A Hidden Gem: The Little Crooked House | Hope’s Yard, Uppingham

There’s a hidden corner of Uppingham that I always seem to slow down for.

Tucked just off the High Street in Hope’s Yard is The Little Crooked House, one of those places that’s incredibly easy to miss, but once you’ve noticed it, you’ll never quite walk past in the same way again.

It’s a small, almost secret passageway that forms part of Uppingham’s Heritage Trail, and it’s exactly the kind of place that rewards you for looking up, slowing down, and noticing the details.

Every time I walk through here, I spot something different. On this visit, it was the beautiful old timber beams overhead as I passed through the yard, the kind of historic detail you would easily miss if you weren’t paying attention, but once you see it, you can’t unsee it.

Hope’s Yard sits in one of the oldest parts of Uppingham, where the early Saxon settlement is believed to have developed along the ancient ridge route between Oakham and Rockingham. This historic crossing point helped shape the town we see today, with some of the earliest homesteads forming along what is now the High Street and surrounding yards.

Within Hope’s Yard, traces of that early history are still visible.

The Little Crooked House, at No. 4, is believed to be one of the oldest continuously occupied residences in Uppingham. It is described as an ancient freehold 'from time immemorial' and is thought to have originated as a late medieval hall house. Remarkably, 15th-century roof timbers are said to still survive within the structure, along with elements of the original hall and Tudor fireplaces. The old screen passage still forms part of the right of way through the building, with cellar and buttery spaces believed to lie beneath nearby buildings.

Just a few doors along, at No. 5, the Old Cobbler’s Shop preserves an original medieval oak mullioned window, a detail revealed during renovation work in the 1970s when the yard was restored and reimagined as a series of small boutiques.

Hope’s Yard, as it's been called for much of the 18th and early 19th centuries, was known as Bullocks Yard, linked to a family of bakers who lived and worked in the area. The name we know today comes from the Hope family, three generations of chemists whose shop and home at No. 15 High Street East shaped the yard during the 19th century. The family story began with William Hope's arrival from Cheshire in the early 1800s, followed by his son and grandson, before the chemist’s shop eventually changed hands in the early 20th century.

By the mid-20th century, like many historic yards, Hope’s Yard had fallen into decline, and parts were derelict. It was only in the 1970s that the late Tony Traylen rescued the area from becoming a car park, restoring the buildings and transforming them into the beautiful buildings that remain today. His work not only preserved Hope’s Yard but also helped inspire the wider regeneration of Uppingham’s hidden yards.

It’s a wonderful reminder of how much medieval, Tudor, and Georgian history still survives quietly within Rutland’s market towns, often hidden behind shopfronts and everyday streets, waiting to be noticed.

Hope’s Yard is also one of the stops along the Uppingham Heritage Trail, which explores the town’s historic streets, courtyards and architectural details. The trail highlights the hidden gems that you might walk past a hundred times without ever realising what lies just a few steps off the High Street.

After delving a little deeper into its history, I ended up on uppinghamhistory.org.uk, created by the Uppingham Local History Study Group, and completely fell down a rabbit hole of local research.

Old maps, photographs and detailed notes bring Hope’s Yard and the surrounding buildings to life in a completely different way, and it’s well worth a browse if you enjoy discovering the layers behind familiar places.

It’s one of those hidden parts of Uppingham that always catches my attention. Even the smallest corners of Rutland still hold centuries of history waiting to be discovered.

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Charlie

@rutlandblog