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United Kingdom
England
East Midlands
Rutland

Uppingham

The best walks and hikes around Uppingham

4.5

(595)

4,191

hikers

17

hikes

Hikes around Uppingham explore the rolling countryside of Rutland, England's smallest county. The landscape is characterized by gentle hills, open fields, and modest woodlands, with footpaths winding through farmland and along hedgerows. Routes in the area often provide far-reaching views and pass by features like the Eyebrook Reservoir.

Best hiking trails around Uppingham

  • The most popular hiking route is From the highest pub in Rutland to Eyebrook Reservoir loop, a 9.0 mile (14.5 km) trail that takes around 3…

Last updated: April 24, 2026

4.5

(10)

34

hikers

#1.

Rutland Round: Uppingham and Eyebrook Reservoir Loop

14.5km

03:51

150m

150m

Hike the Rutland Round: Uppingham and Eyebrook Reservoir Loop, a moderate 9.0-mile (14.5 km) trail with rolling hills and reservoir views.

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Moderate

Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

Moderate
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Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

Moderate

Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

Moderate

Hard hike. Very good fitness required. Easily-accessible paths. Suitable for all skill levels.

Hard
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Tips from the Community

ACW2018%
April 1, 2026, Old White Hart Pub, Lyddington

Beautiful pub, open 7 days a week offering food and accommodation. stopped off for a quick refreshment in the beer garden.

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lovely quiet village with an important history and a view of the reservoir.

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Great views and ridable in all but the wettest weather

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The Exeter Arms is a lovely drinking pub (no sign of food!) and we were given a warm welcome by the Host, who was unaware of the Pubs lofty status as the highest in Rutland. We both enjoyed a very fine pint of “Inclined Plane” from the local Langton Brewery.

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Adie
December 1, 2022, Uppingham Market Town

Uppingham is a delightful little market town, filled with honey coloured stone buildings. Uppingham School has been providing education since 1584 and houses one of the largest private theatres in the country.

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Enjoy a pint of "Inclined Plane" at, by my reckoning, the highest pub in the whole of little Rutland. A very nice pub it is too, with a warm welcome and excellent beer.

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Lovely garden and excellent staff good place to stop for tea, drinks and lunch

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Adie
August 16, 2022, Uppingham School

Uppingham is a delightful little market town, filled with honey coloured stone buildings. Uppingham School has been providing education since 1584 and houses one of the largest private theatres in the country.

2

0

Frequently Asked Questions

Are there many circular walks starting from Uppingham?

Yes, many trails in the area are circular, allowing you to start and end in the same place without retracing your steps. These loops guide you through the rolling countryside and back to town. A great example is the Wardley Woods Bluebell Forest – Uppingham Market Town loop, which takes you through local woodlands.

What are the trails like around Uppingham?

The hiking trails around Uppingham are characterized by the gentle, rolling hills of the Rutland countryside. You'll typically find yourself on well-trodden footpaths that cross open farmland, follow hedgerows, and pass through small woodlands. Many routes offer expansive views across the patchwork of fields.

Are there any easy, family-friendly hikes available?

Definitely. While most routes are moderately challenging due to the rolling terrain, there are a few easier options perfect for a family outing. These shorter walks stick to gentler gradients and are a great way to introduce kids to the local countryside. Look for routes under 5 miles with minimal elevation gain.

Can I bring my dog on the trails?

Dogs are welcome on most public footpaths around Uppingham. You'll find plenty of space for them to explore in the open countryside. However, you will be walking through farmland, so always be prepared to put your dog on a lead, especially when livestock are present. For off-lead time, the enclosed Gorse Field Nature Reserve near Oakham is a popular choice with local dog owners.

What do other hikers enjoy most about the Uppingham area?

The area is highly regarded by the komoot community. Reviewers often praise the quintessential English scenery, with its rolling hills and tranquil atmosphere. The excellent views of Eyebrook Reservoir and the impressive Harringworth Viaduct are frequently mentioned as highlights.

Are there any trails with good views of Eyebrook Reservoir?

Yes, several routes offer fantastic views of Eyebrook Reservoir, a site historically used for practice by the Dambusters. For a comprehensive experience, consider the Uppingham Market Town – View of Eyebrook Reservoir loop, which provides multiple perspectives of the water from the surrounding hills.

Can I find any challenging hikes in the region?

While the region is not known for mountainous terrain, you can still find challenging hikes. The difficulty here comes from distance and cumulative ascent over the rolling hills rather than steep climbs. There is one hike rated as difficult, but longer moderate routes like the 9-mile loop to Eyebrook Reservoir will provide a good test of endurance.

Are there any walks that go through local villages?

Yes, several trails connect Uppingham with charming nearby villages. You can follow paths to places like Lyddington, home to the historic Bede House, and Seaton. These routes combine countryside walking with the chance to explore the area's picturesque ironstone villages.

What kind of wildlife might I see while hiking?

The area is rich in wildlife, particularly birdlife. The trails around Eyebrook Reservoir and nearby Rutland Water are hotspots for birdwatching, with opportunities to see waterfowl, waders, and even ospreys. In the woodlands and fields, keep an eye out for deer and other common British wildlife.

How many hiking trails are there around Uppingham?

There are over 15 designated hiking routes to explore around Uppingham on komoot. They range from short, easy strolls to more demanding all-day treks, with the majority being moderately difficult loops through the scenic countryside.

Can I start a walk directly from Uppingham town?

Absolutely. Many of the best routes begin right from the edge of town, so you don't need to drive to a trailhead. For instance, the Stoke Dry Wood – View of Eyebrook Reservoir loop is a popular trail that starts and finishes in Uppingham.

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