Free Self-Guided Tallinn Walking Tour: Highlights & Overlooked Gems (With Map!)

Tallinn is one of those cities that never fails to make a positive first impression. It has one of the best-preserved medieval towns in Europe and the cobblestone alleyways, slender steeples and keg-shaped bastions could have jumped straight out of the pages of a medieval book. A large chunk of sights in Tallinn are concentrated in and around the medieval Old Town. A Tallinn walking tour is one of the best ways to see these sights, important landmarks and soak in the charming atmosphere. This post includes a map for a self-guided free walking tour of Tallinn. Enjoy your walk! 🙂

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Why Choose This Free Self-Guided Tallinn Walking Tour?

This free self-guided Tallinn walking tour itinerary is perfect if you are short on time and trying to save some money. With our free map, you can follow the route quite easily without having to hire an expensive guide for the day. The tour will take you past the city’s major attractions, landmark public buildings, places of worship, cultural venues, restaurants, and cafes. You’ll also learn a few lesser-known facts about Tallinn along the way.

The tour will take you through the center of Tallinn, principally focusing on the attraction studded areas of the medieval UNESCO World Heritage Old Town and Toompea.

Tallinn Walking Tour Itinerary

I’ve divided this Tallinn walking tour into a basic and an advanced tour. The basic walking tour covers a total distance of approximately 3.7 kilometers (2.3 miles). This tour starts at the Rotermann Quarter and terminates at the Estonian National Opera. If you feel you’re up for it, you can proceed with the advanced tour in which the main sights are around Kadriorg. The advanced walking tour adds approximately 4.7 kilometers (2.9 miles) to the basic walking tour. So, the basic and advanced walking tours add up to a total of 8.4 kilometers (5.2 miles). Feel free to take a break if you feel jaded along the way. I have included some cafes and restaurants in the map where you can take a breather and grab a bite. On this Tallinn walking tour, you will see:

1. Rotermann Quarter
2. Viru Gate
3. St. Catherine’s Passage
4. Fat Margaret’s Tower
5. Three Sisters
6. St. Olaf’s Church
7. House of the Blackheads
8. Great Guild Hall
9. Holy Spirit Church
10. Town Hall Square
11. Town Hall
12. St. Nicholas’ Church
13. Cathedral of St. Mary the Virgin
14. Estonian Knighthood House
15. Kohtuotsa Viewing Platform
16. Alexander Nevsky Cathedral
17. Toompea Castle
18. Kiek-in-de-Kök
19. Freedom Monument
20. Estonian Drama Theater
21. Estonian National Opera
22. Kadriorg Park
23. Kadriorg Palace
24. KUMU Art Museum
25. Russalka Memorial

1. Rotermann Quarter

Kick off your Tallinn walking tour in the Rotermann Quarter. The Rotermann Quarter is an area that consists of former decaying factories and warehouses established in the 19th-century by the industrialist Christian Abraham Rotermann. Neglected during much of the Soviet era, in 2007 the district underwent a major redevelopment and is now home to properties that are prime inner-city redevelopment territory. The local architects got creative by not demolishing these industrial buildings, and just modernized them by adding additional floors and glass windows, which look like glass cubes or spinners. The result is pretty cool and these sleek architectural buildings now house swanky bars, cafés, boutique shops, offices, and restaurants.

2. Viru Gate

The iconic Viru Gate serves as one of the chief entry points into the Old Town. Its two picturesque, skewed stone towers are one of Tallinn’s major sightseeing attractions. The pair of towers that make up the gate date to the 14th century and are surrounded by a stretch of the city wall dating back to the 16th century.

3. St. Catherine’s Passage

Next up is St. Catherine’s Passageway, one of my favorite places in the Old Town. It is an enchanting medieval alleyway joining Vene and Müürivahe streets with uneven stone walls and overhead vaulting. I love how it gives you the feeling of stepping back in time. The passage runs along the surviving wall of St. Catherine’s Church, which was built in 1246 and was formerly the largest church in the city. You can still notice several gravestones here, some dating from the 14th century. Nowadays, the passage is home to an ensemble of arts and craft workshops. You can watch applied artists work with stained glass, ceramics, leatherwork, millinery, and jewelry and check out their wares.

