The action-packed market will be returning on Thursday 28 May 2026, transporting the town centre back to the 1940s with a range of free entertainment for the whole family to enjoy!
Soak up the atmosphere with live music, a replica Spitfire, street entertainment, wartime displays and impressive 1940s attire.
The event will take place during the school holidays again and run alongside the popular weekly Thursday flea market – the perfect time to get the family together.
Entertainment on the day includes:
Outside Market Hall
- Display of classic cars and military vehicles – 10am to 4pm
- 1940s Mining display – 10am to 4pm
- Escape artist / glass walker – 25-minute displays starting at 10am, 1pm and 3pm
Market Place
- Full-sized Replica Spitfire – 10am to 4pm
- Vintage Fire Engine – 10am to 4pm
- Laurel and Hardy Magicians (walkabout) – 11am to 4pm
- Bombardiers (walkabout) – 40-minute performances starting at 12 noon, 1.15pm and 2.30pm
Market Square (outside Santander)
- Natasha Harper (singer) – 30-minute performances starting at 10.30am, 12.20pm and 2pm
- Kyle Evans (singer) – 30-minute performances starting at 11.30am, 1.10pm and 2.50pm
Outside Crown and Cushion
Shire horses – 12 noon to 1.30pm
New Square
- Hurricane Plane and Diamond T Truck – 10am to 4pm
- The Daisy Belles (singers) – 30-minute performances starting at 10.15am, 12.15pm and 2pm
- Kalamazoo Dance Band – 30-minute performances starting at 11am, 1pm and 2.45pm
Outside McDonald’s (10am to 4pm)
- Chesterfield Museum displays
- Post Officers throughout the years
- Sparky Ink Studio Ltd offering kids animation workshops (10am to 3.30pm)
The Shambles
Viva La Vintage – 30-minute performances starting at 10am, 11.50am, 1.30pm and 3pm
The Yards
Lady Lindy – 30-minute performances starting at 11am, 12.40pm, 2.20pm and 3.30pm
Burlington Street (10am to 4pm)
Royal British Legion
The Parish Church of St Mary and All Saints (Crooked Spire)
- Soldiers Camp and Drill – 10am to 4pm
- Jayne Darling (singer) – performances starting at 10am, 11.30pm and 2.10pm
- Johnny Victory (singer) – 30-minute performances starting at 10.50am, 1.20pm and 3.15pm
- Tower Tours – 2.30pm. Tours are priced at £10 for adults and £5 for children under the age of 16. Family tickets (2 adults and two children under 16) are available for £20
This event is delivered by Chesterfield Borough Council thanks to support from by the Chesterfield Town Board Pride in Place programme, which is funded by the UK Government.
