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.
Last updated: October 10, 2026
4.6
(19)
80
hikers
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)β¦
4.1
(7)
47
hikers
3.71km
01:00
50m
50m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

4.8
(34)
169
hikers
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
4.7
(19)
58
hikers
4.51km
01:19
120m
120m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
4.7
(11)
39
hikers
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
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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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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.
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.
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.
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.
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.
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.
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.
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.
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.
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 β Buckholt Wood loop from Cotswold Commons and Beechwoods, offering scenic routes through ancient trees.
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 β Buckholt Wood loop is about 1 hour 48 minutes.
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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