Update in case anyone searches for a similar topic:
Our favorite meal: Chatham Wine Bar
The food at this tiny spot was absolutely incredible. It's a very European menu (Spanish and Italian). I had the crab cake, some of a cheese plate (fig almond cake was fantastic), lobster bisque, seared scallops over beet and carrot purees, and a Boston creme cake bomb for dessert and everything was prepared perfectly.
I also liked our lunch at The Goose Inn based on our appetizer of lobster rangoons. We were honestly not very impressed with our meals at Chatham Bars Inn.
Go-to shops: Sea Bags (made from recycled sails), The Black Dog (Martha's Vineyard-based), Sara Campbell (Boston-based), and Violet's. I also really liked the Chatham Candy Manor.
Must-do activity: whale watching (we saw 6-8 whales!!) and touring the Chatham Bars Inn Farm in Brewster, MA. The Chatham 4th of July parade was indeed worth going to and 100% Americana.
I wish we had enough time to see the Cape Cod Chips factory. Traffic on the Cape is very real during the summer and especially on the weekends when people are arriving/departing. Instead of going to the potato chips factory, we left the Cape very early on Saturday so we wouldn't get stuck in traffic. We used the extra time to shop on Newbury Street in Boston before our flight.