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Dripping Springs Songwriters Festival — Day 1 Artist Guide (Friday, Oct 16)
Your artist-by-artist guide to Day 1 of the Dripping Springs Songwriters Festival — who's playing, what they sound like, and where to find them across 8 stages in downtown Dripping Springs.
The 12th Annual Dripping Springs Songwriters Festival kicks off today — Friday, October 16, 2026. From 1:30 PM to 8:00 PM, 40+ songwriters will perform in Nashville-style "in the round" sessions across 8 stages in historic downtown Dripping Springs. Every downtown show is free. Here's your artist-by-artist guide to Day 1 — who's playing, what they sound like, and where to find them.
📅 FRIDAY SCHEDULE AT A GLANCE
Four rounds, 75 minutes each, with 25-minute breaks between:
• Round 1: 1:40 – 2:55 PM
• Round 2: 3:20 – 4:35 PM
• Round 3: 5:00 – 6:15 PM
• Round 4: 6:40 – 8:00 PM
8 stages: The Barber Shop Bar, Acopon Brewing, Mazama Coffee Co., Hudson's on Mercer, Warehouse, Winehouse, Haus of Jayne, and Dog & Bone.
🎸 THE FRIDAY ARTISTS
🤠 BRIAN ALLISON — Americana
Nashville-based Americana singer-songwriter originally from Chicagoland. Three-time Josie Music Award winner, including Americana/Folk Artist of the Year. Performing professionally for over 20 years and full-time since 2016. Toured internationally in 2025. His songs are the kind of heartfelt storytelling that the festival is built around — think classic Americana with a Nashville polish.
Where: Round 1 (1:40 PM) at The Barber Shop Bar
🎸 TIM STYLES — Folk / Blues / Country / Rock
A modern-day troubadour born and raised in the Arrowhead Range of northern Minnesota. His dynamic approach seamlessly blends country, blues, folk, and rock — the quality and content of his songwriting belie his youth. Tim is featured in three consecutive rounds on Friday, making him the artist to follow through the afternoon.
Where: Round 1 (1:40 PM) at The Barber Shop Bar → Round 2 (3:20 PM) at Haus of Jayne → Round 3 (5:00 PM) at Mazama Coffee Co.
🎵 ROBERT EUROPE — Blues / Americana / Folk
Austin-based singer, guitarist, and songwriter originally from Long Island, NY. Full-time musician for 10+ years, specializing in soulful acoustic music — blues, Americana, folk, classic rock, and country. His Marshall Tucker Band covers are legendary on YouTube. If you want blues with a Texas edge, start your festival here.
Where: Round 1 (1:40 PM) at The Barber Shop Bar
🎹 ANDY SYDOW — Americana / Rock / Folk
An accomplished multi-instrumentalist whose lyrics paint a picture of poetic realism. Americana, rock, and folk with a songwriter's eye for detail. Based in Colorado, Andy brings a different flavor to the festival — think Rocky Mountain Americana meeting Hill Country listening rooms.
Where: Round 2 (3:20 PM) at Haus of Jayne
🌊 WILL OVERMAN — Americana / Alt-Country / Folk Rock
Virginia-raised, Nashville-based singer-songwriter. Genre-bending storytelling approach — born on the East Coast, tested on the road. His densely layered tunes reward both new listeners and longtime fans. An entirely independent artist at 29, Will represents the next generation of Nashville songwriters.
Where: Round 2 (3:20 PM) at Haus of Jayne
🎶 RAY PRIM — Soul / Americana
Austin-based "Singer Soulwriter." His music takes you back to the days when songs were inspiring, meaningful, and thought-provoking. Performs with his backing vocalist Mexican Chocolate — their live shows are known for humor, heart, and soul. A regular at the Saxon Pub in Austin. If you want something with a soul groove among the acoustic sets, this is your stop.
Where: Round 3 (5:00 PM) at Mazama Coffee Co.
👴 GEORGE ENSLE — Folk / Country
A Texas legend. Part of Houston's 1960s folk scene, George shared stages with Townes Van Zandt, Guy Clark, and Billy Joe Shaver. 15 albums released, inducted into the Houston Folk Music Archives and Corpus Christi Songwriters Hall of Fame. A Texas Commission on the Arts Touring Roster Artist with 58+ years of performing. If you want to hear where Texas songwriting started, don't miss George.
Where: Round 3 (5:00 PM) at Mazama Coffee Co.
🎤 VAUGHAN SEGERS — Singer-Songwriter
Vaughan Segers brings his songwriting to the festival's premier indoor venue. Performing Friday evening at Hudson's on Mercer Street — the festival's main stage with professional sound and lighting. A rising voice in the Texas songwriter scene.
Where: Friday 7:00 PM at Hudson's on Mercer Street
🎸 CHARLIE ARGO — Southern Blues / Country
An unmistakable blend of southern blues and country influences. Charlie brings a gritty, soulful edge to the festival lineup. Catch him at the Dripping Springs Visitors Center stage.
Where: Friday 5:00 PM at Dripping Springs Visitors Center
🎪 DEAN JOHANESEN — Circus Swing / American Roots
"Without a Net" is Dean's musical approach — literally. He plays Circus Swing and American Roots music, a genre-blending style that's unlike anything else at the festival. Based in Florida, he's a songwriter and guitarist who tours the festival circuit. If you want something different from standard Americana, Dean is your pick.
