Wessex Crossing

On this ride you will cross the ancient kingdom of Wessex from Weston-Super-Mare on the Bristol Channel coast to the historic capital at Winchester.

The trail winds its way through the Mendip Hills in Somerset, before crossing Salisbury Plain and then traversing the Avon and Test Valleys. Along the way, you will pass the iconic landmarks of Cheddar Gorge, Wookey Hole and Stonehenge, ride through Longleat Park and visit the impressive cathedral cities of Wells, Salisbury and Winchester.

  • 124 miles / 202 kms
  • 12,140 feet / 3700 metres
  • 2-3 days
  • Weston-Super-Mare - Winchester

By starting in Somerset and heading east you have a good chance of cycling with the wind behind you. However those riding east to west are rewarded with a finish beside the Severn Estuary on Weston Super Mare promenade.


As the trail ends in Winchester you have the opportunity to extend your trip by continuing along the South Downs Way to Eastbourne or following the Pilgrims' Way to Farnham. The North Downs Way starts in Farnham and ends at Dover on the Kent coast, which means you can cycle from coast to coast across Southern England - a fantastic achievement. The distances shown are a guide only and depend on the accommodation you choose each night. Large groups may need to use hotels and inns in towns nearby.

Mendip Hills, Somerset, England

Two Days

Cycling the trail over a weekend is a decent challenge for serious riders and requires good trail and weather conditions. You can return home or back to Weston Super Mare using mainline train services from Winchester railway station.

Day 1 - Weston-Super-Mare to Warminster - 62 miles / 101 kms
Day 2 - Warminster to Winchester - 62 miles / 101 kms

Winchester Cathedral, Winchester, England

Three Days

A 3 day cycling trip has overnight stops in Frome and Salisbury. The shorter third day gives the option to transfer back the same day rather than stay overnight at the end. At Winchester you can cycle up the Itchen and Wey Valleys to join the North Downs Way.

Day 1 - Weston-Super-Mare to Frome - 50 miles / 80 kms
Day 2 - Frome to Salisbury - 49 miles / 79 kms
Day 3 - Salisbury to Winchester - 26 miles / 42 kms

There are several long term car parks in Weston Super Mare and the town has a train station with connections to Taunton, Bristol and London Paddington. Winchester has long term parking too of course and there are railway connections to London Waterloo and the South Coast. The journey time by road between Winchester and Weston Super Mare is 2 hours 30 minutes for a minibus pulling a trailer.



Landranger map 182 includes Glastonbury, Polden Hills, Cheddar Gorge and Chew Magna

Yeovil & Frome

Landranger map 183 includes Sherborne Castle, Cheddar Gorge, Wells, Shepton Mallet and Frome

Salisbury & The Plain

Landranger map 184 includes Stonehenge, Salisbury Plain, Salisbury and Old Sarum

Winchester & Basingstoke

Landranger map 185 includes Andover, Romsey Abbey and the South Downs Way

GPS: Weston to Nunney

Download GPS points of the trail from Weston-Super-Mare to Nunney

GPS: Nunney to Salisbury

Download GPS points of the trail from Nunney to Salisbury

GPS: Salisbury to Winchester

Download GPS points of the trail from Salisbury to Winchester

Hotels & Inns

We have listed some of the better hotels and inns with links to TripAdvisor where you can read customer reviews and check prices and availability.

When booking accommodation ask if there is secure storage for your bikes and the time breakfast is served in the morning. All should be able to provide packed lunches. For those starting late or cycling long distances, check when evening meals end. If you plan to arrive mid afternoon check that the country inns are open as many close between 3 and 6 pm.

As one would expect from an English seaside resort there is accommodation for all budgets in Weston Super Mare. Once you leave the town there are lovely inns and small hotels to be found in the Somerset and Wiltshire countryside. At Winchester there is plenty of choice too and with its restaurants and bars it is a lovely city to enjoy the final night of your trip.