One South Mountain Gap that is not talked about is Buena Vista Springs. After the Civil War this area became home to a huge resort, but there are accounts of the gap during the Civil War from Union deserters to Confederate soldiers occupying it during the Confederate retreat after the Battle of Gettysburg.
The Monterey Pass Tollgate was located at a very important intersection. This is where the Fairfield, Mentzer’s Gap, Emmitsburg and Waynesboro Turnpike came together. Across from the tollgate, was Pendersville Road and connecting to that was a road that led directly to Buena Vista Springs and intersected with a road that led to the turnpike and what would become Cascade, Maryland.
During the Battle of Monterey Pass, there are accounts surfacing of Confederate troops ending up at Buena Vista Springs as the Union cavalry charged down the mountain. The only way to access the back road that led to Buena Vista today is by hiking a small portion of the Appalachian Trail. The parking area for the Appalachian Trail is located to the left along Route 16 leading toward Waynesboro. The hike will take you through areas of the Monterey Pass Battlefield where the 1st West Virginia Cavalry began attacking the Confederate wagon train.
This hike will take about hour and to start you will walk across the wooden bridge due south and following the white blazes.
This photo is taken from the Rolando Woods Lions Club Park
This is the Old Emmitsburg and Waynesboro Turnpike and is the same area where the Confederate wagon came under attack. The toll house is about 100 yards from this point.
This is the roadway leading toward Buena Vista and is seen crossing the Appalachian Trail
This is the same road looking toward Monterey Pass. From this point you are less than a quarter mile from the actual mountain gap.