North Shore Lighthouse Ride

Local loop thru Winthrop, Salem & Cape Ann
Sat June 23
(~199 miles)

A big rain front was looming south of New England for the weekend, but I’d been spending more time farkling lately than riding and needed to get out and test the new aux tank. I decided to head a bit north to stay ahead of the weather and chose a route along the MA shore north of Boston up to Cape Ann, to collect some lighthouses for the IBA tour.

I rarely have occasion to visit the town of Winthrop MA, isolated on it’s peninsula jutting southward into Boston Harbor, and this was the first time on two wheels. The proximity to Logan Airport seems the town’s main reason for being mentioned in conversation: i.e. “it’s the town all the planes fly over”.

Deer Island, part of the Harbor Islands Park system lies next to Winthrop and is connected via a short causeway. The island has a quite a history, being the site at various times of an interment camp for Native Americans, an immigration quarantine facility, a prison, and now the largest wastewater treatment plant in the state. Despite all that, it IS now a park and there is a very nice paved loop trail that circles the island, offering nice views of Boston, Logan Airport, and the rest of the harbor.

My first quarry of the day was Deer Island Light, located on a reef just off the tip of the island. While there is a paved road that extends most of the way into the island, it is signed for authorized vehicles only (i.e. the wastewater plant) and the general public must park just over the causeway and hoof it from there. Luckily, it was a coolish day in the 60s, so the 2+ mile walk out and back wasn’t too bad in my motorcycle boots and I pretty much had the place to myself.

Towards the tip of the island lies more of the industrialized facility buildings, including this unusual cluster of egg-shaped treatment tanks shown here.

However, just turn around and you are presented with a magnificent view of the harbor, with the skeletal structure of Deer Island Light atop a tiny rock promontory, marking the channel.

There was an actual fireplug-style lighthouse at the location once upon a time, but time and severe nor’easters wore it down and it was dismantled in 1982 and replaced with a unique fiberglass hourglass-shaped job. That was replaced in 2015 with the current skeletal fixture.

I love the odd geology of some of these MA seaside towns with small but striking bump hills on old ledge rock in otherwise flat areas right next to the ocean, where real estate is prime and dwellings have been built almost atop one another.

After snagging a snack/receipt at a local Dunkin to document my ride for the Lighthouse Tour, I continued north along the coast, passing through the usually busy Revere Beach boulevard. The traffic remained light and there were only a few kite-boarders out in the water today.

I cruised on through Lynn and stopped for a quick snap of Nahant Bay in Swampscott.

Past the well-kept and ever-larger homes in Marblehead, I wended my way out onto the Neck to the distinctly designed Marblehead Lighthouse guarding the point. A guy there with his wife asked me about my aux tank and told me that he rode, but wasn’t interested in doing thousands of miles and usually trailered his softail when heading south to the Blue Ridge. I wished him well.

I crossed through Marblehead and into the more familiar streets of Salem MA, though I wasn’t familiar with the stubby little Derby Wharf Lighthouse. My GPS took me to the spot right across from the old Customs House where Nathaniel Hawthorne once worked and then just kept screaming at me: “Turn right! Turn right! Turn right!” caught in a loop that was annoying and amusing. I pulled into a nearby alley way that took me right up to a seawall with a view of the light and resident-only parking. Luckily there was a space free, and I used it to capture the image, after rebooting the GPS lady to shut her up.

Just a mile or so up the road is the very familiar Winter Island park and campground area, where my wife and I usually stay at least once a year to use as a launching point for some scuba diving. The kind lady at the gate waved me on when I told her I just needed a photo of the picturesque Fort Pickering Lighthouse.

Back on the mainland, I stopped for a receipt and noticed a little bakery across the street. I saw the words Key Lime Pie and knew I had to take my wife’s favorite dessert home to her (karma for all this riding I get to do!). It did end up making the trip in my topbox with only some cosmetic damage.

Passing into Beverly MA, I located the Baptist Church that houses the Hospital Point Range Rear Light in the steeple. Being the highest structure on shore in 1927, the Lighthouse Service arranged with the town and church authorities to install lighting equipment pulled from a lightship in the steeple, which would shine in concert with the front range light on shore to show mariners the channel into Salem Harbor.


