New owners for Orcas Freight

Two Orcas couples are collaborating as business owners.

Bob and Gail Toombs and Charlie Jabbora and Madeline Sheplor purchased Orcas Island Freight Lines this summer from Michael and Sarah Aley.

“Neither of us wanted to do it without the other,” said Sheplor.

The Aleys bought Orcas Freight in 2009 from original owner Wayne Foster. The Aleys previously owned and operated Friday Harbor Freight, and Sheplor grew up with the Aleys and their two daughters on San Juan Island.

For nearly two decades, Charlie worked in the freight department at Costco and Sheplor ran the network system for the Bellingham Public Library. They were “hemming and hawing” about moving back to the San Juans when the Aleys called to offer Charlie a job as a driver in 2015. A year after moving to Orcas, Sheplor became the office manager of the company.

Bob, who worked for Sea Island Sand and Gravel for years, joined as a part-time driver in 2016. He first had the idea to join forces with Sheplor and Jabbora after sitting with three other local truck drivers – Tim Holmes, Jerry Schmidt and Jay Sack – on the ferry one day.

“They said, ‘why don’t you guys just buy it’?” remembers Bob.

The budding partnership was perfect timing as the Aleys left for a mission trip to Utah in early 2017. By Aug. 18, the two couples were the new owners.

Orcas Freight hauls a wide variety of residential and commercial items from as far north as the Canadian border and as south as Tacoma, and delivers to all islands, including Shaw, Crane, Waldron, Decatur and Blakely. The company has two flatbeds, four box vans, two box trucks and four semi-trucks.

“Between the Fosters and the Aleys, it’s a viable business,” said Bob. “But we want to improve efficiency and open the freight lines up and down the I-5 corridor.”

The company established a central location at Soniq Transportation in Kent for items be dropped off by customers and carriers like UPS and FedEx in Kent. Freight is staged by Soniq in Orcas trailers and brought back to the islands three days per week.

As a new service, a dedicated truck goes off-island one day a week to pick up residential items from hardware and furniture stores in Bellingham and Burlington. The business also partners with two shipping companies to bring 28-foot trailers to homes for moving services.

“We are great for homeowners too,” said Gail.

Orcas Freight has a contract with the county to haul containers of recycle, electronic recycle and garbage for Orcas Recycling Services.

“We have a good partnership with ORS,” said Sheplor. “We haul for them five days a week – sometimes twice a day.”

In addition to Bob and Jabbora, drivers for the company are Kelly Toombs (the Toombs’ son) and Tyler Patterson. Kelly’s daughter Maggie, a senior at Orcas High School, is also a part-time employee. Family is an integral part of the new management at Orcas Freight.

“We seriously love each other,” said Sheplor.

Added Gail: “Madeline and Bob speak the same language in business. We already feel like they are family.”

To reach Orcas Island Freight, call 360-376-2303 or visit