Cowboys & Hippies
Schedule
Sat Sep 19 2026 at 02:00 pm to 09:30 pm
UTC-04:00Location
86 Ingleside Dr, Winchendon, MA 01475-4506, United States | Winchendon, MA
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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.https://www.eventeny.com/events/cowboys-hippies-concert-27916/
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.
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Where is it happening?
86 Ingleside Dr, Winchendon, MA 01475-4506, United StatesEvent Location & Nearby Stays:
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