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Quincy lawyer, inspired by James Taylor, to walk from Stockbridge to Boston for charity

David Spillane plans to walk 161-miles from "Stockbridge to Boston" for charity.David Spillane

How does an avid walker and die-hard James Taylor fan raise $50,000 for charity?

By walking 161 miles from Stockbridge to Boston, of course.

That stretch, immortalized in the lyrics to Taylor’s soft rock lullaby “Sweet Baby James,” inspired David Spillane, a Quincy lawyer of 30 years and father of three, as he chose his route.

He’s seen Taylor, a Massachusetts native and multiple Grammy winner, in concert 16 times. This is the only Taylor song he can play on a guitar.

“It’s like falling in love,” Spillane, 63, said of his idea. “It just happened.”

At a fund-raiser two years ago, Spillane was touched by the efforts of the Elizabeth Stone House, a Roxbury nonprofit that helps survivors of domestic violence and other trauma reclaim their lives.


“I started thinking, ‘what can I do?’” Spillane said. The lawyer loves to walk.

There’s no better way to see a city, he said.

For years, his family walked long distances in cities around the United States. Eight times they’ve participated in the 39.3-mile Avon 39: The Walk to End Breast Cancer. The event became a part of their vacations, raising an estimated $75,000, he said.

From Nov. 23 through Dec. 1, Spillane will walk residential and rural parts of the state, passing through Northampton, Worcester, Marlborough, Sudbury, Watertown, Cambridge, and other areas before reaching Boston.

Spotters will make sure Spillane is OK as he strolls from Route 20 to Route 9 and back to Route 20. On Dec. 1, he plans to cross the Boston Marathon finish line.

“I told my spotter,” Spillane said, “one of your most important jobs is to find me a place to have lunch. I know how to layer so I’m just going to dress depending on the day. I have rain gear, I have sweaters, I have water-wicking clothes.”


Spillane hopes to average 18 miles a day, listening to National Public Radio or music as he ambles along near the route Taylor crooned about in his 1970 hit song:

“Now the first of December was covered with snow

and so was the turnpike from Stockbridge to Boston

Though the Berkshires seemed dreamlike on account of that frosting

with ten miles behind me and ten thousand more to go…”

David Spillane.David Spillane

“He’s taken this on himself,” said Rebecca Allen, donor relations manager for the Elizabeth Stone House, of Spillane’s goal. “We’ve supported with some stuff on social media and writing thank you letters to donors, but he just said, ‘I’m going to walk and I’m going to raise money for you.’ We’ve never had someone do a fund-raiser like this for us.”

The money will go to the Elizabeth Stone House’s capital campaign to construct a new building, Allen said. The group currently helps 700 domestic abuse survivors — mostly women and children — a year. The new location, which is across the street from the current building in Roxbury, will allow the group to quadruple that number. As part of his training, Spillane has averaged 8 to 10 miles a night since April and considers Thanksgiving the perfect day to start. He’s already raised nearly $25,000.

“I’m not afraid to ask people for money,” he said.

When he reached out to Taylor’s management company online, he said, they wished him good luck.

He’ll surely see some “deep greens and blues,” but mostly Spillane will be surrounded by the fading shades of fall, the tones of winter, and the “song that they sing when they take to the highway.”


“Walking relaxes me and it makes me tired so I can sleep,” Spillane said. “You can’t really appreciate beautiful things when you’re driving by. Walking has a unique perspective.”

Cristela Guerra can be reached at cristela.guerra@globe.com. Follow her on Twitter @CristelaGuerra.