Get ready for a full day of music, community, and good vibes at Cowboys & Hippies, an all-day outdoor music festival celebrating the free spirit of rock, roots, and jam culture.
From early afternoon through sunset and into the evening, the stage will be alive with powerhouse performances from regional favorites and crowd-loving jam bands. Expect soaring guitar solos, tight grooves, soulful vocals, and plenty of moments that make you want to dance, sway, and sing along.
🎶 Featuring live performances by:
Whiskey6 – Bringing high-energy country-rock with a modern edge and a sound made for open air and raised cups.
The Whole Loaf – A genre-blending jam band known for playful improvisation, funky rhythms, and infectious fun.
Bearly Dead – Delivering deep grooves and faithful interpretations inspired by the Grateful Dead, perfect for heads, hippies, and newcomers alike. Get ready, Winchendon!
Waylon & Co. — an incredible Waylon Jennings tribute band — is bringing the outlaw spirit to Winchendon Community Park.
They honor the legacy of Waylon the right way — with grit, soul, and that unmistakable outlaw country sound. This isn’t just a cover show… it’s a tribute to the music, the attitude, and the movement that changed country forever.
🌞 What to expect:
A full day of live music (2 PM–9:30 PM)
A relaxed, festival-style atmosphere
Dancing, lawn chairs, and laid-back vibes
Food, drinks, and community energy throughout the day
Whether you’re a boot-wearing country fan, a tie-dye-loving jam band follower, or someone who just loves live music under the open sky, Cowboys & Hippies is where those worlds collide.
🎟️ Come for a set. Stay for the day. Leave with a soundtrack you won’t forget.
