Walking Tour Walking Tour

Walking Tour of Historic Leonardtown

Stop 1: Tudor Hall Stop 2: Old Jail Stop 3: St. Mary’s County Courthouse Stop 4: Spalding / Camalier House Stop 5: Leonardtown Bank of the Eastern Shore Stop 6: Bell Motor Company Stop 7: Mercantile Bank of Southern Maryland Stop 8: World War I Memorial Stop 9: Deceased Veterans Memorial Stop 10: The New Theater Stop 11: Union Hotel Stop 12: Duke’s Fountain-Bar-Restaurant Stop 13: The Picture Box Stop 14: The First St. Mary’s Hospital Stop 15: Henderson House Stop 16: St. Peter’s Chapel Stop 17: St. Aloysius Catholic Church Stop 18: St. Aloysius Church Rectory Stop 19: Leonardtown Nazarene Church Stop 20: The Leonardtown Mural Stop 21: The Orchard

1. 

   1. Tudor Hall

   A Georgian-style mansion overlooking Breton Bay. Tudor Hall has served as a private home, public library, Town Hall, and now houses the St. Mary’s County Historical Society.

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2. 

   2. Old Jail

   The Old Jail was expanded in 1876 and served St. Mary’s County until 1942. It is now maintained as a museum and is one of Leonardtown’s most recognizable historic landmarks.

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3. 

   3. St. Mary’s County Courthouse

   Leonardtown has had a courthouse since the early 1700s. The courthouse site has been rebuilt and remodeled over time, with a major renovation and addition completed in 2001.

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4. 

   4. Spalding / Camalier House

   This early in-town residence includes Greek Revival details and is associated with several notable local owners. It is part of the historic fabric near the courthouse area.

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5. 

   5. Leonardtown Bank of the Eastern Shore

   Constructed in 1913, this one-story brick building reflects Classical Revival design and the growing role of banking and commerce in early twentieth-century Leonardtown.

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6. 

   6. Bell Motor Company

   Built in 1939 for an expanding Chevrolet dealership, the Bell Motor Company building represents Leonardtown’s twentieth-century commercial growth.

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7. 

   7. Mercantile Bank of Southern Maryland

   This 1921 brick commercial building helped define the southern end of Washington Street and represented Leonardtown’s role as a regional financial center.

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8. 

   8. World War I Memorial

   Dedicated in 1921, this memorial honors local men who died in World War I and remains a focal point for community remembrance.

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9. 

   9. Deceased Veterans Memorial

   This memorial honors St. Mary’s County service members killed or missing in action during World War II, the Korean War, and the Vietnam War.

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10. 

    10. The New Theater

    Originally built around 1945 as a movie theater, this structure later retained its theater space while the front of the building changed over time.

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11. 

    11. Union Hotel

    The former Union Hotel, later known as the Fenwick Hotel, hosted court-day visitors, voters, tradesmen, public debates, and community gatherings.

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12. 

    12. Duke’s Fountain-Bar-Restaurant

    Built in the 1920s, this two-story brick building has housed auto sales, a grocery, event spaces, and later restaurant and retail uses.

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13. 

    13. The Picture Box

    Constructed in 1938, this building began as a photography studio and lab. It later served as a florist shop, shoe repair shop, and real estate office.

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14. 

    14. The First St. Mary’s Hospital

    Before a permanent hospital was built, Leonardtown’s first hospital operated in this Fenwick Street dwelling beginning in 1912.

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15. 

    15. Henderson House

    A Folk-Victorian style building with additions over time, Henderson House was built around 1910 for use as both a funeral home and residence.

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16. 

    16. St. Peter’s Chapel

    This former Episcopal chapel is a vernacular Gothic-style building known for its steep roof, pointed-arch windows, interior woodwork, and restored stained glass.

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17. 

    17. St. Aloysius Catholic Church

    The present Colonial-style church was built in 1962, replacing an earlier 1846 church. Historic elements, including the Jenkins Memorial Bell, were preserved.

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18. 

    18. St. Aloysius Church Rectory

    The rectory was built in 1933 after an earlier residence for Jesuit fathers fell into disrepair. It was stuccoed to visually match the old church.

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19. 

    19. Leonardtown Nazarene Church

    Built in 1915, this Gothic-style concrete block church includes ornamental blockwork and pressed tin panels used on the interior walls and ceiling.

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20. 

    20. The Leonardtown Mural

    The mural depicts different eras in Leonardtown history, moving from a turn-of-the-century theme to scenes from the mid-twentieth century.

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21. 

    21. The Orchard

    This grouping of homes began with the Johnson House and Store in 1919 and reflects the local practice of family members subdividing land to live near one another.

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