Fall Tandem ride

For Holloween, Sara and I were to be out in Leesburg for a party and the parade. We decided to do a tandem ride before the party. Sara had issues before with the Tandem and her knees. I have been doing a experiment where she is not wearing bike shoes but her tennis shoes and toe clips so that her feet can go where ever they want. This seems to be working cause she hasn't had knee pain.
I had found a route that did road from Leesburg to Purcerville and the trail back. That route on bikely was 40 miles and I was looking for us to do something in the 30miles territory. I made it 30miles but messed up the ride greatly because of that. We were riding well, Sara liked going through Waterford, but then after being on Milton Rd, we started hitting dirt. Then with Purceville Rd. it was all dirt. If I had a map I would have had us go a little bit west to the next road which was paved. So we did the dirt road on the tandem with 28mm tires a little too small. Sara got annoyed when I would make sudden changes which were because of pot holes I did not want us to hit. We eventually got to Purceville, and then took the bike path back. We ended up riding for 1:50 minutes so next time I will shoot for us riding around an 1:30. Hoping to ride more with Sara on the tandem in the future.