The American Civil War and the Reconstruction era that followed represent one of the most tumultuous periods in American history. From 1861 to 1865, the nation was embroiled in a bloody conflict over states’ rights and slavery that pitted the Union against the seceded Confederate states. Even after the Confederacy surrendered in 1865, struggles continued during Reconstruction as the country tried to rebuild and bring the Southern states back into the fold. This period left a lasting legacy and much to contemplate even today.
Riddles can be a fun way to engage with history and test your knowledge. Below are 56 riddles about key people, battles, and events related to the Civil War and Reconstruction. Each riddle has the answer provided as well so you can check your work!
Civil War Riddles
People
1. Tall and lanky, I kept the Union together as the sixteenth president: Abraham Lincoln
2. General of the Confederate army, my nickname was “Stonewall”: Thomas “Stonewall” Jackson
3. Enslaved man who escaped and helped the Union, I spoke out for civil rights after the Civil War ended: Frederick Douglass
4. Southern belle who volunteered as a nurse during the war, I founded the American Red Cross: Clara Barton
5. Led Union troops in the west, later became president after Lincoln’s assassination: Andrew Johnson
Battles
6. First major battle of the Civil War won by the South in Virginia in 1861: First Battle of Bull Run
7. Deadly 1862 battle in Tennessee, second bloodiest of the war after Gettysburg: Battle of Shiloh
8. Turning point 1863 battle won by Grant, splitting the South along the Mississippi River: Siege of Vicksburg
9. Civil War’s bloodiest single-day battle on September 17, 1862 with almost 23,000 casualties: Battle of Antietam
10. Major Confederate victory in 1862 led by General Lee in Virginia: Second Battle of Bull Run
Politics & Events
11. Amendment abolishing slavery passed in 1865 under Lincoln: Thirteenth Amendment
12. President after Lincoln assassinated, impeached for firing cabinet member: Andrew Johnson
13. Withdrawal of Southern states from the Union in 1860-61: Secession
14. Lincoln’s 1863 proclamation freeing slaves in rebelling territories: Emancipation Proclamation
15. Network helping slaves escape north to free states and Canada: Underground Railroad
Reconstruction Riddles
Politics
16. Congressional plan requiring 50% loyalty oaths for Southern voters: Wade-Davis Bill
17. Republicans who pushed southern reforms and racial equality during Reconstruction: Radical Republicans
18. Term for Northerners who came south as government workers and teachers: Carpetbaggers
19. Force bill in 1870-71 to enforce black voting rights and suppress KKK: Second Enforcement Act
20. Panic of 1873 started this economic depression lasting over 5 years: Long Depression
Rights & Reform
21. Amendment in 1868 defining citizenship and equal rights that was ratified under Grant: Fourteenth Amendment
22. Legislation in 1875 banning racial discrimination in public places: Civil Rights Act of 1875
23. Plantation system replaced by sharecropping system using these annual contracts: Sharecropping
24. Secret vigilante society that used violence to intimidate blacks and Republicans: Ku Klux Klan (KKK)
25. Grant’s tough laws in 1870 and 71 to combat KKK terrorism: Enforcement Acts
End of An Era
26. Disputed presidential election between Hayes (R) and Tilden (D) settled by special: Compromise of 1877
27. Federal troops withdrawn from South as part of 1877 compromise: Compromise of 1877
28. Marked formal end of Reconstruction era starting “Redemption” movement: Compromise of 1877
29. Term for Southern Democrats who wanted to restore pre-war racial hierarchy: Redeemers
30. Laws created to enforce segregation and strip rights from blacks: Jim Crow Laws
More Civil War & Reconstruction Riddles
31. My assassination by Booth at Ford’s Theatre ended the Civil War: Abraham Lincoln
32. These state’s rights, economic disputes led Southern states to secede, starting the Civil War: Sectionalism
33. General who led Union Army to victory with his “total war” scorched earth fighting style: William T. Sherman
34. President Johnson was impeached but not removed by just one vote of this group: U.S. Senate
35. Supreme Court ruled this 1896 case legalized “separate but equal” segregation: Plessy v. Ferguson
36. Union general known for brilliant battlefield strategies like flanking maneuvers: Joshua Chamberlain
37. Southern war tactic named for military leader, aiming to wear down enemy morale: Guerrilla warfare
38. President Johnson opposed this Constitutional amendment giving rights to free slaves: Fourteenth Amendment
39. Printers spread propaganda and shaped public opinion through newspapers and these: Political cartoons
40. Contested voting rights in South led Congress to pass these Reconstruction Amendments: 13th, 14th, and 15th Amendments
41. Supreme Court case in 1883 striking down 1875 Civil Rights Act protections: Civil Rights Cases
42. General Sherman burned Atlanta then continued destruction to this port: Savannah
43. Confederate surrender at Virginia Appomattox Court House in 1865 by General: Robert E. Lee
44. President after Johnson who won 1868 election to continue Reconstruction: Ulysses S. Grant
45. Union blockade preventing Southern cotton exports aimed to wreck this industry: Cotton
46. Underground network and series of safe houses enslaved people followed to escape: Underground Railroad
47. Thaddeus Stevens and Charles Sumner were faces of this Reconstruction faction: Radical Republicans
48. Soldiers who fought for North were called these: Union
49. Soldiers who fought for South were called these: Confederates
50. Total number of Southern states that seceded was this many: Eleven
51. Supreme Court case ruled federal government couldn’t restrict slavery in territories: Dred Scott v. Sandford
52. General Lee surrendered to General Grant in this tiny courthouse village: Appomattox Court House
53. President tried 10-Percent Plan for Reconstruction, seen as too soft by Republicans: Andrew Johnson
54. In Plessy v. Ferguson, Supreme Court legalized__________ under “separate but equal”: Racial segregation
55. Sharecropping system started when plantation owners broke up land into smaller__________: Farms
56. Poll taxes and literacy tests aimed at _________ specific groups from voting: Disenfranchising
