When I have a long distance ride like this (approximately 100 miles + round trip) I would never take difficult trails. The day will be long enough as it is without people having to negotiate obstacles and try to stay upright.
This type of ride is about seeing the scenery, checking out the POI of the New River Train and the Brushy Mountain Pennetentiary.
Historic Brushy Mountain State Penitentiary
For those that don't know the BMP is a county ran tourist attraction in an old Maximum security prison, the Wardens Table Restuarant is definitely a must do, reasonable prices and good food.
http://www.tourbrushy.com/wardens-table-resteraunt
Optionally you can self guide tour the prison for $12 if interested, allowing about 2hrs to walk the and read and see the history.
Also is the gift shop and the End of the Line distillery they have onsite moonshine and vodka.
It's a good ride, I personally recommend going by trail to it ( about 5 hours with a big group) and take 75% backroads back ( about 2 hours) at that rate it's a 10-11 hour day from departure to return. With several photo OP stops for overlooks and POIs.
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