News Summary
The Iron Horse Hotel in Milwaukee has been acquired by its lender for $15.75 million at a sheriff’s sale after lengthy foreclosure proceedings that began in 2021. The property, famous for its boutique rooms and proximity to the Harley-Davidson Museum, faced financial difficulties linked to the COVID-19 pandemic. Following the acquisition, an agreement was reached allowing the previous ownership group to retain control and provide updates on the hotel’s loan status as it moves forward.
Milwaukee – The Iron Horse Hotel, situated at 500 W. Florida St. in Milwaukee’s Walker’s Point neighborhood, has been acquired by its lender for $15.75 million at a recent sheriff’s sale. The sale comes after prolonged foreclosure proceedings that began in 2021 amid financial difficulties exacerbated by the COVID-19 pandemic.
The Iron Horse Hotel, known for its 102 boutique hotel rooms and a biker-friendly atmosphere linked to the nearby Harley-Davidson Museum, represents a significant property within the local hospitality industry. Since opening in 2008, it has become a popular destination, featuring three public-facing restaurants and bars: Branded, Ash Heart and Bar, and The Yard.
Legal issues for the hotel commenced in 2021 when the lender, identified as RSS, filed a foreclosure lawsuit against the ownership group, Rider Hotel LLC, led by developer Tim Dixon. In 2022, Rider Hotel LLC filed for Chapter 11 bankruptcy, citing the adverse impact of the pandemic and ongoing financial struggles. This bankruptcy filing temporarily paused the foreclosure process, allowing the company to seek potential debt resolutions.
Despite these efforts, Rider Hotel LLC was ultimately unable to rectify its debt situation, leading to Milwaukee County Circuit Court judge approval for foreclosure in June 2023. The subsequent sheriff’s sale took place on August 25, 2023, where RSS, formally known as RSS GSMS2015-GC28-WI RH, LLC, was the sole bidder. Judge Paul Van Grunsven approved the sale during a session on a Monday morning, with the proceeds directed toward paying off Rider Hotel’s outstanding debt of $27.9 million.
Following the auction, which occurred in September 2023 but did not attract any additional bids, a noteworthy development took place two months later. An agreement was reached, allowing Dixon’s ownership group to retain control of the hotel and provide updates on the loan status. Following this resolution, the bankruptcy case was closed in October 2024 after further negotiations with the lender, as Dixon had initially intended to refinance the loan by its maturity date in February 2025.
The Iron Horse Hotel’s legal saga also includes an initial auction in 2023 that did not attract bids sufficient to cover the $24 million owed by Rider Hotel LLC. A foreclosure judgment was posted against the company by Judge David Borowski, indicating that the property’s potential sale would benefit the lender.
In light of the foreclosure ruling in June 2023, Crescent Hotels and Resorts, based in Virginia, was appointed as the hotel’s receiver. This transition further emphasized the challenges faced by the property and its management amidst shifting financial landscapes in the hospitality sector.
In summary, the Iron Horse Hotel’s journey through foreclosure to lender acquisition highlights the difficulties experienced by many establishments in the hospitality industry due to pandemic-related disruptions. The property is now positioned under new ownership as it seeks to navigate future challenges and opportunities in Milwaukee’s competitive hotel market.
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HERE Resources
Iron Horse Hotel in Milwaukee Acquired by Lender for $15.75 Million
Additional Resources
- BizTimes: Lender Acquires Iron Horse Hotel
- Wikipedia: Iron Horse Hotel
- Urban Milwaukee: Iron Horse Hotel Faces Sheriff’s Auction
- Google Search: Iron Horse Hotel Milwaukee
- JSON Line: Milwaukee Boutique Hotel Faces Foreclosure
- Encyclopedia Britannica: Iron Horse Hotel Milwaukee
- Travel Wisconsin: Thursday Bike Night Series
- Google News: Iron Horse Hotel

Author: STAFF HERE MILWAUKEE WRITER
MILWAUKEE STAFF WRITER The MILWAUKEE STAFF WRITER represents the experienced team at HEREMilwaukee.com, your go-to source for actionable local news and information in Milwaukee, Milwaukee County, and beyond. Specializing in "news you can use," we cover essential topics like product reviews for personal and business needs, local business directories, politics, real estate trends, neighborhood insights, and state news affecting the area—with deep expertise drawn from years of dedicated reporting and strong community input, including local press releases and business updates. We deliver top reporting on high-value events such as Summerfest, Milwaukee Film Festival, and the Milwaukee Boat Show. Our coverage extends to key organizations like the Metropolitan Milwaukee Association of Commerce and Visit Milwaukee, plus leading businesses in manufacturing and brewing that power the local economy such as Harley-Davidson and MillerCoors. As part of the broader HERE network, we provide comprehensive, credible insights into Wisconsin's dynamic landscape.