The May Festival, which was first held in 1896, has a varied history. After the Bayreuth Wagner Festival (since 1876), it is the second oldest festival in Germany. Its program included opera, drama, concerts, ballet and other events. Special in-house productions at the opening of the festival were a constant.

Until the beginning of the First World War, the May Festival was all about representation with a view to the Emperor, who often stayed in Wiesbaden, and an international audience. Wilhelm II saw almost 100 theater performances during his stays in the city. He not only attended the festival as a guest, but also financed it entirely and, together with director Georg von Hülsen, determined the program selection. In addition to the imperial family, the nobility and officer corps as well as foreign spa guests were the addressees of the "patriotic festival" and the social events.

The program was initially dominated by the Hohenzollern dramas of Joseph von Lauff. In drama, Victorien Sardou's (1831-1908) "Theodora" as well as Schiller, Shakespeare and Hebbel occupied the top positions. In opera, comic operas by Albert Lorzing, Otto Nicolai and Carl Maria von Weber dominated. In ten seasons from 1900-14, Weber's "Oberon" was on the program, followed by Gluck's "Armide". The great importance of French and English operas and plays is remarkable, as is the absence of Richard Wagner's stage works. Even the new artistic director Kurt von Mutzenbecher was unable to emancipate himself from the dictates of the monarchy after 1903, as the May Festival was considered a festival "by imperial order". The reputation of the festival sank in the press and among the public, who blocked innovation and cultivated a "plush cult". With the outbreak of the First World War and the end of the monarchy, the festival also went under for the time being.

After the end of the war, inflation and occupation, a new concept was needed, which artistic director Paul Bekker presented and underpinned programmatically. Instead of expensive guest engagements in opera, drama and operetta, Bekker focused on his own ensemble performances with an emphasis on international contemporary plays, experimental opera and the revival of rarely performed plays. His aim was to achieve the greatest possible response from audiences who had previously stayed away from the theater; furthermore, the performances should also be reflected in the reviews of the national feuilleton. Despite great artistic successes and world premieres, the May Festival did not cause a sensation with its innovations. Bekker's republican conception of art was strongly criticized by the political right, and he himself was defamed as a Jew. The theater was pilloried and Wiesbaden society did not support either the new artistic start or the high costs of the festival, which was then renamed the "Spring Festival". Ernst Krenek's short operas "Der Diktator", "Das geheime Königreich" and "Schwurgericht" stood out artistically, as did Richard Strauss' "Ägyptische Helena" and Hans Pfitzner's "Palestrina". In drama, there were plays by William Somerset Maugham, Arthur Schnitzler and Max Mell. Bekker also presented light-hearted pieces such as Emmerich Kálmán's "Duchess of Chicago" and Walter Brandon Thomas' (1850-1914) "Charley's Aunt". Among the May Festival operas, works by Richard Wagner, Giacomo Meyerbeer and Giuseppe Verdi stood out.

With Bekker's departure from Wiesbaden in 1932 and the rise to power of the National Socialists, the orientation of the May Festival changed. In order to upgrade the festival, new productions were moved to May. Artistically, well-known works by Goethe, Shakespeare, Mozart, Verdi, Grieg and, again and again, Wagner dominated. There were also works by Nazi playwrights such as Hanns Johst (1890-1978), operas by Hans Pfitzner and a large number of operettas. In 1944, the Gauleiter reanimated the former representative festival as the "Rhein-Mainische Theatertage", at which the bombed-out stages of the neighboring cities were to demonstrate productions as a "showcase of German theater".

In order to revive the May Festival after the Second World War, a new approach and a high level of social and political commitment were required. Lord Mayor Hans Heinrich Redlhammer and Treasurer Heinrich Roos found their artistic director in General Director Heinrich Köhler-Helffrich, who founded the "Wiesbaden International May Festival" by inviting ensembles from all over the world. Many opera ensembles made their celebrated post-war debut in Wiesbaden. Under the label of international understanding and exchange, the people of Wiesbaden saw well-known top productions from opera houses in Barcelona, Belgrade, Brussels, London, Paris, Rome, Vienna and Zurich. The municipality purchased top-class productions and gave a small subsidy because the enormous demand for tickets almost covered the costs. Köhler-Helffrich's "Oberon" production was celebrated in 1953; the people of Wiesbaden loved it for its renewed splendor after the barren post-war years.

Köhler-Helffrich's successor, Friedrich Schramm, gave the Internationales Maidfestspiele a modern direction: Leoš Janácˇek's operas "Aus einem Totenhaus" and "Die Sache Makropoulos", Hermann Kasack and Hans Vogt's oratorio opera "Die Stadt hinter dem Strom", Paul Hindemith's "Mathis der Maler" and Ernst Krenek's "Karl V." delighted the feuilleton, but drove away audiences accustomed to the classics. Towards the end of Schramm's directorship, the program seemed arbitrary, audience numbers and income stagnated. Claus Helmut Drese, another reformer, came to Wiesbaden in 1963 and gave the festival a new program. Based on the close relationship with the Belgrade Opera that had existed since 1953, the International May Festival presented itself as a showcase for the East with ensembles from Warsaw, Prague, Budapest, Leningrad and Moscow. They were to show the most important operas of their country and present new, internationally presentable pieces. The "hub of international understanding" brought inexpensive and opulent guest productions to Wiesbaden that were rarely seen elsewhere. In addition to this "cultural Ostpolitik", Drese established ballet as an important part of the festival. For the Shakespeare year 1964, the Old Vic Theatre came to the International May Festival from Bristol with "The Loss of Love" and "Henry V", the Comédie Française from Paris with "Hamlet", the Munich Chamber Opera with "Othello" and the Berlin Schiller Theater with "The Taming of the Shrew". There were also productions by the Wiesbaden Theater.

Audience numbers and recognition for the International May Festival increased. From 1969, Alfred Erich Sistig continued the wide-ranging guest performance tradition with the Slovakian National Theatre in Bratislava (Pressburg), the Bucharest State Opera and again the Sofia, Budapest and Prague State Operas as well as the Bolshoi Theatre in Moscow. During this time, Imre Keres shaped the ballet productions of the State Theatre and Dr. Rainer Antoine the drama department; Antoine particularly cultivated an exchange with the author Peter Hacks (1928-2003). During this phase, numerous festival performances were broadcast on television. Due to the renovation and reconstruction of the Staatstheater in 1975-78, the possibilities of the new artistic director Peter Ebert (1918-2012) were limited.

After a year without a festival, Christoph Groszer took over the fate of the Staatstheater and the International May Festival in 1978 and called it the "International Festival Days", which extended into November. Criticism of the International May Festival came not only from the left-wing alternative scene, which organized the "Alternative May Festival", but also from the city treasury, which limited the purchase of renowned productions. The year 1987 marked a new approach. If there was to be an International May Festival, it had to be with more guests and a more prominent cast, was the demand of artistic director Claus Leininger. After a long time, the Bolshoi Theater, the Hungarian National Opera, the Geneva Opera and the Munich Kammerspiele were once again guest performers. The expansion of the program was made possible by higher municipal subsidies, initiated by Lord Mayor Achim Exner. A highlight was the 1990 Unity Festival with numerous ensembles from East Germany and Eastern Europe. Under Achim Thorwald and Manfred Beilharz, the festival remained true to its international character.

Since 1988, the Rheingau Music Festival has in many ways replaced the International May Festival in terms of its supra-regional fame and musical significance, but it still offers regional visitors world theater on a local stage.