If your toddler were the travel agent, your itinerary would be organized around the big C’s—chocolate, carousels, and choo-choos!

The next time you're contemplating a family vacation, ask yourself: What if the kids planned it instead?Or, more specifically: What would happen if a three-year-old called the shots?My wife, Joanna, and I—expecting our second child and in an indulgent state of mind—decided to find out. We packed up our car for an August journey from Philadelphia to Pittsburgh with our son, Alexander, and traced a route designed to satisfy every budding whim.

Philadelphia to Hershey: 110 miles

Philadelphia's Please Touch Museum, one of our family's favorite haunts since Alex learned to walk, played into the theme of our trip perfectly, since this excellent children's museum lets kids take control. Alex went straight for the pint-size supermarket—shoppers-in-training get to pick out their own fake fruits and vegetables, milk and eggs, and, yes, cookies and ice cream. They can even take turns working behind the cash register or in the "stockroom." Our other stops: the Where the Wild Things Are– and Alice's Adventures in Wonderland–themed areas, and the scale model of a city bus, where kids jostle for the spot behind the wheel.

Our hand stamp got us into the Franklin Institute's Science Park across the street, with its gigantic climb-through-it Goodyear tire. You can also access Ben's Bistro, at the institute, where we ate pizza before staring up at the 20-foot-tall Ben Franklin National Memorial, in the rotunda. (Note that the Please Touch Museum, which has no restaurant—or on-site parking—is planning an expansion next year, into a facility three times the current size.)

We drove out of Philly on the Schuylkill Expressway, and the closer we got to Pennsylvania Dutch country, the more opportunities we had to moo out the window at cows—it was nice to hear Alex put some of those "Old MacDonald" sounds to good use. Most of Amish country is not aimed at toddlers—antiques and folk art were certainly not on Alex's agenda—so we made a beeline for the Strasburg Rail Road, where you can ride a steam train for 45 minutes through the barn-and-cornfield countryside. (Try to sit toward the back of the train: that's real coal in the engine, and the black smoke billowing out can get a bit thick up front.) We couldn't leave without picking out a souvenir railcar at Thomas' Trackside Station, just down the road, which carries all things related to the beloved blue train from the island of Sodor. We didn't have time to see either the Railroad Museum of Pennsylvania (big trains; across the street) or the National Toy Train Museum (little ones; also nearby), but both are high on Alex's next-time list.

Our final destination of the day: the Hershey Lodge, a ridiculously family-friendly hotel and erstwhile conference center where we'd settle in for two nights while exploring the chocolate-covered town of Hershey—this is a place where you have to specify "white milk" with your meal order. We had dinner at Lebbie Lebkicher's buffet restaurant in the lodge, named after a childhood friend of Milton Hershey, the candy company's founder. Alex had a ball just trying to say the name, so you can imagine his delight at discovering the kids-only buffet—macaroni and cheese, chicken nuggets with chocolate ketchup (!)—and the sundae bar. We had to hide the Hershey's Miniatures that had been left on our pillows.

Hershey: 0 Miles

An important rule to follow when taking a car trip with a three-year-old: Don't overdo the car part. So we scheduled a day off from the drive—and then proceeded right to the twin Turnpike rides at Hersheypark. You can choose an antique car or a hot rod, but in either case even Alex could do the driving (or at least the steering; I was next to him controlling the pedals). Hersheypark has all of the attractions for which big theme parks are famous, and instead of one kiddie area, there are rides for squirts scattered throughout the park. Hello, Dinosaur-Go-Round!

To beat the heat—and to give Joanna, who was six months pregnant, a rest—we went back to the hotel for an afternoon dip in the pool (would that we had packed the water shoes; Alex cut his foot poolside on some poorly maintained concrete). Dinner was at another of the lodge's five restaurants, the Hershey Grill, where we decided against the Reese's Peanut Butter–soy-marinated pork chop, but we can heartily recommend the Hershey's Chocolate Crème Brûlée—or, in toddlerspeak, "really good chocolate pudding."

Hershey to Pittsburgh: 216 miles

Alex was not quite ready to leave Hershey, and it's a testament to his, um, trip-planning skills that Joanna and I weren't either. So before heading farther west we checked out the 23-acre Hershey Gardens, high on a hill over the town of Hershey and the theme park. Alex showed a hidden talent for finding the butterflies amid the dense foliage in the Butterfly House; in the Children's Garden, he loved the giant Kisses that surprise onlookers by shooting random blasts of mist.

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.


Hershey Lodge University Dr., Hershey; 800/437-7439; www.hersheylodge.com; doubles from $259.

Renaissance Pittsburgh Hotel 107 Sixth St., Pittsburgh; 800/468-3571; www.renaissancehotels.com; doubles from $249 (inquire about family weekend packages).


Please Touch Museum 210 N. 21st St., Philadelphia; 215/963-0667; www.pleasetouchmuseum.org; $10 per person.

Strasburg Rail Road Rte. 741, east of Strasburg; 717/687-7522; www.strasburgrailroad.com; tickets $5–$12.

Hersheypark 100 W. Hersheypark Dr., Hershey; www.hersheypark.com; adults $42, children 3–8 $25.

Hershey Gardens 170 Hotel Rd., Hershey; 717/534-3492; www.hersheygardens.com; adults $10, children $6.

Hershey's Chocolate World Hersheypark; 717/534-4900; www.hersheyschocolateworld.com.

Kennywood 4800 Kennywood Blvd., West Mifflin; 412/461-0500; www.kennywood.com; adults $29, children $18.

Andy Warhol Museum 117 Sandusky St., Pittsburgh; 412/237-8300; www.warhol.org; adults $10, children $6.