Photo by Katie Bell

Driving through the vast open plains of Route 240, you can pass by Glasgow’s western outskirts in seconds. But you shouldn’t. Over the bridge with an impossible-to-ignore view of the Missouri River and towering MFA grain silos is a community of friendly people, good food, and enthralling stories. In fact, with a population of a little more than a thousand, Glasgow just might have more delicious dining and interesting history per capita than any other city in the country.

Glasgow was born in 1836 when thirteen men settled in an area that was once home to the Osage. Unlike some river towns before and since, these men bought land that was and still is safe from flooding. One of the baker’s dozen founders, St. Louis merchant James Glasgow, gave the town its name. Early on, hemp and tobacco plantations took root, and the little settlement began to grow and prosper.

Antebellum Glasgow boasted two drug stores, five churches, a law office, a bank, a barber shop, two hotels, a shoe factory, and six saloons.

And it seems as if little has changed since then. The number of churches and local businesses are nearly identical.

On Glasgow’s main drag of First Street, the River Bend is the place to get breakfast. Framed newspaper clippings and old photos are plastered on the walls. Among the décor, an undated photo of First Street reveals that Glasgow closely resembles its appearance at least half a century ago. Fred Foley, the River Bend’s owner and chef, lined the walls with Glasgow’s semi-ancient artifacts. Aside from slinging buttery biscuits and hearty gravy at the quaint diner, Fred is also the town’s mayor.

“I’m actually from Minnesota,” Fred says. While hunting for antiques in the area, he stumbled upon Glasgow and decided to make it his new home. “I just fell in love with the town.”

Although he still splits time between Missouri and his home in Minnesota, where he owns an antique store, he has invested time and money into maintaining and preserving Glasgow.

“Once your infrastructure goes, you go,” he says, explaining that residents have invested thousands of dollars back into the community. He’s not shy when talking about his Glasgow pride or telling stories of the town’s past. But that is a common trait in Glasgow.

“This is the friendliest place,” says Donnie Drew, owner of The Trading Post, the store next door to the River Bend. Donnie is a great example of the very friendliness he talks about. He’s a talkative, tattooed, Hawaiian-shirt-clad father with a heart of gold.

“They don’t care what you look like here,” he says. “I talk to the mayor. You don’t see the town’s mayor talking to a guy who looks like me in every town. Well, maybe in California.”

The friendly people and welcoming community were the reason he moved, but like the mayor, Donnie found the history to be a big attraction.

“I don’t think people recognize the history we got here,” he says. “It makes me crazy.”

Despite these residents’ affinity for its antiquity, the settlers of Glasgow were forward-thinking.

During the height of railroad travel, the Alton Railroad company sought to build a bridge in Glasgow. In April of 1877, the project’s chief engineer, Sooy Smith, learned of a new steel alloy made by a Burlington, Iowa, man named A.T. Hay. Smith then decided to construct the bridge entirely from Hay steel, though iron was typical for such projects. The venture ended up costing more than a half-million dollars by its completion in June 1879, but Glasgow’s Chicago & Alton Bridge became the first all-steel bridge in the world.

Railroad travel didn’t last forever, though. At the turn of the century, automobiles became more common. In 1921, Missouri established a highway commission, and building a toll bridge in Boonville became a priority. After Boonville’s bridge was completed, a delegation from Glasgow proposed a free bridge in their town, and construction followed soon thereafter. On June 4, 1925, the Glasgow bridge was dedicated and drew fifteen thousand visitors from the area. The event was overloaded with automobiles and had a parking problem during a time when there were only 150 cars for every thousand people in the United States.

Glasgow excelled at more than travel infrastructure. Some early residents were business-savvy, too. An apprentice at the time, Dr. Osborne Henderson witnessed a gruesome amputation in the wilderness, and the doctor told him to carry the severed limb to town. A chilling event for the young Henderson, he gave up his career as a physician and opened a pharmacy in 1841. The store was a success.

More than 150 years later, Henderson’s Drug Store still stands. David William Henderson, a fifth-generation descendent of Osborne, owns the store. And David says that his son will take over the shop when he retires. Although the store dates back to the nineteenth century, its vintage neon sign, brick façade, and soda-fountain bar make it seem like a relic of the 1950s—a rare place that still serves real, hand-stirred fountain sodas.

Henderson’s isn’t the only place in town with the aura of post-war America; Englewood Drive-In opened in 1962 as a burger and shake shack, but since 1974, it’s been known as Perry’s.

Today, Joetta Gebhardt runs the joint, cooks up comfort food, serves ice cream cones, and tries to make everything as delicious as her mother did. Mary Lou Perry, Joetta’s mom, originally ran the restaurant and was the first female Glasgow Chamber of Commerce president. Fittingly, Joetta is involved with the business community, and her daughters both have leadership positions at businesses in Columbia. Although both her daughters have degrees and careers, they still work at the drive-in occasionally. What matters at Perry’s are the simple things like keeping the business in the family.

