Road trip (with baby) New Orleans to Austin, March/April

Jackson, MS doesn't have much to offer. It's a state capital which usually tends to mean boring and the small downtown has been struggling to come back for a long time. Jackson probably is best known for its dead shopping mall that has become a successful medical clinic. It's a place that I enjoyed leaving both of the times I was there.

The heyday of blues was decades ago--you'll get a historical perspective from the museum in Clarksdale and Beale Street has some clubs but the Blues these days are mostly in the hands of younger, whiter generation and the new music comes out of elsewhere (like Chicago). The places that gave rise to the classic Delta blues (there are other Blues genres like the Piedmont blues of North Carolina) are the little towns in the cotton growing area between Clarksdale, Greenville, and Greenwood--places like Itta Beta. Driving that area, even now, will give you some idea of what led to the blues. The poverty and social divisions in those places are pretty obvious--it's not a romantic place to drive, but instructive and antidote to celebrating the "Southern way of life" that comes with places like Natchez.

Cabins in the woods are pretty hard to come by in most of the US. You might find a state park lodge in the woods, although state parks are pretty few and far between along your route, which is among the poorest areas of the US. You're describing something that's more likely in New England, the Pacific Northwest or the northern Rockies and even difficult to find in those places.

You may have difficulty finding a boutique-y hotel--perhaps in Natchez or Oxford, but really Mississippi is about roadside places. You can find something hipster-ish in Austin. Places in New Orleans with character will probably come with a big price tag. There used to be hotels like the Monteleone--a mid sized hotel convenient to the French Quarter that were affordable and had character, but post-hurricane Katrina, they have gotten more expensive. You may do better with AirBnB, but you also should make sure you know something about the neighborhood--AirBnB bargains often are in kindof marginal neighborhoods.

You're about 20-30 years too late for Austin--it lost its quirk a long time ago. The Hill Country is pleasant but not exceptional. You will find some good restaurants esp. for bbq, Tex-Mex and "interior Mexican" (actual Mexican food).

Daytime music venues on a weekday are probably not on the menu for any of these places (and I can say the same thing about Nashville if you're thinking about going there), esp. in March when the weather tends to be dreary, grey and often wet. You may get some amateur musicians playing for "donations" in New Orleans during the day on the weekend, but really if you want daytime music on a weekday in the US--it's usually downtown in larger cities during the summer and courtesy of the local musicians union, city government and the downtown business association. On the weekend, you'll get it from a seasonal parade or festival--you'll too late for St Patrick's Day in New Orleans which probably would fun and an example of this.

New Orleans has many art-y venues. The old warehouse district W of downtown has been fashioned into an arts district, but you can find galleries and shops in the French Quarter, the Garden District and the neighborhoods adjacent to them. You're likely to find other venues scattered through the Mississippi Valley but not huge numbers of places.

I've never been to Oxford, but it makes lists of towns to visit often such lists don't mean much--it's a college town where famous authors have lived and from people I've known who've lived there, it's a bit of a cultural oasis, but not enough of one that those people bothered to stay.

Thank you so much @buckguy for taking the time to share these thoughts and insights – hugely appreciated – will be a great help :)
thanks and best,
Adam

We're thinking about the Natchez Trace Parkway for next year; one of the places to stay that has come up a couple of times is this place in Port Gibson: http://www.isabellabedandbreakfast.com/ It looks pretty on the website & the tripadvisor reports sound ok.

Thanks @thematis :)

10 days road tripping through Louisiana, Mississippi and Texas:
(including: Lafayette; Natchez and Natchez Trace Pkwy; Texas Hill Country)
- 4 nights in Austin

"Texas Hill Country" is part of the Austin region.
Make sure you get some time in San Antonio to explore a mission or two (other than the Alamo).

Jackson MS. Such mixed opinions on here... would anyone make a case for / against?

It is common for Europeans posting here to have the notion that seeing a city on a map equates to a worthwhile stop. Visiting Jackson will rid you of this notion quickly.
(FTR, I am of the opinion that just about every place has something, but the issue is whether it's relatively worthwhile compared to other places. Jackson is certainly not.).

Opinions on Natchez Trace Pkwy (southern stretch).

The stretch roughly between Natchez and Vicksburg (which is a small detour away) has a good sample of what you would see on the full route. There are the historic wagon ruts, inns, native mounds, etc. If you only have a brief amount of time, this would satisfy.

Apart from Lafayette, where else in Louisiana. St Francsiville??

Baton Rouge is the location of a major university, and it's easily on the way north. You may find your music (though not necessarily during the day) there, and there are some very good food options (I like Sammy's, because you can get gator other than fried).
However, there really isn't much else there beside the capitol and a historic military vessel.

Interesting things to do on / by Mississippi river – should we be wary of those touristy pleasure cruisers?

A brief cruise on the river would be nice. Try to find one on a paddle steamboat, like this one (I have never used them).

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