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United Kingdom
England
South West England
Gloucestershire
Stroud

Upton St. Leonards

The best walks and hikes around Upton St. Leonards

4.5

(678)

6,331

hikers

18

hikes

Hiking around Upton St. Leonards offers access to the varied landscapes of the Cotswold Hills, characterized by limestone grasslands, ancient woodlands, and prominent hills. The area provides expansive views across the Severn Estuary, the city of Gloucester, and the surrounding countryside. Trails often traverse sites like Standish Wood and Cud Hill Common, which feature diverse flora and geological interest. The region's topography includes gentle ascents to viewpoints and paths through wooded areas.

Best hiking trails around Upton St. Leonards

  • The…

Last updated: April 24, 2026

4.6

(14)

63

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

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

Moderate

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

Easy
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Popular around Upton St. Leonards

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Tips from the Community

Shane
September 6, 2025, View from Coopers Hill Local Nature Reserve

enjoy

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Mark
August 17, 2025, Painswick Beacon

(TP4459) Lat 51.80736N / Lon 2.19252W at 283 Metres

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lovely walk. will go again

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Great curve downhill in beech woodland

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Helen
June 25, 2024, Shag Hill

prepare!

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Discover this pretty secluded woodland located in the western Cotswolds near Gloucester. A network of paths leads around the woods where you can enjoy a diverse range of flora and fauna species, particularly rare butterflies including chalkhill blue, Adonis blue and dingy skipper,

2

0

Cooper's Hill Nature Reserve is an area of woodland, meadows & grasslands in the Gloucester area known for its rich biodiversity including a wide range of plant and animal species.

2

0

Careful on the golf course, stay to the edges. Fantastic views over Gloucester and stroud. If you want an express route down take Stockley and enjoy rocketing into Upton st. Leonards.

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Frequently Asked Questions

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

There are around 18 hiking routes documented on komoot for Upton St. Leonards. These trails offer a variety of experiences, including 9 easy routes, 7 moderate routes, and 2 more challenging options.

What kind of landscapes and natural features can I expect to see on hikes near Upton St. Leonards?

Hiking around Upton St. Leonards offers access to the varied landscapes of the Cotswold Hills, characterized by limestone grasslands, ancient woodlands, and prominent hills. You can expect expansive views across the Severn Estuary, the city of Gloucester, and the surrounding countryside. Trails often traverse sites like Standish Wood and Cud Hill Common, which feature diverse flora and geological interest.

Are there any easy hiking trails suitable for beginners or families?

Yes, Upton St. Leonards has several easy hiking trails perfect for beginners or families. An excellent option is the Painswick Beacon & Buckholt Wood loop β€” The Cotswolds, an easy 2.3-mile (3.7 km) path that features sections through Buckholt Wood and leads to Painswick Beacon, providing panoramic views. Another family-friendly choice is the Painswick Beacon – Buckholt Wood loop from Gloucestershire, a 3.1-mile (4.9 km) trail through woodlands and open common land.

Can I find circular hiking routes in Upton St. Leonards?

Yes, many of the hiking routes around Upton St. Leonards are circular, allowing you to start and end at the same point. Examples include the popular Cooper's 'Cheeserolling' Hill & Buckholt Wood loop and the Painswick Beacon & Buckholt Wood loop β€” The Cotswolds.

What are some prominent viewpoints accessible via hiking trails?

The area is rich in stunning viewpoints. Haresfield Beacon offers expansive views across the Severn Estuary, Gloucester, and the Forest of Dean. Painswick Beacon provides impressive panoramic views, particularly over the Severn Estuary. Cud Hill Common, located directly above Upton St. Leonards, boasts magnificent vistas that include Gloucester, Cheltenham, Gloucester Cathedral, and The Malvern Hills.

Are the hiking trails around Upton St. Leonards dog-friendly?

Many trails in the Upton St. Leonards area are suitable for dogs, especially those that traverse woodlands and open common land like Buckholt Wood and Cud Hill Common. It's always recommended to keep dogs under control, especially near livestock or in nature conservation areas, and to check local signage for any specific restrictions.

What are the typical durations for hikes in this area?

Hikes around Upton St. Leonards vary in duration. Easy routes, such as the 2.3-mile Painswick Beacon & Buckholt Wood loop, can take around 1 hour. Longer moderate trails, like the 6.5-mile Birdlip Descent loop from Gloucestershire, might take over 2 hours. The longest routes can extend to over 3 hours.

Are there any historical or geological points of interest along the trails?

Yes, the area is rich in both historical and geological interest. The route to Haresfield Beacon often passes through Standish Wood, a Site of Special Scientific Interest recognized for its Jurassic rock formations. Cud Hill Common, besides its views, has historical significance as a lookout point. A short distance away, the Devil's Chimney, Leckhampton Hill, is a unique limestone rock formation above a disused quarry.

How can I access the hiking trails using public transport?

Upton St. Leonards is served by local bus routes, which can provide access to the village center. From there, many trails are accessible on foot. For specific trailheads further afield, it's advisable to check local bus schedules and routes that pass through nearby villages or directly to popular hiking spots like Painswick or Haresfield.

Is there parking available near the trailheads?

Yes, parking is generally available near popular trailheads and viewpoints in the Upton St. Leonards area. Many common starting points for hikes, such as those near Painswick Beacon or Haresfield Beacon, have designated parking areas. It's always a good idea to arrive early during peak times, especially on weekends, as spaces can fill up quickly.

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

The hiking routes in Upton St. Leonards are highly rated by the komoot community, with an average score of 4.5 stars from over 600 reviews. Hikers often praise the varied terrain, the stunning panoramic views from beacons like Painswick and Haresfield, and the peaceful atmosphere of the ancient woodlands and limestone grasslands.

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

Upton St. Leonards offers enjoyable hiking experiences year-round. Spring brings wildflowers to the grasslands and woodlands, while summer provides warm weather for long walks. Autumn showcases beautiful fall foliage, particularly in areas like Buckholt Wood. Even in winter, crisp days can offer clear, expansive views, though some paths may be muddy. Always check weather conditions before heading out.

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