Left: Bill, Dick, Jack and Don Montgomery in 1920.

Left: Bill, Dick, Jack and Don Montgomery in 1920.

Montgomery family celebrates 100 years on Orcas

  • Thu Jun 21st, 2018 4:37pm
  • Life

by Krysti Hall and Larry Nyland

Special to the Sounder

Joseph Ray “Monty”’ Montgomery and May Cecil Schlott arrived on Orcas Island in 1918. A century later, on July 4, 2018, their descendants will gather in Eastsound to celebrate “100 Years on the Rock.”

Monty was born in Kansas and raised in gold mining fields from Arizona to Alaska. May was born and raised in Las Vegas, New Mexico shortly after the likes of Jesse James and Billy the Kid made Las Vegas a rival to Dodge City and other “wild west” towns. In the early 1900s, May and Monty arrived separately in Tacoma, Washington, as students at Whitworth College. The two met in choir, married in 1913 and settled in West Seattle where they had two sons: Bill and Jack. Monty bought four milk cows, acquired some lessons in milking, and delivered milk door to door with his horse, Rusty.

Meanwhile, May’s sister Merle came to Orcas Island as a teacher. She met and married Bill Norton, who owned much of Deer Harbor. In time, Bill Norton asked Monty to manage the ranch that then existed on the property where Four Winds Camp is now. Rusty the horse made the move with the family, pulling the buggy to the ferry and church for several years. May and Monty’s third son, Don, was born in 1918. Dick was born in the Deer Harbor store in 1920. Pat was born in 1923.

Having experienced significant rapid change over several years, Monty and May now established stability on the island through their family farm and their solid Christian faith. In 1920 they bought Meadow Farms, a Deer Harbor farm they would run for the next 20 years. They raised sheep, sold milk, and grew vegetables, for which Monty, now known as J.R., won awards at state exhibitions.

The Montgomery sons attended the Deer Harbor School (now the Deer Harbor Community Club) until the school merged with West Sound in 1926. The boys graduated from high school in Eastsound. By then, the family had a Chevy stake truck. That one vehicle sufficed for farm use as well as transportation to and from church and basketball practice. With hay bales in the back, the truck carried the family and many others where they needed to go and home again.

By 1940 it was becoming difficult to make truck farming pay. J.R. and May moved to Los Angeles to help his aging mother. Bill and his bride, Dorothy, took over the family farm. Bill and Dorothy became caretakers of the Kaiser family estate and eventually transitioned into construction. They raised three children on Orcas: Natalie, Ron, and Mark.

Dick and Mary Montgomery returned to Orcas in 1955. Dick drove a truck, did construction work, and served as the music and youth director at the Orcas Island Community Church. He bought and restored one of the oldest homes on Orcas—a hospitality landmark now known by many as the Inn at Ship Bay Restaurant. Countless memorable Montgomery family gatherings occurred in the fireplace room. Two daughters, Dorothy and Kathy, were raised on Orcas Island before Dick and Mary moved to Mount Vernon. Dick returned to Orcas in his later years.

Jack and Gene Montgomery raised their family in Burlington but returned to the island in their retirement years. Don and Rosa lived in Los Alamos for most of their working years and returned to Orcas in their retirement. Pat died in military service in 1944.

J.R. and May returned to Orcas in 1957 to develop the Eastsound waterfront tracts on Montgomery Lane just east of Crescent Beach. Waterfront lots were $2500. For decades, most Montgomery Lane lots belonged to family and friends. The annual “family reunion” picnic on July 4th now includes as many friends as family.

Much of the Montgomery family history is intertwined with the Orcas Island Community Church, from J.R.’s flatbed truck to Jack’s youth group and Dick’s music leadership. Bill and Don both served on the church board and as constant supporters. Rosa’s Bible study continues to this day, long after her passing. Regular fellowship, church sings, and helping out wherever there was a need were woven into the fabric of Montgomery family life.

In 1992, the four living Montgomery brothers—Bill, Jack, Don, and Dick—served as marshals in the Eastsound Historical Parade. Family members came from far and wide to honor the patriarchs and the occasion. As recently as 2003, all four had returned to their Orcas roots. They were living on Montgomery Lane, competing as storytellers, imparting to the next generation how it really was “in the old days.”

Today, Bill, Jack, Don, Dick, and Pat are gone. Ron, Bill’s son, is a full-time resident on Montgomery Lane. Natalie, Bill’s daughter, comes often to their vacation home on Montgomery Lane as do Kathy (Dick’s daughter) and Robyn (Don’s daughter). Several of Monty and May’s great-grandchildren own lots on Montgomery Lane. All have rich memories of beach picnics, hikes in Moran State Park, and family reunions.

“Kudos to the grandparents for deciding to move to Orcas in 1918,” says Ron Montgomery, the family’s current patriarch-in-residence. “They not only impacted this place, they created an opportunity for five generations (and counting) to enjoy an amazing connection to one of the most beautiful spots on the planet.”

In just a few days, Montgomery family members will converge on Montgomery Lane from points near and far to celebrate a long-anticipated centennial. Look for three generations in this year’s Eastsound Historical Parade. You’ll recognize them by their blue t-shirts bearing a photo of Monty and May, and a grateful declaration of their legacy: 100 Years on the Rock: Faith, Family and Future.


Rusty the buggy horse, with Dick, May, Jack, Don, and Bill Montgomery

Rusty the buggy horse, with Dick, May, Jack, Don, and Bill Montgomery