1582 Russia cedes Livonia and Estonia to the Polish–Lithuanian Commonwealth.
1904 The Russian Baltic Fleet leaves Reval, Estonia for Port Arthur during the Russo-Japanese War.
1917 October Revolution: In Tallinn, Estonia, Communist leader Jaan Anvelt leads revolutionaries in overthrowing the Provisional Government (As Estonia and Russia are still using the Julian Calendar, subsequent period references show an October 23 date).
1918 Germany, Austria and Russia sign the Treaty of Brest-Litovsk ending Russia's involvement in World War I, and leading to the independence of Finland, Estonia, Latvia, Lithuania and Poland.
1919 Estonian Liberation War: the decisive defeat of German Freikorps (Baltische Landeswehr) forces in the Battle of Cesis (Võnnu lahing). This day is celebrated as Victory Day in Estonia.
1920 The Tartu Peace Treaty is signed between Estonia and Russia.
1934 Konstantin Päts and General Johan Laidoner stage a coup in Estonia, and ban all political parties.
1940 The three Baltic states of Estonia, Latvia and Lithuania fall under the occupation of the Soviet Union.
1940 The United States' Under Secretary of State Sumner Welles issues a declaration on the U.S. non-recognition policy of the Soviet annexation and incorporation of three Baltic States: Estonia, Latvia and Lithuania.
1941 June deportation, the first major wave of Soviet mass deportations and murder of Estonians, Latvians and Lithuanians, begins.
1944 Soviet Army troops liberate Klooga concentration camp in Klooga, Estonia.
1946 Estonian school girls Aili Jõgi and Ageeda Paavel blow up the Soviet memorial that preceded the Bronze Soldier in Tallinn.
1949 The extensive deportation campaign known as March deportation is conducted in Estonia, Latvia and Lithuania to force collectivisation by way of terror. The Soviet authorities deport more than 92,000 people from the Baltics to remote areas of the Soviet Union.
1988 The Supreme Soviet of the Estonian SSR declares that Estonia is "sovereign" but stops short of declaring independence.
1989 Singing Revolution: two million people from Estonia, Latvia and Lithuania stand on the Vilnius-Tallinn road, holding hands (Baltic Way).
1991 Estonia, annexed by the Soviet Union in 1940, issues a decision on the re-establishment of independence on the basis of historical continuity of her pre-World War II statehood.
1991 The European Community recognizes the independence of the Baltic states of Estonia, Latvia and Lithuania.
1991 The United States recognize the independence of the Baltic states: Estonia, Latvia, and Lithuania.
1991 The Soviet Union recognizes the independence of the Baltic states: Estonia, Latvia and Lithuania.
1991 Estonia, North Korea, South Korea, Latvia, Lithuania, the Marshall Islands and Micronesia join the United Nations.
1996 Pala accident: a wood lorry and school bus collide in Jõgeva county, Estonia, killing eight children.
2001 Pärnu methanol tragedy occurs in Pärnu County, Estonia.
2002 NATO invites Bulgaria, Estonia, Latvia, Lithuania, Romania, Slovakia and Slovenia to become members.
2002 Enlargement of the European Union: The European Union announces that Cyprus, the Czech Republic, Estonia, Hungary, Latvia, Lithuania, Malta, Poland, Slovakia, and Slovenia will become members from May 1, 2004.
2003 In a referendum, Estonia approves joining the European Union.
2004 Bulgaria, Estonia, Latvia, Lithuania, Romania, Slovakia and Slovenia join NATO as full members.
2004 Cyprus, Czech Republic, Estonia, Hungary, Latvia, Lithuania, Malta, Poland, Slovakia, and Slovenia join the European Union, celebrated at the residence of the Irish President in Dublin.
2006 Estonia ratifies the European Constitution.
2007 Estonian authorities remove the Bronze Soldier, a Soviet Red Army war memorial in Tallinn, amid political controversy with Russia.