Dave not only came up with the idea but also carried out much of the detailed organisation. Assisted by Trev Gray, he surveyed the course, drew up the various legs and change over points and supplied maps for those running each section. The original aim was to break a record set by a walkers organisation for completing the route and the first event, held in October 1983 was organised with military precision. The teams left Costello early in the morning in vans and mini-buses and the first runners set off from Filey Brigg at 8.30 in the morning. The event required map reading skills as well as a fast pace, especially in some of the more remote northerly sections of the route where it was relatively easy to go off course. In the event, only the runners on the Sherburn Road to Wintringham and Thixendale to Fridaythorpe legs went seriously off course but the time this cost the runners was not enough to prevent the runners from setting a new record when they arrived at Hessle Haven in some nine hours and twenty-two minutes after leaving Filey Brigg. Later in the evening a high spirited social was organised for the team, supporters, friends and relations in the Ferry Boat Inn.
Over the next few years a number of organisations tried to beat the time but failed and in 1989 the club decided to repeat the relay as part of the "Centenary" Celebrations. This time Paul Peacock was oversaw the organisation. Dave Ainsworth supplied the original maps whilst Paul spent some time with Robb Robinson, Arthur Gill and Pete Chapman on various parts of the course going over the details in the preceding weeks. On this occasion the runners avoided the mistakes of the previous years, although there was a hiccup on stage twelve, the Londesborough to Arrass Hill leg. However, Mike Baggott made up much of the lost time with a storming run on Stage 13, Arrass to Swindale. Even so, it was apparent to all that breaking the record was going to be no pushover and but, Paul Peacock, like all the good movie directors, kept something special up his sleeve for the finish by saving some of his fast runners for an epic finish. On the penultimate stage Adrian Hill and Andy Ulrick could be seen hurdling fences down the Humber after a superb run from Brantingham and at Ferrriby they handed over the batons to Paul Scott and Mike Lake who made the final dash along the Humber Bank to Hessle. The whole team was elated when the pair arrived at the Ferry Boat Inn on Hessle Haven some seven and a half minutes to the good with a time of 9.14.14. Calor Gas struck up a barbecue (Martin Farrell was by now on his sixth hamburger of the day) and handed out very welcome liquid refreshments.
In 1990 East Hull Harriers took up the challenge with relish and on their first outing - over ten rather than twelve legs they completed the full route in 9.25.31. Their team ran the route from Hessle Haven to Filey Brigg - the opposite direction - possibly a harder direction and threw down the gauntlet to City of Hull. The result was an open race between several local clubs the following year. In that race, City of Hull Senior team built up a substantial lead before half way and looked in an unassailable position until one of their team went wildly off course on the leg by Millington Pastures and the City of Hull Veteran team came past them to take a lead which they never lost. The same leg caused problems for the City of Hull team another year and lost them the race.
The Wolds Way not only took a lot of planning but also required an early start. Clusters of competitors and supporters would congregate on Filey Brigg to see the first leg runners start against the backdrop – depending on the weather and time of year – of either a grim and grey or shimmering North Sea. Convoys of cars then chased along quiet lanes and across the open country of the High Wolds to collect at the various changeover points where over all would strain eyes and ears to catch the first glimpse of the incoming runners racing through the fields and hedgerows of this beautiful stretch of countryside or to shout support for their team member on his or her way up some steep chalky path or furrowed footpath. Those who had completed a leg before half-way had time to stop off at the Cross Keys in Thixendale for both food and refreshment before rushing on to catch up with the race on a later leg. The great thing about the Wolds Way Relay was the uncertainty: it was often to predict which team would actually be in front by the line at Hessle Haven. It only took one runner to go off course on one leg for the nature of the whole race to change.