The railing on the roof is most likely to keep snow and ice from falling down on pedestrians in the winter, a common practice.

I love the history in this photo. Kings Chapel Burial Ground to the left of the church is the first burial ground of the Puritan settlers of Boston. Governor Winthrop leader of the Puritans is buried there. The famous Parker House Hotel is to the right of the church. Its history is more modern of course. Ho Chi Minh once worked there and JFK has many connections to the hotel. The history goes on and on with this photo. Just behind the church is the site of the first public school, Boston Latin, in America. Further down Milk Street is the Old South Meeting House of Tea Party fame. If you travel to the right of the photo you would come to the Old Granary Burial Ground. A kind of celebrity burial ground of the American Revolution. Paul Revere, Sam Adams, Johh Hancock, and victims of the Boston Massacre are buried there.
I grew up in Boston and walked this street many times. I lived in the North End of the city and as children we would walk through old Scollay Square and to Tremont Street to get to the Boston Common.
Yet with all this history in and around the photo I saw something that reminded me of a movie I saw years ago. Gene Wilder and Margot Kidder starred in Quackser Fortune Has a Cousin in the Bronx. You can look it up on IMDb or YouTube. Quackser did something similar to the man in work clothes with a shovel and a wagon in the far left of this photo. Look it up and you will see.

those are hat boxes, there was a hat maker, milliner on Summer Street, I think. We have a poster from them hanging at my mother's house. He was probably on the way to the Ritz or maybe the Parker House

Despite he screens atop the Ionic capitals, at least one pigeon has figured out where else to perch and still be able to plop pedestrians.

One seems to have eluded them though to gain the perfect aiming vantage point

This is one of the greatest works of colonial architecture in America. It was designed by Peter Harrison, usually considered the first American architect, and built in 1749-1754. The blunt tower was intended to have an elaborate multi-stage steeple, which unfortunately was never built. The magnificent interior is lined with paired Corinthian columns and features a Palladian window over the altar. Harrison's design was inspired by (but not copied from) the famous church of St. Martin-in-the-Fields in London. Built for the first Anglican congregation in Puritan Boston, this church became America's first Unitarian church after the Revolution. In every respect this is a fantastic building.

Took a while, but finally found it. Nice selection of cards. Is that guard rail along the Chapel roof for any real purpose? Interesting.

Does the absence of the rail mean that pigeons no longer are a concern? I take that back; they relocated the rail to stymie that one clever pigeon and his descendants.

I pass that corner every day. That corner has remained essentially the same. School St is still one way.

The Common Sense Gum Company, whose offices are seen in the background, manufactured Listerated Pepsin Gum (yum!) and boasted that they had "no competitors in the line of medicated gums."

First photo where I see someone thinking: "Gee, in a hundred years I may be on Shorpy!" - the lady in the corner (back row, right) of the sightseeing bus.

But now it's the opposite direction.

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What is that young man right underneath the Tremont St sign carrying?