This isn't as great as shopping as I expected from other reviewers. I spent an hour or two browsing the shops but some of them are absolute crap (sorry). Don't get me wrong there are some nicer stores but its not what I expected. The restaurants here though are great!
If you want a really great shopping experience I would recommend going to Edgartown and get off at the Church St. bus stop and walk towards the waterfront. There is a huge Vineyard Vines store (much bigger than the Circuit Ave location) and a few dozen other shops that are wonderful to visit. There are also some very scenic views of the waterfront at many of the restaurants as well.