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The 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 1901, the building became the Hillside Hotel. The Hillside Inn of Ephraim 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.

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 inn with all of the amenities of a boutique hotel. It closed in 2010 and was reopened by current owner, Diane Taillon, in 2016.

The south cottage, built near the turn of the century, was originally part of Martin Oleson’s house. The north cottage was built late in 1915. Southeast of the hotel was a one story board and batten shed which was built as a workroom in the 1880s. Behind the hotel are two outbuildings which were built in the 1910s; the Oleson family lived in these outbuildings when the hotel was full. 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.

The south section was also added to the hotel in 1908 while the north section was added in 1926. A photograph dated 1913 shows the north portion of the hotel as being only one story tall but otherwise similar to the present configuration.

In the 1890s, Ephraim was starting to attract summer visitors seeking an escape from the hot and crowded cities located south of Door County. At first there were only a few visitors and no hotels. Village residents, many fishermen and lumberman by trade, would rent out rooms of their houses and cook for the summer visitors. By 1896 the county newspaper was lamenting that “Ephraim needs a good hotel.” Four years later as both the fishing and lumbering industries continued to decline, the tourist industry had increased to the extent that inquiries for accommodations for the summer were being made in the early springtime. It was during this time that many hotels and cottages were built and among them was Martin Oleson’s (Olson) Hillside Hotel.

Ephraim had three hotels in 1910 and seven hotels in 1917, by which time the Hillside had expanded to accommodate 40 people. Ole M. Olson, Martin’s son, was for many years the proprietor of the hotel. He developed it to the extent that when he died in 1921, the county newspaper noted that “as proprietor of the Hillside Hotel he was widely known throughout the state, having entertained summer guests from many of the cities of this adjacent states.” The Hillside Inn is the last of the original “Grand” hotels of Ephraim still welcoming guests today.

Meet the Owner: Diane Taillon
Owner, 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 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 Hillside is a thriving, vital part of the Door County community.