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St. Charles is larger in population than we typically recommend for a small town. But the downtown historic district is very impressive and reminiscent of the main street in an old small town. St. Charles was Missouri's first state capital. Its historic significance was as a starting point for wagon train excursions in the western expansion. It lies on the Missouri River, just 20 miles northwest of St. Louis. St. Charles is the eastern terminus of the 250 mile long Katy Trail bicycle path. EARNS OUR HIGHEST RECOMMENDATION