Bailey Island in Maine has one of the most interesting origin stories of any city in the country. It was originally called Will's Island. Will was a freed slave who decided the island was his. It was awarded to him legally and he loved it. Except he loved to party, too -- apparently, he sold the island for a pound of tobacco and a gallon of whiskey to the Baileys. Mrs. Bailey was the priest's wife, and she didn't like the fact that it was bought with alcohol so she told everyone that she loved the island so much that Will gifted it to her. Either way, Will walked away from his home and the Baileys got a beautiful island. Will's Gut is the portion of water that runs under the bridge going from Bailey Island to Orr's Island; this is the only part of the island that still holds the original owner's name.
You and your dog should definitely take a walk around the island because there are some very unique land formations. Land's End is the name of the rocky beach. Then there is the giant rock formation that is resembles a staircase carved out by the sea. If you want to see some cool man-made stuff, you could check out the Lobster Man, which is a bronze statue created for the 1939 World's Fair, or the World War II air control towers on the south end of the island.