You could make two tables in your database. One for dates and one for images. So your tables could be:
ImageId -> PrimaryKey, autoincrement
ImagePath -> varchar(250)
DateId -> PrimaryKey, autoincrement
Date - > datetime
ImageId -> ForeignKey to ImageId from the first table
In the end you will have two tables with one- to-many relationship. On one image corresponds many dates on which this image will be shown.
Then with RadCalendar you could show multiple months with customized date's templates on which you could show the images from database.
You could find the online demo of RadCalendar with multi-month view here:
And online demo of Calendar with special days and templates you could find here:
You could achieve the desired functionality by combining the multi-month view calendar with calendar with special days and templates.
I hope this helps.
All the best,
the Telerik team