August 26, 2026 Portland, Maine

 Wed.  and Thurs. Aug. 26-27, 2026   Gloucester, MA to Portland, ME   85 miles and 8.9 hours 

Our initial thought was that we'd do a short run up to Portsmouth, grab a mooring ball for the night and continue the next day to Portland.  But the weather models were saying swells offshore would build overnight Wednesday and be very uncomfortable for us on Thursday.  So changed our plans and decided to make it one long day of nice cruising on Wednesday.  That involved an unusual for us 6:30AM departure. Water was pretty calm but definitely swells with a long period, so not noticeable until 9 hours later when we hit land and had the body bobbles where you still are rocking even on solid ground. We stopped in Portland on our Down East loop last year.  Stayed across the river in South Portland.  Opted to stay at DiMillo's Marina in the heart of downtown this time.  Decent enough place but very pricey. I'd rather pay less than half for dockage on the south side and Uber into town. Live and learn!

Very calm day on the open Atlantic.  Running in 200'-300' waters.

Twin lighthouses at Cape Elizabeth built in 1828

Pretty sturdy looking.  Matches the rugged rocky coastline 

Closer to Portland and lobstering activity picked up

Portland Head Light built 1791 is the oldest lighthouse in Maine
and sits at the headlands entrance to Portland

Lighthouses are everywhere here due to unforgiving nature of the rocky coast

Fort Gorges built 1858-1865. Modeled after Ft Sumter. Never saw a battle.

DiMillo's famous restaurant in a converted ferry.

 We got in early enough for a quick walk to find somewhere for drinks and dinner.  Stopped at the Portland Beer Hub for libations and got talking to the bartender for recommendations for "cheap eats".  He pointed us to a local's favorite called Tomaso's Canteen.  Every bit of a dive bar we normally would have avoided at all costs.  But the food was good and very reasonable.  Meaty wings in Thai chile sauce for an appetizer.  Then split a Steak Bomb (think Philly cheese steak).   This put us within a few blocks of Shipyard Brewing Company so.... off we went.  Quite a big facility but split into smaller rooms.  Great logo so had to get one of their shirts. Didn't have a couple beers on tap I wanted to try so got talked into trying their seasonal "Smashed Pumpkin" Imperial Pumpkin Ale.  Would have thought it's to my liking - 10.5% abv and bourbon barrel aged.   Couldn't drink it - nasty stuff.  They had a Hazelnut Porter that was decent - the nose on it was incredible. After all that we stumbled back to the boat pretty exhausted and called it a day.

Touristy town. Old Customs House in background.
Cute historic area, cobblestone streets, lots of shops and restaurants.  

Tourist boat rides around the harbor seem to be a thing. 

Loved the ship weathervane on this building.

Got up Thursday and headed to Standard Bakery for some pastries.  Place gets rave reviews, so not surprised to see a line out the door.  Blueberry scone, Morning sticky buns, Pain au Chocolat.  All outstanding.  Went back Friday for more before we left!  We had intentions of going to the Portland Art Museum but decided we really needed a workday.  Boat is filthy after a couple months on board.  Martha took care of the inside stuff.  I got boat washing detail outside.   By the time we were done nothing left to do but take showers and head out for early dinner. Wound up at Highroller Lobster Company.  Rated as having some of the best lobster rolls in Portland. Place wasn't looking familiar to me (maybe due to recent addition??) but Martha swore we had eaten there.  Checked out the blog from last year and she was right - it's where we ate the day we took an Uber over from the southside.

Line out the door at Standard Bakery. Moved quickly and worth the wait. 

My sistership - the 120' Ocean Alexander Wreckless docked while I was cleaning. 
 Available for sale at $12MM

Congvoyage - a 120' Hargrave makes way down our narrow fairway. No room to
turn around so will need to back out when time to leave. 
Also for sale at a more modest $11MM.

Spent the evening working out possible places we could go to next. Figure it'll mostly be mooring and anchoring around Casco Bay for the next week. Decided to head up the NW shoreline of the bay to Freeport.  Home of L.L. Bean.  

Journey for August 26, 2026

August 24, 2026 Gloucester, Mass.

 Monday and Tuesday Aug. 24-25, 2026  Salem Mass to Gloucester, Mass. 14 miles and 1.8 hours

Next stop on our historical tour of Massachusetts is the fishing village of Gloucester.  Can just about see to their harbor from Salem.  Short run up the coast.  Nice sunny day, little swell but barely noticeable.  Martha drove the entire trip.  My duties were to untie the line from the mooring ball in Salem and grab a new ball in Gloucester.   Had some apprehension about Gloucester's harbor.  There's an inner harbor and two outer mooring fields.  All open to the southwest which is the forecasted wind direction for the next two days.  No need to worry as we got a prime ball in the inner harbor.  Not too swelly unless one of the fishing boats comes through a little faster than the posted 5 mph limit - which they all seem to do.   All settled in by 1 o'clock. 

