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Finance

17 Retro Photos of Tailgating at Its Finest

Last updated: July 11, 2025 2:58 pm
Oliver James
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17 Retro Photos of Tailgating at Its Finest
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There’s something timeless about a good tailgate — the clink of bottles, the smell of charcoal in the air, and the buzz of pre-game (or pre-concert) excitement. But look back a few decades, and tailgating had an extra dose of charm. These weren’t curated Instagram moments; they were heartfelt gatherings built around community and love for the game.

Contents
1. Pregaming Before ‘The Who’ Concert in Pittsburgh (Early 1980s)2. Tailgating in a Full Suit at a Packers Game (Late 1970s)3. Creatively Catching the All-Star Game in San Diego (1992)4. Getting Hyped for Wrestlemania (1987)5. New York Cosmos Fans Tailgating at Giants Stadium (1970s)6. Tailgating at a ‘Genesis’ Concert7. Ringing in the Raiders’ Season Opener (1984)8. Grilling at Milwaukee’s County Stadium (1977)9. Throwing ‘Em Back at the Philadelphia Eagles Game (1983)10. Tailgating at Shea Stadium After the Mets Won the World Series (1986)11. Tailgating After a Dirt Bike Race Out in the Boondocks (1970s)12. Tailgate Keg (1950s)13. Going All Out for the Browns vs. Oilers Game (1988)14. The Country Squire Was the Ultimate Picnic Ride (1960)15. The Classiest Tailgate (1954)16. There’s a Full Bar in the Trunk … (1980)17. Tailgate Party for One (1956)Sports, sports, sports!

These retro photos remind us that the best traditions don’t need upgrading — they should just embrace simplicity and a bit of nostalgia.

1. Pregaming Before ‘The Who’ Concert in Pittsburgh (Early 1980s)

A group of people in casual 1980s clothing pose together in front of two parked cars under an overpass; some are sitting, others standing, with relaxed and cheerful expressions.A group of people in casual 1980s clothing pose together in front of two parked cars under an overpass; some are sitting, others standing, with relaxed and cheerful expressions.
AbeScrapes / Reddit.com

2. Tailgating in a Full Suit at a Packers Game (Late 1970s)

A man in a coat stands behind an open car trunk in a parking lot, pouring a drink into a cup and smiling. Several cars and a building are visible in the background.A man in a coat stands behind an open car trunk in a parking lot, pouring a drink into a cup and smiling. Several cars and a building are visible in the background.
smalltown34 / Reddit.com

3. Creatively Catching the All-Star Game in San Diego (1992)

Four people sit beside a pickup truck on a hillside overlooking a stadium at sunset, watching a small TV placed on the ground. Beer bottles and a blanket are nearby, creating a casual outdoor viewing scene.Four people sit beside a pickup truck on a hillside overlooking a stadium at sunset, watching a small TV placed on the ground. Beer bottles and a blanket are nearby, creating a casual outdoor viewing scene.
WhoppaChoppa / Reddit.com

4. Getting Hyped for Wrestlemania (1987)

AxlCobainVedder / Reddit

5. New York Cosmos Fans Tailgating at Giants Stadium (1970s)

blrghh / Reddit.com

6. Tailgating at a ‘Genesis’ Concert

blrghh / Reddit.com

7. Ringing in the Raiders’ Season Opener (1984)

A group of seven people, some wearing Los Angeles Raiders shirts and hats, smile and pose together outdoors during the day, with trees and cars visible in the background.A group of seven people, some wearing Los Angeles Raiders shirts and hats, smile and pose together outdoors during the day, with trees and cars visible in the background.
UserDeleted / Reddit.com

8. Grilling at Milwaukee’s County Stadium (1977)

A group of people gather outdoors for a barbecue, with several standing, eating, and talking near a charcoal grill and coolers. The scene is relaxed, with folding chairs and trees in the background.A group of people gather outdoors for a barbecue, with several standing, eating, and talking near a charcoal grill and coolers. The scene is relaxed, with folding chairs and trees in the background.
FrancisFriday / Reddit.com

