For this artist, the Cape’s pull is strong, not just for its unique lighting but also for the fond memories it holds.

For artist Steve Allrich, the Cape isn’t just a landscape to paint—it’s a place with fond memories, where he developed his craft, met his wife and made lifelong memories that keep him coming back every year.

Allrich first visited the Cape in 1988 at 36 years old. After graduating from the American Academy of Art in his home city of Chicago, he had been living in central Massachusetts for a few years, painting dairy farms and field landscapes on the side while working full time.

He took a huge leap of faith, hoping a gallery on the Cape might see potential in those works. After venturing to Blue Heron Gallery in Wellfleet, he was set—he moved into the gallery owners’ basement unit on a bluff in Truro that first summer, and the rest is history.

“The owners of the Blue Heron, Del Filardi and Harriet Rubin, kind of basically adopted me,” Allrich says. “I stayed with them for the summer, and I painted there, and I just had a blast. I hung out at the gallery a lot.”

Filardi, a sculptor, and Rubin, a potter, treated Allrich like a son, taking him out to dinner in Wellfleet and Truro and showing him the best spots for painting. They also introduced him to a host of artists and collectors.

“It was just a really, really great symbiotic relationship, and it was all against the backdrop of the Cape, which was very new to me. I hadn’t even seen it until I went there to show them my...