Nothing says freedom like a solo road trip. I hit the road Friday afternoon for a trek down to Winchester, Virginia where I made my home until starting the leisurely trip north Monday.

When planning this trip, more than a dozen scenarios were on the table but nothing really excited me. I was studying a map of Virginia when Winchester caught my eye and a vague recollection that Patsy Cline was from here made me pause.

A visit to her museum was one of the highlights of my trip to Nashville this spring and I had to wonder if there were other things to do around Winchester. Turns out this was a silly question. The area is rich in history and natural beauty and there is no shortage of things to do.

In fact, I packed a lot into my long weekend but needed far more time to do everything that looked interesting. I did hit the highlights and saw a lot in places along the way as well.

Sometimes I wish that I had a specific interest- a certain period of time or a field like aviation or rock collecting. It would be nice to be an expert in something.

But that’s not how I’m wired and trips like this make that especially clear.

My activities ranged from Civil War era attractions like Stonewall Jackson’s Headquarters and the battlefield at Mannasess to a flying circus, an awesome cavern and the childhood home of Patsy Cline.

The good news about having such a broad range of interests is that there’s always something to learn and a lot of surprises to enjoy.

The highways were useful when I just needed to make time but secondary routes were more fun when the goal was to sit back and enjoy the view. It was about 50/50, a ratio that worked well given the mountainous terrain of West Virginia, Maryland and Virginia.

This trip was memorable despite the fact I’ve been battling a sinus infection for weeks and still wasn’t feeling my best. For this reason, I took it easier and rested more than normal but still finished each day satisfied with all I had done.

This also helped some with the mental fatigue that’s been dogging me for a few months. I didn’t know what time it was most of the weekend and did not care.

Regardless of how fast or slow I move, I have a knack for attracting people who want to talk.

At the flying circus, I was befriended by a 74 year old gent with a soft Virginia drawl and a curiosity about the sign he saw me taking a picture with. He listened with interest as I told him why solo travel is fun. I also explained that it’s a necessity as I’m not prepared to stop going places simply because I don’t have a mate or someone to go along for the ride.

He gave me two pieces of advice:

1. If you want to retire early, live well below your means and lower your expectations. He should know – he retired at age 54.

2. To never lose my sense of adventure and bravery.

I liked him and appreciated the advice.

On the other hand, a younger man in the same conversation said that no wife of his would be out running around by herself like I do.

I smiled and told him it’s a good thing I’m no one’s wife. Jerk.

I’ll stick with the wisdom of the older man, thank you.

After leaving Winchester Monday morning, I followed the recommendation of a friend and took a detour to Lurray Caverns about an hour south of Winchester. Then it was a meandering journey to Clarksburg, West Virginia by way of Oakland, Maryland. My use of Hotels.com finally paid off and I cashed in a free night’s stay at Clarksburg before heading home the next day.

This was a perfect long weekend. With no real schedule and no one to please but myself, it was easy to just enjoy the adventure without pressure or worry. There are several stories to share including some unexpected things from along the way. Those usually make for the  best stories, those things you don’t plan.

We’ll get started tomorrow with a visit to the Patsy Cline House!