The Cotswold Way route was first suggested some 50 years ago by Gloucestershire-area Ramblers, of which Tony Drake of Cheltenham area and the late Cyril Trenfield of the South Gloucestershire area were principals. Although recognised as a suitable route for a National Trail in due course, the path was initially sponsored by Gloucestershire County Council, who had no powers of footpath creation, and so used only existing rights of way. An early guide to the Way, in the hand-drawn pictorial style of Alfred Wainwright, was produced by another Cheltenham-area rambler, Mark Richards, in 1973. The foreword from Tony Drake says:
"... it is necessary to trace the history of the project to date. Following the passing of the National Parks and Access to the Countryside Act of 1949, which made provision for the designation and creation of long distance paths, I put forward the idea of a footpath route following the Cotswold escarpment. This met with great interest but the plans which the Gloucestershire Committee of the Ramblers Association submitted to the National Parks Commission in 1953, though acknowledged and mentioned in the Commission's annual report of that year, was nevertheless pigeonholed and largely forgotten until Gloucestershire County Council prepared its recreational plan for the countryside in 1968. The County Council decided to designate a Cotswold Way route itself, using existing public rights of way, and the scheme was launched during Footpath Week in May 1970. The Way has had priority in signposting and waymarking programmes but until the Countryside Commission get ministerial approval to create a national route, grants will not be available for maintenance and several very desirable rights of way, where none now exist are unlikely to be created."
A memorial to Trenfield in the form of a bench is on the Way near Dyrham Park.
Besides being popular with walkers, the Cotswold Way is run annually as a 10-stage relay from north to south, usually in late June or early July. The winning team typically takes an aggregate time of about 12 hours. It is run under Fell Runners' Association rules and organised by City of BathAthletic Club. It is traditional for the first leg to start from St James Church, Chipping Campden promptly at 7am. The lead runners finish the final leg outside the doors of Bath Abbey at about 6pm.
In September, the Cotswold Way is run as a single stage race from north to south, leaving Chipping Campden at noon on a Saturday and finishing in Bath from approximately 6am until 6pm the following day in front of Bath Abbey. The race is organised by Cotswold Running.
The official record for running the Costwold Way is held by Nathan Montegue of Swindon Harriers, who on 24 September 2014 ran from Chipping Campden to Bath in 19 hours and 31 minutes.