4. Fat Margaret’s Tower

Out of all of the Old Town’s remaining towers, the Fat Margaret’s Tower is definitely the most outré. This 16th-century tower’s suggestive name comes from the fact that it was the largest part of the city’s fortifications with walls measuring 4 meters thick. It was initially constructed to defend the harbor as well as to enthrall visitors arriving by sea. Later, the tower was transformed into a prison. It is now home to the Estonian Maritime Museum and features an interesting collection of nautical paraphernalia spread out over four levels.

5. Three Sisters

The Three Sisters are three adjoining medieval merchants’ houses that are probably the most captivating and best-preserved of the Old Town’s gabled merchants’ houses. The houses were built in 1362 and were functional mercantile areas, complete with loading hatches and winches to hoist sacks of goods up and down. The houses’ original owners were mainly guild members, town councilors and burgomasters who used the houses to entertain foreign guests. Recently, the houses have been converted into a single luxury hotel in tasteful citrus colors.

6. St. Olaf’s Church

No Tallinn walking tour would be complete without seeing the famous St. Olaf’s (or St. Olav’s) Church. The church was first mentioned in 1267 and named in honor of King Olaf II of Norway, who was canonized for massacring pagans in Scandinavia. Its eye-catching 124-meter spire is a major Tallinn landmark and the church holds a proud place in the city’s history. According to local lore, the citizens of Tallinn wanted the church to possess the tallest spire in the world in order to attract merchant ships and boost trade. The church’s original 159-meter spire reputedly made it the tallest building in the world until a lightning strike burned it down in 1625. Remarkably, the church was struck by lightning 6 or 8 times and burned down twice between then and 1820. The church underwent extensive renovation in the 19th century and as a result, features a rather drab interior.

7. House of the Blackheads

This 15th-century House of the Blackheads served as the congregation place of the Brotherhood of Blackheads, an association of unmarried merchants and shipowners. The building’s unusual name comes from the North African St Maurice, the organization’s patron saint, whose image can be seen on the front door of the building. Although it’s not as beautiful as its more famous namesake in Riga I really like the building’s Renaissance facade with its elaborate stone portal and ornately decorated door.

Unlike in Riga, however, the Tallinn Blackheads also served a military purpose and proved themselves as redoubtable adversaries during the Livonian Wars. The Brotherhood survived until the Soviet invasion in 1940, and today the House of Blackheads serves as a venue for regular chamber concerts.

8. Great Guild Hall

The Great Guild Hall, which dates to 1417, is one of the most important buildings from medieval times that holds a significant place in Tallinn’s history. The Gothic building has retained its original appearance through the centuries, although the windows were restructured in the late 19th century.

The Great Guild served as the home of the most powerful of the city’s guilds, uniting the German-speaking mercantile elite into an organization that effectively controlled Tallinn’s commerce. Its doors were closed to smaller merchants and artisans, who were instead forced to form lesser institutions. Besides being the gathering place for its members, the Great Guild was also the focus of many of medieval Tallinn’s social events. It was often rented out for wedding parties and court sessions and used to be the starting as well as the end point of most festive cavalcades. Today, the building is home to a branch of the Estonian History Museum whose collection of historical artifacts covers Estonian history from the Stone Age to the mid-19th century.

9. Holy Spirit Church

The 13th-century Holy Spirit Church (or Holy Ghost Church) is one of the most attractive churches in Tallinn. A small Gothic building with stepped gables, the church served as the Town Hall chapel before becoming the principal church of Tallinn’s Estonian-speaking population. Its whitewashed exterior and stepped gable are topped by a striking Baroque tower. The ornate clock set into the wall above the entrance, with carvings dating from the late 17th century, is Tallinn’s oldest public clock. The interior of the church is as spectacular as its exterior and features a treasure trove of religious artifacts and architecture. One of the reasons why this place holds a special place in Estonian history is because the first Estonian-language catechisms were formulated here in 1535 following the Reformation.

10. Town Hall Square

The gently sloping, magnificent Town Hall Square lies in the heart of the Old Town and has, for centuries, served as a marketplace. The cobblestoned square is surrounded by an ensemble of pastel-colored medieval houses. Being one of Tallinn’s marquee attractions, the square has become a trademark of both the city and Estonia as a whole, featuring on countless souvenirs and tourist posters. One of the most august buildings lining the Town Hall Square is the Town Hall Pharmacy, famed for being one of the oldest pharmacies in Europe. The building’s exterior dates back to the 17th century, but there is evidence that a pharmacy existed on the site as long back as the early 15th century.

