Remember when you used to take those long car rides with your friends and family growing up? It was always an adventure, but deciding where and when to stop was stressful. We all have memories of being in awe and how our bodies shook with excitement when we spotted a neon sign hinting at the promise of much-desired fast food and comfortable rest of roadside stops. We wish we could go back to those days. But wait, maybe we can! This post will take you on a nostalgic journey exploring some of the most iconic American roadside spots, from famous landmarks that have made appearances on the big screen to hidden long-serving gems with a history providing much-needed on-road comfort. So fasten your seatbelts, turn the radio up, and let’s take an emotion-provoking journey through American roadside history.
Stop By the Second Oldest Burger Chain
We’ll be kicking off this drive through American roadside history with a location that is both charming and iconic. This is a Kewpee diner, and it is a roadside gem that has been in operation for years (since 1928)!
Kewpee Hamburgers is the second oldest hamburger fast-food chain restaurant! Once upon a time, there were over 400 Kewpee diners all over America, but currently, about five locations remain, one of which is this restaurant in Lima, Ohio.
A Former President Was (Technically) at this Wendy's
Here is another pretty amazing piece of American roadside history. At first glance, this could look like just another Wendy’s restaurant. However, that isn’t the case at all! This is a particularly unique Wendy’s with an amazing backstory.
This storefront has been standing for over 45 years and has served tons of motorists. Besides the amazing longevity, this location used to be the Sunnyside Garden Arena, and it even once hosted John F. Kennedy while he was running for president.
Comfort Food For Travelers Near Orlando
If you stay in the Winter Garden, Florida area, or you used to travel along the old Highway 50, this is a sight that will bring huge smiles to your face. This iconic restaurant is a popular attraction for travelers and tourists.
The Maryland Fried Chicken shop boasts a unique architecture with candy cane poles propping up its grand structure. But what really draws crowds is the mouth-watering fried chicken. Sadly, though, after 57 years, this treasured establishment closed for good on April 1st.
This Pizza Shop Was in a Hit Movie
Prepare to be transported down memory lane with this sight. After all, the Lenny's Pizza brand has been serving up delicious pies for a remarkable 70 years. That's a true testament to their dedication and passion for the craft.
Lenny's Pizza became famous after a cameo in the iconic 1977 film Saturday Night Fever. Since then, they've become a household name, beloved by locals and tourists. However, as they say, all good things must end. Lenny’s Pizza closed this year.
Iconic Sliders in Jersey
Do you live in Hackensack, New Jersey? If so, you’ll recognize this amazing structure immediately. It might not look like much now, but you should know that White Manna Hamburgers is a very popular American roadside stop.
This particular shop has been open since 1939, and not much about this diner has changed. White Manna also has a reputation for serving up some delicious food, including its iconic small, square-shaped sliders served on a soft, steamed bun.
Pizza Hut Once had Fine Dining
Next up, we have an exciting example of iconic American roadside history for you. Now you’re probably wondering, “What could possibly be interesting about Pizza Hut?” Unlike what we know today, Pizza Hut wasn’t always a carry-out pizza chain.
Rather, every Pizza Hut Classic location actually used to be a sit-down, dine-in restaurant; tons of amazing memories were made here! Travelers and locals gathered at Pizza Huts in the Midwest to enjoy the buffet of pan pizzas.
Lexington Candy Shop was an Upper East Side Icon
Here we have another American marvel that has unfortunately fallen to time. This is the Lexington Candy Shop, and if you grew up in New York City in the 1950s, you have fond memories of this particular shop.
This luncheonette serving diner-style food opened in 1952 and quickly became a popular spot for locals and tourists. It had a reputation for excellent service. The shop has been featured in several movies and TV shows, cementing its place in New York City history.
“Sopranic” History
This street-side shop is one of the most iconic and historic diners you’ll ever see. If you're a fan of the hit series The Sopranos, you’ll recognize this landmark immediately!
That’s right, this particular “nondescript-looking” building is so amazing that in addition to drawing tons of tourists and travelers, it is also featured in The Sopranos! Pizza Land in North Arlington, New Jersey, has been serving delicious pizzas since the 1900s.
Burger King... The Original
Next up, we have a picture of a Burger King. Burger King has been around for quite some time, and as you’d expect, the brand has undergone some changes. Look at this picture… notice anything somewhat different?
You won't find this type of sign anywhere except at the Myrtle Beach location. Besides the unique logo, this particular Burger King immediately transports you into a diner with a 1990s vibe. Eating here will certainly bring up some nostalgia.
