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Let Your Preschooler Plan Your Trip | T+L Family

Back outside the entrance to the theme park is Hershey's Chocolate World, an ersatz chocolate-processing plant with the kind of do-it-yourself exhibits found at so many company headquarters nowadays. Still, the vats of molten chocolate and candy at every turn go a long way toward making this one quite palatable. Lunch was at the factory's Kit Kat café, where Alex guzzled chocolate milk between yawns—and Joanna and I decided that a straight shot to Pittsburgh would be in order. There's certainly plenty worth seeing in western Pennsylvania, but a high-speed nap on the Pennsylvania Turnpike seemed more appropriate than meandering on country roads.

After a couple of hours on the highway, with four long, dark tunnels through the Appalachians as an exciting distraction, we aimed for Kennywood, one of the nation's oldest amusement parks and a National Historic Landmark. You'll think you're lost as you wind through the local streets off I-376 outside Pittsburgh, in the shadow of shuttered steel mills, but just trust the arrows and you'll end up at this bucolic 108-year-old spread on the banks of the Monongahela River. Follow the toddlers parading toward the giant Art Deco toy soldiers to find the kiddie rides.

A couple of hours at Kennywood were just enough—as were three rides on its big 1926 carousel—so we drove toward downtown Pittsburgh at dusk. The Renaissance Pittsburgh Hotel is a beautifully restored classic overlooking the Allegheny River and a few of the city's many renowned bridges (which are also very cool for kids). This hotel puts you right across the river from five-year-old PNC Park, home of the Pirates; on baseball game nights, a carnival atmosphere takes hold, as the Sixth Street Bridge is shut to traffic and pedestrians fill the streets leading to the stadium. The real reason we were at the Renaissance, however, was its family package, which included two pizzas via room service and a free in-room flick—Alex chose Pooh's Heffalump Movie.

Pittsburgh to Philadelphia: 295 miles

Tired does not begin to describe Alex's state on the last day of our trip. Was all this a bit much to pack into three-plus days?Perhaps. Is there a reason toddlers don't plan their own vacations?Most definitely. But I'd say the trek was worth the effort—Alex was unusually compliant as we checked out of the hotel after yet another pancake breakfast, as if after three days of having every wish come true, he was finally sated. So Joanna and I took the reins and voted, by virtue of a 2-to-1 majority, to make one last stop before the drive home, a detour that was purely for us: the Andy Warhol Museum. Yet somehow, no matter where we went on this trip, we found ourselves coming right back to Toddler Town. After a short nap in his stroller, Alex awoke to the sight of neon-colored bovine lithographs blanketing an entire gallery (Cow Wallpaper—accompanied by more mooing); he then moved on to the room that holds Warhol's Silver Clouds, a dozen or so pillow-shaped Mylar balloons, which the viewer is encouraged to bat around. As Joanna and I watched Alex run giddily through the gallery, whacking balloons left and right, I said to her, with a wink and a nod, that I couldn't have planned this trip any better myself.

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