Prilep spreads across a broad plain in the south of North Macedonia, with a ring of granite hills around it, and it is a city that is both agricultural and historic. Tobacco has long been the crop here, and the surrounding fields produce much of the country's leaf, which is why the town has a tobacco institute and why drying sheds sometimes show up on the edges of the road. The beer and the old bazaar are both part of local life, and the city has a reputation for being a place where people take their time with coffee.
On a hill above the town stand the ruins of Markovi Kuli, the Marko's Towers, a medieval fortress that belonged to King Marko, a Serbian-era ruler who became a legendary figure in Balkan epic poetry. Marko is remembered in song as a hero who fought the Turks and drank wine from a huge cup, and it is easy to imagine him on this rocky spur. Below the fortress, the nearby village of Varoš has an old church with fine medieval frescoes, and the nearby monastery of Treskavec lies higher on the mountain, reached by a rough road. The granite outcrops around the town are strange, rounded boulders that look as if they were left behind by a giant.
The riding is gentle on the plain and more interesting as you climb. The road from Prilep north toward Kruševo climbs into the Baba Mountain foothills, with long rising sections, a few tight corners and views back over the flat basin. Surfaces vary from good to broken. In summer the plain is hot and dry, and by mid-afternoon it can feel like a furnace, so ride in the morning or evening. Spring is green and mild, and autumn is usually clear and warm.
Prilep has over seventy thousand inhabitants, so it has plenty of fuel stations, restaurants and shops. It is a useful place to stock up before the mountain road, and there are enough cafés to keep you busy. A cold local beer after a long day is nearly traditional here, and the quiet evenings on the squares are a pleasant way to wind down.