Widely known as one of America’s most beautiful river towns, Madison has a rich past as a port town along the Ohio River during the early 1800s, so much that it was dubbed a gateway to the West. While today this proud town of 13,000 is known more for shopping and dining than it is for shipping, its merchants and innkeepers have done a stellar job of preserving that small-town charm. They love Madison and it shows. Winery tasting rooms, antiques shops, and bed-and-breakfasts are icons of the town’s newest incantation.