"Oakham & Uppingham Issue Title Is Help Yourself (1944)" - British Pathé on YouTube
This British Pathé film clip from 1944 lasts just one minute and 32 seconds, but manages to visit both of Rutland's towns.
At the time of filming, Oakham looks more like quiet village of thatched cottages than a town. Everything shown is old and beautiful. Footage includes regency houses, the market square with stocks, All Saints church, and the banqueting hall which is the last surviving building from Oakham Castle. Two cars, one driving along and the other one parked, are the only motor traffic present in the town's quiet streets.
A Journey Through Rutland: Exploring the "Delicious" Heart of England
If you’ve ever found yourself cresting the hill by the spot where Longfellow’s famous village smithy once stood, you’ll find a charming descent awaiting you. As you pass the picturesque thatched cottages on the far side, you emerge directly into the main street of a place that feels frozen in the best parts of the past.
Welcome to Oakham, the capital of Rutland—the smallest, and arguably most enchanting, county in England.
The Capital That Feels Like a Village
Though it holds the title of "county town," Oakham has the soul of an oversized village. It is the crown jewel of a county that measures just 17 miles across, a place the travel writer H.V. Morton once described as one of England’s "delicious villages."
Walking through Oakham is like stepping into a living history book. You’ll see sundials perched on the faces of golden-stone houses and feel the weight of centuries-old stories resting on every hearth. The Market Square is a particular highlight, lined with grand Regency houses that speak to a time of elegance and prosperity.
Curiosities and Customs
History in Oakham isn't just something you look at; it’s something you encounter. Take, for instance, the Butter Cross—a circular stone structure that provided shade for market traders centuries ago. Beneath it, you’ll find a quirky set of five-holed stocks. Local legend suggests they were fashioned that way to accommodate a specific "odd man" in town who only had one leg!
Just a stone’s throw away is All Saints Church, a breathtakingly classic example of Early English architecture, its spire reaching high over the rooftops.
The Castle of Horseshoes
Perhaps the most famous landmark is Oakham Castle. While only the Great Hall remains today, it houses one of the most unique traditions in the British Isles. For centuries, a local custom has demanded that every Peer of the Realm passing through the town for the first time must forfeit a horseshoe to the Lord of the Manor. Today, the walls are adorned with an incredible collection of these iron trophies, ranging from simple shoes to massive, gilded ceremonial versions left by royalty.
Beyond the Capital
While Oakham is the heart of the county, its neighbor Uppingham is equally steeped in prestige. Renowned globally for its public school, Uppingham’s educational roots stretch back to 1584, with several of the original Tudor classrooms still perfectly intact today.
If you venture further into the rolling countryside, you’ll find hidden gems like the Norman church at Manton, complete with an ancient belfry that has watched the centuries roll by.
In Rutland, the days may pass and the modern world may hurry along elsewhere, but here, the beauty remains untouched. It’s a tiny county with a massive personality—one that rewards anyone who takes the time to slow down and explore.
The year 1944 was perhaps the most consequential in the long history of Oakham. While the town had seen centuries of quiet market trade and the slow turn of the seasons, this particular year saw the small Rutland capital thrust into the center of a global whirlwind. As the Allies prepared for the liberation of Europe, Oakham was transformed from a sleepy backwater into a vital cog in the machinery of war. To walk through the streets of Oakham in 1944 was to experience a town on edge—tense, overcrowded, and vibrating with the hum of impending action.
A Town Under Occupation (The Friendly Kind)
By early 1944, the most striking thing about Oakham was its population. The census might have suggested a modest number of residents, but the reality on the ground was very different. The town was flooded with soldiers. Most notably, the American 82nd and 101st Airborne Divisions were stationed across the Rutland countryside, with many paratroopers billeted in and around Oakham.
The "friendly invasion" changed the social fabric of the town overnight. The local pubs, such as The Crown and The George, became melting pots of accents—Rutland burrs mixing with Brooklyn brawls and Midwestern draws. For the local children, the Americans were a source of endless fascination, bringing with them exotic luxuries like Coca-Cola, chewing gum, and "nylon" stockings that were otherwise mythical in a town living under strict British rationing. However, for the elders, the influx of thousands of young, energetic, and often boisterous soldiers was a shock to the system that required a very British brand of polite endurance.
