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Upton St. Leonards

Easy hikes and walks around Upton St. Leonards

4.5

(1819)

12,700

hikers

778

hikes

Easy hiking trails around Upton St. Leonards traverse a landscape rich in natural features, situated within the Cotswolds. The area is characterized by rolling hills, ancient woodlands like Buckholt Wood, and limestone grasslands. Hikers can experience sections of the Cotswold Way, offering panoramic views across the Severn Vale and towards distant hills.

Best easy hiking trails around Upton St. Leonards

  • The most popular easy hiking route is Cooper's 'Cheeserolling' Hill & Buckholt Wood loop, a 3.0 miles (4.9 km)…

Last updated: October 10, 2026

4.6

(19)

80

hikers

#1.

Cooper's 'Cheeserolling' Hill & Buckholt Wood loop

4.85km

01:25

130m

130m

Explore the Cooper's 'Cheeserolling' Hill & Buckholt Wood loop, an easy hike that takes you through ancient beech woodlands and offers expansive views. This route covers 3.0 miles (4.9 km)…

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Easy

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy
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Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy
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Tips from the Community

Clive G
September 16, 2026, Buckholt Wood

Very fine Beechwoods that stretch for some distance.

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Clive G
September 16, 2026, Painswick Beacon

Painswick Beacon sits at the highest point of the Iron Age hill fort Kimsbury Camp. It is also in Painswick Golf Club, and some of the holes are very unusual!

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Cooper's Hill is a lovely place with fine mature Beech woods and good paths throughout.

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A real highlight of this part of the Cotswold Way is the chance to look down the intimidatingly steep 200 yard slope that is the scene of the world famous Cooper's Hill Cheese-Rolling and Wake, held every Spring Bank Holiday. Here people risk life and limb to chase a wheel of Double Gloucester cheese to the bottom - they never catch it of course, but the first past the winning line at the bottom is awarded to cheese as a prize. A fair number of people also end up in the medical tent...

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As the way contours round along the edge of Witcombe Wood you can occasionally look down to Witcombe Reservoir and beyond to the Severn Valley.

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Looking down the slope of the famous Cooper's Hill Cheese-Rolling and Wake you can see how intimidatingly steep it is!

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Shane
September 6, 2025, Buckholt Wood

love the woods

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Frequently Asked Questions

How many easy hiking trails are available around Upton St. Leonards?

Upton St. Leonards offers a wide selection of easy hiking trails, with over 470 routes specifically categorized as easy. These trails provide accessible ways to explore the diverse landscapes of the Cotswolds.

What makes Upton St. Leonards a good place for easy hikes?

Upton St. Leonards is ideal for easy hikes due to its location within the Cotswolds, offering gentle rolling hills, ancient woodlands like Buckholt Wood, and limestone grasslands. Many trails provide panoramic views across the Severn Vale without requiring strenuous effort, making them perfect for a relaxed outdoor experience.

What do other hikers say about the easy trails in Upton St. Leonards?

The easy hiking trails in Upton St. Leonards are highly regarded by the komoot community, boasting an average rating of 4.5 stars from over 600 reviews. Hikers frequently praise the well-maintained paths, the stunning Cotswold scenery, and the accessibility of routes that lead to beautiful viewpoints.

Are there any circular easy walks in Upton St. Leonards?

Yes, many of the easy trails around Upton St. Leonards are circular, allowing you to start and end at the same point. A popular option is the Cooper's 'Cheeserolling' Hill & Buckholt Wood loop, which is 3.0 miles (4.9 km) long and takes you through woodlands and near the famous Cooper's Hill.

Are the easy trails in Upton St. Leonards suitable for families with children?

Absolutely. The easy trails are generally well-suited for families. Routes often feature gentle gradients and clear paths through woodlands and meadows. For example, the Painswick Beacon & Buckholt Wood loop is a 2.3-mile (3.7 km) path that offers rewarding views without being too challenging for younger hikers.

Can I bring my dog on the easy hiking trails?

Many of the easy hiking trails in Upton St. Leonards are dog-friendly, passing through public footpaths and open countryside. However, it's always recommended to keep dogs on a lead, especially when passing through livestock fields or nature reserves like Cooper's Hill Nature Reserve, to protect wildlife and farm animals.

Are there good viewpoints on the easy trails around Upton St. Leonards?

Yes, the area is known for its spectacular viewpoints. Easy trails often lead to elevated spots offering panoramic vistas. You can enjoy views from Painswick Beacon or Haresfield Beacon, which provide sweeping sights across the Severn Vale, Gloucester, and even the Malvern Hills on a clear day. Nut Hill also offers expansive views over Gloucester.

What kind of natural features or landmarks can I expect to see on these easy hikes?

Easy hikes around Upton St. Leonards showcase a variety of natural beauty and interesting landmarks. You can explore ancient woodlands like Buckholt Wood, discover the historic Nut Hill with its unique sunken pillbox, or pass by the famous Cooper's Hill, known for its annual cheese-rolling event. Many routes also traverse limestone grasslands and offer glimpses of the Cotswold Way.

What is the best time of year to go hiking in Upton St. Leonards?

Upton St. Leonards offers enjoyable hiking experiences throughout the year. Spring brings wildflowers and lush greenery, while autumn provides stunning foliage in the woodlands. Summer is ideal for longer days and clear views, and even winter walks can be beautiful, especially on crisp, clear days, though some paths might be muddy.

Are there any easy trails that pass through woodlands?

Many easy trails in the area incorporate woodlands, providing shaded paths and a different natural experience. Buckholt Wood is a prominent feature in several popular loops, such as The Cotswold Way – Buckholt Wood loop from Cotswold Commons and Beechwoods, offering scenic routes through ancient trees.

How long do the easy hikes typically take?

The easy hikes around Upton St. Leonards vary in length and duration, but most can be completed within a few hours. For instance, the Cooper's 'Cheeserolling' Hill & Buckholt Wood loop takes approximately 1 hour 24 minutes, while the The Cotswold Way – Buckholt Wood loop is about 1 hour 48 minutes.

What kind of terrain should I expect on easy hikes here?

The terrain on easy hikes in Upton St. Leonards typically consists of well-defined footpaths, bridleways, and some quiet country lanes. You can expect a mix of grassy tracks, woodland paths, and occasional gravel sections. While generally gentle, some routes may include minor ascents and descents characteristic of the Cotswold escarpment.

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