Series III · July 18, 2026 · Annapolis, Maryland
Maryland Crawl
A five-stop chapter through the historic taverns of Annapolis — from West Street to Church Circle, Main Street, and the City Dock.
Route dossier
A five-stop field guide through the taverns of Annapolis.
Stop 01
Ram’s Head Tavern
33 West St, Annapolis, MD 21401
Operating on a site that dates back to 1703, this location became a tavern and boarding house in 1792. It features a traditional, cozy pub, multiple dining rooms, and a wisteria-covered patio serving hearty, scratch-made tavern fare alongside an extensive beer list.
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Stop 02
Reynolds Tavern
7 Church Cir, Annapolis, MD 21401
Built in 1747, this is one of the oldest taverns in the United States. It offers a unique three-tiered English afternoon tea service in its sunlit parlor, while the cellar houses the rustic 1747 Pub with exposed stone walls and a walk-in hearth.
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Stop 03
The Maryland Inn
16 Church Cir, Annapolis, MD 21401
Home to the Drummer’s Lot Pub — housed inside a building dating back to the late 1700s, this subterranean pub serves historic-inspired cocktails (like rum punch) in a revolutionary-era setting.
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Stop 04
O’Brien’s Tavern
113 Main St, Annapolis, MD 21401
Originally called the Rose & Crown when it opened in 1774, The Middleton Tavern opened on the cusp of the American Revolution. It served as a portside communication network and a common meeting place where both Royalists and Revolutionaries gathered.
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Stop 05
Middleton Tavern
2 Market Space, Annapolis, MD 21401
Established in 1750, this is one of the oldest continuously operating taverns in America. George Washington, Thomas Jefferson, and Benjamin Franklin were all known patrons. Today, you can enjoy fresh Chesapeake oysters and local drafts on the first floor, or visit the second-level piano bar.
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From the Annapolis Record
Histories of the Old State House City
Until the photographs of Series III arrive, let the record show why Annapolis was chosen — few American towns carry more of the Revolution in their brick and cobblestone.
Fact I — 1772
The Oldest Working State House
The Maryland State House is the oldest U.S. state capitol in continuous legislative use — and the only one ever to have served as the nation’s capitol. Built in the Georgian style, its cornerstone was laid in 1772 and construction finished in 1779.
Fact II — 1783–1784
The First Peacetime Capital
The Continental Congress met in the building’s Old Senate Chamber between November 1783 and August 1784, making Annapolis the young republic’s first peacetime capital.
Fact III — December 23, 1783
Washington Resigns His Commission
On December 23, 1783, George Washington came before Congress in the Old Senate Chamber to resign his commission as Commander-in-Chief of the Continental Army — cementing the precedent of civilian control over the military.
Fact IV — January 1784
The Treaty of Paris Is Ratified
In January 1784, Congress ratified the Treaty of Paris in the State House, officially ending the American Revolutionary War — steps from the very taverns on our route.
Crawl commencement ceremony
UNITED WE CRAWL!
— Annapolis, Maryland / Series III · July 18, 2026 —
By authority of the Colonial Crawlers… and in grateful remembrance of those who thirsted for Liberty… let all assembled draw near and give ear!
On this most glorious Eighteenth Day of July, in the Year of Our Lord Two Thousand and Twenty-Six—
We, the Crawlers, gather here in fair Annapolis, where Patriots once raised not only their voices and sails, but their tankards in a noble cause.
Let it be known throughout this Republic—and to any lingering Loyalists among us—that we assemble this day to celebrate Two Hundred and Fifty Years of Life, Liberty, and Libations!
Raise thy glass to General George Washington, who laid down his commission and surrendered his sword—not to a King, but to his fellow citizens!
Raise thy glass to that noble House wherein Peace was ratified, and a grateful Nation first embraced the blessings of victory!
Raise thy glass to the Patriots and Founders of this Republic, who gathered in these historic taverns, where the cause of Freedom grew ever stronger!
Now let every step honor those who came before us, every timber bear witness to our fellowship, and every spirit be lifted—
By this proclamation, I do declare the Colonial Crawl officially commenced!
UNITED WE CRAWL!