Trek on 7/11/2013 2:14:00 PM:
Although we've started trips in Columbia, for the out of towner I'd suggest either starting in Rocheport or riding there before heading on eastward. Abigail's and the Rocheport General Store are good places to eat in town, as well as Les Bourgeois on top of the bluff northeast of town. The A-frame at Les Bourgeois has a good river valley view. Boonville can be seen from the bluff to the west ten to twelve miles away. There is also a good BBQ restaurant just behind the bike shop at the trailhead. Rocheport also has the tunnel on the west edge of town and just east of town are several interesting railroad related things such as the old ammunitions bunker. We've stayed at the Schoolhouse B&B which was nice, but our room was pretty small for the dollar charged.
Hartsburg has Dotties Café which is a welcome spot, very friendly and good food. We haven't been to the Hartsburg Grand, but it gets good reviews here. We've not stayed in Hartsburg, but would like to stay in the Caboose sometime.
In Jefferson City, which is a short ride off the trail, we've stayed at Cliff Manor B&B and several of the hotels just south of the capital grounds. All were nice accommodations and reasonably priced. We've eaten at Madison's a few times. Aris pizza is good food (Columbia location anyway) and the Central Dairy is a good stop too. All three of those are just a few blocks from the capital.
We've stayed several places in Hermann in years past. A lot of the places there now require a two nights stay, which at the rate charged is no longer a good deal for us. Nice places like Hermann Hill and Hermannhof are good stays, but are pricey. There are other places though. The Stonehill Winery is a good place to eat German food and the tour of the prohibition period wine cellar is worth seeing. If you're going to buy wine, Loutre Market just south of McKittrick is less expensive than at the wineries and they have a decent selection. Hermannoff winery has a nice patio