East out of downtown and down a quiet side street, I located the Hospital Point Front Range Lighthouse.

Unfortunately, as I’ve been learning during this tour, there are a great many lighthouses where you simply cannot get so up close and personal. A few miles up MA-127 brought me into Manchester-by-the-Sea, where I turned off into some waterfront residential streets to try and catch a glimpse of Baker’s Island Lighthouse. I’m used to seeing this one from a much closer distance in a boat, but this is about as close as a motorcycle can get, so I made use of my SLR zoom camera to get the shot from Harbor Street.

Out of the corner of my eye, I spotted another lighthouse across the small harbor on another populated peninsula. Strange…the next one on my list wasn’t until after crossing onto Cape Ann. I scrolled around on the GPS (love the bigger screen on the 595 for this purpose) and determined where I needed to go exploring.

I circled through the town and found myself cruising slowing through the ULTRA-wealthy private neighborhood on Smith’s Point. Tiny little lanes bedecked on both sides by trees, huge dwellings, immaculate landscaping, and the odd objet d’art out in the yard. I finally turned a corner and there it was – a towering square lighthouse smack in the middle of another palatial house with gated grounds and fancy sculptures flanking the driveway that I could see. Not sure what the story was and not wanting to linger too long during my discreet sortie, I snapped the shot and continued on my loop, marveling at the opulence that exists in pockets of land like this.

I noted the name of the area and later looked it up online. The home values that came up were in the millions of dollars (no surprise) and the tower – though never a real lighthouse at all, but rather a converted 11-story WWII fire tower – ended up having a pretty interesting history. It now serves as a guesthouse for the wealthy owners.

I continued hugging the coast through little Magnolia and circling all the way around Gloucester Harbor and down the eastern shore.

Ten Pound Island Lighthouse, hidden in plain sight out in the middle of the harbor, is another one requiring some creativity and a good zoom lens to capture from land.

I’d visited Eastern Point Lighthouse before and knew the drill of getting there through the private community that controls the road in and out. Just let them know you’re going to the lighthouse or the bird sanctuary and act respectfully, and the gatekeepers will generally let you pass. Low speed cruising will get you out to the Audubon Sanctuary parking area just outside the lighthouse grounds.

As a bonus for getting out to Eastern Point, Dog Bar Breakwater Light is housed atop a small church-like enclosure at the end of the breakwater protecting Gloucester Harbor. I’d traversed the breakwater before, but wasn’t feeling up to the task in my MC boots plus paying $10 to park at the sanctuary parking lot. My zoom lens once again saved the day (and some cash).

I reversed direction back into Gloucester and began my loop around Cape Ann on MA-127, entering Rockport. The twin lighthouses of Cape Ann Light Station on Thacher Island are a welcome sight whenever I’m in the area, and I took this shot from Loblolly Point after scrambling up an overgrown path and some loose rock.

Another couple miles further, Straightsmouth Island Lighthouse is another one best seen from the water. I managed to find a vantage point from another residential side street, this one with slightly more modest homes.

I was again thankful for light traffic as I went through Rockport and continued my loop north around Cape Ann and over to the small village of Annisquam on the western side of the island. Annisquam Lighthouse is in another hard-to-reach (or even see) location by land, now being ensconced within yet another private seaside development. I’d seen the lighthouse before, however, though from a distance. I found my way to Squam Rock, in a small park-like preserve atop a hill. From there, there was a mostly obstructed view of the lighthouse down what appears to be a man-made lane through the trees.

Not really happy with the shot (I have another which includes my flag), I decided to once again trust upon the good manners of private neighborhood folks. On my way out of town, I turned into the development and made my way through the small lanes down to the shore, passing a group of folks with open beverage containers who appeared to be attending a function with a big tent in someone’s yard. A couple of them gave me the hairy eyeball but didn’t challenge my presence. I made it to the lighthouse, now shielded by a private residence and almost completely hidden from the road by vegetation and the house. There was a right-of-way out onto the rocks of the cove where I may have been able to get a photo but, not wanting to press my luck and feeling the call of home, I decided to call it a day. I may go back and try this one again some time.

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