It’s hard to believe two+ decades have passed since that first trip in ’99. Sorting through these images has produced a mix of feelings ranging from warm nostalgia to blunt reality – time passes quickly. Many of my early experiences in Estonia have been lost to a failing memory. Nonetheless, these ordinary snapshots stir emotions of a special time and place. Their enduring significance could never have been anticipated in the moment.
After returning from my brisk walk to the TV Tower on that first morning, Viki and Villu picked me up at the Pirita Hotell. On our way into Tallinn, we travelled along a gently curving, picturesque stretch of Pirita Avenue. On the right side sat the expansive Tallinn Bay. On the left, we passed a large, multi-faceted, Soviet-era, concrete structure that was clearly designed with a purpose in mind. Yet, what that might be remains something of a mystery to me. We also passed the Song Festival Grounds, another must-see on my list (but, for another day). Ahead were the outlines of church spires in Tallinn’s Old Town district. Of course, this was at the very top of my list and Viki was eager to show off Tallinn’s crown jewel.
The photo below is the first of what became a frequent subject. This is Viru Street, one of the main entryways into Tallinn’s Old Town district. By the way, Old Town is known locally as Vanalinn (literally “Old Town”). This area of Tallinn dates back to 1154. However, throughout much of its history it was known as Reval. The name Tallinn was adopted only at the beginning of its first independence in 1918, a nod to its Danish heritage. In Estonian, “Tallinn” means Danish Town.

Tallinn’s Old Town is considered one the most well-preserved in all of Northern Europe and is recognized as a UNESCO World Heritage Site. The narrow cobblestone streets are lined with four-story merchant buildings dating to medieval times. The grand churches, large squares, quaint passages, towers, bastions and moat are fascinating. It doesn’t require much imagination to transport yourself back in time.
The above photo shows one of the main entrances to Old Town known as Viru Gate. It is guarded by two, nearly identical, towers on each side. These towers are important fixtures in a very large and complex defensive fortification dating to the 14th century. The Gate itself was situated further back from the towers and was part of a wall that surrounded the entire city. While much of the wall still exists, modern transportation requirements (horse-drawn tram) necessitated Viru Gate’s sacrifice in the late 1800s.

After Viru Street we headed for upper Old Town, known as Toompea. This is where Estonia’s seat of government is located. Next was Piiskopi Platform on the west side and Kohtuotsa Platform on the east side. For an American new to “Old Europe”, my first experience with Vanalinn was nothing short of stunning. Truth be told, it’s always been that way. Each time I return, I can’t wait to take that first stroll through this magical slice of history.





