Gloucester, the Original Working Waterfront

“It’s pronounced ‘GLOSS-tah’, not,…’gl-OW-stir’”, our friend Julia corrected as she swiped through my iPad and reviewed my destinations, including Gloucester, on Cape Ann just north of Boston. Like a second daughter to us, Julia is from nearby Scituate (pronounced, “SIT-chew-it”), and joined us for a few days of sailing on Buzzards Bay this season.

So upon leaving the Cape Cod Canal at 8 a.m. a few days later, and armed with the correct pronunciation, I set a course for Gloucester for the first leg of a solo return trip to Maine. The engine did all the work on a rare windless trek across Cape Cod Bay and I finally throttled back inside Gloucester’s inner harbor, 60 nautical miles later.

I fell in love with Gloucester Harbor on the spot. Lowering the anchor into history-rich mud, I was amazed to be anchored right in the middle of it all. It figures that seafaring Gloucester would remember the transiting sailor and leave precious space for me to anchor inside. Not surprisingly, as it was the second week of September, I was the only boat in the small anchorage (there are several town moorings available nearby).

Gloucester is a real working harbor. Scanning the fully developed shoreline that appears industrial from a distance, a closer look reveals there’s more to Gloucester Harbor. Evidence of the historic fishing industry is present today in the big trawlers that come and go. The shoreline, though, has given way to a recreational boating movement that looks unique to the town; unique in that the wood-planked fishing dories that worked the sea a century ago are actually part of that recreation. And that recreation isn’t new, either, as they’ve been racing Gloucester Dories, under oar power, in the harbor for more than 50 years.

Sitting on your anchored boat in the middle of it all, it’s hard not to imagine the centuries of history that took place on this interesting working waterfront. I watched a pair of Gloucester Dories row just off my port deck while a huge rusting fishing trawler steamed by on my starboard.

Gloucester Harbor is a unique mix of living history and maritime industrial energy today that says unapologetically, “This is Gloucester, take it or leave it”.

Later, I rowed to the nearby public dinghy dock and took a walk around the small city. Gloucester is in transition on shore. Future plans are underway for a harbor walk and other public access improvements. I peeked over the shoulder of a street painter engrossed in the urban seaside scene ahead. This harbor has drawn artists for centuries. Overlooking the harbor, the famous artist Fitz Henry Lane — today immortalized in bronze sculpture — has an urgency in his form and sketchpad as he captures a fleeting moment typical on this waterfront. Everybody sweats a little in Gloucester, even the artists.

The downtown is a blend of a working waterfront together with an energetic vibe of galleries, businesses, shops, stores, and restaurants. A hard-working bohemia pulses through the streets. It’s got a past, it’s got life, and it’s on the move. A unique harbor, Gloucester. Take it or leave it.

I love it, and I’ll be back.