The Oaks Waterfront Inn Undergoes Major Renovations

Since the early 1900s, The Oaks Waterfront Inn, formerly known as the Pasadena Inn, has been a unique destination just outside of St. Michaels. The Inn, now under new ownership, will undergo enhancements on the property with a number of renovations that will carry it into future decades.

This artist’s rendering showcases the exterior enhancements taking place at the historic The Oaks Waterfront Inn. Rendering courtesy of McHale Landcape and Design.

The new owners, Scott and Tracy Wagner, Doug Stewart and Jennifer Stevens, have enlisted the design expertise of McHale Landscaping and began the enhancements by cleaning up the tree line on the property and across the street. Beautiful trees and white fencing were added in those areas.

The Inn was closed for a few weeks in July to install a new roof, replace the yellow vinyl siding with white hardy plank, add new windows, seal the crawl space and pave the driveway as well as parking lots.

A longer closure will take place after the last wedding in 2022, from November to April 2023, to complete the remaining renovations. Plans include adding an elevator, redecorating the rooms, renovating all bathrooms and adding three new cottages on the property.

The Oaks’ new owners and staff are looking forward to the upgrades to this beautiful historic property and are excited to welcome guests. There are still several weekends available for wedding bookings in 2023. Contact Lamond Conover at 410-745-5053 for details or visit

The History

According to The fascinating history of the recently renovated Oaks Inn dates back to the 17th century. The Inn resides on property from an original land grant deed to the Benson family by Lord Baltimore in about 1680. The entire plot of land consisted of 740 acres. A 42-acre portion of that property, where the Inn now sits, was sold to the Harper Family in 1884 for $5,900. They farmed the land, and it became known as Oak Hall.

Frederick Harper and his wife, Louise, started running the Inn as a boarding house in 1902 to help with the expense of the farm. Guests would travel by steamship from the Western Shore to nearby Claiborne and then catch the train to the Inn.

The Harpers sold the farm in 1971 to the German Company Schwaben International who continued to run the Inn as a corporate resort and cultural conference center. In 1996, a St. Michaels couple purchased and completely renovated the Inn. Instead of small road-front rooms with bathrooms “down the hall” you will now find spacious rooms, many with water views and modern conveniences like Whirlpool tubs, gas fireplaces and king-sized beds.

Fun Fact

During the early 1900s, one of the last silent films, “The First Kiss,” was filmed in Easton. The stars of the film, Gary Cooper and Faye Wray, stayed at the Inn during filming. Faye Wray was married on a skipjack on the Miles River while making the movie.

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