Even though the water is warmer on the sound side, I prefer bay all the way. Beaches from Mayflower to Skaket are great for family & kids. Sandy beaches, never see any sea weed (sound side can suck) and with the flats, low tide exploring with kids is fantastic.
First Encounter is definitely a fun place for young kids. There will always be a bay side vs sound side debate I prefer sound side others in my family prefer bay side.
Some other stuff to do:
Brewster General Store - Ice Cream and penny (sort of) candy
Chatham Fish Pier - 2-3pm fishing boat off load at the dock and you can watch from above as they unload dogfish and cod while the seals swim around the boat.
Chatham Lighthouse - Great overlook.
Sundae School Ice Cream, Dennis, MA - Classic Ice Cream
Hybrid Mode
