On a typical day most of us drive through a dozen towns, maybe more. But how many of us can say that we’ve stopped, walked around or explored any of those towns to see what they have to offer? Probably not many. Even one rainy weekends where complaints of boredom are echoed, the odds are unlikely that we’ll take that time and simply drive around or explore a new place.
I know myself, I drive each day from Middletown to Essex without giving as much as passing thought to the towns I’m driving passed. Their enormous green road signs blur together in my subconscious as my mind wanders to the day ahead.
When I’m on the boat however, that’s a different story. I can search around on Active Captain for hours looking for a secluded or hidden harbor to explore (I even click around in harbors overseas, you know, incase I suddenly need to find an anchorage in Italy). In fact, it was during such a planning session that I spotted a small little Brewer marina a few miles north in a town called Deep River. Our current Brewer membership awards us two free nights at Brewer locations so I figured, what the hell, why not go check it out?
So with that we packed the requisite cooler, sheets, and pillows and cruised north. Boat traffic had dramatically dropped off since the leaves began to change color, so our hour-long trip north was pretty darn peaceful (a nice change of pace from our recent sporty trips across the Sound).

With plenty of open moorings in Deep River, we picked a nice spot off by itself and got settled in. The marina would prove to be up to Brewer’s high standard. There was a clean in-ground pool, clean facilities, plenty of propane grills for guests to use etc.
I recalled seeing that the historic Gillette Castle wasn’t too far from the marina and when I asked a dockhand how far it was he nonchalantly responded, “oh not far at all, go just around the corner and you’ll see it.”
And with that grossly undersold measurement of distance we hopped in the dinghy with its 3.3 hp outboard and went to go check it out. Now, the dockhand wasn’t exactly lying, you could see the castle from there, the problem was the giant castle looked like a spec off in the distance and motoring against an incoming tide had us motoring at a turtle’s pace. We plowed through our snacks and drinks before making it halfway there.
Against the odds, and the tide, we eventually made it to a small stretch of beach beneath the castle; things were looking up. It was an absolutely beautiful day and I wasn’t particularly in the mood for an indoor tour but again we figured, why not? We sprung for tickets and headed up to the towering stone castle for a tour.
We step inside the castle and hand our tickets to an overly enthusiastic guide. Ms. Peppy then says, “let’s just have you wait here a minute while the group ahead of you gets ahead.”
“Alright, is it a big group?” I ask.
“Oh, it’s a group of about a hundred seniors that are here on a bus trip.”
A long pause ensues before I mumble to Karen, “a simple yes, would have sufficed.” She of course rolled her eyes.
Now let me reiterate, it was a stinkin beautiful day outside; it felt like a July day. And I strongly dislike crowds. And I respect my elders just like I was taught to, but listening to the shuffling crowd complain, “Oh, that bus was too cold!” “You’re right Muriel, I’m going to say something to the bus driver.” “I thought it was cold too, Dorothy, much too cold,” well, that just wasn’t how I wanted to spend my Saturday. If we could just scoot ahead of them I thought.
And with that I dragged Karen passed what I’m sure were many interesting rooms until we were ahead of the group, finally. We walked through the next door, which ended up being the end of the castle, and you’re “not allowed” to go back the way you came. We had missed practically the whole castle. But I smelled the fresh air and wasn’t about to go back and hear more about the great temperature debate; I promised Karen we’d come back another day.
Back on the boat sipping a cold beer, I had no regrets. In the evening we walked about a mile into town where we enjoyed a great dinner outside at a barbeque restaurant called the Red House. We ate too much meat and cornbread, if that’s even possible, before making out way back to the boat. The following morning we’d enjoy a nice walk through the quaint little town that boasts only a handful of stores, and not much else. We ate breakfast at a popular little hole-in-the-wall breakfast spot called Hally Jo’s. It’s a happening little spot on a Sunday that seems to attract the entire town.
Too soon after we’d head back to Essex and our mini adventure in Deep River was over. Not only did the quiet little town provide a welcome escape after a busy week, it reminded me that if you slow down and look around once in a while you might just find a fun adventure hiding in plain sight.