About Our Historic Door County Inn

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The Historic Hillside Inn has a long and rich history in Door County.
Read below to learn more about the Inn’s beginnings, and how we got here today.

The Hillside Inn (formerly Hillside Hotel) was started by Norwegian immigrants Martin and Maria Oleson and his family who purchased a four-room log cabin from Reverend Andreas Iverson in 1866. Over the years, the family built additional bedrooms and began renting these rooms out to guests in the summer of 1893. Additions over the years allowed for more and more guests accommodations and in 1901, the building officially became named the Hillside Hotel.

The Historic Hillside Inn of Door County is on the National Register of Historic Places as one of the first hotels in Ephraim, as the area transitioned from lumber and fishing to tourism. It included the wooden hotel, cottages and outbuildings, with one structure built as early as 1864. A one story porch with turned wood columns and a plain wood balustrade spanning the entire front of the hotel was built in 1908 and still exists today as part of the largest porch in Door County.

In 2002, it was remodeled by Jim and Claire Webb with close attention paid to maintaining the original integrity of the outside structure while becoming a luxury historical Door County inn with all of the amenities of a boutique hotel. It closed in 2010 and was reopened by current owner, Diane Taillon, in 2016.

Meet the Owner – Diane Taillon
Owner, Historic Hillside Inn / Owner & Broker, Arbor Crowne Properties

Expect the best from this organized, enthusiastic real estate broker with a contagious, positive attitude. Diane brings experience, efficiency and calmness to your real estate transaction. In real estate since 2003, she is an accomplished Broker in the states of Wisconsin, Illinois and Florida. In addition to being named as one of the Top Ten Realtors, she is a member of the Professional & Ethics committee of the Door County Board of Realtors. Di is a Graduate of the Realtor Institute as well as the Institute for Luxury Real Estate.

Formerly a Pediatric Orthotist, she developed the largest Orthotic practice in Northeastern Wisconsin in addition to developing several medical patents. Her practice was recognized as the Small Business of the Year in Wisconsin. A graduate of the State University of New York at Buffalo and Northwestern University, she was a teacher in Nairobi, Kenya while part of the US Peace Corps and led the African National Conference on Malnutrition in Africa. For relaxation, she enjoys sailing and international travel.

Diane has recently purchased The Historic Hillside Inn in Ephraim where her real estate office is located. She is excited to work with her management staff of the Hillside as owner to welcome both Door County tourists to this historic property as well as local community groups to utilize the Inn. It is her goal that The Historic Hillside is a thriving, vital part of the Door County community.

Learn more about Arbor Crowne Properties.