Jersey’s Best Milkshake on Route 35
If you haven’t grabbed a milkshake here and you live or drive around Colonia, New Jersey, that’s something you’ll want to remedy as soon as possible. You’re missing out on delicious frozen treats and American nostalgia.
This Colonia Dairy Maid opened in the 1950s and has been a beloved stop for travelers along Route 35. Asides from having a long, rich history, the Colonia Dairy Maid also retains its old-school decor and seasonal flavors.
A Sweet Pit Spot on Skidway Road
If you used to live or travel in Savannah, Georgia, you’ll immediately recognize this sign. What makes this roadside gem iconic and memorable is the amazing delicious doughnuts this shop serves. However, this is more of a tribute than a review.
Residents woke up on a Monday to find that the store had closed for good. This was one of the very few Krispy Kreme stores that still had the original 1960s signage, and this particular store was by far the best!
The Treasure Of Margate
At first glance, you’d think this is a part of a circus performance. However, if you stay in Margate, New Jersey, you’ll definitely know better! This is Lucy, popularly known as the treasure of Margate, and she is a pretty historic treasure.
Lucy has been standing since 1881 and has been a very popular roadside attraction. Lucy is considered to be America’s oldest roadside architectural novelty. Despite her age, Lucy has been well-preserved and continues to stand tall, inspiring wonder among visitors.
Horne's Was Once a Thriving Road Stop
This structure might not look like a rundown shack, but if you live in Lawtey, Florida, and you’ve stayed there for years, you’ll certainly have numerous fond memories of this place. The building you’re looking at here used to be a former Horne’s restaurant.
As a traveler, the first thing that catches the eye is the building's unique “A” shape. The smell of amazing fried chicken once reeled you inside. This American roadside gem served some amazing food that kept people coming back for more.
The Big Duck in The Hamptons
This odd and amusing roadside attraction in New York has a fascinating history. Behold the famous Big Duck – a whimsical structure that looks like it belongs in a storybook rather than on the side of the road.
Legend has it that the owners of this marvel were inspired by the giant coffee pot house. Constructed in 1931 at 20 feet tall, the Big Duck is one of the largest and most iconic roadside attractions in America.
That Sapp Pie is a Trucker's Favorite Dessert
There are several famous truck stops in American roadside history, but this one is one of the most popular. This is a Sapp Brothers truck stop in Clearfield, Pennsylvania, and this sign is so iconic that you can’t miss it.
This Sapp Bros. Cafe is an iconic truck stop eatery serving some of the Midwest's best comfort food and pie. While the Sapp Bros. Cafe menu is filled with classic diner food, like burgers, fries, and milkshakes, the real star is the pie.
Only One Mr. Waffle
If you're a frequent traveler, you know that there are few things more satisfying than starting or ending a long day's journey with a delicious waffle. That said, there are lots of waffle houses in South Carolina, but there is only one Mr. Waffle!
In Gaffney, South Carolina, Mr. Waffle has been serving mouth-watering waffles since its opening in 1975. Although it's been open for years, this beloved establishment still attracts tourists and travelers who can't resist the temptation of its delicious offerings.
Frozen Custard is a Must at this Roadside Shop
No, your eyes are not deceiving you! This really is a functioning Frozen Leon’s Custard shop! If there’s anything Milwaukee is famous for, it’s its amazing collection of frozen custard shops. However, this one stands at the head of the pack!
Do you remember the taste of frozen Leon's custard on a hot summer day? That creamy goodness would make your mouth smile. It's been years since we’ve had a scoop, but the memories are still sweet. Opened in 1942, Leon’s Custard remains open today!
The Authentic Deli Experience
We talked about popular roadside stops, but here's a hidden gem you’ve probably not heard about. Wilson’s Delicatessen is a roadside stop you’ll be familiar with if you’re from or stay in Ulster County, New York.
Wilson’s Delicatessen serves some of the best subs you’ve ever eaten. It has been open since 1966 and remains a popular stop for travelers. The exterior might not look like much, but trust us when we say this is one place you should visit.
A Real Tastee Treet
Next up we have Tastee Treet, a store that was and still serves as the sweet spot of Prineville, central Oregon. If you’ve never heard of Prineville, let’s just say it qualifies as the most popular hidden gem.
Prineville once had a thriving lumber, cattle, sheep, and tire business. Even Apple and Facebook established a presence here too. These workers require nourishment, and Tastee Treet is that place in Prineville. Tastee Treet has served since the 1950s, and not much has changed.
The Big Shoe is a Must See in Pennsylvania
This might look like something out of a Disney fairytale, but we assure you, this shoe house is very real. The Shoe House, located in Hellam Township, off Route 30, has been around for a long time and has drawn curious travelers.
