Pikk, whose name simply means 'Long Street' in Estonian, runs through Tallinn's Lower Town from the old harbour gate up to the foot of Toompea hill. For centuries it was the road merchants took from their ships into town, and it is still lined with the halls of the guilds that ran medieval Tallinn. Walk it end to end and you pass from Hanseatic trade to Soviet surveillance in a few hundred metres.
Pikk Street at a glance
- Where: in the Lower Town of Tallinn's Old Town, from the Great Coastal Gate and the Fat Margaret tower in the north to the Pikk jalg gate tower below Toompea.
- Origins: a medieval street; most of its guild halls and merchant houses date from the 14th to the 16th century, with later façades.
- What it is today: a cobbled street of guild halls, merchant houses, museums and cafés, part of the Old Town listed by UNESCO in 1997.
- Time needed: 20–30 minutes to walk it end to end; one to two hours with a museum or a coffee on the way.
The merchants' road
Tallinn, then called Reval, was a member of the Hanseatic League, and Pikk was its main trading street. Goods came in through the Great Coastal Gate, and many of the tall gabled houses along the street were both homes and warehouses: look up and you can still see the hoist beams under the gables that lifted goods into the lofts. The town's merchants organised themselves in guilds, and their halls stand along Pikk. The richest belonged to the Great Guild, whose hall was built in 1407–1410; craftsmen met in St Canute's and St Olaf's guilds; and young unmarried merchants joined the Brotherhood of the Blackheads.
The guilds lost their role over the following centuries and were dissolved in 1920, two years after Estonian independence. In 1940 the Soviet Union occupied Estonia, and the Blackheads, by then mostly Baltic Germans, left for Germany. Under Soviet rule a building near the northern end of Pikk became the headquarters of the Estonian KGB. Today the guild halls are a museum, concert halls and event spaces, and the street is one of the busiest in the Old Town.
What to look for
- Fat Margaret: the squat cannon tower from the early 16th century beside the Great Coastal Gate at the northern end, now home to the Estonian Maritime Museum.
- The Three Sisters: three medieval merchant houses side by side near the northern end of the street, with steep gables and hoist beams, now a hotel.
- The House of the Blackheads (Pikk 26): the Renaissance façade from the late 16th century, decorated with reliefs and coats of arms. The brotherhood's patron, St Maurice, appears on its emblem as a dark-skinned head. It is the only Blackheads house in the world that has survived intact.
- St Canute's Guild Hall (Pikk 20): rebuilt in the 19th century in neo-Gothic style; look for the two statues standing in niches on its façade.
- The Great Guild Hall (Pikk 17): the tall Gothic hall with blind arches and a pointed portal, built in 1407–1410 and now home to the Estonian History Museum.
- The Church of the Holy Spirit: at the corner opposite the Great Guild, with a painted wooden clock on its wall carved by Christian Ackermann in the late 17th century, often called the oldest public clock in Tallinn.
Pikk 59, the KGB building
The house at Pikk 59 was the headquarters of the Soviet KGB in Estonia until 1991. Its ground-floor windows were bricked up so that no one could see in or out, and you can still see the infill today. A plaque in Estonian by the door says that the building housed the repressive organ of the occupation regime. The cells in the basement are now a small museum. A grim joke from Soviet times said that Pikk 59 was the tallest building in Tallinn, because from its basement you could see Siberia.
Tips for your visit
- Walk the street downhill from Pikk jalg towards Fat Margaret, or the other way round to end at the climb to Toompea: either way, the guild halls are in the middle.
- Early morning or evening is best for photos of the façades without crowds and cruise groups.
- The cobbles are uneven and can be slippery in winter; wear shoes with a good grip.
- Stop for coffee opposite the Great Guild, then step into the Holy Spirit church to see its carved interior.
Nearby
- Town Hall Square: the medieval market square with its Gothic town hall, a couple of minutes' walk along Pühavaimu from the Holy Spirit church.
- Toompea: the upper town on the hill, reached through the Pikk jalg gate tower, with Toompea Castle and the Alexander Nevsky Cathedral.
- St Olaf's Church: the Gothic church with the tall spire, just off the northern end of Pikk.
- Lai Street: the parallel 'Broad Street', quieter than Pikk, with more medieval merchant houses.
See Tallinn with World City Trail
Our Tallinn scavenger hunt turns the old town into a game you play on your phone. The route links 10 stops and takes around 2 hours, with about 38 minutes of walking. It includes Viru Gate, the Alexander Nevsky Cathedral and Town Hall Square.
If you prefer a different format, there is also a self-guided walking tour and an outdoor escape game in Tallinn.
Play the Tallinn scavenger hunt →
Take the self-guided walking tour of Tallinn →
Play the outdoor escape game in Tallinn →
Facts checked in October 2026.