Tallinn

Tallinn may be small, but it’s full of stories. About a third of the city is still surrounded by its medieval wall, and you can climb towers that once defended it.

The Old Town’s cobblestone streets and red rooftops are so well preserved that UNESCO named it a World Heritage Site. Kids will love knowing this city was once ruled by knights, merchants, and even pirates.

The city grew rich in the Middle Ages as part of the Hanseatic League, a trade network across Northern Europe. Merchants filled the Town Hall Square with goods from Russia, Germany, and beyond.

The Great Guild Hall still stands as proof of their influence. But Tallinn’s wealth also made it a target.

Danish crusaders captured it in 1219 at the Battle of Lyndanisse. A legend says Denmark’s red-and-white flag fell from the sky during the fight, giving the Danes victory.

Control of Tallinn shifted often. The Swedes ruled in the 1500s, followed by the Russian Empire after the Great Northern War in 1710.

That war devastated the city with plague and hardship. In the 20th century, Tallinn endured Soviet and Nazi occupations during World War II.

Bombings in 1944 destroyed much of the city outside the Old Town, though the medieval core survived. Estonians finally regained independence in 1991, with Tallinn leading the Singing Revolution, where people resisted Soviet rule with music and protest.

Walking through Tallinn today, you can see every layer of its past. Climb Toompea Hill to visit the castle where rulers once sat, and see Estonia’s parliament there now.

Step inside St. Olaf’s Church, once one of the tallest buildings in Europe, though some say it may have been the tallest in the world.

For families, the Seaplane Harbour museum brings naval history to life with real submarines and planes.

And if you want to feel the city’s medieval spirit, head to Town Hall Square, where markets and festivals still fill the same space as they did 600 years ago.