The Shoe House has a rich history as one of the most popular roadside stops. While it was once an ice cream shop and museum, it will soon be transformed into an Airbnb by the new owners.
Sunroom-ed Wendy’s
When we step into a Wendy’s or drive past one of the locations, we cannot help but feel a little twinge of nostalgia concerning how different Wendy’s restaurants look now compared to what they used to look like.
It's been a while since we’ve seen a Wendy's with a sunroom. It was like dining in a greenhouse, but with delicious burgers and fries instead of plants. There’s a sunroom Wendy's in Valis Gate, Orange County, New York, that you should really visit!
Dutch Haven was a Popular Tourist Attraction in PA
Do you remember Dutch Haven, that charming little store in Lancaster County, Pennsylvania, that sold delicious shoofly pies and other Dutch treats? Of course, you do! This quaint store was once one of the biggest attractions in Lancaster County.
The giant windmill could see a mile away. Who could forget the amazing trademark shoofly pie? We could almost taste the gooey molasses filling and crumbly, buttery crust. Dutch Haven is now closed, but the owners left everything in place, including the recipes.
Who else Got the Sticky, Sweet Chickens?
These days, very few people can relate to the sticky sweet fried goodness that is Yogi Bear’s Honey Fried Chicken. Yogi Bear’s has been around since the late 1960s, and while the fast-food joint enjoyed amazing success, the chain is currently all but done.
Above is a Yogi Bear’s Honey Fried Chicken store in Hartsville, South Carolina, and this branch is believed to be the last standing store. Famous for its sweet, sticky honey sauce that perfectly complemented the savory chicken, it was a popular roadside stop.
Coffee In A Coffee Pot
If you have ever traveled across the highway in Bedford, Pennsylvania, you’ll be familiar with this particular American roadside stop. The Coffee Pot opened in 1927, but the structure still stands today.
If you've visited this famous structure, you’ll remember how it always smelled like freshly brewed coffee and sizzling bacon. The Coffee Pot also served some of the best breakfast in the area. Unsurprisingly, it quickly became a preferred stop for travelers on the Lincoln Highway.
The Pink Motel was a Classic Road Stop
If you stay in Cherokee, North Carolina, you’ll probably have driven past this motel several times without realizing you’ve been driving past an amazing piece of American roadside history. Now you’re probably thinking, “This motel? Really?”
The Pink Motel was more than just a place to stay. It was a vibrant and colorful landmark that embodied the spirit of the 1950s and 60s. The pink and white exterior felt like something out of a movie.
Route 66: A Legacy Of Amazing Dining
Continuing our journey through America's most iconic roadside stops, we come to the Route 66 restaurant. This gem of a diner was located right off Route 66 in Santa Rosa, New Mexico, and was a must-visit destination for anyone passing through the area.
Opening in the mid-1960s, the Route 66 restaurant quickly became a beloved local institution. For decades, the Route 66 restaurant was a staple of the Santa Rosa community and a popular stop for travelers. But in 2019, the diner closed its doors for good.
Big Dipper’s Sweet Treats
Summer is synonymous with ice cream. For those who grew up in the small town of Missoula, Montana, the Big Dipper was the go-to spot. The Big Dipper is an ice cream parlor on Higgins Avenue, a short walk from the University of Montana.
Despite how it looks, The Big Dipper has been serving delicious ice cream since 1995! Their ice cream is made from locally-sourced ingredients, which gives it a unique and fresh taste. This store remains a favorite of students and residents in the area!
Old, Sweet Ice Cream
If you're a regular traveler along Route 11, you know that a trip down this scenic highway wouldn't be complete without a stop at the Big Dip. Even those en route to dinner can't resist the temptation of a quick, delicious dessert.
The hard ice cream is some of the finest in the area; each flavor is crafted from family recipes. The Big Dip holds a special place in the hearts of those in the Onondaga County area, recognized as the oldest ice cream stand around.
Miracle Half Mile
Arby’s is not a new sight to you if you travel along America’s highways frequently. However, this particular Arby’s is special for several reasons. If you travel along Route 11 a lot, you’ll recognize this particular Arby’s immediately.
This Arby’s still sports the early 10-gallon neon hat signage that was popular around 1975. This Arby’s is right in the middle of three other iconic American roadside stops. It’s fondly referred to as the “Miracle Half Mile.”
The ThunderBird Was an American Roadtripper's Spot
So far, most of the American roadside stops we’ve considered are diners and ice cream places. However, there’s another important part of on-road traveling – sleep! Driving long distances is tiring. The ThunderBird is a haven for sleepy travelers who need to rest.
