> England Hiking Tours > Cotswold Way > Challenging Hikes > 5-Day / 4-Night Challenging

Cotswold Way

Read More About The Cotswold Way

Your Self-Guided Hiking Tour Includes:

  • Top-Choice Accommodation
  • Detailed Itinerary, Maps & GPS Tracks
  • Baggage Transfer
  • Breakfasts
  • Insider Tips
  • 24/7 Support
  • Access your tour details & documents on the go with your designated Hillwalk Tours account
from £599 per person*
*An additional Single Supplement Charge also applies where a single room is booked (A room for one person) BOOK NOW
  • Day 1 Arrival in Chipping Campden

    From your point of arrival, use the public transport information we provide to make the journey to Chipping Campden.

    Please remember that, as there are no bus connections between Moreton-in-Marsh and Chipping Campden on Sundays, you will need to take a short taxi ride.
  • Day 2 Chipping Campden to Winchcombe

    18.6 Miles / 30 Km 7-10 Hrs 680 Metres

    The quintessential Cotswold village is packed with history, beautifully maintained and full of wonderful old buildings – Chipping Campden, Broadway and Stanton all epitomise these qualities. The ancient ruins of a Cistercian monastery at Hailes and Sudeley Castle, not far from Winchcombe, are other stunning examples of the region’s rich history.

  • Day 3 Winchcombe to Leckhampton Hill

    17.4 Miles / 28 Km 7-10 Hrs 750 Metres

    Far-reaching views from the top of Cleeve Common (at 317m – the highest point of the walk) where the Brecon Beacons in Wales are visible on a clear day. Lineover Wood, where some trees date back over 700 years is particularly impressive.

  • Day 4 Leckhampton Hill to Painswick

    12.4 Miles / 20 Km 5-7 Hrs 490 Metres

    Early in the day, you pass through Crickley Hill Country Park with wonderful views from the escarpment over the plains below. The quiet walker will have a good chance to spot some of the wild deer that roam the majestic beech tree forests close to Birdlip. The trail descends via a golf course into the picturesque little town of Painswick.

  • Day 5 Departure from Painswick

More information on the Cotswold Way