5.37.6 A Weekend In Uppingham | Things to Do Near Uppingham Click here to use our accessible website
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Where to Walk in Uppingham

It’s surprising how many steps you can clock up just by simply meandering around the town, dashing in and out of the shops and walking to the cake counter and back. But following the Uppingham Heritage Trail is another great way to see all the historic sights in one foul swoop. The trail ticks off 20 spots including the post office, railway station, the town hall and Uppingham School.

For us, a weekend well spent isn’t quite complete without an opportunity to pull on your wellington boots and take a stroll through the fields. And a good walk in the great outdoors is one of the reasons we love the countryside. From brisk three mile routes to five hour hikes, the Uppingham walks are plentiful. Perhaps one of the most well-trodden routes (and not just because it starts and ends at the Exeter Arms) is a nine mile hike that takes in views of nearby Eyebrook Reservoir. The town’s tourist information is a hub of helpful information and various maps and official walking routes can be found inside. But sometimes, a little self exploration is the best path to follow.

What to Wear for a Weekend in the Country

If you’ve got your trip to Uppingham booked, but you’re unsure what to pack in your weekend bag, we’ve got you covered with our countryside outfit ideas.

Like most towns in the British countryside, there’s no particular dress code in Uppingham unless you’re a student at the school. But it’s a place that offers the opportunity to really consider your style, should you want to and it’s that freedom that we love most about it. 

When it comes to women’s country clothing, a pair of well-fitting jeans, a striped top and a trench coat creates the perfect weekend attire. Equally a dress, tweed or quilted jacket and women’s fedora hat would certainly never look out of place on the streets of this charming town. When venturing outside the realms of market square to enjoy the surrounding walks, opting for a pair of wellies is a sensible choice. If your visit takes place in the colder months then tall wellies will ensure maximum protection from mud and rain, while short wellies are a better call for the warmer months of the year.

Similarly for men’s country clothing, Uppingham is all about embracing a comfortable but cool aesthetic and no matter the time of year you’re visiting, layering is a simple way to achieve this. A well made sweatshirt paired with a quilted gilet is the perfect balance between country and contemporary. Well cut jeans or even a pair of chinos and leather Chelsea boots will polish off the look.

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