The Thunderbird Motel was a popular roadside stop along the historic Route 66. With its distinctive mid-century architecture and neon sign, the Thunderbird Motel stood out from the other roadside motels. Although the motel has undergone renovations, it retains its mid-century charm.
Potato Camping
If we could have a big kettle and a big duck, then a big potato seems to be perfectly normal. Have you ever heard the saying, “They grow them big in Idaho?” If you have, then now you know why.
This is the Big Idaho Potato Hotel, one of America’s favorite roadside stops. The potato is an Airbnb you can rent for the night. Don’t be deceived by the exterior; this roadside stop has a chic interior that’ll leave you in awe.
Blow off Steam at Timber Bar
The Timber Bar is located in Big Timber, Montana. The Big Timber is a place that keeps drawing people because it is such a beautiful place, and travelers on Interstate 90 always make it a point to stop here.
Of course, travelers and residents alike need a place to blow steam and just chill and for Big Timber, that place is Timber Bar. Open since 1957, travelers still haven’t gotten tired of coming here!
White Manna Burgers are Famous in Jersey City
There are many pretty historic burger places all over America’s roadside. However, there is no doubt that this particular store stands at the very top of these locations. This is the White Manna, a slider-style burger joint in Jersey City.
This particular store has been around for a while, and the burgers were so good that it was a popular stop among travelers. But beyond the amazing food, the White Manna building had a unique design and glowing neon sign.
Ghosts Of Shopping Past
Ladies and gentlemen, we give you Ames, the place where America used to shop. That claim isn’t a stretch because the discount department store was once so popular that there were hundreds of different locations.
Now Ames stores haunt our streets like the ghosts of America's past. There were so many amazing memories made here, and it’s sad to think that there won’t be any new memories made in an Ames store again.
World’s Greatest Fried Chicken
You’ve heard of “The Golden Arches,” a nickname that refers to McDonald's. However, we’re willing to bet that very few people know that there used to be a very big restaurant chain called “The Golden Skillet!”
When the Golden Skillet was still operational, this restaurant chain had over 200 locations. The fried chicken was reportedly so good that someone even declared it the greatest food in the world. There are still a handful of Golden Skillet locations in the U.S.
Dairy Queen, Milkshake Kings!
For frequent travelers along the Central North Carolina road, this Dairy Queen is a sight that’ll bring a lot of smiles to faces. It remains one of the most popular stops along that road, and it’s a stop “road trippers” are always partial to.
This particular Dairy Queen has been up and running since 1950! This stop is charming because the staff here are so friendly. Dairy Queen might not be as popular as it once was, but there’s no questioning the fact the legacy lives on.
Hal’s Pure Horseradish was a Tourist Hot Spot
If you're a fan of spicy condiments and love a good dose of nostalgia, this next post is for you. So far, we’ve explored different iconic American roadside gems, most of which are diners and motels. This one, however, is different.
This is Hal’s Pure Horseradish, a condiments store that used to be operational in Banning, California. Hal’s has been closed since 2014, but memories of Hal's Pure Horseradish – which used to be made with only the freshest horseradish root and vinegar–remain fresh!
A Motel Of Memories for the Rolling Stones
If you grew up in the '60s and '70s, you remember the Memory Motel. This iconic motel in Montauk, New York, has been a haven for artists, musicians, and free spirits for decades. The giant whale sculpture and neon lights make it iconic.
Despite what it looks like now, this motel has hosted a who's who of celebrities, from Bob Dylan to Andy Warhol to Paul McCartney. Also, legend has it that the Rolling Stones’ “Memory Motel” hit was actually inspired by this building here!
You Had to Get A Shake at The Dari-ette Drive-In
Remember when you could pull into the Dari-ette Drive-In and have a friendly waitress bring your food to your car window? It was like going back to the 1950s, complete with poodle skirts and classic cars. The burgers were truly something special.
Made with fresh, never frozen beef and cooked to perfection, they were always juicy and flavorful. No trip to the Dari-ette Drive-In was complete without trying one of their creamy milkshakes. Unfortunately, this iconic stop is now closed.
HBO, Wi-Fi, and Everything Else
The Shell Beach Inn’s huge blue sign is a popular marker along Highway 101. Many a weary traveler’s eyes have lit up upon sighting this because it promised good food and rest, which are very important after a long day on the road.
At its prime, the Shell Beach Inn was one of the coziest retreats in the country, sporting luxuries such as Wi-Fi, a pool, and even HBO! This inn also offered guests breathtaking ocean views and easy access to the beach.
So there you have it, 40 of the most iconic road stops in American history. How many did you recognize, and which one had you shed a tear or two? Let us know in the comments below!