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East Midlands
Rutland

Uppingham

The best family-friendly hikes and walks around Uppingham

4.5

(595)

4,191

hikers

17

hikes

Family friendly hiking trails around Uppingham are characterized by rolling hills, expansive farmlands, and tranquil woodlands. The landscape is shaped by underlying Jurassic geology, featuring limestone and iron-containing strata that form elevated areas. Hiking routes often incorporate significant natural features such as Eyebrook Reservoir and Stoke Dry Wood. A network of footpaths and hedgerows crisscrosses the countryside, providing accessible routes through varied terrain.

Best family friendly hiking trails around Uppingham

  • The most popular family friendly hiking route is Rutland Round:…

Last updated: May 3, 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

How many family-friendly hiking trails are there around Uppingham?

There are over 15 family-friendly hiking trails around Uppingham, ranging from easy strolls to more moderate adventures. This guide focuses specifically on routes suitable for families, ensuring a pleasant experience for all ages.

What kind of landscape can we expect on family hikes near Uppingham?

The Uppingham area is characterized by its beautiful rolling hills, expansive farmlands, and tranquil woodlands. You'll find paths winding through fields, along hedgerows, and into small woods, often offering scenic views of prominent features like the Eyebrook Reservoir and the wider Rutland countryside.

Are there easy walks suitable for families with young children or toddlers?

Yes, Uppingham offers several easy walks perfect for families with young children. These trails typically feature well-maintained footpaths and gentler gradients. For example, you can find shorter loops that explore the town's open spaces or offer glimpses of the surrounding nature without being too strenuous.

Are the family trails around Uppingham accessible for strollers or wheelchairs?

While many paths are well-maintained, the varied terrain of rolling hills and woodlands means that not all trails are universally accessible for strollers or wheelchairs. We recommend checking individual route details for specific surface information. Shorter, flatter sections within town parks like Tod's Piece might be more suitable.

How long do family walks near Uppingham typically take?

The duration of family walks varies. Shorter, easier routes might take around 1.5 to 2 hours, while moderate trails like the Stoke Dry Wood – View of Eyebrook Reservoir loop from Uppingham can take around 2.5 hours. Longer routes, such as the Uppingham Market Town – View of Eyebrook Reservoir loop from Uppingham, could take 3.5 to 4 hours, depending on your pace and stops.

Are there circular family walks available around Uppingham?

Absolutely! Many of the family-friendly routes around Uppingham are circular, allowing you to start and end at the same point without retracing your steps. Examples include the Rutland Round: Uppingham and Eyebrook Reservoir Loop and the Uppingham School – Uppingham Market Town loop from Uppingham.

What interesting landmarks or attractions can we see along the family-friendly hiking trails?

Many trails offer views or pass by notable landmarks. You might catch sight of the impressive Welland Viaduct, a historic masonry structure, or enjoy the scenic beauty of Eyebrook Reservoir. The nearby Rutland Water also offers extensive paths and a nature reserve for wildlife spotting.

Are the family-friendly hikes around Uppingham dog-friendly?

Yes, many of the trails around Uppingham are suitable for dogs, provided they are kept under control, especially when passing through farmland with livestock. Always remember to clean up after your dog and respect local signage regarding dog access, particularly in nature reserve areas.

What is the best time of year for family hikes in Uppingham?

Uppingham's trails are enjoyable year-round. Spring brings blooming wildflowers and newborn lambs, while autumn offers stunning foliage. Summer is ideal for longer days and picnics, and even winter walks can be beautiful, especially on crisp, clear days. Always check weather conditions before heading out.

What do other hikers enjoy most about hiking in Uppingham?

The area is highly rated by the komoot community, with an average score of 4.5 stars. Reviewers often praise the diverse and picturesque landscapes, the well-maintained network of footpaths, and the opportunity to combine natural beauty with glimpses of historic landmarks like the Eyebrook Reservoir.

Are there opportunities for wildlife spotting on family walks?

Yes, the varied habitats of woodlands, farmlands, and reservoir edges provide excellent opportunities for wildlife spotting. Keep an eye out for various bird species, including barn owls and woodpeckers, as well as deer and badgers. The Rutland Water Nature Reserve, a short drive away, is particularly renowned for birdwatching.

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