Hammond Castle outside of Gloucester. Built between 1926 and 1929 as a home,
laboratory and museum for John Hays Hammond Jr.  A prolific inventor
with over 800 patents for 400 inventions largely dealing with remote control. 
 He was also an avid collector of medieval artifacts. Now a museum.

Multiple lighthouses guard the entrance to Gloucester harbor

Old Manufactory Building across the harbor in Rocky Neck

Still an active fishing village with vessels of all shapes and sizes

Hail the free launch service for a quick trip to the town wharf and start exploring.  The Maritime Gloucester Museum is right at the town dock. Contains info on the shipbuilding and repair industry that supported the commercial fishing industry the town is famous for.  Ships from here went in search of cod and haddock on Georges bank off Cape Cod and up to the Grand banks off Newfoundland.  The city is considered America's first seaport with a history now dating back over 400 years. The town is still an active fishing port with vessels of every type and style - large and small and continues to have several processing facilities.  Gorton's Seafood of Gloucester has been in business since 1849 with headquarters and a processing plant still in town.  You know Gorton's by their iconic "Man at the Wheel" fisherman.  While growing up, many a Friday night meal during lent in our house consisted of their frozen fish sticks.  My usual plea to mom "Can I just have the mac and cheese please?"

View to the town wharf and the sailing ship Adventure. 
 Two smaller ones are used for daily tourist tours

Nice floating docks at the town wharf

Just not very forgiving when the tide goes out.

"Man at the Wheel" statue commemorated in 1926 in celebration of the
 towns 300th anniversary.  Gordons Seafood used it for their iconic logo.

Very elaborate city hall attested to the town's wealth

Fitz Henry Lane built this 3 story house in 1849 as his home and artist studio 
overlooking the harbor using the locally quarried granite.

Tuesday back into town and a visit to CAM (Cape Ann Museum).  Started over 150 years ago.  Reopened after a major remodeling. Information regarding the town's fishing heritage was expected but also found out they were famous for their granite quarries starting in the early 1800's through about 1935.  Their granite was particularly hard and used as cobblestones for street paving in many US towns.  The granite curbing you see in older towns historic districts was another product that came from these quarries.  All came to a screeching halt quickly as towns found paving streets with cement was quicker, cheaper and smoother

In the park where his home sits there is this statue of Fitz
depicting him working on a sketch of harbor activities.

Cape Ann (which includes Gloucester and surrounding areas) was also an active summer artists' colony.  The museum had a special display of artwork from three artists who worked closely during summers in the 1930's and 1940's here - Milton Avery, Adolph Gottlieb and Mark Rothko. Much of the exhibit focused on their sketches and paintings showcasing the local area but also showed how dramatically their style and paintings changed over the next few decades into large modern art pieces. I kind of found their development story more interesting than some of their artworks.  

Interesting statue of the Gloucester Sea Serpent.   Numerous sightings
 have been reported over the centuries with surprisingly similar descriptions. 

Early 1920's Milton Avery picture showing the impressionistic 
oil painting style favored by the art colony at the time

During the 1930's and 1940's his style had morphed to 
 watercolor paintings depicting time at the beach.   
By the 1960's he was painting large abstract canvases in bold colors.

The permanent exhibit they are known for is the works of Fitz Henry Lane. He was a local artist, built a granite house on top of the hill overlooking the harbor and was known for his finely detailed paintings primarily of ships and harbor scenes.  Most of his work was done from 1830's to 1865. I have a hard time understanding most modern art so really enjoyed close up inspection of his realistic art.  Seeing the detail and finesse of every brush line. 

Picture of Gloucester from across the harbor.  Town being cast in white light was
 a style he incorporated in numerous landscape paintings of towns

Some of his ship paintings were fascinating for the level of detail.
Every rope for the sails intricately laid out and finely drawn 

On first glance it seems like a landscape picture.  Then the 
sailor looking over his beached ship comes into focus.

Part of the museum contained information on local history. Two of the displays of interest were the carved Virgin Mary statue that once stood atop the catholic church between two bell towers.  She's holding a ship in her arm instead of the infant Jesus.  It was a very noticeable landmark for fishermen who saw her giving well wishes for a safe voyage or glad tidings at their safe return.  The other item of interest was the story of Howard Blackburn.  At age 24 in January of 1883, he was fishing off the coast of Newfoundland setting lines in his dory when a storm came up and separated him from the schooner Grace L. Fears.   He spent 5 days rowing in the cold open Atlantic before finally landing in Newfoundland where a local family took him in and nursed him back to health. Frostbite was so severe he lost all his fingers and several toes.  He eventually returned to Gloucester as a hero.  Unable to fish he opened a successful saloon, The Blackburn Tavern.  Growing restless, he sailed twice single-handed across the Atlantic.  Once in 1899 and again in 1901.  The 25 foot Gloucester fishing sloop Great Republic used in his second crossing is also on display.

The much larger than life hand carved statue of Mary holding a ship

The church now has a more durable fiberglass copy of the carving

Portrait of Howard Blackburn.  Diorama below him shows all the different
sizes and styles of sailing fishing boats used over the years in Gloucester

The 25' Great Republic used by Howard Blackburn on his second Atlantic crossing.   
Made it to Portugal in just 39 days.

