
There was a big question in the air about what we’d do the weekend after our wedding. We had the kids set with their own plans, but Jocelyn and I waited until the last minute to decide where we were going. It was Labor Day weekend, so prices were steep, and that added a little apprehension. Still, we knew we wanted time together, just the two of us. After working a wedding in Alexandria Bay earlier this year, I’d been reminded of the simple beauty there and what it meant to me. That settled it: the Thousand Islands would be our place.

I found the 1000 Islands Hart House online and immediately connected with its owner, Jamie. He clearly cared not only about running a welcoming bed and breakfast but also his guests experience and about Wellesley Island itself. When we arrived Saturday night, we were greeted warmly — well wishes, cold drinks, and plenty of tips for how to spend our time. Each room carried its own theme and character, and the house itself had history. It was once part of Hart Island’s Boldt Castle before the Boldts decided it didn’t fit and moved it across the water. A smart decision, because this place was worth saving.

I made dinner reservations for two restaurants that looked promising both for celebration and for gluten-free options. Our first night we sat outside at The Boat Yard in Clayton. The reviews praised the flavors and atmosphere, and in practice it mostly held up. The staff wasn’t as confident with the gluten-free menu as we’d hoped, but we landed on some great dishes. The Black and Blue Nachos were unique and piled high, the Garlic Chicken hearty, and the Mediterranean Platter had unexpected depth. The star, though, was the platter’s hummus — smoky, rich, and unlike any version I’ve had with Mediterranean food before. The Boat Yard was a great choice for flavor as well as starting to feel the atmosphere around us.
The next morning brought a surprise. Over breakfast at the Hart House, Jocelyn spotted a familiar face: one of her kids’ former teachers, staying there with her husband. The four of us ended up laughing through the meal, sharing stories and coffee as though we’d planned it. I looked across the table at my wife, grateful again for the joy she so naturally shares. These are the small moments that remind me how lucky I am.

We spent the day exploring, guided by Jamie’s recommendations. Thousand Island Park was our first stop, also the site of our second dinner reservation. Along the way we ducked into The Guzzle, a boutique-style grocery and coffee shop that doubled as a game space and mini arcade. I grew up with pinball machines, so seeing an old baseball-themed pinball game made me light up. Jocelyn, meanwhile, reminded me she’s the real gamer in the family by absolutely crushing me at pool. Places like this — small, quirky, alive with character — are what make travel so memorable.
Later we drove down the St. Lawrence to a few smaller riverside towns. This was Jocelyn’s suggestion based on her own history. Her grandparents had a place nearby, and she has fond memories of summers spent exploring. Walking through Cape Vincent and Clayton with her as my guide was like stepping into her nostalgia. The shops were small, the people friendly, and even at the end of the season the towns felt vibrant. I love connecting with people when we travel, so that energy gave me a spark.
We had high hopes for dinner at the Wellesley Hotel. The building itself felt like a piece of history — polished woodwork, simple design, a reminder of a time when grand hotels filled Thousand Island Park. Most of those are gone now, victims of fire or time, but the Wellesley remains as the last in that line. Walking in, it carried the kind of weight that makes you expect something special.

The start was promising. We shared Truffle Pomme Frites, crisp and fragrant, though we quickly learned each bite needed a good hit of parmesan to really sing. Still, it set the tone for what we thought would be a refined meal.

For mains, we ordered steak with Gorgonzola cream sauce and tried the Korean short rib. Both sounded perfect for a celebratory evening. The flavors were there — that sauce in particular was superb — but the execution left us wanting. Her steak wasn’t cooked to order, and the sauce portion was too light to balance the dish. My plate was even more unbalanced: one small rice pancake, a tiny streak of chimichurri, and no vegetable to round it out. It looked elegant, but it simply wasn’t enough to stand as a main course.

The kitchen clearly had the right ideas on flavor, but the proportions missed the mark. At this price point, and with the elegance the Wellesley represents, we expected more.
And yet, as we lingered in that old dining room, I found myself less concerned with the meal and more with the company. My bride and I laughed at the mismatched plates, shared what worked, and left with a memory that will last longer than any entrée. The hotel stands as a relic of history, but the real treasure that night was time together.
Our last morning was quiet. Another breakfast at the Hart House, a few more goodbyes, and then we were on our way. We left knowing this little slice of New York was one we’d return to. The Thousand Islands have a calm and charm that feel exactly right for us. My new bride and I need that, and I can’t wait to share it again — with her, and with those we love.

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