On this episode of Unexpected Essex, your host Eri Berry deep dives into the murky world of 18th century highway robbery. Today, we answer the question: just who was Dick Turpin, how was he connected to Essex, and exactly what was the real deal with highwaymen?
This episode explores the life of highwayman Dick Turpin, the circumstances of his eventual execution, and how society came to romanticise the figure of the gentleman highwayman in popular culture. Turpin was born in Hempstead, a small village in the north west of Essex. Initially working as a butcher, it isn't long before he's drawn into a shady world of poaching, robbery, and even murder.
Timestamps:
00:00 Intro
00:17 The Concept of the Highwayman
04:13 The Origin of Dick Turpin
07:25 The Gregory Gang a.k.a The Essex Gang
21:36 Turpin on the Run
26:53 A Fateful Letter
29:15 The Trial
31:02 Execution
34:25 The Legend Begins
38:52 The Myth of the Highwayman in the 20th Century
40:44 Introducing the Turpin Tally
41:19 Thanks for Listening!
41:48 Credits
Key Names and Places
Dick Turpin, Hempstead, Epping Forest, York, London, Thaxted, Waltham Forest, Lincolnshire
Show Notes and Image Attribution
Click here.
Socials and Subscribe Links:
YouTube: Unexpected Essex
Instagram: @unexpectedessex2026
TikTok: @unexpectedessex
Facebook: Unexpected Essex
Website: www.unexpectedessex.co.uk
Contact: unexpectedessex@gmail.com
DISCLAIMER:
While I do my best to bring you accurate, well-researched content, I’m only human! If you spot a mistake, have a correction, or want to share additional context, please feel free to reach out via email at unexpectedessex@gmail.com.