Imagine a medieval city on a hill above the sea, surrounded by a high stone wall fortified with round towers like a giant castle. Then imagine sitting at the top of the wall with a glass of wine. You don’t have to imagine if you visit Tallinn, Estonia.Kate Dolan visits a cool bar in Tallinn

I have to admit I’d never heard of Tallinn until the name showed up in a travel brochure. I’d heard of Estonia, one of those countries that used to be behind the Iron Curtain, but I couldn’t have told you anything about it except that it was somewhere in Europe.

I can tell you more about it now, and someday hope to learn much more.

Over the centuries, the city of Tallinn was conquered by the Russians, Swedes, Poles and Danes, and it shows. The Estonians seem to have no trouble adopting aspects of other cultures while retaining a distinct identity of their own. Our tour guide spoke flawless English; she said learned it as a child from watching Cartoon Network. But as she told stories of the Estonians’ struggle to gain independence from the Soviet Union (including the “singing revolution,”) her sense of patriotism showed clear through. Watching American TV did not make her want to become American. Kate Dolan loved taking pictures of Tallinn

What interested me most were her stories from the medieval days when life in Tallinn was confined to the city walls and the city was divided into an upper and lower town. The upper town housed the ruling class of aristocrats while the merchants and workers lived in the lower town. Each part of the town even had its own separate government. Gates between the two sections were locked at sunset. While the upper town residents were socially superior, they were often in debt to the merchants in the lower town. Can you say awkward?

Tallinn has all the ingredients for a great story: oppressive foreign princes, deposed  diplomats, rich merchants vying for power, and all of them served by an oppressed local peasant class who might have sided with any of these powers or tried to thwart them all.

Kate Dolan visits the gate across from McDonalds in Tallinn

This was right across from the town McDonald’s…

I loved the town from the moment I saw the torches burning by an opening at the base of the wall and saw the sign urging us to come drink wine in the bar at the top. I have to admit, I like the way the city plays up the fairy tale look. In addition to the torches, there were archery targets set up on one side of the wall, and a guy dressed like Shrek (with a life-sized stuffed donkey) looked completely at home. Almost like a never-ending Renfest.

Kate Dolan spots Shrek in Tallinn EstoniaKate Dolan finds the bar at the top of the Tallinn wall

To get to the top of the wall for that glass of wine, we had to climb up steep winding stone stairways that were so narrow, I had to smash my face into the rock to make room for others to squeeze past me on their way down. Definitely not handicapped accessible. The bar at the top brought up supplies from the outside of the wall with a winch because the staircase was so difficult to traverse. When we finally reached the top, though, it was worth it. I felt like I was sitting in a mammoth tree house. I didn’t get the promised glass of wine, however. Instead, I ordered dry cider which turned out to be Estonian pear cider. It was great. I bought another bottle just before we re-boarded our cruise ship and it was still good, even though instead of sitting at the top of the quaint town wall, I was standing outside the gift shop of the not-at-all quaint cruise terminal. I would have bought even more to bring home except that I was pretty sure it would explode in my suitcase (don’t ask me how I know this).

So Tallinn ended up being my favorite stop on a trip that included visits to seven different countries. Despite the fact that our tour guide described Estonian weather as “nine months of hope followed by three months of disappointment,” I am anxious to return and learn more about this fascinating city and its irrepressible people.