22. Riverside, Connecticut (Average Household Income: $309,401)

This town cozies right up against Old Greenwich, another wealthy town mentioned later down on this list. The luxurious Riverside Yacht Club is one of the primary attractions of the community.

Notable residents of Riverside include retired NFL player Tiki Barber, actress Kathie Lee Gifford, and former NHL player Marc Staal. They likely appreciate the beautiful views of the cove and the easy train ride to and from New York City.