“We don’t try and compete with big-box stores and franchise,” Joetta says. “We just try and do what we do best.” Perry’s is succeeding in creating a welcoming, family-run atmosphere with delicious soft-serve ice cream. Like most businesses in town, it doesn’t have to worry about competition from franchises. There’s no Dairy Queen or McDonald’s in Glasgow. A drive through and around downtown will only lead to one franchise: a Casey’s gas station. Almost all of the businesses in Glasgow are independent and locally owned. For groceries, there’s Charlie’s Quik Check. For steaks and fine dining, Beckett’s would be the place to go. And of course, there are plenty of places to explore and shop for knick-knacks, art, and antiques.

“I don’t know how a town of a thousand people supports it,” Donnie Drew says.

But ask around about the place to visit, and people will likely say one thing: The Rolling Pin Bakery. Known for its pies, the bakery has other goodies for those with a sweet tooth, plus top-notch sandwiches for lunch. Because the Rolling Pin is a destination for pie-lovers, many people think its popularity keeps the town going. However, that assertion is unfair because Glasgow has so much to offer. The best food might also be the best-kept secret.

The intoxicating scent of delicious meat occasionally wafts from the dead end on First Street’s west side. There’s no formal restaurant there and no tables; the only chairs are already taken by men relaxing and talking in front of a big meat smoker.

“My favorite part about Glasgow is you can set a lawn chair in your driveway,” Chris Damron says, “and in about an hour and a half, you’ll have seven friends sitting by you.”

Chris is the man behind the food. As informal as his barbecue business might seem, Chris is serious about flavor. He offers traditional fare such as pulled pork and beef brisket sandwiches, but specialties such as barbecue nachos with smoked cheese and barbecue bacon make the stand one of the most exceptional barbecue spots outside Kansas City.

Aside from friendliness, Chris shares something with the mayor, the owner of the Trading Post, Gene and Susan Marksbury, owners of the Winery on First Street, and many others in town: He’s not a Glasgow native. Outsiders are welcome. It seems to be a trend, anyhow.

“The people in town are very educated; they are hard workers,” Chris says. “But you don’t have to live here for thirty years to be a part of that. They take everyone in very quick.” For the record, natives like to stay, even if they try to leave. Megan Watts is one of them. “I’ve moved away, and every time, I come back,” Megan says.

She works at the town’s still-in-print weekly newspaper, The Glasgow Missourian, and helps out at the Glasgow Community Museum. Although the museum displays interesting pieces from Glasgow’s past, it’s a bit ramshackle. However, the only area without display cases is the real attraction.

Up a flight of stairs from the musty basement is a stunning old chapel with ornate stained glass windows and remarkable stories in every nook. After the church’s membership dissolved, it was turned over to the town to use as a museum in 1975. The building had housed a Presbyterian congregation since 1866. Built by Baptists in 1861, the Presbyterians purchased it after their church was destroyed in the Battle of Glasgow.

That Civil War battle that transpired on Glasgow’s soil is why many history lovers celebrate the town’s past. Megan, the museum curator, helps organize the annual reenactment of the battle. Her favorite account is a gruesome tale from the era.

According to Megan, the tale begins with Benjamin Lewis, one of the richest men in Glasgow during the Civil War. Lewis, who gained his wealth through tobacco and hemp production, was one of the state’s largest slave owners. Before the Civil War, though, he had a change of heart and freed his slaves and paid them.

At the onset of the Civil War, he was a Union colonel and saw battle. During one skirmish, the notorious Confederate guerilla Bloody Bill Anderson shot one of Benjamin’s fleeing soldiers in the back, so Lewis put a $6,000 reward on Anderson’s capture. Anderson did not take kindly to this. He took Lewis hostage in his mansion and tortured him for days before dragging him by horse through town.

“Benjamin Lewis was strong enough that he lived for sixteen more months, but was never able to walk again,” Megan says. “He proved he could outlive a barbarian.” Anderson was killed in Missouri just days after his attack on Lewis.

Although Lewis’s death was tragic, Glasgow inherited the Lewis Library, which was used by those who attended a school founded with his personal fortune, Lewis College. It is now the town’s public library. Libraries aren’t a typical tourist destination, but the Lewis Library, the first west of St. Louis, is a must-see when in Glasgow.

Built in 1866, the building itself has a rich history and also houses some important and curious pieces of the past. Anyone at the library will say the most remarkable artifact is the Glasgow battle flag. In 1861, women sewed a flag from donated fabric scraps including a woman’s blue silk dress and presented it to men attending a state convention that would determine whether Missouri would remain loyal to the Union. Among the men was General Sterling Price, who sided with the Confederates. Those who remained loyal to the Union, however, kept the flag as their own. On October 15, 1864, Sterling Price would meet the flag again at the Battle of Glasgow. The old flag is still a beautiful sight and point of pride for residents.

It has been almost 150 years since Glasgow endured the Civil War, but the town still honors those soldiers with historical markers, museum displays, and of course the residents’ shared appreciation for history. With such a welcoming and united community, it’s hard to imagine the town was ever so violently divided.

But that’s where Glasgow succeeds. Places like Perry’s and people like Megan evoke countless good memories. The town’s triumphs are celebrated and turmoil forgotten. In this scrappy river town, it’s all water under the bridge.

Glasgow feels at once like a dream, a memory, and home—something everyone should feel every now and again.

This story originally ran in the October 2013 issue of Missouri Life. For more stories like this, subscribe to Missouri Life