August 31, 2026 Anchoring In Maine's Casco Bay Area - Snow Island

 Mon.-Tues. Aug. 31-Sept. 1, 2026  Freeport, ME to Snow Island   20 miles and 2.7 hours

Report on the Whoopie Pie for dessert last night.  The thing was huge.  We cut it in half and then quarters.  Martha and I each ate a quarter.  About all we could do.  Will save the other half for another nite.  It was pretty good.  Cake was moist and chocolatey.  Filling was a buttercream style.  Some of them are marshmallow based which we don't think would be as good.  I'm trying to picture a school aged kid getting one of these pies as a "treat" in his lunch bag and eating the whole thing. Talk about a sugar rush!!!  

Whoopie Pie - the official state treat of Maine

Buttercream filling on ours - some have a marshmallow creme

No skimping on the buttercream here

Enough about Maine's official state treat - on to cruising details. We like these planned short trip days where there's no hurry to get going.  Took our time hoisting the dingy back onboard, had a little breakfast, dropped the mooring ball lines and headed over to the marina dock for a pumpout. Martha at the controls trying her hand at docking with a little more challenge than usual.  Wind blowing at the bow but current pushing at the stern. Normally we'd dock into the current but the pumpout fitting is on our port side that needed to go against the dock. Working both the breeze and current while docking was a first for Martha. Wisely took an extra maneuver to safely back away and re-group before making a successful second approach and eased it right into position.  Good job Martha!!!

Pumpout dock straight ahead. Spin 180 degrees and lay her up on the port side 

Maine's best cruising grounds are broken into 4 sections.  Casco Bay starts around Portland and goes east for about 20 miles, The Midcoast with Boothbay in the center and perhaps 15 miles wide, Penobscot Bay about 25 miles across with Rockland and Camden on the western boundary, and Mount Desert Island Region about 25 miles across with Bar Harbor at its center and Acadia National Park completing it to the west.  That's as far as we'll go.  The coastline continues northeastward but with much less development terminating up the Bay of Fundy with it's crazy 20+' tides.  

Tending his lobster pots

Plenty of lobster fishing boats out and about up here

This starts basically a week of anchoring out for us.  First stop is Snow Island.  Fight the incoming tide as we exit Freeport and make way through the narrow entrance.  Then nice cruising southwest winding around and between numerous islands before finally heading out into the ocean.  Long period swells creating nice gentle rollers. Make our way around the tip of Harpswell Island and then Bailey Island, before heading north inland and up Quahog Bay.  Turn in behind Snow Island to an anchorage we visited during our Down East cruise last year that we had given high marks.   Nice protected and picturesque anchorage.  Came in at close to full tide with 10' of extra water.  Couple of other boats here and a few more joined us for the evening but plenty of room for everyone.  Good news is lack of any lobster floats in here since water is so shallow.  

Incoming tide and turbulence going out the Freeport channel 

Nice private island, house and beach

Sailboat squeezed in between two islands.  Braver or dumber than me?? 

   

Drone shot of As You Wish resting easy in Snow Island anchorage

Birds eye view of the anchorage as evening falls

Martha doing her best to become a certified drone operator

Surprising to see some serious rock ledges materialize as the tide went out.  Read one review where an anchored boat wound up sitting on the rock ledge when the tide went out overnight.  Had to wait for the next high tide to remove it.  Nothing much to report whenever we're at anchor.  These are primarily fairly isolated areas but good for rest, relaxation, recouping, and reading. 

Couple of small islands protecting our cove

Same scene as the tide was going out. Good reminder to watch those navigation
 charts carefully - never know what lies just a few feet below the surface

Birds eye view of the setting sun

Water level views of the sunset

Journey for August 31, 2026

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