But on Friday he put aside his musical instruments and took to the saddle to lead as Langholm Cornet.
And in doing so the 27-year-old university graduate achieved a lifelong ambition.
“It’s hard to describe how it felt,” he said afterwards. “Being in that position and seeing all the crowds filling the town is very special.
“It was a very proud moment.”
The part-time organist and choirmaster, who plays at Langholm Parish Church, Westerkirk and Ewes, joined the Castle Craig club in 2011.
Before that, he was already involved with the common riding through his duties as a trombonist and flautist with the town band and flute band respectively.
But even his experiences representing the town at common ridings through the bands, failed to prepare him for what it would feel like leading the celebrations as cornet.
“You think you know what to expect, but when you are in that position everything you feel is times 10,” he said.
“It’s hard to take it all in.
“And in Langholm, with the High Street being so narrow and small, it seems even busier, and the atmosphere all that much bigger.
“For me the main thrill of the day was going up the Kirk Wynd. It is just like a continual rolling cheer as you go up.”
Henry was appointed as cornet in May, after winning the public vote against two opponents in his second year of standing.
And the timing could not have worked out better, for this year he followed in the footsteps of his late great-uncle Andrew Jeffrey, who was cornet 60 years ago.
Henry added: “It was special because on the hill you get to choose an ex-cornet to give the flag to take around the hill. I was able to give it to my uncle Andrew, the 1988 cornet, who carried it on behalf of his father on that anniversary.”
Having led each of the town’s previous five rideouts, alongside his right and left-hand men Iain Little and Stuart Murray, Henry was invested as cornet on Wednesday evening when investing lady Michaela Maxwell, daughter of common riding chairman and officiating magistrate Roger Maxwell, presented him with his crop and sash.
Beside him each step of the way were his lass Lara Falconer, parents Gavin and Frances Jeffrey and sister Claire.
View all our photos here: https://www.thesouthernreporter.co.uk/news/people/in-pictures-langholm-common-riding-1-4975206
And on Friday, Henry led the procession of hundreds on both foot and horseback, through each of the town’s cherished ceremonies. Thousands lined the steep slopes of the Kirk Wynd and Mount Hooley to witness the spectacular gallop and then to hear the fair cried at the Castle Craigs.
After inspecting the ancient boundaries, the cavalcade, which this year included jubilee cornet Billy Laidlaw, circled the monument built to John Malcolm in 1835.
The cavalcade then made its way to Whita Well and Mount Hooley and was met by the bearers of the common riding’s emblems, the thistle, the floral crown, the spade and the barley bannock, as well as hundreds of children with heather besoms.
The procession, now complete with bands and emblems too, was led back to town, where Rae Elliot cried the second part of the fair from the back of a horse, following once again in the footsteps of his father, grandfather and great grandfather.
After safely crossing the River Ewes and rounding the sod that was cut on the Castleholm, a rousing cheer welcomed the cornet and his followers as he galloped past the grandstand at Castleholm.
“All the rides were really well supported and we had super weather at all of them,” Henry added. “And on Friday the weather just got better and better as the day went on.
“I’ve been a really lucky cornet.”