When my good friend Tina mentioned that she would be heading to San Diego for four months to escape winter and play lots of golf, my immediate response was:
“ROADTRIP! Let’s make it an Alliventure!”
A cross-country road trip was something I had always dreamed about. I can’t say I ever pictured myself doing it in the dead of winter or through a bunch of states I'd mostly been to, but that didn’t really matter. I was here for the experience and determined to make the most of it, no matter what.
Planning the Route
In the weeks leading up to the trip, we spent time mapping out our route, booking hotels, refining the route, rebooking hotels, etc.
The final plan?
A nine-day journey from New Jersey to San Diego with overnights in eight different cities. When broken down into manageable daily drives with planned stops, it felt exciting rather than overwhelming.
We front-loaded the longest drive on Day 1—an eight-hour trek from Hoboken, NJ, to Wytheville, VA. To break it up, we padded in some stops along the way.
Stop #1: Brunch in Harrisburg, PA
Three hours into the drive, we arrived in Harrisburg, PA, where Tina has friends. We met them at Yellow Bird Café in downtown Harrisburg, enjoying a laid-back brunch filled with great food, stories, and laughter.

Stop #2: A Quick "Hike" in Shenandoah National Park
With five more hours to go, we found the perfect midway stop: Shenandoah National Park.
We entered at the Front Royal entrance and drove a short stretch of Skyline Drive, enjoying the sweeping views. A kind park ranger recommended Fox Hollow Trail, a short hike that would fit into our limited time.
We stopped at a lookout point, where the winter landscape left the trees bare and the surroundings shades of muted browns, but still beautiful in its own way. Then, we set off on Fox Hollow Trail, excited to stretch our legs.
Minor issue: I was wearing Converse sneakers. The trail was still covered in snow, and my not-so-hiking-friendly footwear made for a cold and slippery experience. After some cautious (and slightly comedic) steps, we decided to cut the hike short. Even so, we were grateful for the chance to breathe in the fresh air and catch a small glimpse of Shenandoah.
Final Destination: Wytheville, VA
Why Wytheville? Strategic planning! This stop ensured a shorter drive on Day 2, giving us plenty of time to make our 1:20 PM tee time at our next destination.
Turns out, Wytheville has some fun claims to fame:
🛣️ "Crossroads of America" – It sits at the intersection of I-77 and I-81.
🇺🇸 Historic Roots – Birthplace of Edith Bolling Wilson, First Lady and wife of President Woodrow Wilson.
⚔️ Civil War History – A vital hub for settlers traveling on the Great Wagon Road, a major colonial-era migration route.
✏️ A Quirky Landmark – Home to the last remaining "Big Pencil," a 30-foot landmark attached to an office supply store.
Dinner & Rest: The Perfect End to Day 1
Wytheville also gave us the perfect dinner stop: 7 Dogs Brewpub—a relaxed, welcoming spot where we enjoyed a delicious meal and a well-earned ½ pint of beer.
After that, we checked into our basic but comfortable Tru by Hilton, the perfect place to crash before hitting the road bright and early for Day 2.
Final Thoughts
The longest driving day of the trip? Done.
The first of many fun stops? Done.
The excitement for the road ahead? Through the roof.
Day 1 was a total success, and I was fully pumped for everything that was to come over the next 8 days!
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