Chesterfield is set to step back in time to the 1940s as one of the town's most anticipated annual events returns later this month. The beloved 1940s Market will take centre stage in the town centre on Thursday, May 28, from 10am to 4pm, offering vintage entertainment, live music, and family-friendly activities.
Spitfire Replica and Wartime Displays
A full-size replica Spitfire will be the highlight in Market Square, celebrating 90 years since the aircraft's historic first flight. Classic cars, military vehicles, and wartime displays will fill the streets, while children can climb into a Hurricane plane for photos. Street performers, 1940s dress, and dancing add to the nostalgic atmosphere.
Event Details and Council Support
Organised by Chesterfield Borough Council, the event coincides with school holidays and the weekly Thursday flea market. Councillor Kate Sarvent said: "The 1940s Market is a highlight of our events calendar. After the refurbishment of New Square and Market Square, we hope to see families enjoying another fantastic day." The event is supported by the Chesterfield Town Board Pride in Place programme, funded by the UK Government.
Full Entertainment Schedule
Outside Market Hall (10am-4pm)
- Classic cars and military vehicles
- 1940s Mining display
- Escape artist/glass walker at 10am, 1pm, 3pm
- Bombardiers walkabout at noon, 1.15pm, 2.30pm
Market Place (10am-4pm)
- Full-size replica Spitfire
- Vintage Fire Engine
- Laurel and Hardy Magicians walkabout from 11am
Market Square (outside Santander)
- Natasha Harper (singer) at 10.30am, 12.20pm, 2pm
- Kyle Evans (singer) at 11.30am, 1.10pm, 2.50pm
Outside Crown & Cushion
- Shire horses from noon to 1.30pm
New Square (10am-4pm)
- Hurricane Plane and Diamond T Truck
- The Daisy Belles (singers) at 10.15am, 12.15pm, 2pm
- Kalamazoo Dance Band at 11am, 1pm, 2.45pm
Outside McDonald's (10am-4pm)
- Chesterfield Museum displays
- Post officers throughout the years
The Shambles
- Viva La Vintage at 10am, 11.50am, 1.30pm, 3pm
The Yards
- Lady Lindy at 11am, 12.40pm, 2.20pm, 3.30pm
Burlington Street (10am-4pm)
- Royal British Legion
- Parish Church of St Mary and All Saints (Crooked Spire)
- Soldiers camp and drill
- Jayne Darling (singer) at 10am, 11.30am, 2.10pm
- Johnny Victory (singer) at 10.50am, 1.20pm, 3.15pm
- Tower Tours at 2.30pm (£10 adults, £5 children under 16, family ticket £20)
Location: Chesterfield, Derbyshire.



