Itinerary Help Needed
 

My wife and I want to visit a number of people & places in the month of September. We live near Houston, TX. Can someone suggest a possible itinerary for us? The places we want to stop include:
Clarksville, TN; Dayton, OH, Pittsburgh, PA, Bridgewater, VA, Strasburg, VA, Williamsburg, VA, and Washington, DC. We will be driving from Texas. I didn't know whether to start with Clarksville, then head to Dayton and Pittsburgh. After Pittsburgh, the rest of the stops are in VA & DC. Thanks for your advice!

Ohio, no problem: I71 from Louisville to Cincinnati, pick up I75 to Dayton, then I70 to I79 to Pittsburgh. Try to see the US Air Force Museum when you're near Dayton.

The VA part looks more complicated. After Pittsburgh, you might want to hit Strasburg, then DC, then Williamsburg, and finally backtrack to Bridgewater. Or some other variant. Or you could do everything in reverse order. Don't miss seeing Charlottesville with UVa and Monticello if you're in the area.

Are you visiting people or significant sites in Clarksville, TN? If not, and you're only going there because of the Monkees' song, you could save yourself the detour. The city's name was only used because it sounded good.

Not much help, I'm afraid. Have a great trip!

How long do you have for this? Are all the stops equally important--how long you want to stay?
Clarksville is a major army base--could have some pull for the OP.

Let me tweak this. There are some changes. Here is what I am trying to "flesh out" now.
Day 1 Houston, TX to Natchez, MS
Day 2 Natchez to Tupelo, MS
Day 3 Tupelo for family genealogy
Day 4 Tupelo for family genealogy
Day 5 Tupelo to Clarksville, TN
Day 6 Visiting friends in Clarksville
Day 7 Visiting friends in Clarksville
Day 8 Clarksville to Dayton, OH
Day 9 Dayton. Air Force Museum. Wright Brothers.
Day 10 Dayton to Bridgewater, VA
Day 11 Bridgewater. Visit college friends.
Day 12 Bridgewater to Manassas, VA
Day 13 Manassas. Visiting niece and family in Ashburn, VA
Day 14 Manassas to Williamsburg, VA
Day 15 Williamsburg
Day 16 Williamsburg
Day 17 Williamsburg to Knoxville, TN
Day 18 Knoxville to Laurel, MS
Day 19 Laurel to Houston, TX

Just chiming in to thank you for the Bridgewater shoutout!! I am a proud Bridewater College graduate.

I found a nice AirBNB in Bridgewater for when I go for my reunion in October. If you are interested, I can post it for you.

Seems like a lot of time in Williamsburg, which is more than a bit boring unless you're riding coasters at Busch Gardens.

Those last 3 days are all 6.5 hour drives (plus). That seems rough.

Unless your days for visiting Ashburn/Manassas and Bridgewater are fixed, I would suggest switching those two in your itinerary, Manassas first and Bridgewater second.

Manassas to Williamsburg can be a lousy drive on the I95 portion of it. The last hour on I64 should be no problem.

Bridgewater to Williamsburg on I64 is an easy drive and the first part of it though VA's Piedmont is very pretty. You will pass Charlottesville on the way and could stop to see Jefferson's Monticello if time allows. You'll likely be passing C'ville again on your way to Knoxville, day 17, but that is already a full day of driving.

Big Russ is the forum's resident Williamsburg hater. Take his comments with a grain of salt.

Good advice obx!

I'll echo obxgirl's advice on switching up that part of the drive. Good call. And good thing you explained the Bridgwater stop --that was a head-scratcher (and I live about 15 min from there).