As a squadron of the 18th Pennsylvania Cavalry entered the woods, portions of the 1st and 5th Michigan cavalry advanced, with the 5th Michigan sent to the right and part of the 1st Michigan ordered to dismount and continue on the turnpike. This pressure caused Captain Emack’s men to slowly fall back farther west until General George Custer’s Brigade gained the eastern half of Monterey Pass. At the Monterey Inn, Kilpatrick discussed the area roads and their destinations, and resident David Miller informed him of Mount Zion Road leading into Smithsburg and Leitersburg. Using Charles Buhrman as a guide, Kilpatrick ordered the 1st Vermont Cavalry to head off the wagon train as it entered the Cumberland Valley. He also sent part of the 1st Michigan Cavalry, using Hetty Zielinger and James McCullogh as guides, to intercept the Confederate wagon train coming into Fairfield Gap. Planning to strike the wagon train from both rear and front, Kilpatrick then aimed to cut it in half by sending Custer’s Brigade forward to Red Run.