The city by the border with North Macedonia boasts several special features: its cherries, its important transport location, and its mineral springs. We are not sure about the cherries, but the Romans definitely appreciated the rest of the place's advantages and soon after they established their control over the region Pautalia was born.
By 106 Pautalia had become significant enough and Emperor Trajan made it a city. The city thanked in the usual way: by adding the emperor's family name, Ulpius, to its own.
Several decades later, under Antoninus Pius, Ulpia Pautalia started minting its own coins. These are evidence not only for the economic power and ambition of the city: The images on them provide precious information about the religious life and architecture of Pautalia. Temples of gods and goddesses like Asclepius, Sabazios, Zeus, Hera, Apollo, Hermes and others appear on local coins, together with depictions of copies of famed ancient statues. Having a replica of, say, the long-dead Greek genius Praxiteles was all the rage in the Roman Empire, and the people of Pautalia didn't stay away from the trend. They could well afford it.
Pautalia was a fortified city. Its walls were heavily repaired after the Gothic invasion of 270, and in the second half of the 4th Century a fortification was built on the neighbouring hill. Unlike Ulpia Pautalia, whose name is not in any historical sources after 553, the fortress survived the end of Antiquity and people lived in it until the Ottoman invasion, when it was abandoned. The people moved to the remains of the ancient Pautalia.
Pautalia's mineral springs are the most memorable remains from Roman times which you can see in modern Kyustendil. Steaming in cold days in the central garden, they are still here, under the few brick-and-mortar walls of the baths of an asclepion, or a shrine to Asclepius, the god of health. But most of the ancient structure cannot be seen, as the Ottomans built their own public bath over it, and in the early 20th Century it was replaced by a modern bath. It is still operational.
The Late Antiquity fortress on the Hisarlaka hill is preserved too, but a recent "renovation" has robbed it of its authenticity.