"Major thoroughfare through town offers a little of everything along the way."
Colonial Drive (also known as State Road 50) runs the entire length east-west through Orlando. From near UCF in the east (with easy access to Waterford Lakes), through Winter Park (lots of shopping, plus a decent size mall, Fashion Square), then through Downtown and out past the fairgrounds (the fair is coming up soon, check it out). I enjoy coming to the little viet district around Mills Avenue for Dim-Sum occasionally.