Colourful character Edward Toon was well-known in the town. As well as having performing dogs and prize-winning birds, he was a keen singer, ballroom dancer and ran his own business as a carpenter, joiner, cabinet maker and undertaker.
When he died in January, 2007 at the age of 96, part of his legacy to Uppingham was an annual Christmas present of £50 each for anyone over 80 who has lived in Uppingham or Ayston for more than two years.
This is the first year the Edward Toon Charitable Trust has been able to award the money.
The qualifying date is November 1, 2008, and anyone who is eligible should contact trustee Ron Simpson on 01572 823465 or e-mail rons@clara.net for an application form.
Mr Simpson, said: "Always mindful of the fact that it was only with the support of the people of Uppingham that he was able to make a living, Ted's last wishes were that money from his estate should be used for the benefit of the families of those who had helped his business to succeed in the past.
"He gave more than £100,000 to Rutland Memorial Hospital and a similar sum to the doctors' surgery at Uppingham to be used for the benefit of townspeople."