To be honest, when I first arrived by car, in mid-July 2019, to the lovely hotel estate of “Baron’s Cove,” where I’d be staying for the next three nights, I was entirely surprised. The grandeur, the magnificence…all while still being so proximal to everything else you’d ever want to be close to while on vacation—like a town, nightlife, theater, restaurants.

            As the shuttle van pulled into the gravel driveway of thissuperb hotel on that first day, I immediately noticed how close it was to the waterfront and to the docks, as well! While the proximity to the life of Sag Harbor is paramount, I came to find that Baron’s Cove also provided beach service to its guests. For most of any day, a regular shuttle is offered to take guests from the hotel to any beach, and back.

            But before physically arriving to Baron’s Cove, I had been told of the many amenities the inn included. After hearing about them, I assumed that the hotel was located far from the actual town and from Main Street of Sag Harbor. “There’s no way this hotel could provide a large heated salt water pool, a yoga room/fitness studio, bars, a tennis court, and a spa all on a property that’s within walking distance to the waterfront and the town,” I remember thinking. 

            I really didn’t want to have to walk that far—was my real concern before getting there.

            But man, my thinking was way off…and thank GOD it was.

             The truth was that all of the classic facilities and comforts existed right there, right on the one tight lot. All of those amenities were exactly where the shuttle van dropped me off. An excessive amount of walking wouldn’t be necessary.

            I knew it; I was on vacation!

         I also noticed a large number of people that were staying at the hotel, but who were already enjoying its numerous amenities. People were all around the front of the place when I first arrived—in the pool, by the pool, on the porch, in the lobby. Because I was the newest arrival and was already unfamiliar with the setting, I figured that all the guests already knew each other, too.

I was entering a massive summertime celebration that I was on the outside of…or so I thought.

            But I was wrong—about them all knowing each other. 

            But, summertime celebration?

         Why, yes. It was definitely that.

            And as I got closer, I finally saw the forest for the trees. Everyone adored the sun, the pool, and the summertime season in each of their own factions—from individuals, to couples, to families with young children. That’s what I was seeing from a distance. Don’t get me wrong; there were still professional and social groups who’d decided to take their big summer vacations together. As these large groups of partying people existed too, I was probably most intimidated by them. I always envy seeing the groups of friends. 

How many of us feel alone because we’re on the outside of a large group?

Because I was not in the company of a group, much less a single other person, I didn’t have friends to protect me. I didn’t have others to rely on, to talk to, to defend me, to vouch for me, or to even get me a drink. I had none of that.

            But what I learned from watching these groups for several minutes was to decide to take matters into my own hands. I met with an old family friend, who I’d known previously, on the porch of the hotel. This older woman is Tucker and her late husband had attended the same university as my own father, and her daughter went to the same college as my oldest brother. Today,Tucker happens to be a prolific historical nonfiction writer whose books, for the most part, chronicle the history of Sag Harbor, the very place where I was! She gave me suggestions on where I could go in town and on the shore, during my very short stay, butto do my own thing that night.

            That evening I decided to forego a “silly” comedic jazz show at the town’s performance space, as Tucker had recommended, for a walk down Main Street. I was able to buy Tucker’s book, Images of America: Sag Harbor, at the local bookstore. Later, I was able to dine at the bar/restaurant of my choice. 
         Dining alone is really when you can be most resourceful. Finally you’re forced to branch out and meet new people. 

         Eating alone allows you to become engaged with world around you.

         Even to ask a simple question of the staff, such as, ”Which dishes would you recommend,” or to ask your fellow diners, “Could you please grab me a napkin from the pile next to you,” can go a long way to affording you a good night and a pleasant conversation no matter where you dine.

            That first night, I behaved like a Goldilocks character, popping my head into several different restaurant bars, determining “No, that one’s too dead. That one’s too crowded, and finally, this one is just right.” 

            And it was. 

            On my first night, which was a Monday, I dined at Page, a busy bar/restaurant with a casual, and stylish, vibe located right on Main Street. And I thought I was also spying a celebrity at the bar there. Way to kill two birdswith one stone, I thought. Sag Harbor is where celebrities come to live normally. I get it. I’ll dine next to one,or so I thought.

            In the end, it turned out I was mistaken about the sighting, as the celebrity I was thinking of had died two years before, so in spite of appearances the woman I spied at the bar was not Carrie Fisher. Despite mistaking identities, I was right about choosing where to have dinner. The food was delicious, and I became fast friends with the ladies I met at the bar that night, including the Carrie Fisher look-alike. After dining next to them that first night they invited me to dinner the following day, and then to the beach on Wednesday.  

            Between that lovely group of women taking me under their wing and the exceptional amenities provided by “Baron’s Cover,” I was never without something meaningful to do.

            On Tuesday morning at 9am I participated in a yoga class at my hotel taught by a seasoned and venerable instructor, Karen. And on Wednesday night I had the pleasure of again seeing Karen—but this time in the lobby of the hotel where we got to listen to the jazz being performed.

But all the while, no matter what occurred inside the walls of Baron’s Cove, there always existed rocking chairs on its front porch. From the first day, when I sat in those chairs to catch up with my longtime family friend to the last night when I got to watch a breathtaking sunset lower across the docks on the water, I knew I’d be back.

            And just like that…

            My tradition began.

You heard it here first, folks! 

My annual pilgrimages to Sag Harbor, N.Y. started in July 2019 and will continue indefinitely.