I would contact Oakville Green asking what trees/big shrubs would grown in large planters. I would design all the plants with wheels on them
The plants with wheels could be locked in place. Moved when necessary there would be a "skirt" around the planters so wheels are not showing. I would have a small but well run volunteer booth to give information and promote events, activities etc. Tranquil music in back ground. Attract all age groups, some people might just like to sit. Dog cooling area. Bike rack, wifi hook up or recharger, presentable garbage cans. As I see the town presently, it appears to be for women only, Look at the stores around. Very little to nothing to really attract men business wise, or socially. I have taken a picture of the seating in front of Roy Thompson Hall I will try and send it. Worth your while to see.