1 ► Maryland, Caroline County, Andersontown — North-South Boundary Between the State of Maryland and the State of Delaware —

On Shore Highway (Maryland Route 404) near the State Line, on the right when traveling east.

2 ► Maryland, Caroline County, Choptank — 25 — Choptank Landing — Escape from Poplar Neck — Harriet Tubman Underground Railroad Byway —

On Water Street.

3 ► Maryland, Caroline County, Denton — "29, Let's Go!" —

On South 4th Street north of Randolph Street, on the right when traveling north.

4 ► Maryland, Caroline County, Denton — 6 PDR. Nordenfeldt 57 M.M., Rapid Fire Gun. —

On Legion Road, on the right when traveling south.

5 ► Maryland, Caroline County, Denton — American Legion — Post 29 —

On Legion Road, on the right when traveling south.

6 ► Maryland, Caroline County, Denton — Bell from First Methodist Church —

On 5th Street south of Franklin Street (Maryland Route 404), on the right when traveling south.

7 ► Maryland, Caroline County, Denton — 33 — Caroline County Visitor Center — Abolitionists Abound — Harriet Tubman Underground Railroad Byway —

On Crouse Park Lane west of Gay Street (Maryland Route 404), on the right when traveling west.

8 ► Maryland, Caroline County, Denton — Caroline Court House —

On Market Street near Between 1st and 2nd Streets, on the right when traveling west.

9 ► Maryland, Caroline County, Denton — 31 — Caroline Courthouse — In the Shadow of Justice — Harriet Tubman Underground Railroad Byway —

On Market Street at North 2nd Street on Market Street.

10 ► Maryland, Caroline County, Denton — 35 — Choptank River Heritage Center — Steal Away by River — Harriet Tubman Underground Railroad Byway —

On River Landing Road.

11 ► Maryland, Caroline County, Denton — Denton —

On 5th Street at South 6th Street, on the right when traveling north on 5th Street.

12 ► Maryland, Caroline County, Denton — Denton Schoolhouse — 104 South 2nd Street —

On South 2nd Street south of Franklin Street (Maryland Route 404), on the left when traveling north.

13 ► Maryland, Caroline County, Denton — Early Commercial Agriculture —

Near Detour Road east of Harmony Road (Maryland Route 16), on the right when traveling east.

14 ► Maryland, Caroline County, Denton — Edmondson's Reserve —

Near Detour Road, 0.4 miles east of Harmony Road (Maryland Route 16), on the right when traveling east.

15 ► Maryland, Caroline County, Denton — Emancipation's Close Call — Did Union Troops Suppress the Vote? —

On Market Street at North 2nd Street, on the right when traveling west on Market Street.

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16 ► Maryland, Caroline County, Denton — Great Wars of World Conflict —

On Market Street at 1st Street, on the left when traveling east on Market Street.

17 ► Maryland, Caroline County, Denton — Hubs of Activity — Terminals, Wharves and Landings on the Choptank

On River Landing Road, 0.4 miles north of New Bridge Road (Maryland Route 328), on the right when traveling north. Reported unreadable.

18 ► Maryland, Caroline County, Denton — John Wilkes Booth — Escape of an Assassin — War on the Chesapeake Bay

On 2nd Street at Gay Street, on the right when traveling north on 2nd Street. Reported permanently removed.

19 ► Maryland, Caroline County, Denton — Maryland Steamboat Company's Joppa Wharf at Denton — The Wharves at Choptank Crossing —

On River Landing Road.

20 ► Maryland, Caroline County, Denton — Maryland's Eastern Shore — Hundreds of Enslaved and Free Black Men Enlisted

On North 2nd Street at Gay Street, on the right when traveling north on North 2nd Street. Reported permanently removed.

21 ► Maryland, Caroline County, Denton — Moses and the Hounds — Harriet Tubman Underground Railroad Byway —

On Foot of Gay Street.

22 ► Maryland, Caroline County, Denton — Mystery Ship —

Near Martinak State Park Road, 0.4 miles south of Deep Shore Road, on the left when traveling south.

23 ► Maryland, Caroline County, Denton — Neck Meeting House —

On Maryland Route 404 at Maryland Route 328, on the right when traveling west on State Route 404.

