For the next 15-plus years, Richard and Phil would return twice each year—in September and October—and the Wallaces became close friends with the couple. “His ashes were scattered in the creek—that’s how close we became,” Ann says, referring to Phil, who passed away in 2008. Now Phil’s son, who lives in D.C., comes to stay at the cottages with his family every other year.
It’s common for Ann and her son Scott, who manages Chatham Seaside Cottages, to see children who grew up coming to the cottages return once they’re older with families of their own. “They want to come and recreate the memory,” says Scott. “You think back on what tradition your parents had when you were a kid. And then you go back to it and it just brings it all back—it’s like a song.”
For Scott and Ann, it’s all about providing their guests an environment in which to make memories—whether it’s spending the day on the beach, watching the sun set into the ocean on a fall or winter’s night, or even proposing marriage. “One couple were sitting out on the porch, and a plane went by with a sign saying, ‘Karen, will you marry me?’” Ann recalls. The cottages have become a sought-after honeymoon destination as well—a guest book entry dated Dec. 18-27th, 1999 reveals the newly married Gerri and Tink Olmsted, ages 80 and 82 at the time, thoroughly enjoyed their honeymoon at Bayberry Cottage.
While chatting with Ann and Scott at the property on a warm Saturday in mid-June—the telltale sounds of an ice cream truck playing in the background at Ridgevale Beach—Scott had to break away momentarily to greet a group of three women who had just arrived for their stay. Sitting in the screened porch of the third cottage, Ann’s—which the Wallaces renovated soon after purchasing the property to comfortably serve as their home, adding on a second floor—the views are mesmerizing, the crisp breeze drifting through further inducing a sense of serenity. When Scott returned, he mentioned the conversation he had with one of the women, who told him, “We’ve been looking forward to this for a full year. Every couple weeks or months I go on your website and I look at those curtains blowing in the wind.”
“We take it for granted—we live here,” Scott says. “You really get it when people tell you, ‘This is the most beautiful spot I’ve ever been to.’ We get that from people all over the world.” He is not exaggerating, as they’ve hosted guests from across the U.S. as well as countries like England, Israel and Germany—Ann still keeps in touch with the German couple. “I think they come for the simplicity,” Ann says of their guests, who always seem to enjoy the timelessness of the experience.
Sarah McCaffery has made a tradition out of spending every summer on the Cape since she can remember. That tradition continues now with her husband, Simon, and their three kids, Hudson, Oliver and Julia. This June, Sarah and her family spent their summer vacation at Bayberry Cottage—their first time at Chatham Seaside Cottages. Sarah, who describes the cottages as “quintessential Cape Cod,” says what stood out the most to her about their stay was the hospitality. “I can’t say enough good things about them,” she says of Ann and Scott. “They’re on top of everything, making sure that we’re comfortable, and they’re happy to play concierge for us, happy to share their favorite places for us to explore.”
“Ann has been over-the-top kind and helpful,” Sarah adds. “She went to the grocery store and offered to pick up milk for the kids because she knew we ran out.” Sarah also recalls a memorable moment from their first day at the cottages: “Ann was making a delicious dinner and we commented, ‘Oh, that looks like a great recipe you’re making,’ and later on Scott came over and delivered a plate of it to our door—she made us shrimp fritters for an appetizer. They’ve been amazing.”
From her children’s perspectives, Oliver, age 8, says he loves that are plenty of spots to go tide pooling with lots of things to catch, like crabs. Hudson, age 10, says he loves that the cottages come with kayaks. “And not just one kayak,” Sarah notes, “but enough that our whole family was able to go on a kayak trip. And they’re very kid-friendly—the boats are wide and stable, so they’re hard to flip.” And Julia, age 5, says she enjoyed swimming in the calm waters near the cottage.
Although there have been some sad moments during their time at the cottages—like Gordon’s passing at the young age of 55 in 1991—and a few close calls—like when Hurricane Bob hit—by and large, Ann says, it’s been happy moments. “When you walk into these cottages, I swear you feel it—you feel the happiness that people have had in these places,” she says. “There’s just a lot of happiness around here.”
Glancing at her old photographs of the cottages, Ann remarks, “It all worked out.”
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