Ethan Kay, 10, who has an ambition to become an aid worker in Africa, raised more than £100 from the raffle of donated items by local businesses and bought enough toothbrushes and sanitary items to make up 98 packages.
He headed out on December 23 with mum, Rachael Phillips to hand deliver the packages.
Rachael said: “Ethan was very emotional, all the people in need were very, very happy.”
Ethan said: “I met a lady called Kylie who runs the Lincolnshire Rucksack Project in Sleaford and gave her 15 packages. She was delightful, overwhelmed and thankful. We had some toothbrushes and deodorant left over, so I gave them to her as well.
“Then we headed to the YMCA at Lincoln but along the way we met a few homeless people in Lincoln town centre. “Just seeing their faces made me emotional and I had a warm glow inside and cried happy tears.”
They dropped off more packages at the YMCA. “Then we had a look inside where they eat dinner - it felt welcoming and a friendly environment. The manager showed us the very large roast dinner they were preparing for Christmas, it looked delicious.”
Ethan now plans to make more well being packages which include air fresheners, a colouring pack and maybe fidgets for people at the YMCA.
He summed up: “I wish I could do more for those in need. The feeling I felt, the smile on their faces and the gratitude I received is beyond any words. I am truly thankful to everyone who has supported me so far.”