Discover Oakham
High Street

Oakham High Street serves as a vivid timeline of English history, where medieval stone rests alongside Victorian grandeur.

 

Far from being a static museum, the street is a living artery of Rutland’s county town, where every storefront seems to hide a story from a different century.

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The Medieval Power of Flore’s House

One of the most significant domestic survivals in the country is Flore’s House (located at 34 High Street). This Grade II listed building dates back to the late 13th or early 14th century and was the ancestral seat of the Flore (or Flower) family.

Its most famous resident, Roger Flore, was a political titan of his day, serving as the MP for Rutland twelve times and being elected Speaker of the House of Commons on four separate occasions between 1416 and 1422—an unprecedented feat at the time.

While the frontage has been altered over the centuries, the "bones" of the house remain medieval. Inside, the thickness of the walls and a 14th-century piscina (a stone basin) in the hall hint at the building’s ancient origins. It stands as a reminder that during the Lancastrian era, this very street was home to one of the most powerful men in the English Parliament.

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Victorian Ambition Victoria Hall

Further down the street, the architectural mood shifts to the mid-19th century with the imposing Victoria Hall. Built in 1858, the hall was originally known as the Agricultural Hall, reflecting Oakham’s status as a bustling hub for the surrounding farming community. It was designed to be the town’s premier social space, a role it officially cemented in 1899 when it was renamed in honor of Queen Victoria’s Diamond Jubilee.

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The building is a masterclass in Victorian classicism, featuring elegant pilasters and a grand first-floor ballroom. For generations, this room flooded with light from high arched windows has hosted the town's most important celebrations, from lavish hunt balls to modern-day art exhibitions.

 

Interestingly, a 2004 renovation stripped away a 1950s false ceiling to reveal the original vaulted timber roof, restoring the hall's internal majesty.

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Folklore and Trade The Buttercross and Beyond

As the High Street opens into the market area, you encounter the Buttercross, a hexagonal sheltered structure that has watched over the town since at least the early 1600s. In the days before refrigeration, it provided a cool, shaded spot for farmers’ wives to sell "white meats"—butter, milk, and eggs.

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Inside it sit the town’s famous five-holed stocks. Local legend playfully suggests the fifth hole was for a one-legged wrongdoer, but they more likely served as a warning to the rowdy crowds of the twice-weekly market.

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A Legacy of Modernity

Even the more "modern" additions to the High Street carry historical weight.

 

The arrival of the railway in 1848, which famously intersects the town at the Melton Road level crossing, signaled the end of the Oakham Canal era but gave the town its iconic Signal Box. Built in 1899, this specific box became a household name across the UK not for its railway function, but because it was chosen by Airfix as the model for their railway kits, making a piece of Oakham High Street a staple of hobbyist bedrooms for decades.

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From the medieval halls of Roger Flore to the model-perfect signal box, Oakham High Street / Melton Road remains a rare example of a town that has evolved without losing its soul, successfully balancing its heritage with its role as a vibrant modern center.