9. Throwing ‘Em Back at the Philadelphia Eagles Game (1983)

BirdsAndBeersPod / Reddit.com

10. Tailgating at Shea Stadium After the Mets Won the World Series (1986)

A group of people wearing New York shirts tailgating in a parking lot, smiling and preparing food at a grill beside parked cars on a cloudy day.A group of people wearing New York shirts tailgating in a parking lot, smiling and preparing food at a grill beside parked cars on a cloudy day.
nyrsnoopy / Reddit.com

11. Tailgating After a Dirt Bike Race Out in the Boondocks (1970s)

Four young men relax outdoors around a parked car and motorcycles in a grassy field. Three are shirtless, and one wears a plaid shirt and cap. The scene appears casual, with sunlight casting long shadows.Four young men relax outdoors around a parked car and motorcycles in a grassy field. Three are shirtless, and one wears a plaid shirt and cap. The scene appears casual, with sunlight casting long shadows.
mradda / Reddit.com

12. Tailgate Keg (1950s)

MyDogGoldi / Reddit.com

13. Going All Out for the Browns vs. Oilers Game (1988)

A group of people dressed warmly celebrate on and around an orange station wagon painted with “Go Browns” in a parking lot. A homemade doghouse and team decorations top the car, showing enthusiasm for the Cleveland Browns.A group of people dressed warmly celebrate on and around an orange station wagon painted with “Go Browns” in a parking lot. A homemade doghouse and team decorations top the car, showing enthusiasm for the Cleveland Browns.
uncle-woody / Reddit.com

14. The Country Squire Was the Ultimate Picnic Ride (1960)

A station wagon with its tailgate open displays a picnic spread of sandwiches, bread, fruit, and baskets, set up in a nearly empty stadium parking lot under a sunny sky.A station wagon with its tailgate open displays a picnic spread of sandwiches, bread, fruit, and baskets, set up in a nearly empty stadium parking lot under a sunny sky.
FNaXQ / Reddit.com

15. The Classiest Tailgate (1954)

A group of five people sit and stand by vintage cars, enjoying drinks and a picnic on a grassy area, with trees and more parked cars in the background. The scene appears to be from the 1950s.A group of five people sit and stand by vintage cars, enjoying drinks and a picnic on a grassy area, with trees and more parked cars in the background. The scene appears to be from the 1950s.
14thCenturyHood / Reddit.com

16. There’s a Full Bar in the Trunk … (1980)

Five people sit and socialize at a tailgate party beside two cars. The open trunk is stocked with various bottles and glasses, and there are plates and food on the table. It's a sunny day in a busy parking lot.Five people sit and socialize at a tailgate party beside two cars. The open trunk is stocked with various bottles and glasses, and there are plates and food on the table. It's a sunny day in a busy parking lot.
Live-Gas7226 / Reddit.com

17. Tailgate Party for One (1956)

A young man in a sailor uniform sits on the open tailgate of a classic station wagon, holding a decorative bottle and a cup. He is outside, with trees and a garage in the background.A young man in a sailor uniform sits on the open tailgate of a classic station wagon, holding a decorative bottle and a cup. He is outside, with trees and a garage in the background.
MyDogGoldi / Reddit.com

Sports, sports, sports!

The next time you’re hanging around a tailgate, check out some of our latest sports stories. Victory, Defeat, and Glory: 15 Sports Moments That Shook the World will leave you feeling all the feels, while 10 Expensive Sports Contracts That Broke Records might leave your jaw on the floor. And don’t miss The 10 Most Expensive Game-Worn Sports Attire Ever Auctioned for some seriously pricey jerseys.

The post 17 Retro Photos of Tailgating at Its Finest appeared first on Wealth Gang.

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