… you will find us in the hilliest & healthiest country in the world. I would recommend to you to come & return by different routs. the shortest and levellest is by Fairfax court house, Songster’s, Brown’s, Slate run church, Elk run church & Orange court house. the best country and entertainment, tho’ along a hilly road, is by Fairfax C. H. the Red house Prince Wm. C. H. Fauquier C. H. Culpeper C. H. and Orange C. H. the worst, longest, & most uninteresting road is by Fredericksburg.
To Henry Dearborn, August 13, 1803
Patrick Lee’s Explanation
Thoughtful leaders encourage exploration and provide options.
Jefferson was at Monticello for two months, escaping what he called the “sickly season” along the coast and tidewater region, where the yellow fever sickened and killed many in late summer. Learning that Dearborn, his Secretary of War, was traveling with his family to see James and Dolley Madison at their home, the President invited him to come 30 miles further and visit him.
While this region of central Virginia was dotted with towns, there were no public roads to speak of, only acknowledged bare-earth segments or trails from one courthouse, tavern or inn to another. Fording creeks and climbing hills in a horse drawn carriage, especially after a rain, added extra challenges. Ever the explorer, Jefferson advised Dearborn not to come and go by the same route but to see more of the countryside.
Jefferson suggested the three most likely routes:
1. The shortest, fastest and most level (If you just want to get here)
2. The most appealing, though hillier (Challenging but enjoy the journey)
3. “the worst, longest, & most uninteresting” (You have been warned!)