A Century-Old Building Could Soon Have Both a Saloon and a Hotel Room

Aviad Tapiro plans to reopen the saloon while adding a four-suite hotel upstairs

Juan Carlos Montoya News Writer
Former Trail's End Saloon space (Image credit: Google Earth Image)

Trail’s End Saloon, the two-story, 4,500-square-foot building at 1320 Main St in Oregon City, has a new owner with a big vision for the space. Aviad Tapiro, owner of Tapiro Group, a design and construction company specializing in home remodels, purchased the property in June for $655,000, after the saloon closed in November and the building sat vacant.

Tapiro plans to reopen the saloon and restaurant on the ground floor, bringing back live music and dancing, while converting a long-unused upstairs apartment space into a four-suite boutique hotel, all built around an Old West theme. Oregon City currently has no overnight lodging along Main Street or anywhere in its downtown core, something Tapiro hopes the hotel will change. He’s still looking for an operator or business partner to run the food and beverage side of the business.

He received conditional approval for a $100,000 grant through the Tourism Small Business & Entrepreneur Acceleration Grant Program, a Clackamas County program, to help fund the hotel renovation, according to the Oregonian.

The building itself carries deep local history. In the 1880s, the site housed Freytag’s Grocery, believed to be Oregon City’s first grocery store. A fire around 1905 led to the current structure, which later held a Chinese restaurant in the 1940s before Dan and Jean Montjoy bought the property in 1992 and turned it into Trail’s End Saloon.

Tapiro said he hopes to reopen the bar within about six months, though that timeline could move faster with the right operator. He’s open to hearing from other business concepts as well, saying he wants to celebrate both the building’s history and Oregon City’s role as the end of the Oregon Trail.

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Juan Carlos Montoya discovered his love for storytelling through sports, creating social media content in high school before pursuing a bachelor's degree in Journalism in Costa Rica, where he graduated in 2025. Since then, his career has taken him through the halls of Teletica Radio, the biggest mass communication company in Costa Rica, and into the world of digital media as a Social Media Manager for an iGaming platform. Originally from Honduras, Juan Carlos brings a global perspective to every story he tells. He believes that every interview is an opportunity to make a genuine human connection, and that food is one of the most powerful ways to understand a culture and its roots. When he's not tracking down the next big opening in Sacramento or Portland, he's probably watching Football, or planning his next adventure. What Now is his new home, and he's just getting started.
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