24 ► Maryland, Caroline County, Denton — Neck Meeting House Native Garden —

On Meeting House Road.

25 ► Maryland, Caroline County, Denton — Nest of Traitors — The Denton Arrests

On River Landing Road, 0.4 miles north of New Bridge Road (Maryland Route 328), on the right when traveling north. Reported missing.

26 ► Maryland, Caroline County, Denton — On this spot Sept. 5, 1938 stood Franklin Delano Roosevelt —

On Market Street, on the left when traveling west.

27 ► Maryland, Caroline County, Denton — Peter Still: The Kidnapped and the Ransomed —

Near Detour Road east of Harmony Road (Maryland Route 16), on the right when traveling east.

28 ► Maryland, Caroline County, Denton — President Roosevelt's Speech — 1938 — "The Biggest Day That Denton Had Ever Seen" —

On Market Street west of North 2nd Street, on the left when traveling west.

29 ► Maryland, Caroline County, Denton — Revolution or Fraud? — Emancipation in Caroline Co.

On Market Street at 2nd Street, on the right when traveling west on Market Street. Reported permanently removed.

30 ► Maryland, Caroline County, Denton — Ruth Ann Crouse —

On South 5th Avenue south of Legion Road, on the right when traveling south.

31 ► Maryland, Caroline County, Denton — Steamboats on the Choptank River — Connecting Denton to the World

On River Landing Road, 0.4 miles north of New Bridge Road (Maryland Route 328), on the right when traveling north. Reported damaged.

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32 ► Maryland, Caroline County, Denton — Sydney Still: "Sydney's Choice" —

Near Detour Road east of Harmony Road (Maryland Route 16), on the right when traveling east.

33 ► Maryland, Caroline County, Denton — The County Alms House, then Plaindealing — Stark Realities… Stately Home, c. 1792 - 2017 —

On South 5th Avenue south of Legion Drive, on the right when traveling south.

34 ► Maryland, Caroline County, Denton — The Denton Arrests — "Arresting … treasonable characters" —

On Crouse Park Lane west of Gay Street (Maryland Route 404), on the right when traveling west.

35 ► Maryland, Caroline County, Denton — The Doncaster Dwelling: A Perfect Substitute —

Near Detour Road east of Harmony Road (Maryland Route 16), on the right when traveling east.

36 ► Maryland, Caroline County, Denton — The Food Sources of Enslaved Afro-Marylanders —

Near Detour Road east of Harmony Road (Maryland Route 16), on the right when traveling east.

37 ► Maryland, Caroline County, Denton — The Martinak Boat — 50th Anniversary —

Near Martinak State Park Road, 0.4 miles south of Deep Shore Road, on the left when traveling south.

38 ► Maryland, Caroline County, Denton — RM-1239 — Thomas Carney — CA 1760-1828 —

On Market Street.

39 ► Maryland, Caroline County, Denton — 34 — Tuckahoe Neck Meeting House — Living Their Beliefs — Harriet Tubman Underground Railroad Byway —

On Meeting House Road.

40 ► Maryland, Caroline County, Denton — Two Neighbors * Two Governors * Two States — The Citizens of Denton and Caroline County Honor Two Native Sons — Sherman W. Tribbitt, Governor of Delaware, 1973; Harry Roe Hughes, Governor of Maryland, 1979-1987 —

On Franklin Street (Maryland Route 404) at South 2nd Street, on the right when traveling east on Franklin Street.

41 ► Maryland, Caroline County, Denton — War Along the Chesapeake — A Divided Region —

On North 2nd Street just south of Gay Street (Maryland Route 404), on the right when traveling north.

42 ► Maryland, Caroline County, Denton — White Tenant Farmers —

Near Detour Road east of Harmony Road (Maryland Route 16), on the right when traveling east.

43 ► Maryland, Caroline County, Denton — 30 — William Still Center — Families Divided & United — Harriet Tubman Underground Railroad Byway —

On Detour Road.

44 ► Maryland, Caroline County, Denton — William Still: "Father of the Underground Railroad" —

Near Detour Road east of Harmony Road (Maryland Route 16), on the right when traveling east.

45 ► Maryland, Caroline County, Federalsburg — A Paradise For Smugglers — Nanticoke River, 1861-1863 —

On South Main Street (Maryland Route 308) north of Smith Street, on the right when traveling north.

