The owner didn't dress up in period clothes - she is a docent at a history museum, but her only dress is too fancy for serving food. She did say she was planning to get a wash dress made before the next time. It was one of those things we have to fudge, and for that I am fine - she's opening up her inn to us, and we have to make concessions under those circumstances. But I know she wanted to participate more, and that is pretty neat
Food turned out to take up the most consideration in planning. For lunch we did a picnic. Some people brought food, and the rest paid for me to pick up stuff at the local grocery store - cheese, sausage, pickles, preserves, etc. Dinner was tricky - bed-and-breakfasts in Wisconsin have strict regulations about what meals can be served, by whom, and how. I kicked around several ideas, including some likely restaurants nearby and even just letting people do dinner on their own. In the end, we ended up having food catered by a local restaurant. It was period-esque - ham, beans, mashed potatoes, cornbread, all foods that resemble period dishes but not cooked with period recipes - which we paid for the innkeeper to serve us. The Gentleman Friend had to go and pick it up, but he didn't mind driving "the magic carriage" (and I think he enjoyed the break, since this was his first living history experience).
For next year I'm looking into different options or ideas to see if we can . Good thing we have 12 months to think on it