The century-old building that once housed Oregon City's best-known blues venue is getting a new lease on life, with plans for a four-suite boutique hotel upstairs and a revived saloon and restaurant on the ground floor. Aviad Tapiro, owner of Tapiro Group, bought the property at 1320 Main St. in June 2026, and he says the vacant, 4,500-square-foot structure needs a lot of work before it can reopen.
Tapiro's plans include converting the upstairs apartment space, which had just one leased unit in recent years while the remaining units sat uninhabitable, into a four-suite boutique hotel with an Old West-inspired theme, according to The Oregonian/OregonLive. The property, which sold for $655,000 according to county records, includes a 10-space parking lot and a basement Tapiro sees as a potential redevelopment opportunity down the road. Tapiro lives in West Linn and owns Tapiro Group, a design and construction company that specializes in home remodels; the outlet's reporting forms the backbone of what's known so far about the project.
A Building With Deep Oregon City Roots
The site's history stretches back to the 1880s, when Freytag's Grocery, believed to be Oregon City's first grocery store, occupied the location. The structure was rebuilt after a major fire around 1905, and in the 1940s it housed a Chinese restaurant before later serving as apartments. Dan and Jean Montjoy purchased the property in 1992 and transformed it into Trail's End Saloon, which closed in November 2025 after decades as a fixture of downtown Oregon City nightlife.
Before its closure, Trail's End Saloon was recognized as one of the top venues in the regional music scene, winning the Cascade Blues Association's Muddy Award for Best Blues Venue, per the Cascade Blues Association. The saloon regularly hosted notable Pacific Northwest blues artists and jams, including Muddy Award-winning singer Rae Gordon and the late harmonica player Paul deLay, according to the Louis Pain Blog. Tapiro has said he plans to bring back live music and dancing as part of his vision for the space.
Grant Funding and a Bet on Downtown Oregon City
Tapiro received conditional approval for a $100,000 grant award to help fund the upstairs hotel renovation. The money would come through Clackamas County's Tourism Small Business & Entrepreneur Acceleration Grant Program, a one-time, competitive grant cycle administered by the Clackamas County Office of Economic Development that offers individual awards of up to $100,000 from a $500,000 total pool and requires awardees to provide at least a 25% matching contribution for capital improvements, according to Clackamas County.
Tapiro's Oregon Construction Contractors Board license, CCB #211994, confirms his firm's history in residential whole-home remodels, kitchen renovations, and general contracting across the Portland metro area, according to Oregon Construction Contractors Board licensing records. He said he believes in Oregon City and thinks it will be a big thing, adding that the city has big plans of its own. He envisions the reopened building as a family-friendly destination that celebrates both the structure's own history and Oregon City's role along the Oregon Trail.
Filling a Gap in Downtown Lodging
Oregon City currently has no overnight lodging options along Main Street or anywhere in its downtown core, despite sitting within walking distance of major regional draws like the Oregon City Municipal Elevator, Willamette Falls viewpoints, and the Museum of the Oregon Territory. Any boutique hotel Tapiro opens would need to comply with local transient lodging taxes, which range between 6% and 8% in Clackamas County, along with standard business permit registration, per guidance from Cascadia Getaways.
The property sits within Oregon City's Mixed-Use Downtown district, which explicitly permits hotels, lodging facilities, and ground-floor eating and drinking establishments while capping building heights relative to the 58-foot historic Masonic Hall, according to city zoning code. That zoning designation lines up well with Tapiro's plans to reopen a bar and restaurant on the first floor while running lodging upstairs.
Still Searching for a Food and Beverage Partner
Tapiro is seeking an operator or business partner to run the food and beverage side of the operation, and he has said the bar reopening could move faster with the right partner in place. He hopes to reopen the bar within six months, though the timeline for the full hotel renovation remains less certain given the scope of work the building needs.
The project adds to a wave of adaptive reuse taking hold in downtown Oregon City, where Clackamas County recently approved a wrecking ball for the historic courthouse to make way for a five-story mixed-use residential and retail project from Level Development NW. Downtown Oregon City was named a national Great American Main Street Award winner in 2018 by the National Main Street Center, which credited the area with nearly $42 million in public and private investment and commercial revitalization since 2009, according to the Milwaukie Review. Statewide, Oregon's designated Main Street programs generated more than $24 million in private investment and supported 293 building rehabilitation projects in 2024 alone.
