Shadows of Auld Reekie: Edinburgh’s Medieval Wynds, Castle Crags & Literary Lore

Draped across an ancient landscape of volcanic crags and glacial valleys, Edinburgh possesses a gothic silhouette unlike any other city in the British Isles. High above the cobblestone spine of the Royal Mile looms Edinburgh Castle, anchored to an extinct volcanic plug that has repelled invaders since the Iron Age.

For centuries known affectionately—and occasionally disparagingly—as “Auld Reekie” due to the dense coal smoke that once hung over its tenement chimneys, Edinburgh is a city built vertically. Medieval builders, constrained by city defensive walls, erected fourteen-story stone tenements that were among the earliest skyscrapers in Europe.

Exploring the Secrets of the Closes and Wynds

Branching off the Royal Mile like the ribs of a spine are hundreds of narrow, shadowy alleyways known as closes and wynds. Walking down Lady Stair’s Close or Advocate’s Close feels like slipping through a seam in time.

Beneath the South Bridge lie the South Bridge Vaults—a series of 120 stone chambers constructed in 1788 that once housed tradesmen and cobblers before being abandoned to Edinburgh’s destitute underworld, smugglers, and bodynatchers during the 19th century.

“Edinburgh is a city of shifting mists and volcanic shadows, where Robert Louis Stevenson conceived Jekyll and Hyde simply by observing the dual faces of Old Town and Georgian New Town.”

Field Itinerary Highlights:

1. Arthur’s Seat: A hike to the summit of this ancient volcano rewards with 360-degree views across the Firth of Forth to the kingdom of Fife.
2. The Scottish National Portrait Gallery: Red sandstone neo-gothic palace adorned with friezes of Scottish heroes.
3. Dean Village: A quiet 19th-century grain milling village nestled along the forested banks of the Water of Leith.