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The story of Lonesome Valley began in the 1800s with the immigration of the Jennings family from St. Ives, England to the United States.  Throughout the 1800s and early 1900s the Jennings Family became prominent in Pittsburgh’s business and social life.  In the late 1800s, Edward Henry (E.H.) Jennings made his first of many ventures to “Sapphire Country,” known today as the Cashiers-Highlands area.  He quickly fell in love with “this most spectacular of places” and began acquiring various tracts of land. 



In 1895, the visionary E.H. Jennings joined with a group of other gentlemen to purchase 35,000 acres across Western North Carolina and create the Toxaway Company.  Recognizing the natural beauty and attraction of the area, E.H. Jennings developed several fine Inns throughout the region, including the two most notable in this area, the Toxaway Inn and the Fairfield Inn.


Throughout the early 1900s, “Sapphire Country” saw tremendous growth and development.  In 1911, the Toxaway Company was forced into bankruptcy.  As one of the largest stockholders, E.H. purchased the Toxaway Company in foreclosure for $100,000, and thus acquired and owned approximately 27,000 acres of land as well as the Toxaway, Fairfield, and Sapphire hotels.  The Jennings family returned annually to spend several weeks each summer at the Inn. 

Upon E.H. Jennings’s death, his eldest son Richard G. Jennings Sr. assumed responsibility for the family business.  He purchased an additional 550 acres in the box canyon adjacent to Lonesome Valley.  During his tenure, several parcels of land were sold, including a tract known as Panthertown.  Richard Sr. had three children, Richard Jr., Melchior (Mike), and Mary Colwell. 

After the passing of Richard Sr. in the late 1940s, Richard, Jr. and Mike acquired Lonesome Valley from their father’s estate.  Over time, Richard, Jr. purchased the balance of the Valley from Mike.  Like his grandfather, Richard, Jr. fell in love with these mountains.  He never regretted moving to Lonesome Valley, as there was no other place he would rather reside.


Richard Jr. and his wife Frances moved to Lonesome Valley in 1952 and began mink farming and raising trout.  Their family quickly grew to include three children: Sally, Richard III (Dick), and Binford.  Life as a young family in Lonesome Valley took on an almost pioneer existence, and though demand for mink diminished, the Cashiers Valley Trout Farm sustained them. To this day, the Jennings trout farming activities continue under the guidance of daughter Sally and her family at the Sunburst Trout Farm in Waynesville.


Developers began to take notice of the magnificent vistas, rolling green meadows, and clear mountain streams. To preserve their father’s commitment to preserving the integrity of the land, Sally, Dick, and Binford realized that if change and development were inevitable, then they preferred to undertake the effort themselves.



With a plan deeply rooted in the past, the Jennings siblings decided in 2005 to reestablish and expand their family farmstead. Taking inspiration from the natural cow-shaped image found on Cow Rock Mountain – one of two massive granite walls that define the eastern rim of the canyon – the Lonesome Valley logo was established, along with the vision for a community that rekindled childhood joys and freedoms.


Lonesome Valley began its first stages of development with the construction of roads, utilities, conservation areas, and the creation of responsible deed restrictions and thoughtful architectural guidelines.



Canyon Kitchen opens to the public.  Canyon Kitchen offers a humble yet extraordinary connection to food that both sustains and entertains the senses. Massive oak beams define the structure of Jennings Barn and its open-air dining. The restaurant is named "The Most Romantic Restaurant in North Carolina" by Food & Wine and as an Open Table Diners’ Choice Award for Top 100 Scenic View Restaurants in America.


The cottage belonging to the caretaker of Lonesome Valley from 1954 to 2007, Mr. Henry is renovated to become Canyon Spa. Canyon Spa is open to the public and offers a full array of natural body and facial treatments, therapies, and products.