Zaraysk is a small town with a very long memory. Some twenty thousand years ago, Ice Age hunters camped on the banks of the Oka near here, and the archaeological site they left behind yielded carved mammoth-ivory figurines, including small female statuettes, some of the oldest works of art found in Russia. The town itself first appears in chronicles in the thirteenth century, linked to a famous icon of St Nicholas, which was reputedly brought here from Crimea, and the name Nikola Zarazsky became a regional byword.
The centerpiece is the Kremlin, built in the 1520s of white stone under Grand Prince Vasily III as a southern outpost against Tatar raids. It is one of the few stone kremlins in the Moscow region, and one of the smallest in Russia, and it stands on a hill above the river with cathedrals inside its walls. The Cathedral of St Nicholas is a handsome building with tall belfry, and the walls and corner towers are well preserved. Fyodor Dostoevsky spent boyhood summers on his father's small estate at Darovoye, a few kilometers from here, and his experiences of village life fed his novels, a connection the town takes pride in.
Riding is easy and rural. The road from Kolomna runs south across the Oka floodplain, with long, flat stretches, wide fields and views of river meanders, and the surface is generally decent on the main roads. Villages with wooden houses, painted shutters and wells appear at intervals, and storks and cranes nest on poles. Wind can be strong on the open plain, and summer thunderstorms are sudden, so keep an eye on the sky. Farm vehicles, horse carts and the odd cow can appear on side roads.
Zaraysk is large enough for fuel, shops and cafes, and it is the best place to stop before the long run back or onward. The best months are May to September, with warm days and long light, though midsummer heat can be intense. Spring and autumn bring mud on the side roads, and winter is cold and snowy, with frost that can last for months. Local cooks make the most of the river's fish, and regional pastila, a soft apple sweet, is a speciality of nearby Kolomna.