Main Street Memories // A Look Back at Life in Our Small Town

By Cindy Jones

There was a time when you could head down to the hardware store on Winslow Way and buy a refrigerator. And while you were downtown you could go to the department store, get your car fixed and pay your power bill in person.

That was back when all the streets outside of town were nameless, numbered rural routes. Just a few thousand people lived here year-round then although the population would practically double from June to September, when families from Seattle would summer here in Crystal Springs, Rolling Bay and other waterfront locales.

Take a look through old photos of Winslow Way and you might spot a sign that simply reads “Department Store,” though locals referred to it as Allen’s or Childers’, depending on which family was proprietor at the time.

The drugstore would have been Archie’s or Vern’s, and for years the hardware store was either Holger’s or Anderson’s. Depending on the era, you bought shoes at Yeackel’s or ice cream at Horluck’s. Is it clear that everyone on the island pretty much knew everyone else?

If you were a little kid growing up near town, that meant there was almost always an adult looking out for you. Ann Bopp then Ann Alpaugh lived right up Ericksen in a house that her family still owns. When she was a little girl in the 1940s, just five or six years old, she’d walk down to Winslow Way with a sister who wasn’t much older.

The two of them would cross the street—“there was never any traffic”—and go to the grocery store to buy a treat. It was Thriftway back then; it would be years before Town & Country had its grand opening on the same spot in 1957.

Bopp knew every one of the grocery checkers, including Mrs. Koura, whose family name would later be bestowed upon one of those rural routes. After she and her sister had chosen their treats and paid for them, one of the checkout ladies would phone Bopp’s mother to let her know the girls were on their way home.

The Nakata family ran the grocery store in those days and they run it now. In fact, they started operating stores on Winslow Way long before there was either a Thriftway or a Town & Country. Another old photograph this one from the early 1900s depicts the family’s first store, a meat market, sitting where Bainbridge Island Museum of Art is now.

For many years, in the 1940s and ’50s especially, Winslow Way would regularly burst into a stream of sound and color, as parades took over the street for one reason or another the Strawberry Festival, Fourth of July, Homecoming or even the Scotch Broom Festival, which always began spontaneously and featured a tiddlywinks contest and a ragtag parade led by a scotch-broom-waving queen who’d been pulled from a nearby shop or group of passers by.

There’s little in the old photos to suggest the prospect that art galleries and gift shops would one day line a street featuring manicured landscaping, wide sidewalks, and bits of sculpture here and there. But back in the first half of the last century, Winslow Way reflected how life was lived in a small community at the western edge of a still mostly rural nation.

And in general, it was a life of few luxuries. People mostly bought the basics and often raised their own food. (Although, with the prolific chicken coops and vegetable gardens found on Bainbridge today, perhaps we are returning to that simpler time.)

Judy Dulay, an islander who also grew up here in the 1940s and ’50s, remembers paying the local pastor with eggs and chickens and milk from their cow Bessie. Dulay—then Judy Jones—was born in Rolling Bay, which was far enough from Winslow that a big snowstorm kept the local doctor, Dr. Shepard, from getting there for the event.

Instead he got on the phone with her father and gave him some encouragement: “How many times have you birthed Bessie, Shorty? This is just the same. Then you wrap that baby up and put it in the oven’s bun warmer and I’ll get out there as soon I can.”

Apparently the bun warmer did the trick, because Dulay thrived and soon was running around with her friends and siblings, riding bikes and playing baseball in the empty lot where the Bay Hay & Feed nursery is now. In the evenings after dinner, Dulay’s whole family would gather in the kitchen and sit watching the radio while their favorite programs aired. “I tell my grandkids that we watched the radio,” Dulay said, “and they look at me like I’ve lost my mind.”

It’s true that kids growing up today have more sophisticated entertainment with more interesting visuals, but back in the day, a good time meant sneaking out during a pajama party at a friend’s place in town and seeing if everyone could squeeze into the phone booth in front of the drug store. Seems like kids and phones have always been a thing.

But even as the times have changed, a few things have stayed the same around the island and along Winslow Way. Sandy’s Barber Shop still offers haircuts in a classic old-time setting. Esther’s carries on as one of the longest operating fabric stores in the state, and the Christian Science Reading Room still sits serenely in the spot it has occupied longer than any other single store along the street.

Groups of locals still hang out at Isla Bonita, just like they did when it was the Ibis, or the Winslow Coffee Shop, or the Lemon Tree before that. Every year on the Fourth of July, Winslow Way still bursts to life with floats and banners, marching bands and classic cars.

And every year, although less predictably, a Scotch Broom parade will suddenly, spontaneously, erupt out of nowhere. Hopefully, some things will never change. If you have Winslow history to share, visit