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Today's chief town of Harmanli came into being in about 1510 along the road that connects Europe and Asia. The first historical records of it date back to that time. They belong to the Slovene Benedit Kuripeshich, who would sojourn there as an interpreter in his mission. The location of the town along the roadway gives reason to a writer Gencho Stoev to say that 'Harmanli does not need  to travel because the world goes through it.'

Skilful masters built a solid caravansary on the right bank of the Harmanli river (then Oludere).

This first imposing building was intended to provide shelter to travellers and horses, as well as easy travelling of trade and economic ambassadors along the big national highway Constantinople - Belgrade. It also protected the poor peasants from the roundabout villages against incessant bandit incursions - at first seasonally, when they threshed their sheaves at the public threshing-floor near the caravansary, and after that all the year round. The settlement was called Harmanli by the name of the spacious sultan's threshing-floor (harman).

To facilitate travellers, caravaners and threshers a vaulted bridge over the river in Arabic style traditional in that epoch was built in 1585 by the order of the Turkish vizier Siviush Pasha. The marble inscription on the bridge reads as follows: 'The world is a bridge, across which the way of the king and the poor man passes'. The hunchbacked bridge has been saved almost intact till our day. At that time an historic fountain was built at the White-legged Girl's Spring (Ak baldar cheshmesi), half an hour way from the bridge. The legend about Guergana, eternalized in the beautiful poem by Petko Slaveikov, interweaves with another legend relating that boyar Valkashin, father of the legendary Krali Marko, was killed near this spring fighting the Turks. Although the fountain is an object of local lore disputes, even if it is a fiction story, it is an emblem of Harmanli.

Another symbol of the Bulgarian nation's resolution to survive during the slavery time is the St Athanasy old church. The church and iconostasis were built in 1835 with funds and donations of the patriotic Bulgarian population. The studious Bulgarians set up a school in the Hadji Lacho's shop in 1833.

Bulgarian municipalities were charged with some fiscal, administrative  and other functions in 1834. The written rules, called 'Instructions for mayors, masters and village criers,' which were a herald of the first Bulgarian Act of local self-government, are of interest.

In the decline of the slavery - in 1870, Harmanli inhabitants founded their reading club 'Fraternal Love,' renamed to 'Friendship' in 1899. Even today it is a centre of spiritual life, a keeper of the revival ideas, a stage of expression of the creative talents of different generations.

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