Annapolis & Frederick: Maritime Capital & Mountain Town

Tour the oldest state capitol building in continuous legislative use in the country — the only state house to serve as the US Capitol (1783–1784), where the Continental Congress ratified the Treaty of Paris ending the Revolutionary War and George Washington resigned his commission. The original Senate chamber is intact, the dome is the largest wooden dome in America built without nails, and the building doubles as a functioning state legislature.

Lunch at the city dock's oldest operating tavern — a colonial ferry house and inn since 1750, now serving Maryland crab soup, steamed shrimp, and raw oysters on the harbor-facing patio.

Walk through the Naval Academy grounds open to the public — the Visitor Center exhibit on naval history, the Bancroft Hall dormitory facade (the largest dormitory building in the world), the Naval Academy Chapel with Admiral Farragut's tomb, and the impressive bronze statue of Tecumseh, the Navy's good luck mascot, in Tecumseh Court where midshipmen toss pennies before exams.

Dinner at this Eastport waterfront institution looking back across the harbor toward the State House dome and City Dock — Chesapeake Bay seafood, particularly the rockfish and crab cakes, with one of the best sunset views in Maryland.

Sleep at this Maryland Avenue boutique hotel with rooms themed around Annapolis sailing culture — steps from the Historic District, City Dock, and the Westgate Circle farmers market for a morning detour before Frederick.

Wander downtown Frederick's 33-block historic district — one of the most intact 18th and 19th-century townscapes in Maryland, with Federal, Georgian, and Victorian commercial buildings housing galleries, antique shops, and independent restaurants along Market and Patrick Streets. The dual church steeples that Barbara Fritchie allegedly waved the Union flag at Stonewall Jackson still tower above the roofline, and Carroll Creek Park's urban waterway passes under the district's main bridges.

Lunch at this celebrated Frederick restaurant in a restored 1890 Victorian mansion — locally sourced, seasonally driven cooking from a kitchen that has put Frederick firmly on the Maryland food map.

Explore the only museum dedicated to the medical story of the Civil War — a collection of surgical instruments, hospital train cars, and medical supply depots in a building that itself served as a Civil War embalming station and casket depot. Frederick sat at the crossroads of multiple campaigns (Antietam, South Mountain, Monocacy) and the museum explains how wartime medicine evolved from pre-scientific guesswork to systematic triage within four years of conflict.