The history of Cliffside Cottages began in 1936 when Orlo Arnsberger, his wife Anna and their daughter Barbara traveled from Ohio, USA to Wiarton and the Bruce Peninsula. They were in search of a place to build a summer home and a place to alleviate Barbara’s asthma.
Upon their arrival in Wiarton, the Arnsbergers hired a boat to take them out into Colpoy’s Bay to enjoy the beautiful landscape. While on their way to Cape Chin along the rugged shoreline, Orlo spotted a lot on Spragge’s Hill. He tracked down the owner Burford Rydall and paid him a visit to see if he was interested in selling the land. “Will you sell this ground?” Orlo asked. “It’s Sunday and l don’t do business on the Lord's Day” Burford replied. Orlo was insistent and the deal was completed that day (ALBEMARLE, Albemarle Township Historical Society, Wiarton, 1991).
One month later, Orlo built his summer home on the rugged ground below the top of the cliff. Some of the local farmers and businessmen thought he was out of his mind to buy that rock covered piece of ground but Orlo could see his dream taking shape and vowed to prove them wrong.
The initial idea of building a summer home soon changed as requests from visitors and friends to rent the first cottage encouraged Orlo and his family to build in 1942 a small unit, known as the Honeymoon Cottage. In 1943, Orlo purchased an old log building from a farmer in Purple Valley, Ontario. He built a foundation on which to re-assemble the log building and built a rock fireplace in the centre of his third cottage. In 1944 and 1945, he constructed a building that contained three different units on two levels. Finally, in 1948, he started the construction of a log cabin at the top of the cliff with a stunning view of Colpoy’s Bay. This became the Arnsberger's main residence.
In 1948, Anna and Orlo divorced and Orlo managed Cliffside Resortby himself until he met Ruth Sandlie and married her in 1967. Ruth was born in Norway and had honed her skills in many art mediums prior to coming to North America. She loved drawing, weaving and painting in watercolors, oil painting and pen and ink. Ruth was also an avid cross-country skier and designed the terminal cairn at the northern terminus of the Bruce Trail in Tobermory and Queenston and restored the Emily Carr rugs at the Tom Thomson Memorial Gallery. She became a very famous artist in the Bruce Peninsula area. Ruth painted several pictures inspired by the beauty of Cliffside and the surrounding area. In 1970, Ruth and Orlo opened a cross-country ski shop at Cliffside Resort and promoted cross-country skiing in the Wiarton area.
After Orlo passed away in 1989, Ruth and her friend Ross operated and maintained Cliffside Resort until Ruth´s death in January 2008.
Currently, Cliffside Cottages is owned and operated by Orlo’s daughter Barbara, his grandson Michael Millar and Michael's wife, Cristina Guzman.