When I was a teenager, my family used to spend a week at the end of the summer in The Hamptons, or Out East as we called it. Growing up I never thought it was fancy, just a faraway place with a smattering of stores, some gorgeous boats, a few good restaurants, and a relaxing summer vibe. When my son Matty was young, I continued the tradition of taking him with me Out East at the end of the summer after he returned from camp.
Matty looked forward to the double fudge brownie ice cream in those huge homemade waffle cones and thick chocolate shakes at Big Olaf in Sag Harbor, great shopping at Blue and Cream in East Hampton, bacon, egg and melty cheese sandwiches from Schiavoni’s, lazy days by the pool or on the beach, hilarious competitive shopping games at Kmart to pass the time on rainy days, late night snack binges at 7-11, and driving around with the windows down and the music blasting as we sang together in the car. As he got older and started working during the summers, I was brave enough to venture Out East by myself.
The first time I booked the trip without him it was to be my first solo vacation ever and I wasn’t the least bit nervous. I told a few people at work that I planned to go unaccompanied and they asked a million questions. You’re going alone? Not with a friend? Won’t you be lonely? You’re not meeting people out there? Is a group joining you? Yes alone, and it’s just me! Why was that so hard to believe? I enjoy my own company very much and I was excited for the adventure. I’d been there so many times, I knew the lay of the land, and I was thrilled to do what I wanted when I wanted. And it couldn’t have gone better. I woke up early to run. I sat on the balcony to pour over the local magazines. I went to all of my favorite farm stands. I took the ferry to Shelter Island and sat on the beach reading a book. I napped at 3 in the afternoon. I saw the gorgeous sunsets right over the harbor. I engaged in a little retail therapy. I was able to recharge and relax. And of course I visited Big Olaf for their amazing ice cream. It was absolute heaven!
So it became a habit. Every summer I would plan a week for myself to go Out East unescorted, and I loved every single trip. I embraced the table-for-one mentality, comfortably dining al fresco to enjoy a decadent lunch. I liked browsing the small towns, stopping to sit and people watch or shop like I was on a mission. It was a huge dose of healthy selfishness. COVID obviously put a wrench in my annual plans and I haven’t taken a solo trip since the summer of 2019. But I was so proud of myself for venturing out and leaning into the quiet peacefulness of being with my thoughts, and a good book, and quite often a freezing cold milkshake Big Olaf style.
So on this unofficial last day of summer, I hope you enjoy every ray of sunshine, every mouthwatering bite of deliciousness hot off the grill, and especially the company you’re with. But if per chance you’re alone, well then lucky you! Make the most of it while it lasts– a table for one definitely has its advantages.
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