How To Spend A Day in Connecticut

Checking Off Connecticut

Connecticut was much like Delaware, in that I had no clue where to start to make the state worth visiting. We were doing the drive from Atlantic City in New Jersey, up to the Eastern State Penitentiary in Pennsylvania, across Connecticut and into Cape Cod, Massachusetts for the night. It was quite an aggressive day plan, but that was goal.

Fall River Connecticut
The Drive

I decided that the best way to check out the scenery in Connecticut was in Gillette Castle State Park. The drive to get into the park was spectacular in itself. A secret woodland hid serene country houses with grass greener than the White House lawn in its autumn foliage. These were some of the best colors I’d seen in any of the eastern states yet and there were no other cars on the road to take away from the peace.

Aerial View White Home
The Hidden Homes

We rolled over an old stone bridge, crossing a small pond. Here, the colors reflected in the water like the mirror pool in Luray Caverns. The only movement appeared at the dam, where the still water tipped over the edge, gliding down until it was fast enough to be called a brook. We continued down the backroads until we arrived at the entrance for Gillette Castle State Park.

Gillette Castle State Park

I couldn’t believe how many cars were here. This was the busiest park I’d ever scene. Families with pumpkins on their heads and matching flannels were taking portraits in the autumn leaves. I followed the flow of people winding up the cobblestone path until low and behold, the castle appeared in all of its glory. This 148 acre estate was built by actor, William Hooker Gillette, who passed away in 1937. Though his legacy clearly remained after the property was bought by the State of Connecticut in 1943, it looked like it was in the wrong country. 

Gillette Castle
Gillette Driveway

Instantly being transported into Ireland, I looked up at the stone tower. With twenty-four rooms inside, I began to wonder just how many friends this guy had. The magnificent estate overlooks the Connecticut River, gifting a grand panoramic view to anyone who visits. A few boats jetted through the wide river below, slicing the body of water into sections.

Gillette Castle Drone View

As you may have guessed, the fall foliage here was even more fantastic than the woodland drive. Up above, I could see the hills for miles, dotted with every variation of red, orange and yellow that you could dream of. It was perfect. Much like my experience in Delaware, I was pleasantly surprised. However, I wasn’t done with Connecticut just yet; we had one more mystical city to check out (hint, hint).

A Sunset in Mystic Seaport

Mystic Seaport was less than an hour down the road and I was hoping to catch a good sunset. As we turned off the highway and into town, I was shocked. Again, there were SO many people here. We could hardly drive the car down main street with all of the pedestrians running back and forth to the boutiques and breweries (I know, quite the combo). A sign stating there was a film festival this weekend made me realize what all of the commotion may be about. Eventually, after a game of dodge, duck, dip, dive and….dodge, we arrived at the marina.

Mystic Seaport
Mystic Seaport

This was much less pedestrian-friendly than I’d pictured in my head and the sun was gobbled by a cloud before making its grand debut over the horizon. I resorted to reading the boat names for entertainment instead, wondering how someone possibly came up with the idea of calling a boat Jalapeño. Nonetheless, I was inspired by it.

Checking Yelp, I found that there was a well-rated Mexican spot nearby and we beelined it back into the crowds to see it through. Maybe the restaurant owned the ship and used it as inconspicuous marketing. If they didn’t, they owe someone an affiliate link.

A Dinner of Reflections

I sat back, with carne asada in one hand and a paloma in the other, thinking about how, of all of the places in the world, I ended up in this small town at their only taco joint, watching the moon rise tonight. I think that’s the beauty of travel— it’s unexpected.

You can make an itinerary as detailed as possible or book flights months in advance, and still have no clue where you’re going to end up, when you’re going to be there, or who will be sitting by your side. I took this thought with a grain of salt…or a rim of salt, I suppose, as we drove back off into the moonlight, heading to our final destination if the day: Barnstable, Massachusetts.

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