Wessex Crossing

  • MTB Rides /
  • 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
  • Group Support Available

Our Services

Luggage Transfers

Your bags and cycle gear are moved between hotels, inns and B&Bs leaving you to enjoy each day without a heavy pack or cycle panniers.

Prices depend on the distance you intend to cycle each day and the number of bags transported. There are large discounts for group bookings.

Group Transport

With our minibuses and trailers we can transport your group, luggage and bikes from your home or airport to the start and back to your parked cars, home or airport at the end.

Please note that if you require transport only then you need private vehicle hire (a taxi service), which we are unable to provide unfortunately.

Trail Support

For large groups we can provide full trail support where a driver, minibus and bike trailer follow the group each day providing assistance when needed.

The driver is first aid trained and is able to help with mechanical repairs to your bikes. Tea, coffee and biscuits are provided and your personal gear is stored in the vehicle.

Cycle Rescue

We provide an emergency roadside repair and recovery service. We can also transport you and your bikes to your hotel if weather conditions prevent you completing the ride.

The cost of the service depends on the distances and time involved. Should you run into difficulties please call our 24 hour support line for assistance.

Tell us about the trip you are planning and the services that you would like us to provide. We will then confirm availability and provide prices. Bicycle hire is available to groups booking other services, trail support or transport for example.

Please could you provide as much information as you can so that we can check availability of vehicles and trailers and provide an accurate price for your trip. Please include the transfers you would like us to provide, collection from an airport for example, and if hiring bicycles the heights of riders.


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. We can provide transport for the group and bikes between the trail and your accommodation.

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. Transfers back to your cars can be provided, or you can return home 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.

If you are travelling by car we can provide transport at the start and/or end of your trip for your group, bikes and luggage. The journey time between Winchester and Weston Super Mare is 2 hours 30 minutes for a minibus pulling a trailer.

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.