← The Weekend Getaways
🏛️ CulturalLong weekend · from Washington, DC

Annapolis, Antietam & Confederate Capital

Three days through the mid-Atlantic's most concentrated history: Annapolis, the 1779 state house and colonial port where Washington resigned his commission and the Treaty of Paris was ratified; Antietam, the bloodiest single day in American history; and Richmond, the Confederate capital whose Tredegar Iron Works now houses the finest Civil War museum in the country.

Day 1 — Annapolis, MDDay 2 — Antietam & Frederick, MDDay 3 — Richmond, VA
Day 1Annapolis, MD

Day 1Annapolis, MD

🚗 45 min driving📍 5 stops
🌅
Morning
🚗
Drive
Washington, DCAnnapolis Historic District
45 min8:00 AM8:45 AM
Maryland State House & Historic Annapolis
Maryland State House & Historic Annapolis
4.7
The 1779 State House is the oldest continuously operating state capitol in the country and served as the national capital for 14 months following the Revolution — it is where Washington resigned his commission as commander-in-chief on December 23, 1783, and where the Treaty of Paris was ratified on January 14, 1784. The surrounding streets follow the 1695 Baroque street plan radiating from Church Circle; the brick rowhouses on Maryland Avenue constitute one of the finest concentrations of 18th-century domestic architecture in America.
🍽️
Lunch
🍽️ Lunch9:45 AM
Reynolds Tavern
Reynolds Tavern
A 1747 tavern built by hatter William Reynolds on Church Circle directly across from the State House, now operating as a restaurant and inn. The colonial-era menu includes peanut soup, spoon bread, and game pie served in a room with wide-board floors and low-beamed ceilings. One of the most historically grounded lunch stops in the mid-Atlantic, in a building that has been in continuous operation on the same site for nearly three centuries.
4.3Restaurant📍 Maps →
4 options · tap to switch
☀️
Afternoon
William Paca House & Garden
William Paca House & Garden
4.6
Built 1763–1765 by William Paca — signer of the Declaration of Independence and three-term governor of Maryland — the five-part Georgian mansion is among the finest colonial houses in Maryland. The terraced 2-acre pleasure garden behind it was restored through systematic archaeology to its original 18th-century layout, including the fish-shaped pond, the parterres, and the wilderness garden at the lower terrace. The restoration is considered one of the most rigorous examples of colonial garden archaeology in America.
🌙
Evening
Carrol's Creek Waterfront Restaurant
Carrol's Creek Waterfront Restaurant
4.6
Dinner on Spa Creek with views of the Naval Academy across the water and the sailboat anchorage that makes Annapolis the sailing capital of the Chesapeake. The menu is built around Chesapeake seafood prepared seasonally — steamed crabs in summer, oysters in fall, rockfish year-round — and the sunset view from the dining room across the harbor is one of the most pleasant in the region.
🛏️
Graduate Annapolis
A well-positioned boutique hotel near City Dock and the historic district, with nautical-themed decor that plays off Annapolis's sailing identity. Walking distance to the State House, the Naval Academy gate, and the restaurants along Ego Alley. A comfortable base for the evening and an easy morning departure toward Antietam.
Day 2Antietam & Frederick, MD

