I was last in Billings in early July and, as usual, I immediately walked around Montana Avenue to see what was going on—doing that walk has been a tradition for me for over 40 years.

Do you remember what Montana Avenue was like in 1985–well here’s two views if you don’t recall, or were even around in 1985. It was a mix of second hand, rummage, stores, “antique” stores, flophouses, and an emerging galley scene, led by Toucan Gallery.

There was an oasis—the restored Rex Hotel, with one of the city’s best restaurants, and next door, the Rainbow Bar, an oasis of a far different type. Thankfully both businesses, with some changes, remain anchors to the district today.

On the opposite side of the street—despair. The imposing 1907 Northern Pacific Railroad depot was boarded up, forgotten and deteriorating. The reality was a puzzle to me because already in Great Falls and Missoula investors had restored and reopened historic Milwaukee Road depots. Why not Billings?

Five years later, 1990, it had gotten worse instead of better at the depot. When graffiti begins to mark a historic building the end is often near. On the other side of the street, however, new investment kept the historic buildings moving forward.

Changes were afoot at the McCormick Block where two adjacent one story 100 year old buildings had been torn away to create a parking lot.

And the district had a new east end, with the conversion of a 20th century building into the Coulson Bar. I loved the reference to the river town that was a precursor to Billings.

The 1990s was when the historic preservation movement transformed Montana Avenue. The Montana Avenue Historic District was listed in the National Register of Historic Places, thanks to the vision of property owners supported by the city and the State Historic Preservation Office and the work of Chere Jiusto.

When I next visited in 1998, I found the depot, finally, restored and serving as a new anchor.

The new courtyard at the Rex was quite the place to be and be seen. I even saw Hollywood stars there in 1998. the 21st resurgence of Montana Avenue was ready to begin.

How many of you used the Internet cafe at the McCormick Block? I did in 2000 when I took the image above.

Fast forward to July 2025. The once neglected district is a city downtown hub, hosting a street event and businesses booming. What a change from 1985.