Madison, Indiana, is a preservationist’s dream town. A whopping 133 blocks of its downtown is a Historic District and a National Historic Landmark.
Founded in 1810, the town competed with Louisville and Cincinnati as Ohio River port cities. It grew rapidly into the railroad age of the mid-1800s, but railroads leading to those other two cities performed better than the one leading to Madison. Indeed, Madison’s railroad failed in 1862. Even though its line ended up becoming a part of the vast Pennsylvania Railroad system, the die was cast. After the Civil War, Madison’s growth stalled.
Madison’s antebellum loss is our modern gain as it largely froze the town in time. You’ll find all the major architectural styles from the nineteenth, and even some of the twentieth, centuries in downtown Madison.
Residences surround the downtown commercial area, and most of the homes are simply stunning.
The river is just a few minutes’ walk from anywhere in Madison’s historic district. Goods are not received at any port here anymore — you’re far more likely to see powerboats racing here. It’s been happening in Madison for at least 100 years. An annual powerboat race, now known as the Madison Regatta, has been held annually since 1929 over the Independence Day weekend.