A fun visit and productive use of the day.  About it for today.  Well, I did get a haircut.  After 3 months I was overdue as things were getting a bit bushy.

We never got any decent sunsets while here, so I'll leave you with one more of Fitz's paintings

Here's the detail from the bottom left corner

Journey for August 24, 2026

August 22, 2026 Salem, Mass.

 Sat. and Sun. August 22-23, 2026   Boston Mass to Salem Mass.  24 miles and 2.9 hours

More tight maneuvering to get out of our slip at Constitution Marina but we made it out without damage to us or anyone else. Always a good start to the day.  Weather isn't ideal.  Overcast, chance of light rain, winds from the NE.  Slow out of the no wake zone of Boston Harbor.  Follow aside a container ship out the harbor for a bit until he takes a turn to starboard out the main channel. We make a slight turn to port and head straight into a bit of short period swells. Knew it would be a bit rougher but thankfully a shortish run up the coast to Salem. 

Passing the megayachts on our way out at the downtown Boston marinas

Ever Fond veers off headed south for her next stop - per AIS, it's Baltimore

Get to the harbor which has a mostly NE facing opening so not flat calm but doable.  Call the marina for our mooring assignment and they send a skiff out to take us through the mooring field to our assigned spot.  Would never have found it ourselves as markings are pretty small.  Decent spot a bit further back in the harbor.  Get settled in, short nap and call the launch to run us into town.  Late afternoon so some things like the National Parks buildings are already prepping for closure.  Little walkabout and then sample flights at the two breweries in town.  Nothing overly impressive.  Back to the boat for dinner.

In the 1800's Custom Houses like this one collected tarrifs on imported goods.
 

Derby Wharf stretches over 2,000 feet into the harbor.  At one time
 it was lined with warehouses holding imported goods waiting
 to be counted or weighed by Customs employees.

The Narbonne House was built in 1675 and is one of 12 buildings
on the Salem Maritime National Historical Park property. Families lived
here until 1965 when it was sold to the Park Service

Into town Sunday for serious tourist duty. Seems like there are 2 distinct factions in town.  The history buffs and the witchies.  For history buffs this is the birthplace of novelist Nathaniel Hawthorne of "The Scarlet Letter" and "The House of Seven Gables" fame.  Both these houses are now museums.    Lots of other history as a shipping port, seafood port and industrial center. Salem Maritime Historic Site is a National Parks area which includes numerous buildings, a wharf, the sailing ship Freedom. Good job describing the heyday of Salem when it was a major import center of goods for the West Indies Company during the 1700's. 

The house of seven gables. 

Statue of Nathaniel Hawthorne.  Interestingly, he was shunned and left Salem
 to never return after publication of "The Scarlet Letter" where his
 first chapter gave a scathing portrayal of members of the Custom House
 where he was employed for several years.

Town turned to textiles in the mid 1800's and had a good run until the great fire of 1914 burned several mills down and displaced over 20,000 residents.  Most famous mill was the Naumkeag Steam Cotton Mill which made Pequot brand sheets sold worldwide. They rebuilt the mill and continued operations until the 1950's.   Building has been repurposed and still sits on the waterfront.  The textile industry never fully recovered as the business was transitioning to the south.  The Peabody Essex Museum is part history museum and part art gallery with fascinating displays. Started by several of the West Indies merchants to display artifacts gathered from the many cultures they crossed - especially in the orient.  These merchants were some of the first ones to gain access to Japan.  The museum has an actual 1700's Chinese merchant families compound on site - The Yin Yu Tang Home. Buildings, walls, courtyard - everything. The building was painstakingly disassembled in China, shipped here and reassembled.  Unfortunately, it was closed for some renovations, so we didn't get to see anything but photos.  Other exhibits included the history of Salem, the witch trials, Japanese Art room, and Korean Art room.  They also own and maintain numerous historical homes in town. 

Museum has a bit of everything such as this original N.C. Wyeth illustration 

And this Norman Rockwell painting

The Maritime Room was loaded with figureheads and other seafaring items

Town is obviously famous for the witch trials of 1692-3. For the witchies there's the Salem Witch Museum, Museum of Torture, Monster Museum, Dungeon Museum, Salem Witch Village, etc.   All great for tourism but just seems to undermine the actual atrocity of that period where 25 innocent people died. 

A sampling of the witchy crowd...you get the idea

The old burial grounds and the witch's memorial had plenty of visitors
 but was already closed for the day as we passed by

Back to the boat once we got chased out of the Peabody Essex Museum at closing time.  Walked through town snapping pictures of their city art works.  Whereas Plymouth had those seals, here they are a figurehead mounted on light poles around town. 

I actually find her face rather unnerving
no matter how she gets painted - it's the eyes!

 Dinner was leftover Chicken Marsala from La Famiglia Giorgio's with fresh veggies from Haymarket Market in Boston.  Followed that up with a decent sunset as rain and clouds finally started moving out.

Journey for August 22, 2026