West Kent Cotswolds 2026 Walking Holiday
Group Holiday to the Cotswolds - Fully Booked
All spaces at the hotel and on the walks are now fully booked. If you are interested in future group holidays then contact Mark Lavenstein on marklavenstein@gmail.com
Monday 27th April
Sherborne Estate Circular
Distance: 5.5 miles
Time: 2.5 hrs
Ascent: 332 ft / 101 m
Start time & meeting point: 12.30 at National Trust Ewe Pen Barn car park, Sherborne Park Estate, Gloucestershire, GL54 3DT
Car Parking: National Trust Ewe Pen Barn car park is ½ mile (0.8km) off the A40, between Cheltenham and Oxford. Turn off the A40, following signs for Sherborne and Clapton (opposite the brown sign for Lodge Park). Ewe Pen Barn is ½ mile along this road, sign posted to the right.
Free for NT members and £4 per day otherwise
Walk Leader: Mark Lavenstein
The Walk: A nice easy walk to stretch your legs after the drive. The walk begins at the Ewe Barn car park, heading past the Cheltenham Lodges and into the landscaped grounds of Sherborne Park. Once part of the Dutton family estate and later managed by the National Trust, the park reflects centuries of careful stewardship. After crossing Sherborne Brook, the route climbs between Ragged Copse and the old quarry, opening into broad farmland with long views across the valley. A gentle descent leads towards Sherborne House, an elegant 18th-century mansion, before the path loops back through quiet fields to the village.
Tuesday 28th April
Bourton-on-the Water to Stow-on-the-Wold Circular
All Options
Start time & meeting point: 10.30 at Harrington House, Sherborne Street, Bouton-on-the-Water GL54 2BY
Option 1
Distance: 12 miles
Time: c. 6 hours
Ascent: 1013 ft / 309 m
Walk – Bourton-on-the-Water to Stow-on-the-Wold Circular – We begin in Bourton-on-the-Water, leaving its lively riverside and following footpaths through Greystones Farm into open countryside. Gentle climbs across fields and dry-stone walls give us wide Cotswold views as we make our way to Stow-on-the-Wold, where we stop for lunch around the historic market square. Heading south, quieter tracks lead us downhill into the valley to Upper Slaughter, a serene village of honey-coloured stone. We then follow the River Eye to Lower Slaughter before crossing fields back to Bourton, completing the circular walk.
Walk Leader: Mark Lavenstein
Option 2
Distance: 6 miles
Time: c. 2.5 hrs
Ascent: 506 ft / 154 m
Walk –This is the same as option 1 but finishes at Stow-on-the-Wold where you can explore the town or simply get the 801 bus back to Bourton-on-the-Water.
801 Bus Timetable
Wednesday 29th April
Winchcombe, Sudeley Castle, Belas Knap & Cleeve Common 11 or 7.5 miles
All Options
Start time & meeting point: 10.30 am Back Lane Car Park, Winchcombe. Approx 13 miles from hotel
Car Parking: Back Lane, Winchcombe, Cheltenham, Gloucestershire. GL54
Ringo App: 9058 Cost £1 per day
Option 1
Distance: 11 miles Time: c.5 hours
Ascent: 1390 ft / 424 m
Walk – The 11-mile loop from Winchcombe takes us past Sudeley Castle, Belas Knap, and Cleeve Common, creating one of the most varied walks in the Cotswolds. From the town’s old streets, we head toward Sudeley Castle before climbing the Cotswold Way to the Neolithic long barrow at Belas Knap, where wide valley views open around us. The route then rises onto Cleeve Common, the highest point in the Cotswolds and sweeping escarpment scenery. A gentle descent leads us back into Winchcombe.
Walk Leader: Mark Lavenstein
Option 2
Distance: 7.5 miles Time: c 3.5 hours
Ascent: 996 ft / 304 m
Walk – We walk as one group with Option 1 for the first 4 miles to Belas Knap, we simply miss out the section to Cleeve Common before heading back to Winchcombe
Walk Leader: David Baylis
Thursday 30th April
Broadway Tower and Chipping Campden
All Options
Start time & meeting point: 10.30 am Milestone Ground Long Stay Car Park
Car Parking: Milestone Ground Car Park, Childswickham Road, Broadway, Worcestershire WR12 7HB
Ringo App: 20723 Cost £4 per day
Option 1 –Broadway to Chipping Campden and return via Broadway Tower
Distance: 12 miles
Time: 5.5 hoursAscent: 1232 ft / 375 m
Walk – This scenic 12-mile circular walk links the honey-stone villages of Broadway and Chipping Campden in the heart of the Cotswolds. Starting in Broadway, the route climbs through rolling countryside and quiet farmland before descending into historic Chipping Campden with its elegant high street. The return leg follows open ridge paths with sweeping views, passing Broadway Tower where expansive panoramas stretch across the surrounding hills, before descending back into Broadway.
Walk Leader: Mark Lavenstein
Option 2– Broadway & Broadway Tower
Distance: 7 miles
Time: 3 hours
Ascent: 872 ft / 266 m
Walk – This walk starts with Option 1 but does not include Chipping Campden but does finish with a nice climb to Broadway Tower before descending back into Broadway.
Walk Leader: Fiona Mills
Friday 1st May
Burford to Barrington Circular
Start time & meeting point: 10.30 am at Guildenford Car Park, Burford
Car Parking: Guildenford, Burford, OX18 4SE. This is a free carpark with toilets.
Option 1 –Burford to Barrington Circular
Distance: 8.5 miles
Time: 3 hrs
Ascent: 429 ft / 130 m
Walk - This easy-going route tracks the River Windrush from Great Barrington to Burford, cutting through open fields, quiet woods, and classic Cotswold scenery. The terrain stays blissfully flat, perfect for a final holiday walk when you want beauty without the effort. Skirting Taynton and Upton, it mixes calm riverside stretches with wide, open views before rolling gently into historic Burford — a simple, satisfying finish to the trip.
Walk Leader: Mark Lavenstein
Option 2 –Burford to Barrington Circular - extended to include a deserted Church
Distance: 12 miles
Time: 3 hrs
Ascent: 750 ft / 229 m
Walk- As Option 1 but when we return to Burford, if people wish we can head back out from Burford to Widford. Widford is a tiny, riverside hamlet on the River Windrush, centred on its historic St Oswald’s Church and a handful of stone buildings, with surrounding meadows showing traces of its deserted medieval village origins.
Walk Leader: Mark Lavenstein