46 ► Maryland, Caroline County, Federalsburg — Civil War Memorial —

Near Bloomingdale Avenue (Maryland Route 315) west of Old Denton Road, on the right when traveling west.

47 ► Maryland, Caroline County, Federalsburg — Exeter / Idlewild Mill —

On Denton Road, 0.2 miles north of Laurel Grove Road, on the left when traveling north.

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48 ► Maryland, Caroline County, Federalsburg — Federalsburg Hometown Veterans Memorial —

On Rosser Road south of Federalsburg Highway (Maryland Route 313), on the left when traveling south.

49 ► Maryland, Caroline County, Federalsburg — Former Clubhouse at Federal Field — Home of the Federalsburg Athletics — The Eastern Shore League —

On University Avenue North at Greenridge Road, on the right when traveling north on University Avenue North.

50 ► Maryland, Caroline County, Federalsburg — Marshyhope Creek Bridge —

On East Central Avenue (Maryland Route 306), on the left when traveling west.

51 ► Maryland, Caroline County, Federalsburg — The Historic Nanticoke Lodge Masonic Temple —

On North Main Street (Maryland Route 315) just north of West Central Avenue, on the left when traveling north.

52 ► Maryland, Caroline County, Federalsburg — These Dead Shall Not Have Died in Vain —

Near Veterans Drive, on the right when traveling south.

53 ► Maryland, Caroline County, Federalsburg — Veterans Memorial —

Near Bloomingdale Avenue (Route 315) west of Old Denton Road, on the right when traveling west.

54 ► Maryland, Caroline County, Greensboro — Choptank River Park —

On East Sunset Avenue (Maryland Route 314) west of Greensboro Road (Maryland Route 313), on the left when traveling west.

55 ► Maryland, Caroline County, Greensboro — Goldsborough House —

On West Sunset Ave. at Church Street, on the right when traveling west on West Sunset Ave..

56 ► Maryland, Caroline County, Greensboro — Greensboro —

On East Sunset Avenue (Maryland Route 314) at Greensboro Road (Maryland Route 313), on the right when traveling west on East Sunset Avenue.

57 ► Maryland, Caroline County, Greensboro — 33 — Greensboro — Threatened by Ideas — Harriet Tubman Underground Railroad Byway

On North Main Street (Route 480) just south of Cedar Lane, on the right when traveling south. Reported missing.

58 ► Maryland, Caroline County, Greensboro — Letter to Lincoln — Chaos on the Eastern Shore —

On Main Street (Maryland Route 480) at Bernard Avenue, on the left when traveling south on Main Street.

59 ► Maryland, Caroline County, Greensboro — Peter Harrington — Revolutionary Officer, founder of Greensboro —

On Md 480 Main Street at Cedar Lane, on the right when traveling south on Md 480 Main Street.

60 ► Maryland, Caroline County, Harmony — “Sailing Away to Freedom” — Gilpin Point — Harriet Tubman Underground Railroad Byway —

On Holly Park Drive.

61 ► Maryland, Caroline County, Harmony — William Richardson —

On Holly Park Drive.

62 ► Maryland, Caroline County, Hillsboro — Frederick Douglass — Tales of Horror —

On Main Street (Alternate Maryland Route 404) 0.4 miles west of Ridgely Road (Maryland Route 480), on the left when traveling west.

63 ► Maryland, Caroline County, Hillsboro — St. Paul’s Episcopal Church — (St. John’s Parish) —

On Church Street at Maple Avenue, on the right on Church Street.

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64 ► Maryland, Caroline County, Jumptown — 35 — Adkins Arboretum — Slavery's Arboretum — Harriet Tubman Underground Railroad Byway —

On Eveland Road.

65 ► Maryland, Caroline County, Marydel — Sapling from 400 Year Old Oak Tree —

Near Crown Stone Road (Maryland Route 454) at Fire House Lane.

66 ► Maryland, Caroline County, Preston — Charles Dickenson —

On Auction Road (Maryland Route 621) at Harmony Road (Maryland Route 16), on the right when traveling east on Auction Road.

67 ► Maryland, Caroline County, Preston — Choptank —

On Choptank Road at Maryland Ave., on the left when traveling south on Choptank Road.

