On July 8, 2023, The Fun Shop closed its doors on West Washington Street after 66 years, and Middleburg lost the place where it bought birthday presents, christening gifts, toys, tea towels, lampshades, board games, hunt country prints and whatever else it had forgotten until the last minute. Five days later, Town Council stood up to say thank you. "It's not sweet at all. It's bitter," Mayor Bridge Littleton said, though he was happy for the family. ▶ video

Ten Cents a Day

Nancy Lee Coble grew up in Winchester playing "shop" with the neighborhood children and watching her father, A. Lee Coble, run several businesses there. She married Howard Allen, a Winchester boy who had driven an ambulance in Africa and Italy during the war, in 1948. In 1955 they moved to Middleburg, where Howard had bought the local photography studio after its owner died (the Eccentric, 2008).

Mrs. Allen found there was nowhere in town to buy children's clothes or toys. So in 1956, with a loan from Howard's mother, Dorothy Gilpin Allen, who also gave the place its name, she opened The Fun Shop, one of the first woman-owned businesses in Middleburg. It started in a small building near today's Safeway. One day, she liked to recall, she took in a total of ten cents. Customers kept asking for other things, and she kept adding them. In 1960 the shop moved to West Washington Street (the Eccentric, 2015), and Howard's studio ended up upstairs. "Then we merged. I've been losing space ever since," he told the Eccentric in 2008. By 2004 he had been "pushed up to the third floor" (the Eccentric, 2004).

The shop grew to fill two floors of three buildings, about 9,000 square feet by 2019, and it sold nearly everything. A customer once told Mrs. Allen, "If the Fun Shop doesn't have it, you don't need it!" and the family adopted it as the shop's motto. The Eccentric, in 2004, called it "The Macys of Middleburg."

The Family Business

Daughter Betsy started helping at nine and joined the staff as office manager in 1976; her sister Page joined about a decade later as manager and buyer. Their mother kept working into her eighties, still writing house-charge tickets by hand and keeping the sales tax at home until it was due (Loudoun Now, September 30, 2019). Betsy remembered her as "a tough businesswoman" who would tell a salesman his best-selling product was "not here it isn't." The unofficial motto was "service, service, service."

The family served the town as well as the shop. Howard Allen sat on Town Council from 1957 to 1962. Betsy Allen Davis served on Council from 1998 to 2006 and as Mayor from 2006 to 2018. Whenever somebody needed to step up, Littleton said, "Betsy and Page were there."

And Jacqueline Kennedy, in the years the Kennedys rented Glen Ora, never came to Middleburg without visiting the shop, and always asked to see Howard. Many came to regard him as the Kennedys' unofficial photographer in Hunt Country. One evening near closing time, Betsy remembered, Jackie sat cross-legged on the floor of the back room with his hunt photographs spread around her, teaching yoga to a young granddaughter (the Eccentric, 2015).

Nancy Allen died in July 2015 at 92; Howard died later that year. Vice Mayor Darlene Kirk remembered then that when her own mother died, Mrs. Allen "came to visit me, brought food and visited." Bundles Murdock remembered her "wicked smile," used while beating her at poker hand after hand.

Closing Time

In 2019 the sisters put the property up for sale, with Betsy saying she hoped a buyer would keep the shop running. "Nobody wants us to go away," Page said. In March 2023 Council sold the Fun Shop the unused strip of South Pickering Street right-of-way that runs between its buildings, for $20,000, so the property could pass whole to a new owner. Vice Mayor Peter Leonard-Morgan said that was the way to bring in a new business instead of another empty storefront. The last weeks were a sale. Customers bought "all the merchandise at the last and even our fixtures," Page said.

The staff, more than 100 people over the years, threw the sisters a surprise party at the coffee shop the night before Council's tribute. Littleton said the family's biggest legacy was "the way in which they cherished their employees." Page agreed. They had, she said, "one of the best crews ever anywhere." Councilmember Chris Bernard, a toy-store owner himself, thanked them for "a lot of smiles and joy to not just kids." Councilmember Bud Jacobs said his grown daughters always made the shop a stop when they came home. ▶ video

Council adopted its resolution 6-0. Betsy told Council her parents had said, not long before they died, "you really need to settle and go have some fun and do some things on your own." Page thought her mother was "looking down, smiling." The Town set aside a bench at the new Town Hall for a Fun Shop plaque, and the Middleburg Museum planned a party for the family and staff at the Pink Box that August.

What Comes Next

The buildings at 115 and 117 West Washington Street are being remade. Loudoun Now reported in January 2026 that the property had been acquired by the owners of the Piedmont Steakhouse in Culpeper, and that developer Kevin Ash was planning a ground-floor restaurant, an upstairs club for members of his Leesburg social club The Chase, Middleburg's first rooftop garden, and eight apartments in the addition behind Howard Allen's old studio (Loudoun Now, January 7, 2026). The Town approved the plans, and construction is under way. This month Ash, who bought the Fun Shop and two houses behind it on The Plains Road for $3.26 million, showed residents a second phase: a three-story building with 12 condominiums and three small shops (Loudoun Now, October 13, 2026).

The shop is gone. The motto isn't: if The Fun Shop didn't have it, you didn't need it.

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Sources: the Middleburg Town Council meeting of July 13, 2023, its video and the Town contractor's transcript; the Middleburg Eccentric's own reporting, linked in the text; and Loudoun Now, cited in the text. See also the July 2023 Town Council Report.