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Shrouded In Mystery, A Holiday Tradition Was Born

Before this website’s major revamping of 2012, most of the blog posts prior to that time were intentionally wiped out and destroyed. A few memorable ones I made the effort to salvage, mostly from 2010-2011, in which a number of Madonna Timelines played a part, and in order to preserve the continuity and completion of that series I brought them into the update. Other than that, however, the time period before that is a bit hazy, which is why the very first Holiday Stroll I did with Kira remains part myth, part magic, and part lost history.

The nearest I can tell is that it took place in 2011 or 2012, relatively soon after Kira had returned to the Boston area from Florida. That’s when we fortuitously reconnected and started hanging out again, as if her ten years away hadn’t even happened, as if my time in Chicago and Albany were but a daydream. Old friends, especially the good ones, are like that. We picked up exactly where we left off, instantly in sync and totally in tandem as we ventured through Boston and the calendar ticked toward its yearly end.

That first Holiday Stroll was nothing more than a whim, a catchphrase I casually threw out half-jokingly as we scampered through the Boston Public Garden beneath a gray sky spitting snow. We linked arms as we passed by the walking bridge, carrying ourselves in ridiculously haughty fashion as if it were a century ago, then crossed to Beacon Hill where we did some window-shopping. That was about it, and that was enough. Our Holiday Stroll tradition was born. The next year we repeated it when we found ourselves together at Christmastime again, incorporating a dim-sum lunch in Chinatown and a fireside highball in some hotel lobby. Again, it was nothing but our usual shenanigans, given heightened import thanks to the season and the festive air.

By our third year, it felt like it might become a tradition, and we expanded it into a Holiday Stroll weekend, beginning with a Friday night stop at the lobby of the Liberty Hotel, and finishing up with a Sunday brunch somewhere in the city. It was around this time that I started making an itinerary. That immediately sapped some of the joy from the impromptu nature of all previous proceedings, but I liked the sense of gravitas it attempted to conjure.

A year or two later the itinerary had grown so detailed it was down to the minute – I had plotted out the route in ten-minute increments, down to specific ‘casual’ops at hotels for five-minute rest breaks. It was too much, and the universe saw to it that we were saddled with rain and wind, throwing a wrench into my carefully-planned schedule, and rendering it all moot. The first store I had down for us to visit was closed, and we never quite recovered, hitting only four or five of the dozen or so listed stops. Since then I haven’t done a full itinerary in the hope of recapturing the original whim of the first few years. It’s far more enjoyable that way.

A Holiday Stroll should be flexible enough to allow for last-minute inspirations and spur-of-the-moment hairpin curves. Kira never allows herself to be bound to time, and it’s a lesson I’ve slowly learned after years of hanging out with her. For our Holiday Stroll 2019, I only have our annual showing of ‘The Man Who Came To Dinner’ planned as of this writing – the rest will unfurl as the spirits of Christmas intend.

Whether this is our 8thor 9thor 15thHoliday Stroll, it really doesn’t matter. I’ve tried holding onto traditions thinking there was some magic in that, when the real magic is not in doing the exact same thing over and over again, but in being with those who mean the most to us. As I learn to wrap my head around that, I hold those I love a little closer, and the world spins more wildly around us.

Here, to the best of my archival search abilities, is a list of our documented Holiday Strolls:

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