11. Town Hall

The Town Hall, which dates back to 1404, is one of the most hallowed symbols of Tallinn. It boasts an elegant arcade of Gothic arches and a slender steeple. The narrow windows and crenelated parapet complete the building’s dignified facade. Don’t forget to spot the waterspouts in the form of green dragons just beneath the roof and the 16th-century weather vane in the form of a stout, spear-wielding sentry near the summit of the steeple.

12. St. Nicholas’ Church

Next stop on this Tallinn walking tour is St. Nicholas’ Church, my favorite out of Tallinn’s churches and one of the city’s must-see attractions. This Gothic landmark was originally erected in the 13th century but almost all that remains is from the 15th century. You’ll notice a stone skull and crossbones carving at the entrance to the chapel, near the church’s main door. Stone carving was an important element in Estonian architecture, was largely done in dolomite and sandstone.

The building has served as a museum since it was extensively restored during Soviet times after being damaged by Soviet bombing raids in World War II. It is home to most of Tallinn’s medieval artworks – many of which were destroyed in the Protestant riots of 1524. According to legend, however, St. Nicholas’ Church escaped being ransacked due to the quick thinking of the church’s warden, who sealed the door with melted lead. The 15th-century frieze Danse Macabre by Bernt Notke is definitely the chef-d’œuvre of the church. Only a portion of the 30-meter original remains.

13. Cathedral of St. Mary the Virgin

The Cathedral of St. Mary the Virgin is popularly known as Dome Church and is rumored to be the oldest church in Estonia. This cute church was built as a wooden church in 1240 by the Danes and has undergone vast rebuilding over the years. The austere whitewashed Gothic exterior dates from the 14th century, while the beautiful interior boasts an elaborate Baroque pulpit and an organ built in 1878.

14. Estonian Knighthood House

The Estonian Knighthood House is one of the prettiest buildings on Toompea Hill. The Neo-Renaissance building was built in 1848 to serve as the headquarters of the knighthood, a major component of the local aristocracy. It was home to the Foreign Ministry during the first independent republic of Estonia, which lasted from 1920 to 1940 and during Soviet times the building housed the Estonian National Library.

15. Kohtuotsa Viewing Platform

One of the perks of being on Toompea is that you are awarded breathtaking views of Tallinn from here. The Kohtuotsa Viewing Platform is on the hill’s eastern side and from here you are accorded a stunning view of the Old Town`s rooftops and Tallinn’s modern skyline which lies in the background. If you have ever seen any pictures of Tallinn, chances are they included a mural saying “The Times We Had”. You can find it here at Kohtuotsa.

16. Alexander Nevsky Cathedral

The imposing Alexander Nevsky Cathedral is Tallinn’s most striking Russian Orthodox Cathedral. It was built in 1900 when Estonia was under Czarist Russian rule as a reminder to the local Estonians of their subordinate status during that era. Loathed by most Estonians at the time for being a symbol of Russification policies, the Alexander Nevsky Cathedral was planned to be demolished in 1924, but the plan was never executed. The cathedral is dedicated to the Prince of Novgorod, Alexander Yaroslavich Nevsky, who vanquished the Livonian Knights on the banks of Lake Peipsi in 1242.

The cathedral’s Neo-Byzantine exterior is richly decorated in mosaics and icons and its bulging black domes and golden iron crosses are visible through most of the Old Town. The interior is relatively spartan compared to other renowned Orthodox cathedrals but impressive nonetheless.

17. Toompea Castle

Toompea Castle’s placid pink facade belies its history. The castle complex is now home to Riigikogu (Estonia’s Parliament), but for some 700 years, it belonged to various occupying foreign powers. The castle stands on the former site of a 9th-century wooden fortress which was conquered by the Danes in 1219, who built the stone fortifications around the hill, much of which still remain. The structure has been modified by everyone who has conquered it since then and the Parliament building which was built in 1920-1922 is the sole expressionist parliament building in the world. The northern and western walls of the castle, include three defensive towers, the most laudable of which is the 50-meter tall Pikk Hermann, dating from 1371. These crumbling towers were often depicted in old Soviet films, especially fairy tales.

18. Kiek-in-de-Kök

The Kiek-in-de-Kök Tower was built in 1475 to provide a home for Toompea’s main artillery. It is definitely one of the must-see sights on this Tallinn walking tour. Its 4-meters thick walls made it one of the most impregnable cannon towers 16th-century Northern Europe. The tower’s unusual name comes from the Low German expression “to peek into the kitchen”, indicating that sentries had a good vantage point over the adversary. After falling into disuse in the mid-18th century, the tower now houses a museum devoted to Tallinn’s history. The exhibits here include suits of armor, rusty-looking artillery and cannon replicas.

