Excellent detective 'footwork' by Vintagetvs to determine the location of the photo. Not much of the building is viewable in the original photo, but what can be seen matches quite well with the building on the SE corner of Charles and East 31st Street. The location also helps explain at least part of what makes this such an exceptional photo. The parade occurred on the evening of June 17th, 1958, and given the viewpoint, the setting sun would have been behind the photographer, bathing the street in warm glowing colors.

Given the fancy chauffeured ride, one wonders what type of bed that bear slept in ?

Using the parade route posted by stanton_square I "drove" the route looking for the building they are standing in front of and came up with this possibility.

It's not a perfect match, but the architecture is similar and I think I see one of those concrete balls behind the guy in the black shirt.

There have probably been a few changes in the last 54 years also.

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There were a few in the crowd that didn't seem to have a "ho-hum" attitude. Check out the kids in the front row, just above where the car's hood ornament is located; they seem a bit nervous being that close to a real bear.

He bought it from the widow of an executive living near us in New Jersey and used it to travel between home in Chatham and Lafayette, Indiana where he attended Purdue University. He told me he recorded 120 MPH on the Ohio Turnpike one time returning for Thanksgiving. I was 6 years younger and thought this car was the greatest thing I had ever seen.

[Darn, I thought you meant the bear. - tterrace]

The Bear does seem to have a muzzle on and there appears to be a chain running down from his neck.

"Convertible Bear: 1958" is truly the most incredible photo I've ever seen on Shorpy, and that's quite a statement. It's so unassuming but so terrific.

The up-to-date modern sharpness of the wonderful convertible, with those wide, wide whitewalls, the cool casualness of the lady driver, who's apparently done this before, the nonchalant bear tamer and of course . . . what else is in the back seat, with no restraints, guards, guns or other safety measures?? Oh yes, it's a live bear.

Have you seen that in a recent parade? Nope. And what are most folks in the crowd thinking? Ho-hum, interesting. Now, wonder what the next float will be?

See what I mean? An absolutely incredible photo.

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Baltimore Sun, June 18, 1958.

Parade Seen by 150,000

Circus March is City's First in 3 Decades

Baltimore turned out for Barnum in a big way last night. … Tonight the circus, the Ringling Brothers and Barnum and Bailey Circus, begins a five-day open-sky stand at Memorial Stadium with seven performances scheduled. …

The thousands who fought some big traffic tie-ups to hurry to the curb with their kids last night were able to see: Eight good-sized tigers, pacing in or scowling from small cages, Twenty elephants, A little steam calliope on the back end of a pickup truck, A very leggy blonde performer in black mesh hose plus several other circus ladies of interest, riding in convertibles. …

The parade started at Exeter Hall avenue and Loch Raven road, moved to Twenty-fifth street, then to Charles, up Charles to Thirty-third and wound up at the stadium.