| c1665 | Lake discovered by William Drummond |
| 1728 | Dismal Swamp Canal proposed by William Byrd |
| 1763 | Lake Drummond charted by George Washington's surveyor |
| 1764 | Dismal swamp Land Company chartered |
| 1787 | Dismal Swamp Canal authorized by Virginia Legislature |
| 1790 | Dismal Swamp Canal authorized by North Carolina Legislature |
| 1793 | Work on the Dismal Swamp Canal began |
| 1802 | William Farange builds first hostelry in Camden County, N.C. |
| 1803 | Thomas Moore wrote "THE LAKE OF THE DISMAL SWAMP" |
| 1805 | Dismal Swamp Canal began limited through navigation for flat boats |
| 1810 | Jericho Canal completed |
| 1812 | Feeder Ditch completed |
| 1814 | First recorded passage of a vessel other than a shingle flat |
| 1818 | President James Monroe visited the Dismal Swamp |
| 1819 | First Lottery held to raise funds for improving the Canal |
| 1820 | Second Lottery held |
| 1822 | Cross Canal completed |
| 1823 | First passage of completely loaded schooner "Rebecca Edwards" |
| 1825 | Erie Canal completed |
| 1826 | U.S.Congress purchased 600 shares of Dismal Swamp Company |
| 1826 | Dismal Swamp Canal enlarged as a shoal draft ship canal |
| 1829 | Third Lottery held |
| 1829 | Lake Drummond Hotel built |
| 1829 | President Andrew Jackson visited the Dismal Swamp Canal |
| 1829 | Federal Government purchased 200 additional shares of stock |
| 1830 | "Lady of the Lake" first steamer designed to ply the canal |
| 1830 | North West Canal completed |
| 1867 | State of Virginia's 600 share holdings sold at auction |
| 1871 | North West Canal closed by dam built to conserve water |
| 1878 | Congress sold it's shares in the Dismal Swamp Canal |
| 1890 | Emma K - Dismal Swamp's favorite vessel - was built |
| 1899 | Dismal Swamp Canal enlarged in substantially its present form |
| 1929 | United States Government purchased the Lake Drummond Company |
| 1974 | Great Dismal Swamp National Wildlife Refuge created |