Holidays are, by definition Holy Days. We kind of tend to forget this and think more about celebrating with friends and family a lot of the time, but I think it's important to keep the Holy aspect in mind. It is true that friends and family being present makes them much,much more enjoyable and in many cases it's not even conceivable to celebrate a holiday alone simply due to lack of motivation or depression. Years ago I was between Kindreds and I had been celebrating Yule alone for several years. It became more and more difficult to do so, and that was something that really amazed me because I had never really thought of myself as a "Yule" type before... But as I went along in my practice, as I became more serious about every aspect of it, I began to see each holiday as being important and it really weighed on me. My partner at the time, was not even pagan much less heathen but due to the fact that he saw my plight he found a public Yule rite not far from our home. I went to it and saw how differently I viewed Yule from the general public. To me, it's much more solemn, though joyous, and I felt out of place. As time has gone on, I think that this has been pretty much my attitude in general to most of the holidays.
I think that part of the reason for my attitude toward the holidays is that when I started to practice Heathenry, it was just me and the person who brought me in, so we played down the holiday aspect to things a great deal and it was almost a 'just another day' type of deal with recognition that the holiday(s) did exist. I was not highly educated as to the meaning of each of the holidays in and of themselves. It was not until several years later, when we became friends with another Heathen who was studying for her gydhia license that I began to really understand what the holidays were about entirely. At that time we founded a Kindred together and I began to learn from her what the basics were. We were still pretty small as Kindreds go, and we didn't do great big things for the holidays, everything was very organic and everyone had something to do in creation of the blots which I think means a lot. My sense of the holidays was joyful, but still muted a bit by the amount of work that went into the Kindred, especially as I was the primary person to host events which meant lots of cooking and cleaning. For me holidays were rooted in work, which to me kind of rings true for the way I was raised too come to think of it. Togetherness and work with joy and reverence to me that's really what holidays are about.
Of course each holiday has it's own particular definition and meaning, that is a fact and something we should be attentive to. But in some respects I think that it is the excuse for people to gather together, and that this was most likely especially so in times past. Because the Gods and the spirits of the land as well as the ancestors were a part of each individual's every day life, they were conscious of them in a way we no longer are. Now we use the Holiday(s)as an excuse to worship,rather than as an excuse to gather. Kind of backward thinking if you ask me. But we are what we are,society changes and with it our conscious choices.
One holiday that I think most people do not give nearly enough credit to, is the Charming of the Plow.It is at this time that the tools for the year are blessed so that they can allow for productive work throughout the year. Many people consider this purely to be an agricultural holiday and thus sweep it under the carpet and kind of ignore it, but I have used it to bless supplies for crafting,writing and so forth and it has done quite well by me. I think anyone who looks at this as an opportunity to look within themselves and find that which drives them can benefit greatly from celebrating this with great sincerity.
Is the Pagan/Heathen Wheel of the Year artificially created? Most likely it is, but it works. It gives us pause that we would not take otherwise.
( There are holidays that have more or less meaning for me than others. )