We're planning a major road trip from Massachussets to Mexico, officially ending the US portion in Laredo, Texas. We'd love to make this roadtrip as special as possible, and want to get some recommendations for restaurants and/or accomodations along the way that are not your typical Motel 6 and fast food drive thru. Our trip will take us from Lee, MASS through Allentown, PA, through Maryland to Roanoake, VA, Knoxville and Memphis, TN, eventually towards Baton Rouge, LA, Houston and San Antonio, TX down into Laredo.
Anything you can share with me on unique stopping points or hotels along the way will help to make this trip extra special and will give us things to look forward to along the way.
Thanks in advance!

Sounds like fun! I have no specific tips to offer, but you may want to consider checking out http://www.roadfood.com/.

Actually, now that I think about it, here's a place that's right near your route. I've always wanted to go there, but I've never been in the neighborood: http://stormking.org/

You'll also be close to the US Military Academy at West Point. I visited once, and thought it was quite interesting (and scenic).

thanks! Will definitely check this out. Please keep more ideas coming!

From Memphis to Baton Rouge is a ROUGH road! Honestly, you'd be wiser to go from Memphis to Little Rock, Dallas, and San Antonio. It's a better road, and also a lot more direct.

Start dropping south in middle TN and take the Natchez Trace from Nashville. When you get to the end of the trace in Natchez its only a little way to Baton Rouge, LA. No Traffic lights and no traffic make for an enjoyable ride.
http://www.nps.gov/natr/

This summer a New York Times writer did a cross country trip for the travel section in segments. I don't remember where all, as I only read part of it but you might look around in their archives.

Have fun and write us a great trip report afterward!

Yes, if you've got the time, take the Natchez Trace! There are historic sites to see, and Natchez at the end of the road has everything from a Native American museum and burial grounds to recreations of plantation life. Yummy food in that town, too!

...I took a little road trip in Mississippi a few years ago, from the coast up through Hattiesburg to Vicksburg, then down to Natchez. I liked Natchez the best! Though of course Vicksburg is quite monumental. If you're interested, maybe you could hit Gettysburg in PA, then Vicksburg on your way south...

We used to drive this route quite a bit, but in the reverse from Louisiana to Mass. From Knoxville, I recommend that you head down to Chatanooga (go to Lookout Mountain) and then on through Birmingham via I-59 and then on down to New Orleans. At New Orleans, do some touring there, and then take US90 (Future I-49) via the Crescent City Connection. Wind your way through Cajun Country back up to I-10 at Lafayette and then onto Houston. While in Cajun Country, visit St. Martinville, it's a picturesque town.

You will definitely want to stop in San Antonio for a few days as well...