At Lollipop Shoppe, Portland Has a Brand-New Spot for Late-Night Southern Food

A shrimp po’boy from Lollipop Shoppe
Image: Courtesy Lollipop Shoppe
Those in the know, especially when it comes to cheeseburgers (one of our favorites in the city!) and Wednesday corn dog specials, know that Tulip Shop Tavern is just as much about the food as it is about the bar. So when Tulip Shop co-owners Tyler and Devon Treadwell teamed up with Lose Yr Mind festival cofounders Elizabeth Elder and Bryan Wollen to create Lollipop Shop, the new music venue housed at the former Dig a Pony space (736 SE Grand Ave), they created a food menu that looks just as intriguing as the lineup of shows.
Dig a Pony, which often had lines around the block on weekends for DJ nights, closed in June 2022; when Elder and Wollen heard that the venue might be selling, they took it as an opportunity to start the venue they’d been dreaming of. They reached out to the Treadwells to see if they’d be interested in handling the food and beverage side of things. Lollipop Shoppe officially opened its doors on October 28.

Beef debris po’boy
Image: Courtesy Lollipop Shoppe
Behind the menu, which the team describes as "Gulf Coast–inspired," is chef Nick Seabergh, who hails from Mississippi and also headed the kitchen at Tulip Shop Tavern. The Tulip Shop crew visited New Orleans to do some research for their menu, which centers on po’boys. “The thing that I was really drawn to was roast beef, or beef debris,” says Tyler Treadwell. “I’m from Seattle, and every time I’ve had a po’boy, it’s been oysters or prawns.” Beef debris, so named for the bits of meat that fall off while the meat slowly cooks and releases drippings, makes its way onto the Lollipop Shoppe menu in po’boys and on top of loaded fries. Other po’boy options include fried popcorn shrimp, catfish, and fried cauliflower with olive salad. Also look for gumbo, coleslaw, red beans and rice, and what Seabergh refers to as a “soggy salad”—iceberg lettuce that’s marinated overnight in an intensely garlicky vinaigrette.

Mint julep
Image: Courtesy Lollipop Shoppe
The cocktail menu is composed entirely of classic cocktails you might find in New Orleans, including hurricanes, Sazeracs, daiquiris, mint juleps, and an absinthe frappé that Treadwell describes as “a boozy Good & Plenty.” There’ll also be low-ABV spritzes on draft. Look for tap beers from breweries like Wayfinder, Fort George, and Living Häus, plus tallboy cans including Treadwell’s favorite Canadian cheap beer, Kokanee.
In the coming months, Lollipop Shoppe owners plan to add a to-go window that’ll allow customers to order and pick up food from the sidewalk, which will come in handy on days when the venue is packed. It’s also one of the few late-night options in the area. The venue closes at 1 a.m. Sunday through Thursday and 2 a.m. Friday and Saturday, and they’ll be taking food orders up to 30 minutes before closing. Plus, once the crew settles in, keep an eye out for specials like the Jazz Fest–exclusive creamy pasta dish crawfish Monica, plus boudin balls (think arancini with Southern-style gravy), dirty rice, and the occasional whole suckling pig, cochon de lait.
Lollipop Shoppe, 736 SE Grand Ave, open 3 p.m.–1 a.m. Sun–Thu and 3 p.m.–2 a.m. Fri–Sat, lollipopshoppe.com