Was the medieval time merry? - as suggested by Chesterton - or was it miserable as portrayed in popular culture and indeed in popular history.
I am not going to answer that question except to state that it depends on whether or not Christianity is taken into consideration and taken seriously.
Any past era was 'miserable' for most people in the sense that (compared with the past several decades) there was a lot of starvation, disease, warfare, torture, discomfort and dirt.
But in eras of great Christian devoutness - other-worldly eras - these factors carried much, much less weight than they do or would for us.
An interesting test case is Carmina Burana (songs from the Beuern, a monastery), which is a collection of essentially secular lyrics, a selection from which was set to music in a dramatized cantata by Carl Orff during the paganistic era of National Socialism - in other words a modern and non-Christian angle on medievalism.
Carmina Burana is probably my favourite piece of 20th century music, something I find almost wholly enjoyable.
To appreciate Orff's Carmina Burana, I think it needs to be seen dramatized, as in the first-rate 1975 TV version conducted by Eichhorn and currently available in segments on YouTube, e.g:
Orff's CB represents just about the 'merriest' version of the medieval era that is possible minus Christianity - and (yet) it is (taken in total) a terrifying vision of life.
(It also notable the the vulgar vigour of this 1975 dramatization - its 'lust for life', a factor which is absolutely necessary to its positive appeal - would be utterly impossible for the PC-ridden world of 2011.)
A further example of this is the (excellent) novel The Name of the Rose by Umberto Eco. All positive valences attach to modern phenomena (science, philosophy) and the religious aspects are seen as negative, obscurationist, or simply deluded, psychotic, wishful, pitiful.
My contention is that the evaluation of medieval times (or indeed any past era) is for modern people systematically and severely distorted by our habitual subtraction or trivialization of religion from the world view.
Either we miss Christianity out altogether, regard it as peripheral, or regard it purely negatively. All of these are grossly unhistorical biases.
For example, the popular Time Traveller's Guide to Medieval England by Ian Mortimer is solid, engaging and informative so far as it goes - but it contains very little about the Christian life, and completely misses its centrality to the Middle Ages; therefore, ultimately, the book ends by being a travesty of its subject, a massive misrepresentation of the experienced quality of medieval life.
The deeply-entrenched secularism of the modern age is revealed most strongly in such matters: it seems we simply cannot understand what it is to live with religion at the centre of life; or else we can only imagine this an an unmitigated horror.
The idea of a world in which sweetness, beauty and hope; craft, learning, justice and morality, were Christian phenomena - is simply unimaginable to most people, most of the time - and recent literature, art and history are not helping matters.
So if the medievals were indeed merry, as Chesterton argued, then the fact would be necessarily invisible to the modern secular mind-set.