I considered just doing a copy & paste of the same stops we made in 2014 at the start of our trip to bring Ortolan back up to Maine, but that would be way too lazy of me. Rather, you will continue to enjoy more photos and less verbiage.
Amazingly we did depart Deep River on August 1. We soon realized how protected the marina is (well, we did know that) when we stuck our little cat noses out into Long Island Sound after a ten mile trip down the CT River. The Old Lyme Draw bridge tender must have popped a happy pill because he opened up for us in between trains. We thought he’d give us a hard time with our height; the height board read a skimpy 18ft, which is what we are. Not taking any chances we always want 19ft.
Wind and waves on our bow quarter was less than pleasant but hey, we needed a reminder of how it can feel “out there”.
In the above photo you can see people milling about tables near the building. They are selecting free Block Island Wind Farm T-shirts and Frisbees. Yes, we got some too. One or two wind vanes were up and we got a good look at them on our way east to Cuttyhunk.
We spent several nights on Cuttyhunk on a comfy inner harbor mooring. In summer if you want a town mooring, best to get there by 1pm or be prepared to anchor (not good holding) or take a mooring in the outer (not as protected) harbor or anchor out there. We like calm and not squeaky.
Our next stop was a new spot on the south (Vineyard Sound) side of Nashon Island, also part of the Elizabeth Island chain, named Tarpaulin Cove. Low winds out of the north that morning would find us snug in that cove and when the wind switched to SSW we’d be anchored in the lee of Menemsha.
After lunch we headed over to anchor in Menemsha Bight near shore and close to the jetty entrance. President Obama and family were in town. As best we could tell we did get within two miles of the house they rented. Any closer and the Coast Guard would have been mad at us.

Guarding the President is serious biz. We heard a few boats call on VHF to be sure they could enter the harbor, even though these guys were a mile away.
We spent two nights anchored. More beach combing. More great seafood. More cute shops. Lots of chillin’ out. You know that song, “Working on her tan”? Me.
Next stop Lake Tashmoo. Last time there, in July 2014, we had the excitement of s/v Julia Lee. I am happy to report that she’s since been soundly repaired and better than ever. How do I know this? Click What happened to Julia Lee.
Naturally the excitement this visit involved what else- a sailboat. sorry guys nothing personal. First we had teeny incident #1. Well we didn’t have it but we did help to cause it. Gulp. Not our fault, really. Lake Tashmoo was a lake until the skinny section by Vineyard Sound broke through in some storm. Sand loves to move around and a narrow opening means more current and thus more force to move sand. In other words, enter with caution shoaling occurring. But maybe not in the same place as last year, or the year before.
We read all about it in- yep you got it- ActiveCaptain. Wanting to be our usual cautious selves we thought best to not arrive at low tide. Wanting to arrive ahead of the approaching rain, and not able to get an accurate time for tide, we managed to arrive pretty much at low. So we expected the depth alarm to sound (it’s set for 6ft). Enter favoring the “green side” which in this case means left, but then once just inside lord knows what you should do.
As we enter the lake a sailboat hails us, Russ answers at the upper helm before I can grab the lower mic. I knew why and I also knew that the depth sounder was reading 6ft and going down, and Russ needed to pay attention. So he tells the boat the lowest reading he saw was 6.2ft or so but by then even though we are moving slowly, we get a reading of 5.7ft; fine for us maybe not so fine for a sailboat. We anchor, it rains, we hear a boat hail SeaTow. Uh oh. They are aground just inside Lake Tashmoo. Gee, do you think? A short time later they got off and canceled the assist call. Whew.
Next we witnessed more impressive incident #2. The area where most boats anchor, because that’s where the moored boats aren’t, is loaded with eel grass. Not conducive to getting a lasting hold. We watched one boat bring up an anchor LOADED with eel grass and yet another had only a teeny strand. We’d anchored between these two.
Ok I’m getting to the story. Sailboat with older couple makes several attempts to anchor next to us. Russ shares what we learned about calling the Pump Out boat (and works with the Vineyard Haven Harbormaster in the Lake) to request a mooring. Not only is it poor holding but “they” want to replenish the eel grass for several environmentally friendly reasons. If we had known to call, we too would have been placed on an available mooring but since we were already well anchored, we should stay put. Oh but only for three nights, then “they” want you to leave.
Nope, the sailboat captain doesn’t call for a mooring and instead somehow (we missed seeing that exact moment) gets tangled up on the anchor line of a small power boat. He topples overboard. The Pump Out boat races to the rescue and returns the man to his boat (now wearing a PFD) where his wife (I assume) remained at the helm. The Vineyard Haven Harbormaster arrives. The sailboat captain dives in to try to untangle the anchor line that’s become wrapped around his rudder- thus keeping the boat in place. No luck, so the line is cut and a float attached. The sailboat gets a short hip tow to a mooring, the small power boat gets brought to one also since his anchor line was cut. The anchor is retrieved and returned to the power boat.
By this time we are incredulous and yes, feeling a bit ..– no not really so I won’t say we were. We’d seen the power boat’s owner paddle out on his SUP so now what happens when he paddles out and his boat isn’t where he’s been anchoring probably all summer? No worries, things worked out.

Sneak peak at the Wagner’s new house. Their house on Elizabeth Island (Bahamas) is named Top of the World. Maybe this one will be Pride of the Lake.
From the Lake you can walk into Vineyard Haven and enjoy shopping, dining (Black Dog), sightseeing and people watching. But I am sad to report that you cannot visit the wonderful bead shop as it has moved to Virginia Beach.
Friday night- our third and final allowed night, saw all moorings full as boats were having no luck with anchoring and the wind was due to blow with a possible T-storm. One boat dragged. We watched our drag alarm (a visual app on the iPhone); puzzled that it seemed to show us further from the anchor than ever. With one mooring available ( we’d watched someone leave a short while back) we upped anchor and grabbed that ball. Precious little eel grass. Doubt we were dragging, but now we’d sleep well. Saturday, off to Edgartown.
The Vineyard is busier on weekends and we try to not make a move into a popular mooring field on a weekend day, but since we had to leave Lake Tashmoo, Edgartown with its large mooring field edged out Oak Bluffs. Again, arrive early enough for best luck. We did. It worked out and we stayed five nights. More shopping, a long beach walk, more great dining and plenty of R&R.

Seagull joins us for breakfast in Edgartown. The Boch mansion straight ahead- some hotels aren’t that huge
After Edgartown we had a favorable wind/weather day to backtrack to Cuttyhunk and a decent day to go from there to Stonington, CT. I noticed a pirate flag on the boat next to us and really had to smile at the name. Note the sailboat on the right. Look familiar?
This awesome ship was anchored in Cuttyhunk’s outer harbor
So was this lady.
Next stop: Stonington. More seafood, more great dining, a bit of shopping and some R&R time on a windy day.
Our plan was to return to Chester, a town up from Deep River, for the dreaded haulout. Long story short (yay!) we ended up changing to Mystic; but would that be for the best??