Villa Roma - A Family Tradition

Welcome to the Villa Roma

Summer Traditions in the Catskills: A Week of Nostalgia, Nature, and Small-Town Charm

Every summer since 2008, our family has packed up the car and headed to the Catskill Mountains in upstate New York — a region once famed for its grand resorts, fresh air, and classic Americana charm. While its heyday as the vacation capital of the Northeast may have passed, the Catskills still hold a timeless magic for us. It’s not just a vacation — it’s a tradition.

We’ve been fortunate to own a timeshare unit, which has become our home away from home for a week each summer. Coming back year after year, especially since the kids were little, makes each trip feel steeped in nostalgia. Watching them grow up — from chasing frogs to now chasing Wi-Fi signals (though only slightly!) — has made this annual getaway something truly special.

Simple Joys & Classic Fun

What makes the Catskills so magical isn’t flashy attractions or packed itineraries. It’s the simple joys that keep us coming back. One of our favorite traditions is turtle racing — yes, actual turtles, numbered and cheered on as they slowly meander toward the finish line. It’s charming, hilarious, and endlessly entertaining.

Then there’s bingo night, which draws a full house and gets surprisingly intense. The stakes? A big cash prize — not a candy bar or a novelty keychain, but real money on the line. The room gets quiet during those last few calls, and the moment someone yells “BINGO!” is always electric.

But the true fan-favorite in our family is the legendary rubber duck race. Dozens of numbered plastic ducks are dumped down a slide and into the pool, where they bob and spin their way toward the finish line — and yes, there’s betting involved. It’s a ridiculous amount of fun, and Jessica has actually won the duck race twice — with the same duck! We now consider it her lucky duck and guard it like a family heirloom.

Rolling Hills & Moo-ving Moments

Jeffersonville Dairy Farm

One of the things we love most about the Catskills is the connection to nature. One morning this year, we watched a herd of dairy cows calmly heading out to pasture. There’s something so peaceful about it — a perfect snapshot of country life. The rolling hills and farmland are absolutely stunning, especially at sunrise or sunset when the sky seems to stretch forever. The quiet, open space is a welcome break from the pace of everyday life.

Catskills Cravings: Pizza & Pastries

No visit is complete without indulging in some of our favorite local spots. At the top of the list is Peppino’s in Callicoon, where the pizza is nothing short of legendary. The crust is thin and crisp, the sauce is packed with flavor, and it somehow tastes better after a long day of summer adventures. We never skip a stop — and usually, we come back twice.

Jeffersonville Bakery

And for our morning fix or an afternoon treat, we always visit the Jeffersonville Bakery. You can’t miss it — it’s a huge pink building right on Main Street. Their croissants and muffins are fresh, flaky, and delicious every time. The kind of place where the locals chat at the counter, the coffee’s strong, and the baked goods are worth the drive.

A Tradition That Keeps Growing

There’s something truly special about returning to the same place year after year. The Catskills may not be the glitzy resort destination it once was, but to us, it’s even better: it’s tradition, it’s family, and it’s ours. From cash-prize bingo and duck race victories to dairy cows and pink bakeries, every summer brings back memories while making new ones.

Here’s to another year of turtles, pizza, and lucky ducks — and many more to come.