Logo design for a tshirt and ornament for my town

Hi, I'm looking for a logo designer to create a logo for a t-shirt and ornament for my town. I don't have any specific design elements in mind and am open to suggestions, but I do have some ideas that I'm not sure how to incorporate into the design. I'm also open to any color scheme, and would like the logo to have a vintage and nostalgic feel. I need multiple variations of the logo. If you think this is something you can create, please send steps forward with your bid. Thank you!

The town is Westmeath Ontario Canada and this is lookout hill.