Scenic Countryside Walks Near Cheltenham: The Best Routes to Explore

Why Walk Around Cheltenham?

Just a short distance from Cheltenham’s elegant Regency streets, you’ll find some of the Cotswolds’ best walking country. Whether you’re after a short nature escape, a moderate hilltop ramble, or a longer day hike, the footpaths radiating from town let you explore everything from limestone grasslands and ancient woodland to river valleys and open commons.

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1. Leckhampton Hill Circular Walk – Classic Cotswold Views

One of the most popular countryside walks near Cheltenham, this 3-mile circular takes you up onto Leckhampton Hill, an area of rare limestone grassland with wildlife, wildflowers and dramatic views over Cheltenham and the Severn Valley. The route includes woodland, remnants of old quarries and the rocky outcrop known as the Devil’s Chimney.

• Distance: ~3 miles / ~5 km
  
  
• Difficulty: Moderate
  
  
• Why Go: Cliff-top scenery, flora & fauna, great views without straying far from town.
  
  

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‍2. Crickley Hill Country Park – Short & Scenic

Perfect if you want a short stroll with big views, this 1.7-mile circular walk loops around Crickley Hill Country Park. Along the way you pass ancient woodland and open grassland with views out toward the Cotswolds and Malvern Hills. A café and toilets on-site make this ideal for families or a gentle escape.

• Distance: ~1.7 miles / ~2.7 km
  
  
• Difficulty: Easy
  
  
• Why Go: Quick nature fix, good for all ages, café at the start.
  
  

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3. Cleeve Hill Common Walk – The Highest Point in the Cotswolds

For a longer and more rewarding outing, head to Cleeve Hill, the highest point in the Cotswolds. A 6-mile circular route takes you over open commonland with far-reaching views towards the Malvern Hills and Severn Valley, connecting with the Cotswold Way and passing historic landmarks like 17th-century Postlip Hall.

• Distance: ~6 miles / ~9.7 km
  
  
• Difficulty: Moderate, some steep sections
  
  
• Why Go: Superb panoramas; a real sense of space and heritage.
  
  

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4. Lineover Woods & Wistley Hill – Woods to Hilltops

This 3.8-mile circular walk blends wooded sections (Lineover Woods) with open hilltop walking (Wistley Hill). Starting near Dunkertons Park, it follows parts of the Cotswold Way and countryside footpaths, with chances to spot deer and enjoy unspoilt rural scenery.

• Distance: ~3.8 miles / ~6 km
  
  
• Difficulty: Moderate
  
  
• Why Go: Woodland charm + hilltop panoramas, great for spring wildflowers.
  
  

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5. Cranham & Cooper’s Hill Walk – History Meets Landscape

A 4-mile loop east of Cheltenham takes you from the village of Cranham through ancient woods and up to Cooper’s Hill, famous for its wild cheese-rolling tradition. This walk combines leafy paths, fields and wide views across quiet countryside, with a warm pub near the finish.

• Distance: ~4 miles / ~6.5 km
  
  
• Difficulty: Easy to moderate
  
  
• Why Go: Mix of nature and quirky local culture.
  
  

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6. Cheltenham to Winchcombe Walk – Country & Town

For a full-day adventure, try this 8-mile point-to-point walk from Cheltenham to the charming town of Winchcombe. It combines riverside paths, hillside tracks and Cotswold Way sections, making for a scenic and varied journey. Winchcombe itself has plenty of cafés and pubs for a well-earned rest.

• Distance: ~8 miles / ~13 km
  
  
• Difficulty: Moderate
  
  
• Why Go: Great day hike ending in a historic Cotswold town.
  
  

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7. Winchcombe & Belas Knap Circular – History on the Hills

Also starting in Winchcombe, this 5.1-mile loop heads out to the Neolithic burial site Belas Knap Long Barrow before returning with views over the surrounding countryside and glimpses of Sudeley Castle.

• Distance: ~5.1 miles / ~8.2 km
  
  
• Difficulty: Moderate
  
  
• Why Go: Combine landscape with ancient history.
  
  

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🌅 Tips for Enjoying Walks Around Cheltenham

• Best Seasons: Spring and autumn bring colour and wildlife; summer offers long daylight but paths can be busy.
  
  
• Footwear: Many paths are grass or uneven, so sturdy boots are smart.
  
  
• Public Transport: Some routes are accessible by local buses from Cheltenham, but check timetables especially on Sundays.
  
  

From quick woodland strolls and gentle hilltop hikes to full-day countryside adventures, Cheltenham’s surroundings offer scenic walks for every pace and preference. Whether you’re exploring rolling grasslands, looking for spectacular views, or wandering ancient paths, the Cotswold countryside around Cheltenham is ready to be discovered on foot.

Happy walking, and don’t forget your camera!

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For all the latest on what’s happening in the Cotswolds, check out What’sOn?XL in CotswoldXL Magazine.

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