19. Freedom Monument

The Freedom Monument overlooks the Freedom Square, a large open space formerly used for parades on Soviet holidays. It was unveiled in 2009 to commemorate the struggles of the Estonian independence movement of 1918-20. The structure comprises of a large cross mounted on a 24-meter high pillar of dimpled glass, and sort of looks like an ice sculpture that’s on the verge of melting – a deliberate effect meant to signify the movement’s fragile nature. It is, however, a slightly controversial piece of work, with some Tallinn natives regard it too ostentatious.

20. Estonian Drama Theater

No walking tour of Tallinn should be undertaken without paying a visit to the alluring Estonian Drama Theater. The building’s design blends Art Nouveau with Nordic folk motifs to generate a wealth of rustic features. Its roofs resemble the shingles of village huts, and a frieze of age-old bards looms over the chief entrance. Art Nouveau, being my favorite architectural style, makes this building extra-special.

Originally built in 1910 as a German-language theater, the building was purchased by the Estonian Drama Theater in 1939. The theater’s name was changed to the Tallinn Drama Theatre in the Soviet era in an effort to remove nationalist affinities associated with it. However, in 1989 it reverted to its original name.

21. Estonian National Opera

The hulking Estonian National Opera building casts such a large shadow along the stretch of Estonia Avenue that it’s impossible to overlook. This massive edifice houses the Estonian National Opera and its ballet company in one wing and the Estonian National Symphony Orchestra in another. Set up in 1913 through public donations, the Estonian National Opera was meant to showcase Estonian culture that would rival similar German and Russian institutions in Tallinn.

22. Kadriorg Park

Beloved by Tallinn natives, the sprawling Kadriorg Park is one of the city’s major attractions and is home to several notable landmarks. The park stretches for 1.5 km from its southwest corner to the northeast. With its landscaped gardens, forested paths, statues, and ponds, Kadriorg Park is a gem of a place to explore. The beautiful Swan Lake is one of the park’s highlights, and its elegant island gazebo is actually mostly enjoyed by swans. If you’re here in summer, you’ll often see plenty of picnickers and sunbathers.

23. Kadriorg Palace

The Kadriorg Palace was built in 1718 under the orders of the Russian Tsar Peter the Great, who intended it to serve as a summer residence for the royal family. It was later named in honor of his wife Catherine. Kadriorg is Estonian for “Catherine’s Valley”. The palace has an Italian Baroque design with light red walls and a green roof. Determined to honor his wife, the Russian Tsar spared no expense in creating this opulent building. Its main attraction is the ornate Great Hall, which is surely among the finest examples of Baroque architecture in Northern Europe. The palace is now home to the Kadriorg Art Museum which specializes in foreign artworks from the 16th to 20th centuries.

24. KUMU Art Museum

The KUMU Art Museum is built into a limestone bank at the eastern end of Kadriorg Park and is a truly a work of art in itself. Partially underground, this crescent-shaped wedge of Estonian limestone, green-patinated copper and glass juts out from the grassy ridge like a surfacing submarine. KUMU is the headquarters of the Estonian Art Museum and serves both as Estonia’s national gallery and as a center for contemporary art. Its interior is beautifully designed and the three floors of exhibits trace an eclectic mix of Estonian art from the 18th to 21st centuries.

25. Russalka Memorial

The final sight on this Tallinn walking tour is the imposing Russalka Memorial. It was erected in 1902 to commemorate the 177 soldiers who perished when the Russian ship Russalka (or Mermaid) sank en route to Finland in 1893. It features a bronze angel standing on tiptoe, holding aloft an Orthodox cross in the direction of the Gulf of Finland. The rough granite pillar on which the angel stands evokes turbulent conditions at sea. You can often spot newly married couples posing for pictures here.

What Else to See in Tallinn

There is plenty more to see in Tallinn than what we have covered in our walking tour. Places like the bohemian Kalamaja neighborhood, the trendy Balti Jaam Market and the Tallinn TV Tower deserve to be seen. Check out our post on how to spend one marvelous day in Tallinn. And while you’re at it, why not check out our list of the best hotels and hostels in Tallinn? I have made sure to recommend only the best of the best (in terms of quality and value) 🙂

Now, what do you think? Is there something else that should be added to this Tallinn walking tour? Share your thoughts with us in the comments below!