Sailing Downeast - First Stop: Jewell Island, Casco Bay

Preface: Just a heads up, I'm not a sailor, not in the least bit. I do love being on the water though & my landlords happen to own a beautiful 38' Alden Challenger that they've cruised the Maine coast & beyond with for the last 50 years. These two, Dan & Sarah, have been like grandparents to me... Dan was who I went to when I needed a second opinion at the time of purchasing my own boat. He spent hours working on my 1958 Evinrude to get her running, he taught me how to winterize her in the fall & I can't even begin to tell you how many cans of oil he's given me for the numerous times I've forgotten to add oil to a newly filled tank of gasoline for my outboard. Sarah, has always played an encouraging, positive role as well & we've spent many hours working on our gardens together. So when they brought up the idea for us all to go on a sailing trip up the coast of Maine (otherwise known as "downeast") I couldn't have been more excited for the opportunity. 

Dan & Sarah knew my passion for being on the water & exploring the Cape Porpoise islands (which one of these days I'll describe the amazingness that each one of those islands hold) so they wanted to pack a week full of visiting some of their favorite spots/islands along the Maine coast. The only request I had was to visit Jewell Island due to a bunch of research I had previously done on it while helping a friend with a research paper. The island's legends of buried treasure by Captain Kidd & Indian raids & its beaches being haunted by bootleggers are what initially peaked my interest but after reading most of the History of Jewell Island by Peter W. Benoit, my desire to visit this spot specifically was based on much more than folklore. 

First off, the island was described as having some really interesting terrain features. Secondly, in the 1920's through 1940's the island had been used as a WWII military reservation as a primary defense against enemy motor torpedo boats & a secondary defense against aircraft attack. Multiple buildings were constructed & outfitted with heavy duty battery/gun power to take down those potential threats.

The book stated that many of those buildings were still standing today & the island, now being under ownership of MITA (Maine Island & Trails Association), had paths & campsites throughout for visitors to explore & use. Pretty cool right?!

And so my adventure begins...

We set sail Sunday morning, the 21st, leaving from Cape Porpoise harbor. Unfortunately, wind in our faces meant no sailing, just motoring so it took a couple hours to get there. After about 15 nautical miles & passing quite a few islands & lighthouses, Jewell Island was before us.

Approaching Jewell Island from the southwest. 

We pulled around the small strip of land on the west'ard side into a nice protected cove (otherwise known as Cocktail Cove). Upon our approach, we could see many sailboats, catamarans & powerboats anchored here even with it being around 3pm on a Sunday. This spot is a great hangout though for anchoring & swimming & it always holds water no matter where the tide is at. We anchored up after finding a spot to park it & decided to get over to the island to do some exploring.

A portion of Cocktail Cove at low tide. 

On the easterly side of the island is another interesting feature called The Punchbowl. Here's a little snippet that explains in more detail the military use of the island. 

The Punchbowl history. 

The Punchbowl situated on the easterly side of the island. 

This spot on the island is just a short walk; starting at a campsite overlooking Cocktail Cove that leads you down a path through the woods, past a couple of privies. What you see above is a beach on the left containing lots of drift wood & rocks & probably plenty of seaglass too. It's shaped like a bowl, hence its name, but I wouldn't suggest swimming in that water. This was at low tide & stagnant water with low depths tend to get a bit icky.  None-the-less, an interesting spot looking out over the ocean & if you're able to hangout here on a less busy day, it would be a neat place to picnic & relax.

Onward we went, next to the 1st & largest tower, 8 stories with gun emplacements & incredible lookouts. 

8 story tower, Jewell Island. Battery 202. 

Then the next tower, about 1/2 the size of the first one but much sketchier of an ascent going up...

Tower 2 - AMTB M3

All throughout the island are small buildings too, some still standing but barely & lots that were just old foundations & chimneys. The next really interesting part was the underground structure (most definitely need a flashlight to explore this & be careful of holes in the floor... not the best place for kids) which I think was set up as the fire control station with office rooms & such. If you go into the main door (2nd picture below) & head directly straight down the back, when the passage way stops making you go either left or right, go left. 

The left passage will take you outside to a really large gun encampment (first 2 pictures below). The 3rd picture is the exit we just came through to get to the gun encampment.

Most of the island is covered with trees so most of the exploring actually feels less like an island & more like hiking. We did a total of 3 hours of walking around & by the time we returned to the cove where our boat was anchored most of the other boats had cleared out for the evening.  

We sat down for dinner on the boat that night & enjoyed an amazing full moon-rising/sunsetting occurrence. Definitely not something you experience all that often. (The two pictures below were taken at the same time that night - one being our view on the eastern horizon & the other being the western horizon.)

Full moon rising in the east & sunsetting in the west. 

Overall Jewell Island was a pretty cool place, definitely worth exploring. It's not exactly an island to "escape" to, although there were coves tucked away on the southern side that were more private. 

So, Day 1 down, 7 more to go. I think you'll find it very interesting to see how completely different each place was that I visited. Keep posted because there will be more to come very soon!

And as always, thank you for reading & I'd love to hear what you think! Just leave a comment & feel free to subscribe to stay updated with new blog posts.