Chesterfield events

Forthcoming Events

Chesterfield 1940s Market

Chesterfield 1940's Market

Enjoy some classic entertainment as the Chesterfield 1940s Market returns!

Residents and visitors to Chesterfield can shop for all things vintage and enjoy free entertainment including 40s music sing alongs, classic car and military vehicle exhibits and meet the flea market stall holders in period dress.

Why not get in the spirit of the occasion? Visitors are encouraged to dress up in traditional 40s outfits.

Entertainment at the Chesterfield 1940s Market

Highlights of the event will include the return of the popular Kalamazoo dance band! Don’t forget to pop and see them in New Square. There will also be street performers in the town centre throughout the event. Plus, a vintage fire engine and the chance to see an escapologist.

For those who want to have a closer look at memorabilia and artefacts, Chesterfield Museum staff will be bringing objects from their World War Two education box. They will also host a make do and mend activity, alongside Transition Chesterfield.

1940s market Kalamazoo Dance Band

New Square (opposite the Portland Hotel)

  • Kalamazoo Dance Band performing at: 11am – 11.45am, 1pm – 1.45pm and 2.30pm – 3.15pm.

Outside Etienne Curtains and Blinds

  • The Daisy Belles – singers performing at: 10.15am – 10.45am, 12.15pm – 12.45pm and 1.45pm to 2.15pm.

1940s market Spitfire

Market Place

  • Display of classic cars, a vintage fire engine and military vehicles from 10am – 3.30pm.
  • Land Army and 1940s mining displays from 10am – 3.30pm.
  • Escape artist / glass walker / fire eater performing at 10.45 – 11.10am, 1pm – 1.25pm and 3pm – 3.25pm.

Chesterfield 1940s Market

Market Square (outside Santander)

  • Natasha Harper – singer performing from 10.30am – 11am, 12.10pm – 12.40pm and 1.30pm – 2pm.
  • Kyle Evans – singer performing from 11.20am – 11.50am, 1pm – 1.30pm and 2.10pm – 2.40pm.
  • Post Offices through the years. This stand will offer an insight into the history of how the Post Office has progressed and how it supported the country and community throughout the 1940s. Visit from 10am – 3.30pm.

Pavements Shopping Centre (old Massarella’s Unit)

  • Chesterfield Museum – Crafts, handling objects and displays from 10am to 3.30pm.
  • Transition Chesterfield – make do and mend from 10am to 3.30pm.

1940s market Johnny Victory

Rykneld Square (outside the Visitor Information Centre)

  • Jayne Darling – singer performing at 10am – 10.40am, 11.30am -12.10pm and 2pm – 2.40pm.
  • Johnny Victory – singer performing at 10.45am – 11.15am, 1.10pm – 1.40pm and 3pm – 3.30pm.

Crooked Spire Church and Churchyard

  • Tower Tours – adults £10, under 16’s £5 – taking place at 10.30am and 2.30pm.

Vicar Lane are also hosting a trio of singers to complement the event.

Public Transport and Parking

Visitors are encouraged to use public transport to attend the event. However, there is also lots of parking available in Chesterfield. You can find more details on car parks in the town centre here.

Free coach parking spaces are available for groups or organisations visiting the event, but these must be pre-booked here.

The Chesterfield 1940s Market is a free event that aims to bring more visitors and shoppers to the town centre to support local businesses and market traders.


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  • Market Place



  • FREE to attend

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