January 29, 2026
By Cynthia Hochswender
Photographs by Lisa Nichols
It all began with a jigsaw puzzle.
“Whenever he starts working on a puzzle, my mother and I know that some new idea is going to follow,” says Alice Peck, speaking of her father, Darryl Peck.
Darryl is a serial entrepreneur with a particular passion for retail. In Litchfield County, he is best known for launching Outpost.com—both online and at its bricks-and-mortar location in Kent—during the early days of internet shopping. In addition to selling computer hardware and software, he advised Fortune 500 companies on how to bring their products to the web.
In 2006, the Pecks moved to Georgia to care for an elderly family member. To keep himself entertained, Darryl began doing jigsaw puzzles—and soon started thinking about opening an Apple computer store.
“We ended up with 14 shops, from Virginia to Florida,” he says.
After selling that chain to GameStop, he found himself back at the puzzle table. The next idea: a small, independent bookstore. The Pecks opened their first shop on St. Simons Island—then Alice decided to return to Litchfield County.
“Salisbury felt like home to me,” she says, “even though we’d moved to Georgia when I was 9.”
Darryl and Anne soon followed her north and decided to open a bookstore here—and then another.
The first shop opened two years ago on Main Street in Lakeville as Lakeville Books and Stationery. Last November, the Pecks opened a second location in Great Barrington, taking over the beloved former Bookloft space. The new shop is also called Lakeville Books. No one seems confused by the shared name; customers are simply thrilled to have a bookstore again.
“All day, every day, people come in and thank us for being here,” Darryl says.
Social interaction is a key differentiator from the large online booksellers, says Darryl, who handles most of the ordering. Alice manages the Lakeville store, while Anne oversees social media and marketing—alongside her work selling real estate with Elyse Harney.
“My dad especially loves interacting with people and talking about books,” Alice says.
“Bookstores are all about discovery,” Darryl adds. “If you know exactly what you want, you can order it online from home. But here, people browse for 45 minutes, chat with me, and walk out with an armload of books they didn’t know they wanted.”
Children’s books and novels top the bestseller list, but the shop offers a wide range of nonfiction and specialty titles, including automotive books and local interest sections. Jigsaw puzzles (of course) fill the shelves, along with stationery, notebooks, and a curated selection of Japanese pens.
Cookbooks are another standout category.
“If you have 100 cookbooks, you won’t sell any of them. We have 600,” Darryl notes.
Both locations are open seven days a week, and customers can also browse online. Follow Lakeville Books on Instagram (@lakevillebooks) for weekly staff picks and favorite reads.
329 Main St., Lakeville • 860-596-4500
63 State St., Great Barrington • 413-645-3256
—lakevillebooks.com
