Tall Timber Music Festival 2025: Country & Americana Take Over Sugarloaf!

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Tall Timber Music Festival 2025 at Sugarloaf Mountain with live country and Americana bands performing on an outdoor stage, cheering crowd in cowboy hats, and Sugarloaf Ski Resort in Carrabassett Valley, Maine.

Tall Timber Music Festival 2025: Country & Americana Take Over Sugarloaf!

Writer: Gerry Caron | Mar 8, 2025 | 5 min read

Cowboy Boots & Mountain Roots: The 2nd Annual Tall Timber Is Here!

Dust off your hats and grab your dancing boots! From April 4-6, 2025, the Tall Timber Music Festival returns to Sugarloaf Mountain for its second massive year. Building on the legacy of the beloved Broken Hearts & Blackouts, this revamped festival is a high-energy tribute to Sugarloaf’s history, infused with a fresh, soulful Americana spirit.

Set against the rugged beauty of Carrabassett Valley, Tall Timber is the ultimate spring celebration. Whether you’re here for the elite “Big Water” rapids or the high-energy mountain vibes, this weekend promises a world-class lineup of country, folk, and bluegrass that will keep the mountain rocking long after the sun goes down.

The 2025 Weekend Lineup: Three Days of Elite Music

Friday, April 4: Free Après & Nightlife in The Widowmaker

Kick off the weekend with no-cover shows at the heart of the mountain’s social scene.

  • 12:00 – 1:30 PM: Henry Lowery – Maine’s own master of country-blues guitar.

  • 3:00 – 6:00 PM: Silver Heels – A folk-rock powerhouse from Southern Maine.

  • 7:45 – 8:25 PM: Chase Winn – Blending folk and blues into an authentic Americana sound.

  • 8:30 – 11:00 PM: Overserved Again – A high-octane five-piece country-rock favorite.

Saturday, April 5: Free Après & Ticketed 21+ Main Event

Saturday features the festival’s crown jewel: the ticketed evening show in the King Pine Room.

  • 12:00 – 1:30 PM: Nick Casey – Traditional country with a Waylon Jennings soul.

  • 12:00 – 3:00 PM: Henry Lowery – Live at Bullwinkle’s for the ultimate mid-mountain outdoor experience.

  • 3:00 – 6:00 PM: Liz Frame & The Kickers – Rootsy, righteous rock from Boston.

  • The Main Event (King Pine Room – Doors at 7:45 PM):

    • 8:15 – 9:00 PM: Stephanie Ryann – One of country music’s boldest new voices.

    • 9:15 – 10:15 PM: Louie Bello Band – Award-winning Country/R&B fusion.

    • 10:30 PM – 12:00 AM: 12/OC – The dynamic headliners guaranteed to bring the house down.

Sunday, April 6: Soulful Farewells

  • 11:00 AM – 12:00 PM: Henry Lowery – A final soulful acoustic set.

  • 1:00 – 2:15 PM: “Broke Down” – A heartfelt tribute to country storyteller Slaid Cleaves.

  • 2:30 – 4:00 PM: Matt Newberg & The Hearts of Gold – Weaving Maine-inspired folk and a second tribute set to Slaid Cleaves.

🎟️ Ticket & Venue Information

While many après shows are free, the Saturday night 21+ performances require tickets.

Why You Can’t Miss This Year’s Festival

  • Unbeatable Setting: Experience live music at the base and mid-mountain of Maine’s most iconic peak.

  • The Après Scene: Relax with craft brews and world-class mountain culture in the fabled Widowmaker.

  • Exclusive Lineup: From Nashville-recognized singer-songwriters to local Maine legends, the talent is hand-picked for the ultimate Americana vibe.

The Ultimate Sanctuary: Moose River Lookout

Elevate your festival weekend by staying at the Highlands’ premier retreat. Moose River Lookout in Rockwood offers an idyllic riverside escape at the base of the majestic Blue Ridge Mountains.

  • Elite Trail Access: Direct backyard entry to ITS 66 for late-season snowmobiling or the first spring ATV runs.

  • Riverside Luxury: Private dock on the Moose River—perfect for a quiet morning cast or watching the sunrise before heading to the mountain.

  • Adventure HQ: Minutes from the best ice fishing and hiking in the Moosehead region.

Book Your Stay:

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