Beautiful Old Town Tallinn, with its cobblestone streets, Gothic spires, and rich architecture, is a UNESCO World Heritage site, and one of the best preserved medieval cities in Europe. Much of the ovoid-shaped Old Town is preserved green space with pathways, but not all are runnable — the cobblestones can be tough on your joints and your footing. Your best bet is to stick to the parks that surround Old Town — most have paved walkways that are good for running, and you’ll still be able to see most of the sites. On this 4 km route, you’ll pass all sort of interesting structures, including Towers Square, which is lined with medieval structures. If you want to pick your way around the museums and churches in the center of Old Town, you can take a stroll through the cobblestone streets on your cooldown. Inside the walls, design your own route, but they streets/alleys can be narrow, with lots of people and cobblestone footing.
Start out at Linnahall station and head south towards Eesti Meremuuseum. The path bordering Rannamae Tee will be on your left. Follow it southeast towards Viru Square. Use caution at this busy intersection — you’ll need to cross to the east side and into Tammsaare Park. Take a right onto the path through Tammsaare Park and continue west. Where G. Otsa crosses the west end of the park, take a left onto the street briefly and you’ll find the path resume on your right. Follow the path under the train tracks and highway where it passes Jaani Kirik. Just past Vabaduse Valjak, the path turns sharply north towards Raidkivimuuseum. At the museum, take a left onto Komandandi Tee which runs through Harjumagi Park and becomes the Falgi Tee in Lindamae Park. Just past Toompea, take a right onto the main path which will bring you past Eesti Filharmoonia Kammerkoor and north around the pond (Snelli Tiik). Here, you’ll have the best view of the numerous towers of Old Town as you look to your right. Cross over Nunne and into Tornide Valjak along the Rannamae Tee. This windy walled-in sidewalk will spit you back out at Linnahall.