Watermark is the authentic provider of guided historic walking tours in Annapolis, Maryland. With our company’s origins dating back to the 1970’s, our period dressed Colonial guides keep U.S. and Annapolis history alive and have been sharing their passion for history and folklore to adults, students, and groups.of all types for decades. Our tours are a unique and fun option when looking for things to do in Annapolis.

True Annapolis historians! They walk the streets in colonial attire sharing their wealth of knowledge of Maryland’s state capital. Our guides go through an extensive training program that exposes them to authors, professors, specialists, and historic sites. They enjoy spreading the word on how our city came to be with facts, stories, and sheer delight. Many of our Squires and Mistresses have been guiding with Watermark for decades. We are proud to have such a loyal and gifted group ready to show you around town.