Fifty Years. Fifty Miles. $50,000. That’s the plan.

The walk is intended to inspire others to appreciate the connectivity of island life.

  • Friday, July 30, 2021 10:44am
  • News
Toby and Amy Holmes, who love the outdoors, are planning a walk around Vashon’s shoreline to raise $50,000 for island causes (Courtesy Photo).

Toby and Amy Holmes, who love the outdoors, are planning a walk around Vashon’s shoreline to raise $50,000 for island causes (Courtesy Photo).

By Jenna Dennison

For The Beachcomber

Vashon resident Toby Holmes has one goal for his upcoming 50th birthday: to walk 50 miles around the shoreline of Vashon Island in 24 hours and raise $50,000 in the process.

In his quest to raise big money with a very long walk, he’ll be joined by his wife, Amy Holmes. Their walk over cobbled beaches, around the island, will start at 5 a.m. Saturday, Sept. 4 — just shy of one month after Holmes’ 50th birthday, on Aug. 6.

The couple plans to equally distribute the funds raised during his birthday walk to five different local organizations: the Vashon Heritage Museum, Vashon Island Land Trust, Vashon Schools Foundation, Vashon Island Rowing Club and the Vashon Food Bank.

As a board member for Vashon Island School District, Toby appreciates the work of the Schools Foundation, and Amy serves on the board of the Land Trust — two of the five organizations for which they are raising funds.

The walk and fundraising efforts, they hope, will inspire other islanders to appreciate the connectivity of life on Vashon.

“We’re one community, on an island,” Toby said.

However, this will not be the first time a 50-mile walk around Vashon has happened.

In fact, the couple got the idea for the walk after learning about a similar walk that happened in 1938, when George McCormick, who owned Vashon’s Hardware Store, walked the circumference of both Vashon and Maury islands in less than 24 hours, winning a $67 bar bet in the process.

McCormick was supported in his walk by Deputy Sheriff F.J. Shattuck, who reportedly met up with McCormick three times along the way to rub his friend’s feet with alcohol. McCormick also reportedly knocked back a pint of Kentucky bourbon somewhere near Tahlequah, as he approached the end of his walk.

According to a historical account of the walk that appears online at, many in town were in on the bet, including Agnes Smock, then the editor of the Vashon Island News Record, as well as the proprietor of The Alibi, a combined pool hall, card room and restaurant in the middle of town.

Toby and Amy hope their walk generates as much excitement as McCormick’s did — and that it raises much more money.

The couple has been carefully examining maps and tide charts to plan their launch time. There are other challenges they will face, such as likely having to swim or wade through water at the highest tides. Amy has plotted the shorelines and calculated they will cross just over 50 miles of shoreline.

Holmes was born in Dolphin Point in 1971 and left Vashon after graduating high school. He attended Grinnell College, in Iowa, for his undergraduate degree and received his MBA at the University of Washington. He and his wife returned to Vashon about 13 years ago to raise their family.

Holmes is currently serving his second term on the Vashon Island School District board, where he has served for six years.

Updates on the birthday walk will be posted on Holmes’ website at You can also find updates on Holmes’ Twitter and Instagram pages.

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