimp, loaded fries, coleslaw, gumbo, and red beans and rice. The venue closed permanently in November 2025.
The music venue, bar, and restaurant Lollipop Shoppe operated on Grand Avenue at the intersection with Morrison Street in southeast Portland's Buckman neighborhood. Named after the American garage rock band The Lollipop Shoppe, the venue had a small stage and a capacity of 200 people, as well as paintings by Samuel Farrell along a wall with booths and custom mosaic tiles installed by Nicky Kriara. Brooke Jackson-Glidden of Eater Portland said the venue's acts were "a little more art-punk-esque", with some being "somewhere closer to synth pop". The website's Jenni Moore said the venue had a music calendar "usually packed with consistently strong up-and-coming acts, mixed in with a few surprises from the peak-2007 Indie Portland era", with shows "[ranging] from visiting DJs from Los Angeles to Portland indie art rock bands".
The Gulf Coast- and Southern-inspired food menu included Cajun and Creole cuisine such as po'boys with catfish, popcorn shrimp, or fried cauliflower with olive salad as a vegan option. Beef debris (shredded roast beef with sauce) was used on sandwiches and on the loaded fries, which also had cheese sauce, green onions, and pickled Fresno chiles. The menu also included coleslaw, gumbo, red beans and rice, and "soggy salad" made from iceberg lettuce marinated in vinaigrette with garlic. Drink options included cocktails such as an absinthe frappé with absinthe and Meletti Dry Anisette, a Bloody Mary, daiquiris, a French 75, hurricanes, mint juleps, Sazeracs, Vieux Carrés, low-proof spritzes on draught, and beers from Fort George, Kokanee, Living Häus, Wayfinder, and other breweries. The Brandy Crusta had Brandy Sainte Louise, Combier Orange, Maraska maraschino, and bitters.
Lollipop Shoppe opened on October 28, 2022. it operated in the space that previously housed the bar Dig a Pony, which closed in June 2022. Devon and Tyler Treadwell co-owned Lollipop Shoppe with Elizabeth Elder and Bryan Wollen, co-founders of the Lose Yr Mind music festival. Nick Seabergh was the opening chef. In an interview with the Portland Mercury, Elder said of the venue's name:
Prior to opening, the venue made changes to the kitchen equipment and expanded the bar. The remodel took longer than anticipated, so some planned shows were hosted at nearby Swan Dive instead. On opening night, Lollipop Shoppe hosted a Halloween show with music by the Reptaliens, Bijoux Cone, Buddy Wynkoop, and DJ Susan Saranwrap. Other acts that performed at the venue included the bands Rip Room and Spoon Benders, as well as Chipped Nail Polish, Forty Feet Tall, Jakki and the Pink Smudge, Brazilian musician Johnny Franco, Karma Rivera and DJ Lapaushi, Olympia-based Oh, Rose, the psychedelic synth duo Pearl and the Oysters, and Veana Baby. Lollipop Shoppe also hosted "The Thesis", described as a monthly hip-hop showcase, as well as "RNB After Dark" and the lesbian dance party "Dyke Nite". In 2025, Lollipop Shoppe hosted a listening party for a Shadowgraphs album as well as a concert featuring Roselit Bone, Railing, and Cage Mother.
The Treadwells stepped away from Lollipop Shoppe in December 2023. In 2025, the business launched a GoFundMe campaign in an effort to raise $50,000 to pay staff and expand programming, which was unsuccessful. On November 2, the business announced plans to close permanently by the end of the month, citing increased operational costs, crime, and debt as the reasons for the closure. In a statement shared on social media, the owners said, "We put every part of us into this venue. It's hard to say goodbye, but we need to restore our personal and financial balance... There have been many incredible moments in the three years we've been in operation and we hope you'll join us for a few more before our final curtain call." The local band the Macks performed on November 28, the closing night.
Eldorado is slated to open in the space in 2026.
Ezra Johnson-Greenough of Willamette Week described the venue as "open, low-key, approachable, and perfect for showcasing new bands", writing: "Anyone could stumble into The Lollipop Shoppe and not feel intimidated by the cost of entry or hipness of the crowd." Meira Gebel included Lollipop Shoppe in Axios Portland 2024 list of the city's six "most underrated" live music venues, calling it "the ultimate spot for dinner and a show". Reporting on the closure, Hannah Seibold of the Portland Tribune said Lollipop Shoppe offered affordable concerts and "vibrant" cocktails. Nolan Parker of the Portland Mercury called the closure "devastating" and said Lollipop Shoppe was "one of Portland's best small rooms".