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.
Last updated: April 24, 2026
4.5
(10)
34
hikers
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.
4.7
(11)
35
hikers
8.33km
02:14
100m
100m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

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4.9
(11)
38
hikers
11.8km
03:11
140m
140m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
4.5
(4)
20
hikers
10.5km
02:49
120m
120m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
5.0
(1)
7
hikers
18.8km
05:05
250m
250m
Hard hike. Very good fitness required. Easily-accessible paths. Suitable for all skill levels.
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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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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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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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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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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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