August 28, 2026 Freeport, Maine - First Fog of the Trip!!

 Fri./Sat./Sun.  Aug. 28-30, 2026   Portland ME to S. Freeport ME 15 miles and 2.2 hours

Overcast morning. Slight 20% chance of rain.  Nothing showing on radar on my weather apps.  No hurry to leave but as soon as we dropped the lines a light drizzle started. Didn't last long but a harbinger of an interesting morning to come.  Quick 2-hour trip basically just following the shoreline northeast in protected waters to South Freeport. We're in the Casco Bay region.  Somewhat protected by scenic, rugged islands and outcrops making it the start of a favorite cruisers gunkholing area as we head north.  Trick is finding an anchoring area with shallow water, good holding, limited lobster traps and/or mooring balls, and giving protection from changing winds. Decided a mooring ball at Brewsters Marina in South Freeport would be best for our 3-night stay. 

Flat calm seas the whole way up made it easy to spot the smattering of lobster pots. As we were approaching Chebeague Island we noticed what we thought were buoys that kept disappearing underwater.  Finally realized they were seals.  Surfacing, sticking their heads up for a look about and then diving. Still haven't seen a single whale on the trip.  Not sure where all these whale watching boats are taking people.  Anyway, as we're passing by the opening between Long Island and Little Chebeague Island I'm looking over to my starboard to spot a cove that's supposed to be a nice anchoring area.  It is weird.  There is a thick fog bank covering that entire area.  We're making fun of the people anchored there who aren't moving due to the fog. " If they only knew they could cruise a mile out into open water and have these clear conditions we've had since leaving Portland". 

Fogbank hanging over the cove 

Moving out to this Windjammer boat at anchor in deeper water

Then starts to quickly dissipate about the time it reaches the ship

As they say - Karma's a bitch!  Not 10 minutes later we're looking at what appears to be a fogbank straight ahead. We get closer and closer until it finally envelopes us. Reduce speed, navigation lights on, radar on.  We slowly work our way towards Freeport.  Constant watch using our navigation apps to keep us headed in the right direction.  Surprising how easily you can get disoriented with no visual references.  Martha on lookout to guide us around any lobster trap buoys. I'm monitoring for AIS signals, radar blips for nearby islands, rocks and other boats. 

Looks like a decent day .... except for those funny clouds on the water
 to the right of the island.  Exactly where we need to go

Looking much more ominous as we get closer

Yup, we're  gonna get stuck in some fog!!

Tricky entrance into Harraseeket River passing Pound of Tea Island (so named because it was the price paid to the Native Americans for the nearby lands). Thankfully the fog eased up slightly as we enter the harbor area.  Easy grab of the mooring lines and we're all set.   Wind is being fickle today.  None earlier but now blowing 10-15 and constantly changing direction.  We seem to have pointed in every possible direction.  More weirdness all afternoon as we watch fog roll in and disappear at least half a dozen times in a 3-hour period. By evening weather is breaking, and clearer skies are beginning to shine through.

Pound of Tea Island.  Sharp 90-degree turn as you pass next to it.

Picking up our mooring ball as the fog continues to lighten

Then the fog was all gone as we swung around and looked at the marina

Fog rolling back in across the harbor AGAIN!!

Can't see the sun go down since it's behind the trees but it did a nice job on the clouds

Saturday, we woke up to clear skies, sunshine and cool.  Got down to 58 overnight so good sleeping weather. Should warm up nicely to mid 70's.  Take our time with breakfast.  Cook up a couple of eggs and finish off those Standard Bakery pastries from Portland.   Then finally get around to uncovering and launching the dingy since there's no launch service here.  We've been needing some fuel in the dingy and have been waiting for a dock with Marine-Tec Ethanol Free gas.  Finally found it here, so topped off the tank.  Tie up at the dingy dock and hope we won't be sitting in mud when we return at low tide.  Graphs show an almost 10' tide swing here. We watch the folks pouring into Harraseeket Lunch and Lobster on the waterfront.  Open every day but only from 11AM until 4PM. Not near enough parking.  Cars are lined all the way up the street.  Lobster rolls obviously, but they also have a lobster pound.  Pick one out and they'll steam it for you right there.  We'll give them a try tomorrow.   Uber finally arrives to take us into town which is about 3 miles away.  Freeport is home to L.L. Bean.   They originally started as a shoe manufacturer which was the primary industry in town at the turn of the century.  He decided to diversify into outdoor clothing and opened a small retail store.  The rest is history. Headquarters still here along with a huge retail complex.  Over the years more retail outlets have opened stores making the town a shopping destination.  Back at the boat we watch as the last of the full moon crosses the evening sky.

Returning from town the tide is out, land is exposed, but we're still floating.

Safety First! Putting on the inflatable life jacket.

Moonrise over the water.

Nothing much on the agenda for Sunday.  Overcast day with threatening sprinkles most of the day.  They only materialize occasionally. Gives us an opportunity to take the dingy over to the marina docks.  Exchange a few books at the marina office then head to Harraseeket Lunch and Lobster for a late lunch.  They have a pretty varied sandwich menu, but the obvious star of the show is lobster.  Got to see their large holding tanks, scooped out a netful for us to see and even grabbed a jumbo out of the tank so we could see a big one.  Opted for the lobster rolls. Who wants to mess with all that work of a live one when you can just sit back, eat and enjoy? Meat was incredibly tender - perhaps do to having them live and fresh on site to start.  Finished that up with a dingy ride around the harbor. Big yacht pulled in yesterday and I wanted to take a look.  Last of the day spent discussing options for tomorrow's trip, doing some reading and generally just chilling.  Brought back a homemade whoopie pie (Maine's state treat) to the boat for dessert.  Not an actual pie. It's two chocolatey cake rounds with a massive amount of cream filling between.  As they say: When in Maine - eat like a local.

Had to look it up after many wrong guesses. So. Free. Me. - South Freeport Maine

Scooping up a net full of very lively "bugs" from the lobster tank

Lobster rolls Maine style - light mayo dressing

Goodly number of lobster boats like these throughout the harbor. 
 Mega yacht Legacy in background. 2003 127' Burger.  $8.5MM.

Journey for August 28, 2026

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