Where: Friday 3:20 PM (venue per festival program)
🪕 MICHELLE RAYBOURN — Americana / Bluegrass
Americana/Bluegrass singer-songwriter originally from Dallas, TX, now based in Nashville. A member of the Bluegrass Ensemble during college, Michelle blends bluegrass instrumentation with Americana storytelling. Her music is "for the beautiful mess of being human." Catch her at the Visitors Center stage.
Where: Friday at Dripping Springs Visitors Center
🌟 MORE FRIDAY ARTISTS TO WATCH
These festival songwriters may appear in Friday rounds — check the official festival program at Festival Headquarters for their specific times and stages:
• Ben Danaher — Nashville-based country/Americana songwriter from Huffman, TX. Shared bills with Ray Wylie Hubbard and Jack Ingram. Writes songs about family, loss, and personal reflection.
• Eric Ramsey — 2022 International Blues Challenge winner. Arizona Blues Hall of Fame. Soaring vocals and organic arrangements. Blues, Americana, and folk influences.
• Emily Barnes — Contemporary folk singer-songwriter. 2026 COMBO Songwriting Contest winner. Her music breathes life into the characters and stories of everyday people.
• Katrina Cain — Texas-rooted artist, recently toured the UK with the London Homesick Blues Tour. Piano and guitar, powerful vocals.
• Kelsi Creek — Indie-soul artist based in Austin, TX. Heartfelt songwriting with a soul edge.
• Ronny Criss — Nashville-based singer-songwriter. Latest album "Hurricane Heart" released 2026. Music lives at the crossroads of country and rock.
• J. Cruz — Singer-songwriter. Songs include "Wyatt Earp," "Them Boots," and "Simple Livin'." Country and Americana with a frontier spirit.
🧭 HOW TO PLAN YOUR FRIDAY
**Follow an artist through the day:** Tim Styles plays three consecutive rounds at three different venues. Start at The Barber Shop Bar (1:40 PM), follow him to Haus of Jayne (3:20 PM), then to Mazama Coffee (5:00 PM). You'll hear him in different configurations with different co-writers each round.
**Pick a venue and stay:** If you prefer to settle in, each venue hosts a different lineup each round. Stay at Mazama Coffee for the afternoon and you'll get coffee, pastries, and three completely different sets of songwriters.
**The Hudson's headliner:** Vaughan Segers plays Hudson's on Mercer at 7:00 PM — the festival's premier indoor venue with professional sound and lighting. This is your evening capstone show.
**Coffee and songwriters:** Mazama Coffee Co. is both a festival stage and the best coffee in town. Grab a pour-over, find a seat, and settle in for a round. The courtyard is made for listening.
🍺 WHERE TO EAT AND DRINK BETWEEN ROUNDS
25-minute breaks between rounds are perfect for refueling:
📍 Mazama Coffee Co. — Coffee, pastries, and a festival stage all in one
→ https://driptx.com/destination/mazama-coffee-co
📍 Acopon Brewing — Cask ale brewpub, intimate stage, great between-rounds pint
→ https://driptx.com/destination/acopon-brewing-co
📍 Homespun Kitchen & Bar — Farm-to-table, right on Mercer Street between stages
→ https://driptx.com/destination/homespun-kitchen-and-bar
📍 The Grawlix Cocktail Lounge — Craft cocktails, a festival stage, and an arcade side
→ https://driptx.com/destination/grawlix-cocktail-lounge
💡 FRIDAY TIPS
• All downtown shows are FREE — no tickets, no cover. Just walk in, find a seat, and listen.
• Seating fills 15-30 minutes before popular rounds — arrive early, especially at smaller venues like Mazama and Haus of Jayne.
• Bring cash for tips and merch — songwriters sell CDs and merch between sets.
• The festival is a listening-room environment — keep conversations for the 25-minute breaks between rounds.
• Park once, walk everything — all 8 stages are on or near Mercer Street.
• Download the official DSSF app or pick up a printed program at Festival Headquarters for the full stage-by-stage schedule.
• Bring a folding chair — some outdoor stages have limited seating.
🗺️ VENUE MAP
All 8 Friday stages are walkable in downtown Dripping Springs:
• The Barber Shop Bar — Mercer Street
• Acopon Brewing — Mercer Street
• Mazama Coffee Co. — Mercer Street
• Hudson's on Mercer — 381 W Mercer St
• Warehouse — Downtown
• Winehouse — Downtown
• Haus of Jayne — Downtown
• Dog & Bone — Downtown
• Visitors Center — 750 US-290
🎸 FULL FESTIVAL GUIDE
Looking for the complete 3-day schedule? See our full Dripping Springs Songwriters Festival Guide:
→ https://driptx.com/destination/dripping-springs-songwriters-festival-guide
🍷 MORE TO EXPLORE IN DRIPPING SPRINGS
🍷 Wine Trail Guide — 12+ wineries along US-290
→ https://driptx.com/destination/dripping-springs-wine-trail-guide
🍺 Breweries & Distilleries Guide — Twisted X, Jester King, Ghost Note, and more
→ https://driptx.com/destination/dripping-springs-breweries-and-distilleries-guide
🚶 Mercer Street Walking Guide — Park once, walk to every venue
→ https://driptx.com/destination/where-to-eat-mercer-street-dripping-springs-guide
🗓️ 48 Hours in Dripping Springs — Full weekend itinerary
→ https://driptx.com/destination/48-hours-dripping-springs-itinerary
Dripping Springs, Texas — a designated Music Friendly Community and host of the annual Songwriters Festival. Plan your festival weekend with DripTX, your guide to Dripping Springs live music, venues, restaurants, wineries, breweries, and things to do in the Texas Hill Country.
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