When I "officially" started my Druidic Journey 12 years ago, with the Order of Bards, Ovates and Druids, I started as a solitary. Though the order offered a tutor program and there was a grove nearby I started out working completely on my own. Durring this time I started building the blocks that would be the foundations of my future studies in Druidry.
As my studies progressed, however, I found something missing, a void if you will. This void was filled dually with the help of my tutor and the Boston Grove (now Mystic River Grove) of OBOD. At my first seasonal ritual (Alban Arthuan/Winter Solstice) with the Boston Grove I underwent my second (Ovate) initiation with a group, and did find it more meaningful and deep then my first solitary intitiation.
There is much to be said for both paths, and much to be learned on both paths. In truth there is only so far you can go on your own, and only so much you can do in a group. It is really up to you how you want to work and neither way is wrong, but I do advocate both as they are truly both necessary if you wish to progress and gain the deeper understanding of what you have learned. Learning from others gives you the chance to interact with one another and in this dynamic way you learn more.
In the ancient days when one learned magick it was passed from teacher to student and was an oral tradition. This was the only way, in modern times we can open books and practice on our own, but the one thing I think it is important that we don't forget is not to separate ourselves from others and from nature herself. This is because we are all part of this giant living organism we call Mother Earth.