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View over Cotswold village of Naunton, Cotswolds, Gloucestershire, England, United Kingdom

Walking Holidays & Outdoor Adventures in Gloucestershire

Hills, Villages, and the Heart of the Cotswolds

Gloucestershire, in South West England, is the heart of the Cotswolds — a county where walking holidays and outdoor adventures are defined by rolling hills, golden-stone villages, and timeless rural charm. From Painswick and Winchcombe to the sweeping escarpments of the Cotswold Way National Trail, every path offers a mix of heritage and scenery.

Walkers can follow ridge-top trails with panoramic views, explore ancient woodland in the Forest of Dean, or trace the source of the Thames near Kemble. The county is home to the Cotswold Hills National Landscape and part of the Forest of Dean, both rich in wildlife and history. With its combination of escarpments, valleys, and villages, Gloucestershire is a place where English countryside walking feels at its most authentic.

Trails Through Gloucestershire

Cotswold Way
A 102-mile National Trail from Chipping Campden to Bath, with escarpment views, Iron Age forts, and classic Cotswold villages.

Wysis Way
A 55-mile trail linking Monmouth to Kemble via the Forest of Dean and Severn Vale, joining the Cotswolds to the Thames Path.

Thames Path (Source Section)
Meadows and villages around the source of the Thames near Kemble, marking the beginning of this iconic National Trail.

Winchcombe Way
A 42-mile circuit from the walking hub of Winchcombe, crossing fields, woodlands, and historic sites.

Donnington Way
A pub-lover’s route linking all 15 Donnington Brewery inns via scenic countryside walking.

Adventure Highlights

  • Escarpment walking in the Cotswold Hills National Landscape
  • Ancient woodland trails in the Forest of Dean
  • Golden-stone villages: Painswick, Stow-on-the-Wold, Winchcombe
  • Historic sites including Belas Knap, Sudeley Castle, and Neolithic barrows
  • Ridge-top views across the Severn Vale
  • Excellent transport links for short breaks or longer holidays

Explore Gloucestershire

One of the county’s most famous walking bases is Winchcombe, known as a true “walkers’ town” with trails in every direction. Painswick, the “Queen of the Cotswolds,” offers charming streets and yew-filled churchyards, while the Forest of Dean provides woodland adventures and sculpture trails.

Frequently Asked Questions

What is the most famous walk in Gloucestershire?
The Cotswold Way is Gloucestershire’s best-known trail, running along the escarpment through many classic Cotswold villages.
Does Gloucestershire have any National Landscapes?
Yes — the Cotswold Hills National Landscape covers much of the county, and the Forest of Dean is also protected.
Are there easy walking routes?
Yes — village loops, pub walks, and the Thames Path source section are gentle options, while the escarpments offer more challenge.
When is the best time to walk in Gloucestershire?
Spring and autumn are ideal for mild weather and colour; summer offers long days; winter brings quieter trails and atmospheric landscapes.
Can walking be combined with culture?
Absolutely — walks pass castles, abbeys, and traditional pubs, blending countryside with heritage.