20 Vintage Photos That Capture Boston’s Charm and Grit Over the Years

Vintage Photos History April 25, 2025

Last Updated on April 28, 2025 by Colby Droscher

Cobblestone alleys, clam-chowder street stands, and Fenway’s hand-painted scoreboard—Boston has always mixed Brahmin polish with dock-worker grit. The 20 photos ahead take you on a time-travel journey from snowy trolley tracks to Charles River sailboats, proving the Hub’s swagger never needed skyscrapers to shine.

1. Bromfield Street, Boston, circa 1908

anamarcorporate

It almost feels like you’re there.

2. 1895, Lawn Tennis in Boston

Seven men in vintage clothing pose with tennis rackets and balls against a stone wall, some seated and others standing. The group appears to be from the late 19th or early 20th century.
yngdimitriov

These lads could throw down in lawn tennis. No doubt about that.

3. Boston, (Massachusetts) circa 1906

A bustling early 20th-century city street with ornate theater marquees, shops, well-dressed pedestrians, and horse-drawn carriages lining the sidewalks in front of tall historic buildings.
anamarcorporate

The colors really bring this one to life.

4. A 1960 Plymouth Belvedere hardtop on a muddy Boston street in 1964

A muddy, black 1960s Plymouth Belvedere car parked on a dirt road near a blue van, with modernist buildings and construction in the background. The scene looks urban and slightly rundown.
alexylim

I mean, just imagine being able to take a ride around in that.

5. 1933 Boston, the recovery of an auto that plunged into the Fore River drowning 3

A group of people on a docked boat lifts a car from the water using a crane, while others in small rowboats assist beside the boat. Ships and harbor structures are visible in the background.
bwborder

That was certainly no easy feat at all back in the day.

6. Hot dog stand in North End, Boston, 1937

A boy in vintage clothing stands beside a street cart selling frankfurters for 5 cents, drinking from a cup. An umbrella shades the cart, and a busy city street with people and old cars is in the background.
jocke75

Loving the price point there for hot dogs.

7. Boy in a Boston phone booth, 1963

A boy in casual clothes sits in a phone booth with one leg up, holding the phone to his ear. The street and parked cars are visible outside through the booth’s glass. The image is black and white.
deleted

Kid looks like he’s going to be posted up for awhile.

8. 38 Foster Street, North End, Boston, MA, 1913

A police officer on horseback interacts with a group of smiling children and women on a cobblestone street, while two dogs play nearby. The street is lined with old buildings and scattered debris.
slowmovingsloth

Everyone seems to be having a fun enough time out there.

9. Gus P. Napoli Square, North End Boston, 1950s

A group of men in suits and slacks stand and lean near the corner of a city street, beneath signs reading “Moon St.” and “Gus P. Napoli Sq.”, with storefronts and old brick buildings in the background.
oldsoul87579

That’s a whole lot of fellas waiting around for something.

10. Boston back in 1968

A man with an afro and a beard crosses a street in front of vintage storefronts, including signs for hamburgers, lunch, dentists, and liquors, in an urban setting.
susoutthemoon

Got an unshakable feeling that Kemp’s Hamburgers were probably amazing.

11. Boston, Massachusetts, 1907

A crowd of people, early 1900s cars, and a carriage gather outside the ornate entrance of Keith's New Theatre, featuring decorative columns and a large marquee sign above the doorway.
jocke75

Those seats actually look crazy comfortable.

12. Life near Logan International airport (Boston) in the early 70s

A large airplane flies very low over a residential street with multi-story houses and trees, passing just above the rooftops. A parked car is visible on the side of the road.
watsinaname

Now, that can’t have been one of the most peaceful streets to live on, at times.

13. Firefighters and some frozen trucks, Boston, MA, 1920

A firefighter in heavy gear stands near fire trucks and equipment covered in thick ice, surrounded by frozen foam, after battling a blaze in a city with large brick buildings in the background.
quickpresentation11

Truly, an unforgettable shot right here.

14. A Boston winter from a long time ago

A woman in a fur-collared coat walks on a city sidewalk, holding hands with three children dressed formally; two boys in suits and top hats, and a girl in a dress and coat. Vintage cars and buildings line the street.
bumapproach

Not the little lads sporting their top hats to perfection though.

15. Quincy Market in Boston, Mass, circa 1904

A black-and-white photo of a busy 19th-century street market with horse-drawn carriages, people walking, and a long building labeled "Agricultural Warehouse" in the background.
loepke2011

Quincy Market looks like it’s thriving.

16. A 227-gallon teapot above the Oriental Tea Company shop in Boston, Massachusetts, 1934

Black-and-white photo of a busy city street in front of a tea shop with a giant teapot sign above the entrance. People in 1930s attire walk and stand near the storefronts and shop windows.
hjuggernaut

That teapot would fetch a pretty penny nowadays.

17. United States Post Office, Boston, Massachusetts, 1900

Historic black-and-white photo of a grand, ornate building with a mansard roof, large arched entrance, and elaborate stonework; people, horse-drawn carriages, and early automobiles are in front.
myipodstillworks

Seriously though, a building with some striking architecture.

18. Downtown Crossing, Boston, in the 1980s

Four young men pose confidently on a city street in the 1980s; one holds a boombox, another wears an Adidas tracksuit, and all wear hats and sneakers, with people and a building in the background.
haveyy

I just wonder what tunes they might’ve been playing on the jukebox.

19. Some Boston maniacs back in 1975

Three children wearing sunglasses and denim jackets pose confidently with their bikes on a city sidewalk. One child flexes their arm, while the others stand with relaxed, cool expressions. It is a black and white photo.
anonymous

The shades really take the whole crew’s aesthetic to new heights.

20. Three teenage boys on Boylston Street, Boston, 1977

Three teenage boys wearing leather jackets and winter clothing stand on a snowy sidewalk in front of a theater marquee that reads "King Kong." The scene appears to be from a past decade, possibly the 1970s or 1980s.
str33twise89

These guys were working at making leather jackets cool before they were even viewed as cool.

Thousands more historic street views live in the Boston Public Library’s digital photo archive.

Want more city flashbacks? Compare coasts in 20 Vintage Photos That Capture London’s Charm, stroll canyons of steel in 20 Photos of Old New York City, or head west with 49 Vintage Photos of San Francisco (1890s-1970s). Grab your Red Line token—Boston’s past is boarding now.

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