Spread across a ridge in eastern Slovakia, with the jagged peaks of the High Tatras rising on the northern horizon, the Spiš region holds one of Europe's great clusters of medieval monuments. The town of Levoča, the old regional capital, was a wealthy royal free town, and its walls, burgher houses and Renaissance town hall still surround a long central square. Inside the church of St James stands Master Paul of Levoča's carved Gothic altarpiece, finished in the early sixteenth century and the tallest of its kind in the world, an astonishing tower of limewood saints and filigree.
Close by, above Spišské Podhradie, Spiš Castle sprawls across a travertine hill: one of the largest castle complexes in Central Europe, its ruined walls covering a whole summit and visible for miles. Opposite it, on another hill, Spišská Kapitula is a small walled church town with a cathedral and canons' houses, little changed in centuries. Levoča, the castle, the Kapitula and the Gothic church at Žehra, with its remarkable medieval frescoes, are listed together by UNESCO, and riding between them gives you a day of shifting perspectives on the same few hills.
The riding is easy-going and scenic, across rolling farmland, rapeseed fields and woods, with the castle appearing and disappearing on its hill as you approach. The main road between Prešov and Poprad passes through the area and can be busy with trucks; the minor roads to Žehra and towards the Slovenský raj national park are quieter and more fun, with gentle curves and occasional rough patches. Weather can turn quickly, especially with the Tatras so close, and on clear autumn evenings the castle glows orange in the last light.
Spišské Podhradie and Levoča both have fuel and places to eat; Krompachy is another option. Try bryndzové halušky, potato dumplings with sheep's cheese and bacon, and a cold Slovak beer once the riding is done. The castle is a steep walk up from the car park, worth every step for the view over the Spiš basin. In summer the castle hosts historical events, and if you are around in early July, Levoča's pilgrimage to the hill above town draws huge crowds.