20 Vintage Photos of Wagons That Rolled Through Time

History April 8, 2025

Before we saw the rise in the roar of engines across numerous American streets, wagons were out there rolling over dirt roads and transporting families, goods, and dreams. The following collection of photos aims to capture the various wagons that were once responsible for defining transportation in America.

1. Two horses pulling an Imperial Oil Company tank wagon, Winnipeg, 1919

Black and white photo of a man standing next to a large horse-drawn cart with two horses. The cart is in front of a building, displaying the name “Imperial Oil Co.” The horses are adorned with harnesses, and the man is wearing a vest and hat.
infamousleopard383

Those horses look locked in and focused on the day’s work.

2. A line of horse-drawn wagons hauling snow in New York City. January, 1908

A black and white photo of a snowy city street lined with horse-drawn wagons filled with snow. The buildings in the background display various signage, and people are walking along the sidewalks. The scene captures a historic, bustling urban environment.
deleted

Wagons were essential during snowstorms.

3. A family with their covered wagon. Kansas, 1908

A vintage photo shows a family outdoors beside a covered wagon. A man stands by two horses, while a woman and three children sit near the wagon. A dog lies on the ground. The scene is surrounded by trees and leaves.
stilljaguar9174

Is it just me or is the dog on the far left effortlessly stealing the show?

4. Traveling Medicine Wagon circa 1800s

A woman in a white dress stands on the steps of a vintage wooden caravan, tending to birdcages. The caravan has ornate decorations and is surrounded by trees. A bucket is placed on the step.
dunlopsouth

Those traveling medicine wagons came in handy when times got tough.

5. Federal wagon trains moving out of Atlanta in the beginning of Sherman’s March to the Sea

A historical black-and-white photo depicts a busy 19th-century street. Covered wagons pulled by horses travel a muddy road between brick buildings. Pedestrians walk along the sidewalk, and vintage signage is visible on building fronts.
jocke75

Talk about a big turnout of wagons.

6. Covered Wagon of the Great Western Migration, 1886, in Loup Valley, Nebraska

A black and white photo depicts three people standing beside a covered wagon in a vast grassland. Two horses are hitched to the wagon. The scene conveys a historic, pioneer setting.
dunlopsouth

Now that’s a beard.

7. Riding in a horse-drawn wagon in Kolbuszowa, Poland, June 1945

A black and white photo shows a horse-drawn cart on a dirt road. Several people are seated in the cart, smiling and looking at the camera. Trees and a wooden house with a fence are in the background.
catintheshoe

Looks like we’ve got some jokesters on our hands here.

8. The Local Ice Cream Wagon, Columbia, PA, circa 1920s

Two men stand next to a horse-drawn wagon labeled "Purity Ice Cream" on a dirt road. The wagon advertises delivery service. The men are wearing early 20th-century attire. Bare trees and a building appear in the background. Handwritten text below reads “Elwood, Guy, Roberts milk wagn.”
ecostar

Potentially quite a bit quieter from your modernized ice cream truck.

9. An 1870s oil wagon

A black-and-white photo of a man seated on a Standard Oil Company horse-drawn tank wagon in front of a brick building. Two horses are hitched to the wagon. Signs in the background advertise a billiard hall and other businesses.
otherwisetackle5219

Those oil wagons sure kept busy back in the day.

10. Telephone repair wagon and repairman, 1887, California

A man climbs a utility pole while another man sits on a horse-drawn wagon loaded with equipment. Trees and a wooden fence are in the background. The image is in black and white, giving it a historical look.
jocke75

People needed to make sure their phones were accessible.

11. Sheep herder’s wagon in Rosebud County, Montana, 1939.

A covered wagon stands in an open field, with a herd of sheep grazing nearby. The sky is overcast, and rolling hills are visible in the distance. The wagon appears weathered, with items hanging from its back.
catintheshoe

Those sheep are utterly unfazed.

12. Wells Fargo wagon and guards with $250,000 gold bullion from the Great Homestake Mine

A vintage black and white photo shows a group of men sitting on a horse-drawn wagon. The wagon is pulled by six horses and is traveling on a dirt road next to a wooded hillside. The men wear hats and period clothing.
catintheshoe

Those must’ve been stressful shifts with all of the bank robbers out there.

13. Someone was proud of their kids, barn and wagons

Two children sit in a horse-drawn carriage in front of a large barn. The carriage is part of a rural scene, with a wooden cart nearby. The setting appears historical, with the children dressed in old-fashioned clothing.
memorylanepr

Those kids seem like they’re not having the most fun of days.

14. Delivery wagon for E.L. Brady Grocers in front of C.W. Schmid’s Restaurant on 12th Street

A historical black-and-white photo of a bustling 19th-century street. Horse-drawn carriages and pedestrians line the dirt road. Buildings display signs for businesses like restaurants and real estate offices. Overhead wires crisscross the street.
michaelconfoy

You’ve got to love an old real estate office. Land must’ve been a whole lot cheaper back then.

15. The David Hilton family “and their organ” near Weissert, Custer County, Nebraska, 1887

A black and white photo of a rural scene featuring a family with five members posing around an organ in the foreground. Horses, wagons, and cattle are scattered across an open field with fences and barns in the background.
deleted

Some people are adamant about flexing their organs.

16. Coke delivery wagon and workers, Detroit City Gas Co. Circa 1912.

A vintage truck labeled "Detroit City Gas Co." is parked on a residential street. Three men in work attire are present; two are on the truck bed and one stands beside it. The background features early 20th-century houses and bare trees.
anonymous

Nice stache there, sir.

17. A team of timber wolves rescued as pups pulling a wagon for the Minneapolis Cereal Company, 1890s

A black-and-white photo shows a sled pulled by four large dogs in a small town setting. Two men ride the sled, with one steering and holding a whip. Several people stand and observe on the dirt road, dressed in period clothing. Wooden buildings line the street.
eaglemaxedout

Those wolves mean serious business.

18. WWI Medical Wagon Circa 1917

World War I scene showing a horse-drawn ambulance wagon with a Red Cross symbol in the foreground. Soldiers on horses are crossing a bridge above, and sandbags are stacked around a tunnel entrance. The landscape appears barren and war-torn.
lamprey187

Now that’s an impressive shot.

19. A coal man doing his rounds in the Gorbals area of Glasgow in 1960

A black and white photo of a man standing on a horse-drawn cart loaded with bags of coal in an urban street. The cart is pulled by a horse. Rows of old brick buildings are visible in the background under a cloudy sky.
dhorlin

Looks like an especially cold day out there.

20. Draymen hauling barrels of beer in Montreal, in 1908

Black and white photo of a horse-drawn wagon carrying multiple wooden barrels on a cobblestone street. Two horses are harnessed to the wagon, and buildings are visible in the background.
calafiafarms

Those guys were committed to getting their job done well.

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