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Tracing Freedom’s Footsteps: The Revolutionary Annapolis Walking Tour

A Stroll Through Centuries of History

To take an Annapolis walking tour is to step back in time, the city’s fascinating history on display around every charming block, from distinctive 18th-century architecture to historical landmarks like the Maryland State House and the sprawling waterfront campus of the US Naval Academy. Our city, then called the “Athens of America,” had an outsized cultural influence as one of the thriving capitals during the Colonial era and would play an essential role during the Revolutionary War. 

The pivotal tides of history took shape here, shifting like the waters in nearby Chesapeake Bay. Continental Army soldiers spent time in and around Annapolis during the final and crucial years of the Revolutionary War, while later, following our victory over the British, George Washington resigned as General of the Continental Army in the Maryland State House (famously the oldest State House in the country still in use). Four signers of the Declaration of Independence made their home along the same streets you’ll walk today, their gorgeous mansions preserved to look as they did then, living remnants of 18th-century life. Likewise, our inn dates back to the same period, built in the 1770s with a similar classic brick exterior – history abounds and lives on in Annapolis, brick by brick, house by house, and street by street.

When you stay at our Annapolis bed and breakfast, you’ll be in the heart of the Historic District, surrounded by our then-nascent country’s historical chapters around every turn. From the narrow-laned streets branching out from the State Circle to the stately quads at the US Naval Academy, it’s all just a short stroll away. There’s no better way to see and absorb our city’s yesteryear than on an Annapolis walking tour, which will guide you through four centuries of life, culture, and history in Annapolis.

street view of west st. annapolis md

US Naval Academy and Colonial Annapolis Walking Tour

Begin your morning delectably by joining us in the dining room for breakfast, served from 8 a.m. until 10 a.m., starting with coffee or tea, then scones and fruit, followed by an entree of your choice. You’ll be transported back in time by the historical touches throughout the inn – elegantly decorated furniture and period-appropriate art set the scene, a perfect warmup for your Annapolis walking tour.

From our convenient location on Prince George Street, you’ll be just steps away from the marina, where the Colonial Annapolis and US Naval Academy guided stroll begins at 1:30 p.m. every Saturday and Sunday. For decades, local tour guide company Watermark has led this tour, beloved not just for the range of historical topics covered but for the passion of their tour guides. Rather than simply dryly recite historical footnotes, they wear 18th-century attire and embody an Annapolis resident from that time, interpreting history engagingly and animatedly.

During the 2+ hour tour (wear comfortable walking shoes), you’ll get an inside look at the Maryland State House, where the Treaty of Paris was signed in 1784, officially ending several bloody years of the American Revolution, and where the state governor and lieutenant governor still have operating offices today. You’ll also pass by mansions once home to Maryland signers of the Declaration of Independence, such as William Paca and Samuel Chase, both sons of Maryland, esteemed lawyers during their time, and hugely influential members of the Continental Congress, our defacto government during the Revolutionary War. Tour guides will explain how even the street layout of Annapolis showcases history in its design – the circles surrounding the State House and nearby St. Anne’s Parish so impressed George Washington that he helped implement a similar circular spoke-and-hub street layout in Washington D.C. when it became the capital soon after.

Annapolis was built on a hill, and two circles were established on top of that hill, State Circle and Church Circle. Though very close next to each other, they were constructed closely but separated to distinguish and visibly support the separation of Church and State in colonial times.

Your tour group will also walk through the massive 338-acre US Naval Academy, the educational home for Navy midshipmen since 1845. Known as the “Yard” and the “land that leads to the sea,” the campus is unbelievably scenic, with stunning waterfront views and dorms dating back over a century alongside modern sports facilities (the Navy requires every midshipman to participate in a sport). Seeing the tomb of John Paul Jones is always a historical highlight – the “father of the US Navy” has been interred at the campus chapel since 1906.

aerial shot of annapolis harbor

Other Not-to-Miss Sightseeing – Touring the William Paca Mansion and Catching the Naval Academy Noon Formation

Although the Colonial Annapolis walking tour covers many themes and is full of new information for even the most hardcore history buffs, try to make time for an additional guided tour at the William Paca House and Garden. Located the next block down from your Annapolis Inn suite on Prince George St, the 2-story Georgian mansion is an architectural marvel, restored to its original opulence and beauty and enshrined as a historical landmark since 1972. The 2-acre walled garden is just as impressive as the house, with manicured flower beds and a creek running through the sloping lawns. During November and December, guided tours occur five times a day on Friday, Saturday, and Monday, while the property closes down for the winter from January through March, weather permitting.

You’ll get an excellent overview of the US Naval Academy on your guided tour, but stroll back to campus on a different day to catch the “Noon Formation,” which occurs at noon every weekday, weather permitting (the Colonial Annapolis walking tour doesn’t start until 1:30 p.m., which is too late to see it). For over 100 years, all six Navy battalions have gathered at Tamanend Court on campus at noon sharp every school day for an official role call, when they all gather in choreographed formation, followed by the marching band playing the fight song. It’s a rare show of military pageantry open to the public and fascinating to witness in person, another aspect of Annapolis history that lives on.

Stay with us and stroll through the many enthralling chapters of Annapolis history!