Updated Dec, 14th 2012
I liked the cursive over the print, so I stuck with it. I shaded some areas for fun and it looked really nice to me so I kept that for the final result. I may change the color of the shopping bag in the future or take the handle off to leave it as a square.
Round 2 Update
I kept my focus on the shopping bags and thought the implementation of wooden planks over water would help emphasis the name literally.
I'll probably vectorize the logo and use Rockwell as my font for the logo labeled 1. For 2, I'm going to use my cursive and scan it or go over it with a blob brush in Illustrator. 1 grows on me the more I look at it.
Round 1 [old]
I come from what I would consider a medium sized town called Woodbridge. There's not too much to do unless you have a family and like to be home by 10. Our claim to fame is Potomac Mills Mall (and Ikea). When I came to college, I would just say that my high school is across from the mall and everyone knew where I was talking about.
Since the mall plays such a big part in the economy of Woodbridge, I wanted to focus on the shopping experience. Thousands of people roadtrip to Woodbridge just for shopping. The man attractions are the mall and Ikea, but there are lots of other places to shop as well. We've got loads of plazas.
As you can see, I tried to have the shopping experience be synonomous with Woodbridge by using shoppoing bags and packages. I'm not sure which one is best, so it'd be great to have some feedback. I am torn between the heart made of shopping bags and cursive being my favorites.