I was fully self supported and did right at 500 miles.
The weather and trail were fantastic. I had a bit of rain in the evenings, which helps to keep the dust down.
My first suggestion is to search the Katy Trail website. Its very informative and has a trip planing function that I found very useful.
The other thing to do, is to purchase the Katy Trail guidebook, available on the website. It has a short bio about each town along the way, as well as lots of good information and history.
Each town has an information kiosk outlining the towns history, good maps, and info on whats ahead and behind you, so its easy to know what to expect.
As was mentioned in an earlier post, availability of businesses are a bit hard to predict, with limited and unpredictable hours.
As I was late in the season, I met many more day trippers than loaded tourists, but I met alot of great folks.
Some of the highlights were -
Les Bourgeois Bistro, just east of Rocheport. Lock your bike at the rack next to the trail, hike the .3 miles up the bluff for a fine bluff top dining experience, good menu and wine.
Free camping in the Hartsburg Gazebo, with good restaurants nearby.
The Riverview Traders store in Wilton.
Snoddys Store in Boonville, inexpensive deli sandwiches.
Downtown Boonville, cool architecture and restaurants.
Coopers Landing near Easley. Cool general store with a Thai food stand outside, unfortunately I missed it due to limited hours, but heard the food was fantastic. Dont miss Boathenge just west of there.
Turner Katy Trail Shelter, the only hostel on the trail. 32 beds, 2 floors, AC, showers, fridge, microwave, coffee maker, nice decks on both floors, all for $5 per night.
The Katy Roundhouse Campground at New Franklin
Bar food at at the Mokane Bar and Grill in Mokane and the Riverfront Bar and Grill in Portland
I had high hopes for the off trail trip into Hermann, as its touted as the prettiest town in Missouri. I arrived as it started to rain, camped in the city park, cost of $15 dollars which included a fine shower facility, spent the night inside my tent and rolled out the next day headed home. I hope to return to Hermann another time.
The small town of Rocheport, nice little bike/snack shop.
Due to the late season I missed the Katfish Katy Camp Store but did camp at their campground, 3 feet from the Missouri River.
As luck would have it, I had no flats or mechanical issues, weather was fantastic and I will surely return.