A Homestead Once Known as “Yesteryear”
Early Settlement
In the early 1800’s, The Choushatta Indians travelled through the lands that would become the Lake Creek Settlement upon the Choushatta Trace, a trade road from Louisianna into Texas. The Lake Creek Settlement traces its origin back to 1825 when the Mexican government issued colonization contracts to Stephen F. Austin (June 4, 1825) between the state of Coahuila and Texas. Under his 1825 contract, Stephen F. Austin was given six years to settle 500 families in the land between the West Fork of the San Jacinto River and the stream known as Lake Creek – what is today western Montgomery County.
In 1826, Mr. and Mrs. Benjamin Rigby were among the first of the early settlers to arrive in Austin’s “Second Colony”, then known as the Lake Creek Settlement. Rigby applied to obtain a “league of land” from Mexico. On April 14, 1831, his land grand was approved, making Rigby one of sixteen Anglo-American colonists to receive a “league of land” within the boundaries of Austin’s Second Colony. The Rigby homestead was located at what is now the northwest corner of State Highway 105 and FM 149 in Montgomery, Texas. The Rigby’s called their new home “Yesteryear” in honor of their life in the United States.
Founding of Montgomery
In 1837, Montgomery was officially named and chartered. That same year, Mr. Rigby sold the remainder of his land grant to Mr. and Mrs. John F. McCuffin. The town of Montgomery became a local hub for the telegraph line, a newspaper print shop and three stagecoach routes. That same year, Dr. Charles B. Stewart moved to town and later created the artwork for the Texas flag in 1839. Montgomery is officially recognized as “The Birthplace of the Lone Star Flag”.
Montgomery continued to flourish during the 1850’s. On November 22, 1855, Mr. McCuffin sold 1.3 acres of his homestead at “Yesteryear” to Mr. John E. Shelton for the price of $400. Mr. Shelton was a well-known craftsman and builder in Montgomery. Mr. Shelton built several homes in the area that still stand today. He used his skill and vision to build the Main House of The Caroline House Bed & Breakfast.
Transition to the Smith Family
Mr. Shelton sold the home to his friend and business partner, Captain Thomas Wesley “T.W.” Smith on February 2, 1858 for $425. Mr. Smith was a merchant and the sheriff of Montgomery County. He raised eight children in the home with his wife Margaret. In 1872, the Smith family moved to Willis, TX where Mr. Smith owned a successful tobacco plantation and operated cigar factories.
Mr. Smith sold the house to his son W.J. Smith in 1894 for the price of $10. W.J. and his wife Ella Smith remodeled the home in the Victorian style and raised their children in the house. Their daughter, Stella Smith Peynghaus inherited the home in 1905 and made additional renovations in 1922. She added two dormer windows and converted the attic into a second story suite. She also had the original pine floors covered with maple wood.
The Gay and Whisenant Families
In 1924, Thomas A. and Edna Gay purchased the home and added indoor plumbing. They raised their only child, Green Duke Gay II, in the house. In 1949, the house was inherited by Mr. and Mrs. Green Duke Gay II who added a greenhouse to the back of the property with a plexiglass enclosure for growing orchids.
In 1970, the Gay Family Estate sold the home to Kenneth and Mary Whisenant who spent the next three years restoring the home to its original style and character. The Whisenants had the home named a Texas historic landmark and added HVAC to make the home more comfortable.
Becoming The Caroline House
In 2000, the home was sold to Mary Catherine Eckhart Sims who created The Caroline House Bed & Breakfast. Ms. Sims converted the old greenhouse into a three-bedroom Guest House with two bathrooms and a kitchen. She also converted the old slaves quarters into a cozy Honeymooners Cottage.
The Story Continues
In 2025, The Caroline House was purchased by Eric and Connie Renouard. The Renouards love the history and the character of the Shelton Smith House and they have continued the legacy of Mary Sims by keeping the home open as The Caroline House Bed & Breakfast.
