The oldest of Chesterfield's links is with Darmstadt (Hessen) in Germany.
The twinning agreement was signed in 1959 in Darmstadt and 1960 in Chesterfield.
2009–10 was the 50th anniversary of the twinning link, and the anniversary was marked by:
- a civic delegation from Darmstadt for the anniversary of the signing of the twinning agreement
- a social event for representatives of community groups with past and present links with Darmstadt
- Chesterfield and North Derbyshire participation in Darmstadt's annual tourism show
- concert tours by two local groups of musicians (Musicwork and the Phoenix Concert Band) in the Darmstadt region
- a Darmstadt-themed walk, with Darmstadt participants, during the 2010 Walking Festival
- an exhibition showing how the link has developed over 50 years, displayed in various venues during the year
- a Chesterfield food and drink stand at Darmstadt's annual Grenzgang (beating the bounds) walk, staffed by Chesterfield University of the Third Age
- Sabine Welsch giving a talk on Darmstadt's Jugendstil (Art Nouveau) during the Chesterfield Arts and Market Festival
- a beer stall at Darmstadt's Christmas Market, selling Chesterfield beers
Anglo-German twinnings were intended to facilitate contacts between ordinary people, so that the friendships formed would make a future European war unthinkable.
This twinning link has resulted in many visits to and from Darmstadt by schoolchildren, college students, sports clubs, community groups, clubs and societies.
Recent links included the Red Cross, St John Ambulance, ambulance workers, bus drivers, folk-dancers, ex-servicemen, police, and firefighters. Some of these have ended, as their members became older, but others have continued, for example the participation of young musicians in Darmstadt's European Youth Orchestra each year. Two secondary schools still maintain active links, and one of these schools also runs a work experience exchange. A new link has developed between the University of the Third Age, and its Darmstadt equivalent.
A small civic delegation attends Darmstadt’s annual European Weekend, when representatives of Darmstadt’s fifteen twin towns meet to discuss matters of common concern.
The link between Darmstadt and Chesterfield was put to good use in autumn 2010, when it was used to find relatives of Sergeant Dennis Heeley, whose plane was shot down near Salzbergen during the Second World War. Two family members were able to attend the unveiling of a memorial to the flight crew, and visited Sgt Heeley's grave to lay a wreath in his memory.