> England Hiking Tours > Cotswold Way > Challenging Hikes > 5-Day Challenging Hike
  • 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.

  • Day 2 Chipping Campden to Winchcombe

    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

    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

    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