Grottoes is home to Grand Caverns, America's oldest show cave (opened for tours in 1806).

[4] A group of land speculators formally founded Shendun, a combination of "Shenandoah" and the Gaelic word "dun" meaning 'castle' or 'fortified hill', in 1892.

1369 was established 3 miles east of Grottoes, and they built trails and roads into Shenandoah National Park that still exist today.

[9] According to the United States Census Bureau, the town has a total area of 1.3 square miles (3.4 km2), all land.

The geographical location, within 15 miles of Waynesboro, Staunton, Harrisonburg, and Elkton, continues to be a major asset of the town.

Major geographic features in the area include Skyline Drive, Massanutten Peak, and Natural Chimneys.

Previous routes of transport included overland through Brown's Gap to the east, by rail on the Norfolk Southern (formerly the Shenandoah Valley Railroad),[10] or by water on the South Fork to nearby Port Republic and then on the Shenandoah River all the way to Harpers Ferry, WV.