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Anyone who ever sat with a tape deck trying to record a song off the radio understands the power of the perfect song. Jay and I have several “vacation” songs that never fail to make us smile. We crank up the volume and remember the events surrounding us hearing the song, but more importantly the context of the particular vacation where we heard the song.

While on a bus tour of Western Europe, our guide used a distinctive song as a 5-minute warning alarm. When the song played, we had a few minutes to wake up, put on our shoes, or otherwise collect ourselves before the bus stopped for a break. Jay and I had never heard “Bills” by Lunchmoney Lewis before that trip, but by the end of the 15 days, the entire bus groaned every time it played.

WARNING: Most of these songs/videos are NSFW or small ears.

These days, the song makes me smile. While I don’t approve of all the lyrics (I’m not a pearl clutcher, but I don’t appreciate G-D), I can’t help but smile when I hear the opening “doo, doo, doo, doo, doot…I got bills…” We had a great time on that trip traveling with old friends, making new ones, and visiting 7 countries over two weeks.

Fast forward a few years to the Camp Fradd Hallmark Christmas trip. Jay collected another song for our memory bank while at a McGillin’s Olde Ale House our first night in Philadelphia. The historic restaurant looked like a bomb of Christmas decorations exploded prior to our arrival. The dull roar of the crowded pub made conversation difficult. Despite it all, Jay heard “Lonesome LA Cowboy” by New Riders of the Purple Sage for the first time while we ate, and the song lodged itself in his memory.

Why do the songs on this list have questionable lyrics? Maybe I am a pearl clutcher (with a rebellious streak) after all.

Given our ever-growing collection of vacation songs, its no surprise a few song memories have stuck with me from our Scotland adventure. I loaded my iPod (yes, I still have a vintage shuffle circa 2009) with songs for the trip. Previous distance racing experience taught me the distracting power of music when I’m hurting and need help pushing on.

The only time I needed the music came on the day we tackled 19 miles of the West Highland Way. My body started struggling around mile 13 or 14. On other days, our journey would be wrapping up at that those mile markers. Instead we still had 5-6 miles to go. Jay helped me dig snacks out of my bag to refuel for a bit of a boost, all without stopping for a break. I knew at that point if I stopped my body wouldn’t want to start back.

A decent incline lay before us, and we decide to take the hill at our own pace. Since we wouldn’t be walking together, he helped me fish my iPod out of my backpack so the music could keep me company. As the mileage progressed, my spirits (and my ligaments) deteriorated. When Rehab’s “Bartender” hit my earbuds, I began singing aloud. (Are you clutching your pearls?) Emphasizing the song’s profane lyrics helped me dig deep and find that extra boost I needed to keep going.

I switched to listening to our Spotify Scotland playlist I’d downloaded to my cell phone, cueing up specific songs I could sing along to. OutKast “Ms. Jackson” led off the songs, and my “I am fo-reeeeeeeeeal” probably sounded like a dying coyote’s howl. No matter, I was putting one foot in front of the other, and Andre 3000 and Big Boi helped push me along.

In my zone, I didn’t notice when the sweet older Frenchman we’d met earlier on the trail approached from behind. Jay and I had shared a picnic table with him and his wife a few days earlier. While they both spoke a bit of English, his was more limited than hers. By the look on his face as he passed me singing, I have no doubt he struggled to translate my sorry version of the hip-hop song.

My use of headphones wasn’t limited to helping on difficult mileage. In Four Quick Stories About Visiting Scotland, I wrote about listening to the audiobook of How to Train Your Dragon: How to Break a Dragon’s Heart our last day on the trail. While technically about a young Viking boy, the author admits that the isle of Berk is based on an island she visited as a child, which is located just off the west coast of Scotland.

After stopping in at our Air B&B, using the toilet, and changing into fresh socks, Jay and I set out to finish up our last mile of the trail. The original way ended less than a quarter of a mile from where we were staying, but in 2010 the path was extended further into Fort William. I queued up several peppy songs to build the anticipation of finally making it to the end.

Baseball fans know the value of a good walk-up song, and I made my selections thoughtfully. Jay and I had experienced a bit of a heatwave during our week on the trail, and the last day was no exception. Walking on the concrete and asphalt of the road, with no trees to shade us, I felt every extra degree. As we neared the end, I selected one final song.
“Walkin’ On the Sun” by Smash Mouth guided my steps as we approached the small sign that read “End of the West Highland Way.”

“This is it? Seriously?” I said in disbelief. The original trail ending marker had been more remarkable. After getting a good look around, I noticed the Sore Feet statue, as well as the map of the entire trail on the sidewalk. We’d finished!

We posed from some celebratory photos, and posted online about the achievement. You could say, I managed with a little help from my friends.