Along the gravel road ahead, a wooden A-frame reads “Music Fest, this way.” Off to the side, cars line up in a grassy field. Families pull red wagons loaded with camp chairs, coolers and kids. Everyone dances towards a timber-framed stage at the bottom of a gentle slope where potted chrysanthemums dot the edge between amps and speakers. The wooded hillsides enclose the valley like an amphitheater.
Welcome to Middlesex Music Festival.
Most upstate New Yorkers have not heard of this festival and that’s not entirely by accident. But the one-day event has existed in some form for almost 40 years, predating both Grassroots in Ithaca and The Great Blue Heron in Sherman, New York.
Less than an hour south of Rochester, on the eastern shore of Canandaigua Lake, is Middlesex — a small town in Yates County where the population hovers around 1,500. But those folks harbor a secret: an annual event that celebrates the best in local music, from bluegrass and folk to rockabilly and zydeco. In its earliest days, the festival was held at the Middlesex Airport, a grassy strip for private aircraft.
“We set up near the hangars and planes would land during sets,” said Middlesex native Logan Rockcastle, who grew up going to the festival and now runs operations. “It must have been weird to fly over and see a bunch of hippies down on the runway.”
A young Donna the Buffalo played in the early ‘90s along with local legends like Bobby Henry and the Goners. Occasionally, bigger acts like The Horse Flies and Rusted Root would get top billing.
“[An] epic memory I have is giving up my bed and bunking with my brother Skye so Rusted Root could sleep at our house,” Rockcastle said.
After a few too many flyovers, the festival moved to the site it calls home today. With no formal marketing — just word of mouth and a few posters around town — it stayed small but deeply cherished. Locals came each year to eat good food and dance the day away.
Now in his 40s, Rockcastle and his friends are shepherding the festival into a new era. For him, it feels like a birthright (his mother Susie was once in charge); a responsibility to keep hometown roots and homegrown talent at the fore. With no overhead and no budget, Middlesex stays true to itself and doesn’t worry about competing with bigger festivals nearby. Rockcastle volunteers his time, and any revenue goes straight to the bands.
The pandemic brought everything to a halt, but in the quiet years that followed, murmurs rippled through the valley: “When’s Middlesex coming back?” Rockcastle heard it from neighbors, old friends, musicians, even strangers at the bar. By 2024, he was ready.
He called Peter Gerbic, the festival’s founder and owner of the field where the stage still stood (in Rockcastle’s words, “the most epic old timer you’ve ever met”), and Gerbic’s answer was simple: “The property’s ready whenever you are.”
And so, Middlesex came back stronger than ever.
The 2024 lineup featured Eastern Boys in Western Shirts, Bobby Henry and the Goners (keeping traditions alive) and Richie Stearns in cahoots with local songwriter Aaron Lipp. To close the night, Rockcastle tapped Buffalo rockers Folkfaces, led by the ever-enigmatic Tyler Westcott.
Matt Duffy, from nearby Vine Valley, is another native who grew up going to the festival. He plays lead guitar with Eastern Boys in Western Shirts, a zydeco band that also includes Rockcastle on accordion, Colin Swider on drums and other rotating childhood friends who’ve come and gone since the late ‘90s when they first jammed.
“I was just a kid when I first went,” Duffy said. “I fell in love with live music there, and I couldn’t be happier it’s back.”
Remembering their childhood, Rockcastle keeps Middlesex family friendly and safe for little ones. There’s an old apple tree in the field behind the stage and its lower boughs sag just enough for climbing. That’s where the children gather while parents keep an eye from afar without missing the music.
Last year’s weather was perfect, and Rockcastle hopes for the same again. The festival returns Saturday, Aug. 23 with Eastern Boys set to open. They’ll be joined by Mustard Tigers, the Sutton String Band (a new bluegrass group out of Naples) and, of course, Bobby Henry.
“He’s an icon, so I can’t have Middlesex Music Fest without him,” Rockcastle said. (He also hinted at a headliner — Flying Object — out of Rochester.)
The festival’s sense of lineage and tradition makes Middlesex unique, and Rockcastle strives to keep the essence of the valley and its 1,500 inhabitants intact.
“It’s a legacy thing,” he said. “Now I have nieces and nephews running around the festival, and one day, all this will be theirs.” facebook.com/MIDDLESEXMUSICFEST
Jon Heath is a contributor to CITY.
This article appears in Dec 1-31, 2024.
