The buildings home to the city's guilds are all along Pikk Street. It is easy to see the importance of this main street linking the two most important places in a medieval city, the harbour and Town Hall square. The mercantile and guild houses along the street stretching from the Great Coast gate have characteristic gables and warehouse lofts, such as the Three Sisters .
Directly across from the Church of the Holy Spirit is the Great Guild, the number on the Gothic gable refers to its date of construction, 141O. The building used by wealthy merchants and ship owners has retained its original exterior appearance. The metal knockers from 1430 are rare examples of Estonia's medieval bronze-working. The one on the right bears a Latin inscription, "A.D. 1430. Glory to Christ the Lord. Come in Peace.; on the left side, Low German, reading, "God Bless All Who Reside In and Enter This House': The silver cross on a red feld that adorns the facade is the city coat of arms and the Great Guild's seal as well; only guild members could become aldermen. The Guild closed in 1920. Two lunette paintings from the 19th century are extant;one depicts the beginning of the Reformation in Tallinn (T. A. Sprengel) and the other the May King entering Tallinn (L. von Petzold).
The Estonian History Museum is now located in the Great Guild house.
The 19th century Tudor-inspired facade of Canute’s Guild is graced by the figures of Martin Luther and St. Canute. The guild founded in the 13th and 14 centuries included German manual labourers as well as merchants. The Guild was closed in 1920.
Next door is the St.Olaf Guild also from the 13th and 14th centuries, which was open to Estonians. The members, manual labourers, were forbidden to wear silk, velvet and taffeta clothing, as well as fine leather and jewelry, that right was reserved by German merchants. A depiction of the patron saint Olaf appears on the gable, the heraldry of the Burchardts and von zur Muhlen on the facade: The guild was closed in the 17th century.