68 ► Maryland, Caroline County, Preston — Colonel William Richardson — Born 1735, died 1825 —

On Harmony Road (Maryland Route 16) at Wilkins Branch Road, on the left when traveling north on Harmony Road.

69 ► Maryland, Caroline County, Preston — Dover Crossing Timeline —

On Dover Bridge Road (Maryland Route 331) 0.8 miles west of Carr's Creek Lane, on the right when traveling west.

70 ► Maryland, Caroline County, Preston — Escape from Poplar Neck — Harriet Tubman Underground Railroad Byway —

On Water Street.

71 ► Maryland, Caroline County, Preston — 23 — Leverton House — Finding Safe Haven — Harriet Tubman Underground Railroad Byway —

On Seaman Road.

72 ► Maryland, Caroline County, Preston — Linchester — Circa 1681 —

On Maryland Route 331 at Linchester Road, on the right when traveling south on State Route 331.

73 ► Maryland, Caroline County, Preston — Linchester Mill —

On Linchester Road at Maryland Route 331 on Linchester Road.

74 ► Maryland, Caroline County, Preston — 24 — Linchester Mill — Living Dangerously — Harriet Tubman Underground Railroad Byway —

On Linchester Road (Route 817) at Main Street (Maryland Route 331), on the left when traveling west on Linchester Road.

75 ► Maryland, Caroline County, Preston — Mt. Pleasant Cemetery — Dangerous Rendezvous — Harriet Tubman Underground Railroad Byway —

On Marsh Creek Road.

76 ► Maryland, Caroline County, Preston — Mt. Pleasant M. E. Church — 1864 - 1962 —

On Marsh Creek Road.

77 ► Maryland, Caroline County, Preston — Preston —

On Main Street (Maryland Route 331) at Maple Street, on the right when traveling south on Main Street.

78 ► Maryland, Caroline County, Preston — Site of Frazier’s Chapel — Preston, Maryland, 1785 —

On Main Street (Maryland Route 331) at Harmony Road (Maryland Route 16), on the left when traveling south on Main Street.

79 ► Maryland, Caroline County, Preston — The Dover Bridge —

On Dover Bridge Road (Maryland Route 331) 0.8 miles west of Carr's Creek Lane, on the right when traveling west.

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80 ► Maryland, Caroline County, Preston — The Maryland Lot —

On Water Street.

81 ► Maryland, Caroline County, Preston — The Underground Railroad — Seed of War —

On Linchester Road, 0.1 miles north of Maryland Route 331, on the right when traveling south.

82 ► Maryland, Caroline County, Preston — 28 — Webb Cabin — Living Free — Harriet Tubman Underground Railroad Byway —

On Grove Road.

83 ► Maryland, Caroline County, Ridgely — Ridgely Memorial Park — Early History — 1919 - 1938 —

On West Belle Street west of Central Avenue (Maryland Route 312), on the right when traveling west.

84 ► Maryland, Caroline County, Ridgely — Ridgely Railroad Station —

On West Belle Street at North Maryland Avenue, on the right when traveling west on West Belle Street.

85 ► Maryland, Caroline County, Ridgely — Ridgely, MD 1888 - 1917 — A Period of Broad Growth —

On West Belle Road at Cow Barn Road, on the left when traveling west on West Belle Road.

86 ► Maryland, Caroline County, Ridgely — Saulsbury House - Fifer Hospital - Ridgely House — 1934 - 1943 — "The only such institution Caroline County has ever possessed" —

On Central Avenue (Maryland Route 312) at East Belle Street, on the right when traveling south on Central Avenue.

87 ► Maryland, Caroline County, Ridgely — The Drinking Fountain — Erected by the Forget-Me-Not Band of Mercy, 1915 —

On West Belle Street west of Central Avenue (Maryland Route 312), on the right when traveling west.

88 ► Maryland, Caroline County, Ridgely — Town of Ridgely Flag —

On Central Avenue (Maryland Route 312) just south of East Railroad Street, on the left when traveling south.

89 ► Maryland, Caroline County, Ridgely — Wood Ducks —

Near Eveland Road, 0.2 miles north of Sawmill Road, on the right when traveling south.