What's up The Dalles: Downtown The Dalles Builds Momentum with Fall Events, Business Growth

Sep 4

Written By Columbia Community Connection

The Dalles, Ore., Sept. 4, 2025 — The latest episode of “What’s Up, The Dalles” brought together community leaders and local entrepreneurs to spotlight downtown revitalization efforts, upcoming fall events, and ongoing investments in The Dalles’ cultural and business landscape.

Podcast host Tom Peterson, joined by Main Street coordinator Cynthia Kortge, welcomed Natasha Skov of Copa Di Vino and Sunshine Mill Winery, and Julie Wadsworth of Freebridge Brewing for a lively conversation that underscored the evolving vibrancy of downtown The Dalles.

Skov, whose family redeveloped the long-vacant Sunshine Mill beginning in 2004, reflected on the site’s transformation from shuttered grain facility to regional destination. The venue now hosts weddings, community events, and seasonal festivals—including the upcoming Harvesting Sunshine Festival on Sept. 27. The family-run vineyard’s Pinot Noir harvest will be celebrated with face painting, food vendors, roof tours, and booths from downtown businesses like Revival and Terracotta.

The event follows a successful summer for Sunshine Mill, which sold out a special vintage produced for Trader Joe’s. “It was supposed to last the year, but it’s already gone,” said Skov, noting that orders for 2026 have increased.

Wadsworth shared updates from Freebridge Brewing, including the long-anticipated opening of a new kitchen space and preparations for their annual Oktoberfest celebration on Sept. 20. The 10-hour event will include German lagers, bratwurst, pretzels, and games like Hammerschlagen and a stein-holding contest, all streamed alongside Munich’s own Oktoberfest celebration.

Both business owners emphasized the importance of supporting local education. Sunshine Mill and Freebridge Brewing are participating in the Shop and Dine for Schools event during First Friday, with proceeds helping to fulfill teachers’ Amazon wishlists and providing resources for classrooms at Dry Hollow and Chenowith Elementary. “We all know teachers don’t get enough support,” said Wadsworth. “This is a way to step up for them.”

Kortge discussed other upcoming Main Street initiatives, including a Historic Spaces Tour tied to the restoration of the Umatilla House mural and aimed at showcasing both The Dalles’ storied past and its newly revitalized properties. Several downtown buildings—some dating to the 1800s—are being upgraded with support from Oregon Main Street grants and urban renewal programs.

Plans for the Federal Street Plaza and First Street improvements are also moving forward, with groundbreaking expected in spring 2026. Main Street will relocate its office to the plaza, alongside the Veterans Museum, which is gaining additional exhibit space. “It’s going to change how people experience downtown,” said Kortge.

Other fall events previewed included the family-friendly downtown Trick-or-Treat on Halloween, the long-running Witches Walk, and a new adults-only Witches Ball on Oct. 17 at Sunshine Mill.

As The Dalles’ cultural and business districts continue to grow, Neuharth summed up the shared vision: “A rising tide lifts all boats. When we support each other, we build something that lasts.”