Asenovgrad is the last proper town before the Rhodope Mountains, and it sits where the Thracian plain, flat, warm and full of vineyards, runs up against a wall of dark, forested hills. The town is large, with over fifty thousand people, and its streets, churches and markets feel Bulgarian in every detail. It was named after Tsar Ivan Asen II, the medieval ruler who rebuilt the nearby fortress, and the name of that fortress, Asen's Fortress, is what has made the place known to travellers.
The fortress stands on a cliff above the Asenitsa river gorge, a few kilometres south of the centre, and it consists of a ruined wall, a small tower and a surprisingly beautiful church, the Church of the Holy Mother of God of Petrich. The church clings to the rock and is covered with frescoes, and the view down the gorge to the plain is wide. The site has been fortified since ancient times, and Thracians, Romans and Byzantines all held it before the Bulgarians. A steep climb on foot is needed to reach the top, so wear boots you can walk in.
Asenovgrad is also known as a city of churches, and it has so many that it was once nicknamed Little Jerusalem. The old quarter, with its Ottoman-era houses, narrow streets and small chapels, rewards a wander. The area is also wine country, and the Mavrud grape, a dark local variety that produces rich, tannic red wines, is grown around the town. A glass in the evening, once the bike is parked, is a good introduction to Bulgarian wine.
For the rider, Asenovgrad is the gateway to the Rhodope Gorge Route, and the road south toward Bachkovo and Chepelare is a pleasure from the first kilometre. It follows the river through a canyon, with tight bends, rock walls and forest, and the surface is mostly good. Traffic can be heavy within the town, particularly on market days, and trucks use the main road, so be patient. Once you are out of the urban area, the road opens and the riding is delightful.
This is a proper town, with a range of fuel stations, supermarkets, banks, cafes and workshops, and it is the place to stock up before the mountains. Cash is useful in smaller establishments, and prices are low. Take a moment to try a banitsa, the cheese pastry that Bulgarians eat for breakfast, from a bakery near the centre.