The Shadow of the Great Hall
Oakham Castle, as it had for nearly a millennium, remained the symbolic heart of the town, but in 1944, its significance was somber. The tradition of the horseshoe continued, but the town’s focus was less on ancient ceremony and more on the immediate survival of the nation. The Great Hall and its surrounding grounds were often used for civil defense drills and as a gathering point for the Home Guard.
The men of Oakham who were too old or too young for the front lines patrolled the railway lines and the outskirts of the town. There was a constant, low-level fear of German paratroopers—an irony not lost on the locals who watched thousands of American paratroopers training in the skies above them every day. The Rutland landscape, with its rolling hills and open fields, had become a massive rehearsal stage for the drop into Normandy.
Rationing and the "Dig for Victory" Spirit
Life for the average Oakhamian in 1944 was defined by "make do and mend." Despite being surrounded by some of the most fertile farmland in England, the residents felt the pinch of the war just as much as those in the cities. Every available scrap of land was turned over to food production. Allotments sprang up where flower beds used to be, and the "Dig for Victory" campaign was not just a slogan but a necessity.
The local market, usually a place for social gathering and varied trade, was a shadow of its former self. Goods were strictly regulated, and the "black market"—often involving those same friendly American soldiers trading army rations for local eggs or butter—became an unspoken part of the local economy. In 1944, a fresh orange or a real bar of chocolate was a treasure that could stop a conversation.
The Arrival of the Paratroopers: The Run-up to D-Day
As spring turned to summer in 1944, the atmosphere in Oakham shifted from boisterous to breathless. The training exercises grew more intense. The skies above Rutland were constantly filled with the roar of C-47 transport planes. Residents recalled the sight of hundreds of silk parachutes blossoming over the fields near North Luffenham and Cottesmore, a beautiful but terrifying reminder of what was coming.
Then, in early June, a strange silence fell over the town. Almost overnight, the American soldiers vanished. The trucks that had rattled the limestone houses were gone; the pubs were suddenly empty. On June 6, 1944, the people of Oakham woke up to the news of the D-Day landings. There was a profound sense of "empty nest" syndrome, mixed with a terrifying realization: the young men who had been flirting with the local girls and trading gum for smiles just days before were now at the tip of the spear in the invasion of "Fortress Europe."
For weeks afterward, the town waited for news. The casualty lists that began to trickle back hit the community hard. Many of the American units that had been "Oakham’s own" for a few months suffered devastating losses in the hedgerows of Normandy.
The Arrival of the Displaced
While the soldiers went out, others came in. 1944 saw Oakham hosting its share of evacuees from London and other blitzed cities. These "townies" often found the mud and the quiet of Rutland just as alien as the Americans had. Additionally, the year saw an increase in the presence of Prisoners of War. Working on the local farms under guard, German and Italian prisoners became a common sight in the fields. It was a bizarre juxtaposition: the enemies of the state helping to harvest the crops that fed the families of the men fighting them abroad.
The Home Front and the Railway
Oakham’s railway station was a vital artery in 1944. It was the gateway through which everything moved—troops, tanks, coal, and the wounded. The station staff worked grueling hours under the "blackout" conditions, moving immense amounts of freight with only hooded lanterns to guide them. The railway was also a reminder of the war's proximity; hospital trains frequently passed through, a silent testament to the ongoing battles across the Channel.
A Year of Endurance
By the end of 1944, Oakham was exhausted. The initial excitement of the American arrival had been replaced by a weary longing for the war to end. The town had seen its boys go off to fight, it had played host to an international army, and it had survived on the bare minimum. Yet, there was a sense of pride. This small town had stood at the center of the world's attention for a brief, flickering moment in history.
When the Christmas of 1944 arrived, it was a lean celebration. There were few lights and even fewer luxuries, but there was a growing hope. The town had survived the worst of the storm, and though the limestone walls of Oakham Castle were scarred by the vibrations of thousands of passing tanks, they remained standing—much like the spirit of the people who lived within them. 1944 was the year Oakham proved that even the smallest county town could play a giant's role in the story of freedom.
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