BaltimoreEmbark on this 90-minute walking tour to hear the journey of the young enslaved Freddy Bailey who was influenced and inspired to ultimately spread the word of the evils of slavery as the most famous abolitionist orator.
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AnnapolisStroll through the charming streets of the historic district with your colonial-attired guide. Learn the unique history and culture of 18th century Annapolis on this 90-minute tour.
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AnnapolisOn this 90-minute tour, you will be led by our spirited guide through the timeless narrow streets of this old and creaky town. Stopping at spooky spots, stories of those that have passed will be recounted with dramatic zeal.
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AnnapolisOn this 2-hour walking tour, our knowledgeable guide in period attire will share the fascinating history of the contributions made here and regionally by African Americans.
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AnnapolisStroll through the charming streets of the historic district with your colonial attired guide on this 2-hour walking tour. Then continue on to the beautiful and spacious William Paca Garden.
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AnnapolisYou’ll be led through haunted waterways by boat and brave the Historic District by foot while your Ghost Guide entertains you with spooky stories.
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AnnapolisThis 90-minute lighthearted, tongue-in-cheek tour is presented by a guide in the character of a colonial indentured servant who works odd jobs day and night to make ends meet - colonial style.
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AnnapolisEnjoy a 2-hour stroll in Annapolis’ historic district led by a period-attired guide. The tour highlights notable female Marylanders including Harriet Tubman and Barbara Mikulski.
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AnnapolisExplore Annapolis, the museum without walls, on a 2-hour tour led by an architectural historian. Learn about some of the most notable 17th and 18th century architecture in Annapolis.
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AnnapolisDuring the month of October, our ghost walks are enhanced with an exclusive visit to the historic, dimly lit Hammond Harwood House garden.
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AnnapolisLearn more about our special or seasonal walking tours here.
Learn MoreAnnapolis Tours by Watermark offers visitors to the Annapolis and Baltimore region the opportunity to tour some of the nation’s most historic streets with knowledgeable guides that are dressed in period attire.
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.
Watermark’s walking tours provide a great experience for a private group. Whether you are looking for a family. Social, military, or church outing, all of our walking tours are available as a private tour. Click below to contact our group tour specialist or learn more about popular group and private packages.