Regency Ramble: Cotswold Way Highlights from Cheltenham

The Cotswold Way National Trail runs from the market town of Chipping Campden to the UNESCO-listed city of Bath, via swathes of splendid countryside – England at its most irresistibly rural. This flexible self-guided break is based in the Regency spa town of Cheltenham, which provides a convenient and sophisticated base for exploring the northern half of the National Trail.

From Cheltenham, choose from a selection of day walks that will take you out into the lush-green hills, via medieval castles, devilish rock formations, a castle fit for queens, a Neolithic long barrow, a Roman villa and – at Cleeve Hill – the Cotswold’s highest point: stand here on a clear day and you can see all the way to Wales. Mix time in the soul-lifting countryside with Cheltenham’s urbane delights – the town is packed with lovely independent shops, bars, restaurants and cafes.

Tour Overview

The icons below highlight the distance, difficulty and theme of this itinerary.




Walks from 10km to 11km




Rolling Countryside / Connecting Villages & Towns


History / Food & Drink

Activities & Experiences

Walking / Heritage

Regency Ramble: Cotswold Way Highlights from Cheltenham

Here’s everything you need to help you plan your very own walking and exploring break in the Cotswolds. Click on the blue arrow tabs below for more information. To save this itinerary to view later, use the Save to My Rucksack button at the top of the page.

Tour details

This itinerary is being operated by Compass Holidays, who specialise in walking, cycling and activity short breaks and holidays in a variety of UK, European and worldwide destinations.

With more than 30 years’ experience, Compass Holidays allow you to get under the skin of the history, culture and natural beauty of some of the world’s most iconic and spectacular locations.

Compass will arrange your whole tour: you just need to arrange transport to your first location.

  • Accommodation at the stated category with breakfast.
  • Luggage transfers.
  • Full tour pack.
  • Smartphone app with GPS routes.
  • 24-hour emergency helpline.

NOT INCLUDED: Lunch, dinner and drinks; entrance to attractions; buses and/or ferries unless otherwise stated; tourist taxes where applicable.


This self-guided Cheltenham-based trip is available year-round. It is very flexible: choose to stay for three, four or five days; also, the trip can be extended or decreased by changing the daily distance covered. The itinerary below is a suggestion.

Arrive in Cheltenham, the most complete Regency town in the UK, with extensive period architecture, a vibrant cultural life, diverse museums, numerous independent boutiques and a fantastic food scene.

Overnight in Cheltenham.

Start with a good breakfast and a steam train ride on the Gloucestershire Warwickshire Railway from Cheltenham to Winchcombe (on days when trains aren’t running, we can arrange alternative transportation).

Head to Sudeley Castle, on the edge of Winchcombe, surrounded by billowing hills. If you like, you can visit the historic house and its magnificent gardens; Katherine Parr, the last of Henry VIII’s wives, lived and died here, and lays entombed within its 15th-century church.

Head through the Sudeley Estate to begin today’s walk. Climb steadily to the Neolithic long barrow of Belas Knap and on to Cleeve Hill, the highest point in the Cotswolds – the views, to the distant Malverns, are spectacular. Then descend into Prestbury, supposedly the most haunted village in England. From here, head back to Cheltenham.

Walk: 10km. Overnight in Cheltenham.

Take a day to get to know Cheltenham. Stroll its handsome Regency streets and landscaped parks and gardens, and learn the stories of some of the town’s most notable former residents: there are museums dedicated to Gustav Holst (composer of The Planets) and polar explorer, naturalist, physician and artist Edward Wilson.

You could explore via the Regency Cycle Trail, a 10km bike ride around the centre and beyond, or get a taste of the town with a tour of Dunkerton’s Cider or Sibling Distillery. Be sure to refuel too. Cheltenham has a growing number of acclaimed independent restaurants offering everything from French cuisine and award-winning fish and chips to Sri Lankan street food.

Overnight in Cheltenham.

Today, return to lofty Cleeve Hill to continue along the Cotswold Way across Cleeve Common – from here, on a clear day, you can see right to the Black Mountains of Wales. Then, walk onto Charlton Kings Common, with its breathtaking views across Cheltenham and the Severn Vale.

Follow the escarpment past Seven Springs and on to Leckhampton Hill where you’ll spot the Devil’s Chimney – according to legend, the Devil would sit here and hurl stones at churchgoers, but they threw the stones back, driving him underground; now, they say, he uses this rock pillar to release the smoke of hell. From here, head back to Cheltenham via taxi.

Walk: 10km. Overnight in Cheltenham.

Head south to Birdlip, to follow more of the Cotswold Way. Walk past the remains of Great Witcombe Roman Villa, through magnificent beech woodlands and on to Cooper’s Hill where, every May, a crazy event sees brave/foolhardy competitors chase a wheel of cheese down the very steep slope. Emerge onto Painswick Beacon, where the ramparts of an Iron Age hill fort can still be seen.

Finish in picturesque Painswick, the mid-point of the Cotswold Way. Amble along lanes featured in the dramatisation of JK Rowling’s A Casual Vacancy and pop into St Mary’s Churchyard, with its 99 yew trees (apparently, the Devil refused to let the 100th one grow). The nearby Rococo Gardens are also worth a visit. Suggest a taxi back to Cheltenham.

Walk: 11km. Overnight in Cheltenham or return home.


This short break is based in Cheltenham, using either a three-star B&B/hotel/inn or five-star luxury hotel. Please note the luxury version includes some taxi transfers at the beginning or end of some days.

Food & Drink

Cheltenham has a growing number of respected independent restaurants offering everything from French cuisine and award-winning fish and chips to Sri Lankan street food. There is also a wide selection of well-known branded food outlets, family favourites and new restaurants with various awards to their name. Harden’s, The Good Food Guide, The Michelin Guide and The Good Pub Guide all lavish praise on innumerable Cheltenham restaurants.


The grade of this tour is moderate, with rolling hills and some steeper sections.


  • Winchcombe to Cleeve Hill, 10km
  • Cleeve Hill to Leckhampton, 10km
  • Birdlip to Painswick, 11km


Mix walks with other experiences along the Cotswold Way.


The nearest railway station is Cheltenham Spa, which is easily reached from London by train. There will be a short walk or taxi ride to your overnight accommodation, which we are happy to arrange on guests’ behalf.

Cheltenham is also easily accessible via the M4/M5 route or by the A40 from London via Oxford.

Great Western Railway runs a regular service from Paddington station. 


This grade of this tour is moderate. The correct clothes are important to ensure comfort during each walk. We suggest avoiding anything with seams and buttons in sensitive areas. Clothing should take moisture from the body to the outside. Sweatshirts, thin pullovers, and breathable jackets are ideal companions during the cooler days. Take light, waterproof jackets and trousers in case there is rain. On hot days we suggest a cap or hat and sunglasses to protect from the sun.

We advise that you check opening times and booking restrictions before travelling.

Please check out these links for latest advice when in the countryside

Countryside Code

COVID-19 Guidance

Interactive Map

To access the map please click here: Interactive Map

Maps, Guidebooks & Merchandise

The official guidebook and map for the Trail are available from the National Trails Shop along with a wide range of gifts and other merchandise.