Stokesley's new Town signs were installed in 2008 by SPIOTA. The signs had been deteriorating over many years, and quite a number of attempts had been made to redesign them, but funding had always been a problem. In 2007, Frank Cuthbert, in his role as Chairman of SPIOTA, took the matter in hand by searching for potential suppliers of designs and constructions - this after spending much time visiting other towns in North Yorkshire and elsewhere. The whole project came to fruition in 2008.

SPIOTA wholeheartedly joined in the work involved and one of its members, artist Graham Bell, prepared the motif for the signs. The small plaque represents the historic Pack Horse bridge over the River Leven from the High Street.

The whole venture was made possible when Hambleton District Village Regeneration Fund agreed to donate £5,000 towards the cost of a complete renewal of all signs, and to provide new ones where missing. The Stokesley Society also contributed to the funding.

• "Signs of the Times" of Tebworth provided the professionally designed and made name plaques.
• Biker Contracts of Leyburn carried out the demolition of old signs and the construction of the new stone structures.
• Jewsons, of Stokesley, provided the natural stone for the "backboards".
• Members of the "Thursday Gang" finished off the job with their expertise in flower choice and planting, and indeed, it was found possible to return some money to the Parish Council.