Serpukhov is a town on the Oka that has been the southern guard post of Moscow for seven centuries. In the fourteenth century it was the seat of a small principality ruled by Prince Vladimir the Brave, a cousin and comrade of Dmitry Donskoy, who led the Serpukhov regiments at the great battle of Kulikovo in 1380. The town lay on the border between Moscow and its southern enemies, and a white-stone kremlin, built to keep the Tatars out, once stood above the river bend.
Today the old center is a quiet quarter of churches, merchant houses and a kremlin hill where the cathedral stands among surviving walls. Just outside, the Vysotsky Monastery, founded in 1374 by St Sergius of Radonezh, the most revered saint of medieval Russia, sits behind its walls near the Nara River, a peaceful, well-kept complex that holds the Icon of the Inexhaustible Cup, a revered image that draws pilgrims. The town later grew rich on textiles, and its brick mills and old merchants' mansions recall that era.
The riding in the district is a pleasure of its own. Roads south and west follow the Oka through bluffs, pine woods and meadow, and the river's high western bank has chalky cliffs and ravines. The Polenovo estate, home of the painter Vasily Polenov, lies on the river a short ride away, and the nearby town of Tarusa, a gentle riverside settlement, has long drawn writers and artists. The main road, the M2 from Moscow to Tula, is fast and busy, with heavy truck traffic, but the secondary roads are quieter, if patchy.
Serpukhov, with more than a hundred thousand residents, has all the services you need, with fuel at many stations, supermarkets and cafes. It is the right place to start or end a day on the Oka. The best seasons are late May to June, with fresh green and cool nights, and September, when the meadows go golden. High summer can be hot and the roads busy on weekends with city dwellers, and spring thaw brings potholes and mud, so check the surface before pushing the pace. Deer and wild boar are common in the woods at dusk.