The moody, dimly lit interior of Leo, an Annapolis bar and restaurant from the same owners as D.C.’s Lost & Found and Freestone. | Leo America’s Sailing Capital continues to net more local names as of late Between fresh imports like Timber Pizza, Leo (a bar from Lost & Found’s owners), Tatte (a Boston transplant with deep roots in D.C.), Urbano, Moby Dick House of Kabob, and soon-to-arrive Capo Deli, Maryland’s quaint capital is officially a top expansion market for well-known D.C. eateries. Despite its relatively close proximity, the waterfront town saw a post-pandemic surge of year-round residents who work in D.C. Now that many favorite go-to spots are setting up shop in Annapolis — and liberal work-from-home policies staying in place — there’s fewer reasons to make the 45-minute trek into the nation’s capital. Timber Pizza’s co-owner and president Chris Brady says he always envisioned bringing his Petworth-bred pies to his native Annapolis. When the pandemic shut the restaurant industry down in 2020, he moved back home and soon realized he wasn’t the only transplant in town. “I’m as Annapolis as they come, so it was always on the radar,” Brady says.“There’s a certain charm to Annapolis – I always called it 30 miles from D.C. but a world apart.” Timber Pizza/Facebook Pizza comes out of the wood-fired oven at Timber’s Annapolis location. Demand for his award-winning pizza was immediately apparent. Upon opening in August, the 1,850-square-foot import off West Street was flooded with customers. “Annapolis has long yearned for innovative dining in my opinion,” says Brady. “It’s just really great to have a nice new mix of places to go because those are the kind of places that I enjoy as part of my rotation.” That includes his new vegetable-friendly neighbor Leo. Owners Hilarey and her husband Brian Leonard, who also run D.C. bars Lost & Found and Freestone, didn’t intend to open a restaurant when they relocated to Annapolis in 2019. After living in D.C. for 20 years, the couple simply wanted more space for their growing family. But after talking with their friends and new neighbors, they realized there was a hole in the market and opened Leo in 2023. View this post on Instagram A post shared by LEO Annapolis (@leoannapolis) “[Other restaurants] do a lot of business for tourists, which is great, but if you live here, you don’t wanna eat crab cake sandwiches every day,” says Hilarey Leonard. Their varied menu that pulls from local farms and waterways sends out celery bisque, vegan spring rolls, whole grain salads, and a blue catfish with a porcini crust and homemade grits. Moby Dick House of Kabob chief operating officer Alex Momeni says the team eyed Annapolis for years, waiting for the right commercial spot to open up. The DMV-wide Persian kebab shop finally made its Maryland capital debut three months ago. “We opened that location in anticipation for what’s to come in the next couple of years and beyond in that geographical area,” says Momeni. Sales started off “slow and steady,” he reports, and the brand plans to grow with the region. Old Town-born Urbano Tex Mex opened in Annapolis Town Center in September, complete with a private tequila tasting room. The rapidly expanding Mexican spot comes from Common Plate Hospitality, an Alexandria-based restaurant group that recently entered the Maryland market at The Heights food hall in Chevy Chase. Managing partner Chad Sparrow says the decision to expand to Annapolis was easy, saying its family-friendly atmosphere is a good fit for the market. Urbano Tex Mex The vibrant, mural-covered interior of Urbano Tex Mex. European-styled bakery and cafe Tatte, the Boston-based chain that ballooned to 15 locations across the DMV in a matter of years, opened its furthest outpost from the District’s commercial kitchen this month in Annapolis. Located across the street from Urbano, Tatte drew attention even prior to opening. Staff noticed curious onlookers peering into windows of the new 3,900-square-foot, white-tiled space as it was being constructed. Just because this Tatte is a little further from the central kitchen where all the goods are made doesn’t mean the food here isn’t as fresh, management says. “All the desserts and baked items that you see are baked while we sleep at night and then delivered the next morning at 5 a.m.,” says Terry Sorrow, Tatte Annapolis’ assistant general manager. The influx of new residents and restaurants from D.C. is not going unnoticed by Annapolis Mayor Gavin Buckley. “It is less dense and we see a lot of people relocating,” he tells Eater. “They appreciate the proximity to Baltimore and D.C., but with these new places opening up, they don’t have to go far.”