Chapter 3

Before we could get to Newburyport, Massachusetts, we needed to deal with Cape Ann, home of the City of Gloucester and the Town of Rockport.  Cape Ann was first mapped by the explorer John Smith, of Jamestown Colony fame, and colonized in 1623. When Captain Smith showed his map to Charles I, then King of England, he invited the king to name the cape. Cape Ann is named after Charles’ mother, Ann of Denmark. Going around the entire cape, into the Atlantic, would add time and miles to our trip. The other option was to proceed up the Annisquam River, which separates the cape from the mainland and connects with Ipswich Bay. We opted for the river as the  more prudent route. We entered Gloucester Harbor and looked for the draw bridge to enter the Annisquam. Using binoculars, I was able to make out the narrow entrance, and a line of boats waiting. I pointed it out to Tim, and he headed in that direction.

As we waited for the bridge to open a line of spectators started forming along the fence on the street above. It seemed to be a rather curious development. With warning bells ringing and guard rails coming down across the road, the bascule bridge slowly started rising, revealing a line of boats waiting to enter Gloucester Harbor. Once the bridge was fully raised, the boats on the other side had the right of way. Traveling with the current they moved easily between the concrete walls of the bridge, but they did create a good amount of wake, given the limited space for the displaced water to go. When it was our side’s turn to move forward, it became very clear why there was a row of spectators. There were three elements that made this passage dangerous: going against the tide, the narrow opening and the wake from the previous boats.We watched the boats ahead of us speed up considerably as they approached, headed towards the opposite wall of the bridge before turning right to enter the river. With each succeeding boat we saw their bows leap skyward when hitting the wake and then making the turn. It was fortunate that we were not first in line and were able to watch those with local knowledge go before us. Tim followed in kind and we made it through to the calmer water on the other side.

“Are you the launch?” Tim had called to the small boat pulling away from the dock, knowing that it wasn’t.

“No but I can be,” was the response as the boat’s operator  pulled back to the dock.The ride from the dock to our boat’s mooring was only about two minutes in duration. However, during that time our captain announced himself as none other than Bob Crowley, somewhat of a local celebrity. Crowley was the winner of the 17th season of the TV series, Survivor. In addition to winning the $1 million first prize, he won an additional $100,000 as player of the season. We subsequently learned that Bob is a retired school teacher, who lived on a small island in Casco Bay, and sold yurts on the side. That’s the thing about travel: you never know what—or whom—you’re going to encounter along the way.