Day 2Antietam & Frederick, MD

🚗 1 hr 55 min driving📍 5 stops
🌅
Morning
🚗
Drive
Annapolis, MDAntietam National Battlefield
1 hr 30 min8:00 AM9:30 AM
Antietam National Battlefield
Antietam National Battlefield
4.9
September 17, 1862 produced 22,717 killed, wounded, or missing in a single day — more American casualties than D-Day, Iwo Jima, and Normandy combined. The battle stopped Lee's first northern invasion and gave Lincoln the political context to issue the Emancipation Proclamation five days later. The visitor center's fiber-optic battle map clarifies the sequence of attacks; the 8.5-mile auto tour covers the Cornfield (four hours of fighting changed control six times), Bloody Lane (a sunken road that became a killing ground), and Burnside Bridge (where Union troops spent hours taking a bridge that could have been forded in minutes).
🍽️
Lunch
🚗
Drive
Antietam National BattlefieldFrederick, MD
25 min10:30 AM10:55 AM
🍽️ Lunch10:55 AM
Volt Restaurant
Volt Restaurant
Bryan Voltaggio's flagship occupies an 1890s Market Street row house and has maintained its position as the finest table in western Maryland since 2008. The seasonal tasting menu names specific farms, and the wine program has earned Wine Spectator recognition. Reserve 4–6 weeks ahead.
4Restaurant📍 Maps →
4 options · tap to switch
☀️
Afternoon
Frederick Historic District
Frederick Historic District
4.6
The 50-block historic district was founded in 1745 and retains one of the most intact concentrations of 18th and 19th-century commercial and residential architecture in Maryland. Lee's army marched through twice; the wounded from Antietam filled every church, school, and public building in September 1862. The Francis Scott Key Museum (Key was born in Carroll County and practiced law in Frederick) and the National Museum of Civil War Medicine are the two most specific cultural stops.
🌙
Evening
🍽️ Dinner5:00 PM
Brewer's Alley
Brewer's Alley
A Frederick institution since 1996 in the restored 1890s city hall. House-brewed beers run from accessible lagers to barrel-aged experiments; the food covers pub standards executed with more care than expected. The historic building's pressed-tin ceilings and original trim make it the most atmospheric of the craft beer options on Market Street.
4.4Brewpub📍 Maps →
4 options · tap to switch
🛏️
Tasting Room Hotel — Frederick
A sophisticated boutique hotel on Market Street in the heart of Frederick's historic district, with wine-focused amenities and a bar program that stocks the state's best producers. The most comfortable base for exploring Frederick's excellent restaurant scene.
Day 3Richmond, VA

Day 3Richmond, VA

🚗 5 hr driving📍 4 stops
🌅
Morning
🚗
Drive
Frederick, MDRichmond, VA
3 hr8:00 AM11:00 AM
American Civil War Museum — Richmond
American Civil War Museum — Richmond
4.5
The 2019 museum in Richmond's historic Tredegar Iron Works building (where Confederate cannons were cast) is the most sophisticated Civil War museum in the country, presenting the war through three perspectives simultaneously: Union, Confederate, and African American. The Tredegar building itself is part of the Richmond National Battlefield Park and sits at the James River fall line where the city began. The museum's approach to the war's causes and consequences is unusually direct for a Virginia institution.
🍽️
Lunch
Scott's Addition Craft Brewery District
Scott's Addition Craft Brewery District
4.6
Scott's Addition is Richmond's 20th-century industrial district — automotive dealers, cold storage, light manufacturing — that has been comprehensively colonized by craft breweries and cideries over the past decade. Ardent Craft Ales, Väsen Brewing, and Hardywood Park (the district's anchor) all operate within a four-block radius. The concentration of quality and the industrial architecture make this the most compelling brewery district on the East Coast south of Portland, ME.
☀️
Afternoon
Hollywood Cemetery
Hollywood Cemetery
4.7
Richmond's Hollywood Cemetery (1847) occupies a bluff above the James River rapids and contains the graves of two U.S. Presidents (James Monroe and John Tyler), Jefferson Davis, and 18,000 Confederate soldiers — the largest Confederate burial ground in the nation, with a 90-foot granite pyramid erected in 1869 as a monument to the Confederate war dead. The cemetery's hilly topography and river views make it one of the most dramatically situated burial grounds in America, and the Victorian-era monuments are extraordinarily varied.
🌙
Evening
The Eat Restaurant
The Eat Restaurant
4.6
A beloved Fan District institution in Richmond serving creative Southern-influenced comfort food — biscuits and gravy, shrimp and grits, and seasonal specials in a cozy, unpretentious dining room on a classic Richmond residential street.
🚗
Drive
Richmond, VAWashington, DC
2 hr6:00 PM8:00 PM
Plan your own escapeExplore more trips →