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South West England
Gloucestershire
Stroud

Upton St. Leonards

The best family-friendly hikes and walks around Upton St. Leonards

4.5

(1575)

11,879

hikers

17

hikes

Family friendly hiking trails around Upton St. Leonards are situated within the Cotswold Hills, an area defined by limestone grasslands, ancient woodlands, and prominent hills. The landscape features notable hills like Painswick Beacon, Haresfield Beacon, and Nut Hill, which provide panoramic views. Many routes also offer expansive vistas across the Severn Estuary, adding to the scenic diversity.

Best family friendly hiking trails around Upton St. Leonards

  • The most popular family friendly hiking route is Cooper's 'Cheeserolling' Hill & Buckholt Wood…

Last updated: May 4, 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

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
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Tips from the Community

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

enjoy

0

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Tom
September 1, 2025, Wall Descent Trail

eyes up, keep it pinned

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0

Mark
August 17, 2025, Painswick Beacon

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

0

0

lovely walk. will go again

0

0

Great curve downhill in beech woodland

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0

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

Frequently Asked Questions

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

There are 16 family-friendly hiking routes around Upton St. Leonards, with 9 of them being easy and suitable for most families. These trails offer a wonderful way to explore the Cotswold Hills, ancient woodlands, and scenic viewpoints.

What kind of views can we expect on family hikes in this area?

Many family-friendly trails in Upton St. Leonards offer stunning panoramic views. You can expect to see expansive vistas over the Severn Estuary, the city of Gloucester, and the Forest of Dean from prominent hills like Haresfield Beacon and Painswick Beacon. Nut Hill also provides lovely views over urban Gloucester and the wider Cotswolds.

Are there any easy circular walks suitable for families with young children?

Yes, there are several easy circular walks perfect for families. For example, the Cooper's 'Cheeserolling' Hill & Buckholt Wood loop is an easy 4.9 km trail that explores Buckholt Wood. Another great option is the Painswick Beacon & Buckholt Wood loop, which is 3.7 km and includes sections through woodlands and leads to Painswick Beacon for views.

What interesting landmarks or natural features can we discover on these trails?

The area is rich with natural and historical features. You can explore ancient woodlands like Buckholt Wood and Standish Wood. Don't miss the unique geological formation of Devil's Chimney, Leckhampton Hill, a popular natural monument. On the Nut Hill loop from Hucclecote Meadows, you can even find a sunken pillbox, adding a historical intrigue to your walk.

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

The family-friendly trails around Upton St. Leonards are highly rated by the komoot community, with an average score of 4.5 stars from over 660 reviews. Hikers often praise the diverse topography, ancient woodlands, and the stunning panoramic views from locations like Painswick Beacon and Haresfield Beacon, making them ideal for family outings.

Are there any longer, moderate family hikes for older children?

For families seeking a bit more of a challenge, the Buckholt Wood – Painswick Beacon loop from Gloucestershire is a moderate 10.4 km route. This trail offers a longer exploration of the woodlands and open common land, providing a rewarding experience for older children and active families.

Is there parking available near the trailheads for family hikes?

While specific parking details for each trailhead are best checked on the individual route pages, many popular starting points for walks in the Cotswolds, including those near Upton St. Leonards, typically have designated parking areas or roadside parking options. It's always a good idea to check the route description on komoot for the most accurate parking information before you go.

Can we find any attractions or points of interest near the hiking routes?

Absolutely! Beyond the trails themselves, you can visit the beautiful Painswick Rococo Garden, which is a unique attraction nearby. For those interested in history and architecture, Gloucester Cathedral is also within reach and makes for a fascinating visit after a hike.

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

The Cotswold Hills, including the area around Upton St. Leonards, are beautiful year-round. Spring brings wildflowers to the woodlands, summer offers lush greenery and longer daylight hours, while autumn showcases vibrant foliage. Even winter can be magical, with crisp air and unique views. The best time depends on your family's preference for weather and scenery.

Are there any specific trails that offer a mix of woodland and open views?

Many trails in the area provide a lovely mix of environments. The Painswick Beacon – Buckholt Wood loop from Gloucestershire is a great example, taking you through ancient woodlands and then opening up to common land with far-reaching views. This variety keeps the walk engaging for all family members.

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