New Annapolis restaurant Leo serves hyperseasonal dishes in a family-friendly atmosphere

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Hilarey and Brian Leonard used to joke that if they had a boy, they would name him Leo Leonard.

They decided not to follow through when their son joined the family three years ago. Instead, they gave the name to their new Annapolis restaurant.


Leo, which opened on West Street in March, is the latest hospitality business for the couple, who also own two Washington, D.C., bars, Free State and Lost & Found. But the 60-seat New American eatery is their first restaurant.

The Leonards, who moved to Annapolis in 2019, were impressed by the community’s embrace of local businesses during the early days of the COVID-19 pandemic. They were searching for an opportunity to join the capital city’s restaurant scene when Dangerously Delicious Pies closed abruptly last summer at 212 West St.


They toured the pie shop’s space and decided to sign a lease last fall. “We loved that it was in the arts district; we loved that it was a little off the beaten path,” Hilarey said. “We kind of just loved the idea of being on West Street.”

Brian and Hilarey Leonard are the owners of Leo Annapolis, a new upscale casual restaurant on West Street.

Leo offers farm-to-table fare, featuring fresh vegetables, meat and fish sourced from local producers. The restaurant gets greens from Maidstone Farms in Annapolis, steaks from Roseda Farms in Monkton and cheese from Chapel’s Creamery in Easton.

For all the focus on the bounties of the region, you won’t necessarily find crab cakes on the menu.

“There are so many places in Annapolis that have crab cakes and oysters,” Hilarey said. “We wanted to do something a little different.”

The couple brought on friend and former employee Matthew Lego to lead the kitchen at Leo. Lego worked in advertising after graduating with a degree in mass communications from Towson University, but always felt the pull of the hospitality industry. He ended up working as a bartender at Free State and Lost & Found before embarking on a stint in the kitchen at Foraged in Station North.

Roasted beet dip and crostini at Leo Annapolis, a new upscale casual restaurant on West Street. Chef Matthew Lego’s seasonal menu is farm-to-table.

His menu at Leo is inspired, in part, by the hyperseasonal focus of that Baltimore restaurant. Staple dishes will evolve with the changing of the seasons: a butternut squash risotto, for instance, becomes a spring pea risotto as the weather warms, and an angel food cake topped with fresh strawberries in the spring will feature raspberries or blackberries in the summer.

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“The bones of the dish will remain, but will be very largely determined by what’s available to us,” Lego said.

One year-round staple will be the golden crispy grits, a satisfying plate of fried grits sticks served with pickles and a hot sauce aioli. The grits and corn flour used in the recipe are all produced from the same crop of corn grown at Next Step Produce in Charles County. “It’s like a completely self-contained thing,” Lego said.

Dining room at Leo Annapolis, a new upscale casual restaurant on West Street.

The restaurant’s décor is earthy, with forest green and terracotta-colored walls, hanging rattan lamps and plenty of plants. The Leonards commissioned local artist Kimberly George to create textured “sculpture paintings” that hang on the walls. Hilarey, who used to work as a television producer for HGTV, spearheaded the bulk of the restaurant’s design, aside from some carpentry work.

While the restaurant has an elegant look and an extensive cocktail, beer and wine list, the Leonards also want to make it known that Leo is a family-friendly place. That’s one reason they decided to open a restaurant rather than another bar.

“Having a family changed our perspective,” Hilarey said. “It’s nice to go to a place that welcomes people with kids, because that’s what we’re doing now.”

Leo Annapolis

212 West St., Annapolis. 443-782-7549.