On November 28, a day after Thanksgiving, the northeast corner of SE Grand and Morrison was bouncing to the thrashy rock sounds of local Portland band the Macks. Though the tunes were upbeat and lively, the mood couldn’t be anything but bittersweet: It was the final night for the Southern-inspired bar and music venue Lollipop Shoppe.  

The spacious, wood-filled eatery at the mouth of the Morrison Bridge was previously home to Dig A Pony, a bar and dance club that opened in 2011. After more than a decade of service, the team called it quits in June 2022, largely due to the ongoing COVID-19 pandemic. But live music fans didn’t have to wait long— ownership soon passed to Elizabeth Elder and Bryan Wollen, cofounders of the local indie music festival Lose Yr Mind. The two partnered with Tulip Shop cofounders Tyler and Devon Treadwell to reopen the space as Lollipop Shoppe that October.  

Originally, Elder and Wollen handled the bookings and shows while the Treadwells built the menu, drawing heavy inspiration from the cuisines of New Orleans. Lollipop Shoppe impressed diners with its popcorn shrimp, catfish, and po’boys, as well as its array of NOLA drinks, like Sazeracs and Hurricanes. In December 2023, the Treadwells quietly parted ways with the business.  

While Lollipop’s food menu shrunk, its status as a music venue grew. The bar hosted acts like Brazilian rocker Johnny Franco and pop duo Pearl and the Oysters. Regular themed events included Dyke Nite, RNB After Dark, and hip-hop series the Thesis. But despite its popularity, it struggled with finances. On November 2, the Lollipop team took to Instagram with an announcement: The bar would close around Thanksgiving. The post cited rising costs as the reason for closure. “Like a lot of small businesses, we’ve been struggling to make ends meet as operating costs continue to rise,” it reads. “We put every part of us into this venue + it’s hard to say goodbye, but we need to restore our personal + financial balance.” 

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