Christine Williamsburg Road Trip Itinerary
🚗 Cleveland → Hershey → Gettysburg → Williamsburg
🏠 Base: Williamsburg, Virginia
Day 1: Hershey, Pennsylvania
We hit the road early from Cleveland, packed lunches in the car, and made the five-hour drive to Hershey—because what better way to start a family Christmas break road trip than in Chocolate Town, U.S.A.?
Our first stop was the Hershey Story Museum, where we learned how Milton Hershey built his chocolate empire. The exhibits were super interactive, and the kids loved all the hands-on displays. We spent about an hour and a half wandering through before heading to the main attraction—the Hershey’s Chocolate World.
The factory area is free to explore and even has a complimentary 30 minute ride tour. We decided to skip the 45-minute wait (Pro Tip: go first thing in the morning or later in the evening for shorter lines) and instead explored the Hershey store. It’s basically a candy wonderland—free exhibits, fun chocolate displays, and all the Hershey souvenirs you could imagine. Of course, we couldn’t leave without a bag of treats for the road.
We wrapped up our Hershey stop with dinner at Troegs Independent Brewing, a must if you’re in town. Great food, relaxed vibe, and craft beers for the adults—everyone was happy.
After dinner, we took a short one-hour drive to Gettysburg and checked into the Holiday Inn Express. We secured adjoining rooms and relished a restful night. The next morning, we enjoyed a nice complimentary breakfast and set out for the day.
Day 2: Gettysburg, Pennsylvania → Williamsburg, Virginia
We started with a visit to the Gettysburg National Military Park Museum . If you’re traveling with a large family like ours, the Gettysburg Foundation family membership is worth it—it’s cheaper than buying individual tickets for everyone. Plus, if you return in the future, it gives access to several other museums and historic sites in the area.
The Gettysburg National Military Park Museum is packed with Civil War history and artifacts, videos and a demonstration making the past feel vivid and real. After exploring the museum, we set out on a self-guided battlefield tour, driving through the historic fields, stopping at key monuments, and letting the kids stretch their legs while we took in the views.
Before hitting the road again, we grabbed lunch at The Appalacian Brewing Company of Gettysburg, which was the perfect mid-day stop for something hearty and casual along with tasty beers and root beers for the kids. Click here for full guide to Gettysburg!
Then it was on to Williamsburg! The three-hour drive went quickly, and we arrived in time to check into our condo, make dinner, and unwind. We stayed at this condo timeshare which we rented through VRBO. It was centrally located to everything in Williamsburg and had a nice indoor/outdoor pool, pickle ball quarts and 2 free arcade rooms which were a HUGE hit!
Day 3: Exploring Williamsburg
We started the morning with a stroll along Riverwalk Landing in Yorktown, VA, enjoying the peaceful scenery along the York River. It was a quiet and scenic way to kick off the day. For lunch, we stopped at the Yorktown Pub, a casual spot right on the river with fresh seafood and a relaxed atmosphere.
Next, we headed to Busch Gardens in Williamsburg for their Christmas Town event—the largest holiday celebration in Virginia. The park opens at 2 PM, and it was an instant hit with the whole family. We had grabbed our tickets in advance through Groupon, which made entry seamless. Between roller coasters, family rides, and live shows, there was something for everyone. The park is beautifully designed, and the Christmas lights and festive displays were absolutely magical.
Pro Tip: Arrive right when the park opens to make the most of your visit. If you plan to eat onsite, either have an early dinner or bring your own food—by 5:30 PM, the restaurants were packed with long waits.
he next day was all about history at Colonial Williamsburg. This incredible living history museum brings the 18th century to life with costumed interpreters, beautifully restored buildings, and hands-on demonstrations. The kids especially loved watching the blacksmiths at work and seeing what daily life looked like hundreds of years ago. We packed our own snacks, but there are plenty of onsite restaurants if you’d prefer to grab a bite while exploring!
For lunch, we drove across town to Billsburg Brewery in Jamestown for craft beers, live music, and a food truck all with a view of the James river.
We ended our stay with some downtime back at the timeshare—swimming, playing arcade games, and just relaxing after a few busy days on the road.
Trip Takeaways
This road trip had the perfect mix of history, fun, and relaxation. From chocolate and battlefields to roller coasters and colonial streets, it offered a family-friendly route with something new to enjoy each day.
If you’re looking for an eight-hour family road trip that blends sweet treats, history, and theme park thrills, this Cleveland-to-Williamsburg route is a winner.
There are plenty of other historic sites and battlefields nearby that look incredible, but we decided to save some history for our next visit. 😉
✨ Williamsburg Road Trip – Quick Highlights
🚙 Route: Cleveland → Hershey → Gettysburg → Williamsburg
🏠 Home Base: Williamsburg Condo
Hershey, PA
🍫 Hershey Story Museum – Hands-on chocolate history for kids and adults
🍫 Hershey Chocolate Factory – Free exhibits & giant store (Pro Tip: arrive early to skip long lines)
🍺 Dinner: Troegs Independent Brewing– Craft beers and hearty bites
Gettysburg, PA
🏛️ Gettysburg Museum – Fascinating Civil War artifacts and demos
🪖 Battlefield Tour – Drive or walk the historic fields at your own pace
🍻 Lunch: Appalacian Brewing Company Gettysburg
Williamsburg, VA
🏡 Check-In & Dinner: Cook at your Condo
🌅 Morning Walk: Stroll along the scenic York River
🎢 Busch Gardens: Rides, shows, Christmas Lights and family-friendly thrills
🏘️ Colonial Williamsburg: Living history, interactive exhibits, and costumed interpreters
🍺 Meals: Billsboro Brewing, food trucks, and live music
🎮 Condo Fun: Swimming, arcade games, and relaxing downtime
