In 2008, I surveyed the Michigan Road from end to end, documenting the road and its built environment. Here is an installment of that trip report.
Madison is Indiana’s first city. It is said to have been founded in 1809, although the first white settler came in 1808, the city was laid out in 1810, and lots were first sold in 1811. 1809 is also the year surrounding Jefferson County was founded.
Madison rose to prominence between the 1830s and 1850s because of river, road, and rail. Advances in steamboat technology, the building of the Michigan Road, and the building of the state’s first railroad from Madison through Indianapolis to Lafayette made Madison a hub of commerce. Much of old Madison was built during these boom years. But as the railroad overtook river and road as the best way to move goods and people, other rail lines appeared in Indiana and neighboring states. Madison ceased to be a hub, and started to decline in the 1850s. With no significant new industries, and the new construction that goes with it, coming to Madison, the city maintained the buildings it had. This has left the old city nearly intact today, with most of downtown and many other homes and businesses around the city listed on the National Historic Register.
To put the Michigan Road in its proper context, I started at the Ohio River and worked my way north through Madison. At left in this photo the Madison-Milton Bridge carries US 421 over the river. A barge, curiously named Barbara, pushes its way east. I took this photo from a place where spectators gather to watch the annual Madison Regatta, a boat race that has roots back to the 1800s.

Just east of this site lies a boat ramp from the river. On one trip to Madison, I was lucky to happen upon the Delta Queen waiting at the ramp. The Delta Queen has since ceased to cruise the rivers.

The ramp leads directly to West St., which ends six blocks north at the Michigan Road. This photo shows the Madison-Milton Bridge a little more clearly, although I know of a Madison photographer who captured it better than i could ever hope to.

Looking from the top of the ramp, West Street leads north toward downtown Madison and the Michigan Road.

Old Madison is full of old buildings. Some of them appear to need a little TLC, like this one on the northeast corner of 2nd and West Streets. The sign calls it the Cinnamon Tea Room.

On the northeast corner at this intersection is “The Feed Mill,” a consignment and auction shop.

Shepley’s Tavern, in operation since 1867, is at 322 West St. This is just around the corner from Main St., also called State Road 56.

Before we continue north on West Street, let’s explore downtown Madison. Not too long ago, Madison’s Main St. was lined with businesses that served Madison – an assortment of places to buy shoes and clothes, get your prescription filled, take in a movie, deposit your paycheck, or have a soda. Even 50 years ago, many of these buildings were serving their second, third, or maybe fourth purposes. Today, downtown Madison’s focus has changed to antique stores, galleries, bars, and cafes.
The first building I noticed when I reached Main St. was the Ohio Theatre, which anomalously dates to 1936. It replaced a theater on this site that burned. I understand that it shows the movie Some Came Running, which was shot in Madison, once a year. It stands just east of West St. on the north side of the street.

A little bit down the street stands the Madison Bank and Trust Co. building, built in 1833. In this era of bank mergers, it became a Mainsource Bank in 2005, but fortunately this building retains its old signs.

US 421 meets Main St. along Jefferson St. This photo shows the northwest corner.

Downtown appears to end at Jefferson St., so I surveyed the south side of Main St. Here’s the southwest corner of this intersection.

From a different angle, here are the two buildings on the southeast corner today. Inglis Drugs, the brown brick building, is a nightclub now. The building east of it hasn’t seen maintenance in a while, but the building east of that got a new facade along the way.

Here’s what it looks like to stroll along Main St.

I hear that Hinkle Hamburgers is more than just a great neon sign – it’s also great burgers made from beef ground fresh on the premises. Unfortunately, I had my dogs on a leash with me this day and couldn’t go in.

By this time I had reached the western edge of downtown. Here’s the view eastward from here. Except for the modern cars, Main St. looks like a photo plate from an old book.

Still looking eastbound, here’s the intersection with West Street. Turn left and you head toward the Michigan Road.

In the first block of West Street north of Main, the old City Hall stands. It was damaged after a 2006 fire next door. It was built in 1879 and received a new facade in 1925.

Next door to the old City Hall stands the Elks building, a burned-out shell since August, 2006. (More on this building here and here.)

Just north, on the northeast corner at Third St., stands this building, which houses Historic Madison, Inc. It previously housed churches of two denominations and a mortuary.

A home and the oldest operating fire station in Indiana, built in 1848, sit on the northwest corner at Third St.

Moving north to the southeast corner at Fifth St., painted advertisements continue to fade on the Madison Creamery building.

The Michigan Road is in sight. A sign warns heavy trucks to stay off the Michigan Road and follow US 421 instead. A bridge carries the road over a canal.

Here’s a look at the canal, eastbound. This was part of the Indiana Central Canal.

This house, on the southeast corner where West St. meets the Michigan Road, seems to anchor the road.

Many who followed the Michigan Road to northern Indiana’s opportunities did so by following West St. north from the river to where it ended and the Michigan Road began.

Next: The beginning of the Michigan Road along Michigan Hill.
I’ve documented Indiana’s historic Michigan Road extensively. To read all about it, click here.