CALENDAR: September / October 2026 Tuesday, September 1, 2026 • Trivia Night - Free Roam Brewing Company - Boerne • Night Owls - El Milagro Twenty Twelve - Fredericksburg • Toddler Time! - Cafe at the Ridge - Kerrville Wednesday, September 2, 2026 • David Harris - Pioneer Bar - Fredericksburg • Red Cliff - Hudson’s on Mercer Street - Dripping Springs • Wednesday Karaoke Night - Gravity Check Saloon - Kerrville • Ben Beckendorf - Luckenbach
Tuesday, September 8, 2026 • Trivia Night - Free Roam Brewing Company - Boerne • Night Owls - El Milagro Twenty Twelve - Fredericksburg • Maplewood Brothers - Lincoln Street Wine Market - Fredericksburg Wednesday, September 9, 2026 • Blues Wednesdays - Hill Top Cafe - Fredericksburg • David Harris - Pioneer Bar - Fredericksburg • Red Cliff - Hudson’s on Mercer Street - Dripping Springs • Constitution Birthday Party - Museum of Pacific War - Fredericksburg
Thursday, September 3, 2026 • Country Nights Open Mic - Gravity Check Saloon - Kerrville • Not Your Granny’s Bingo - 717 Water Street - Kerrville • Fredericksburg Hop & Sip Kangaroo Experience - Grapetown Vineyard • Bubba Westly - Gruene Hall - New Braunfels
Thursday, September 10, 2026 • Andi Holleman & The Highroad - Gruene Hall - New Braunfels • Trivia Every Third Thursday - Arcadia Live - Kerrville • Open Mic Night - Gravity Check Saloon - Kerrville • KAC Networking Group - Inn Of The Hills Hotel - Kerrville • River Rat Thursdays - River Rose Tavern - Canyon Lake
Friday, September 4, 2026 • First Weekend at the Museum - Pioneer Museum - Fredericksburg • “Stars, Stripes and Stitches” Vereins Quilt Guild Show - Fredericksburg • Vanishing Bees Trio / Karaoke Night - Velvet Lounge - Fredericksburg • Fredericksburg Trade Days - 355 Sunday Farms Rd - Fredericksburg • Labor Day Weekend Neon Glow Party - Texas Wine Country Jellystone Camp Resort • Fall Planting Seminar - Wildseed Farms - Fredericksburg • Warren Rew Band - Rio Guadalupe Resort - New Braunfels
Friday, September 11, 2026 • Brock Stephen - Augusta Vin - Fredericksburg • First Friday Art Walk - 218 W Main St - Fredericksburg • Vanishing Bees Trio - Velvet Lounge Corner Bar - Fredericksburg • Spicy Loops - William Chris Vineyards - Hye • Stoney LaRue - Gruene Hall - New Braunfels • Michael Perez & Jennifer Lynn - Gin Mill Lounge - Fredericksburg • Grandparents Day - TX Wine Country Jellystone Park - Fredericksburg
Saturday, September 5, 2026 • Everybody’s Somebody Fest 2026 - Luckenbach • JNM Acoustic Duo - 1693 Distillery - Fredericksburg • Robert Earl Keen - Floore’s Country Store - Helotes • Trey Gonzalez - Carter Creek Winery - Johnson City • Pat Green & Cory Morrow - Lonestar Premier Outdoors - Cibolo • Redbud Artisan Market - Marktplatz on Main St. - Fredericksburg • Battle Reenactment: Road to Vistory-Peleliu - Museum of Pacific War - Fredericksburg • Heart of the Hills Farmer’s Market - Heritage Star Parking Lot - Kerrville
Saturday, September 12, 2026 • Texas Gun & Knife Show - Happy State Bank Expo Hall - Kerrville • Llano Wild Game Dinner - John L. Kuykendall Events Center - Llano • Marshall Tucker Band - Round Mountain Cider Mill - Round Mountain • Pecan Street Festival - Hill Country Galleria - Bee Cave • Young Eagles Rally - Gillespie County Airport - Fredericksburg • Heart of the Hills Farmers Market - Lot 741 Water St - Kerrville • Nalani Caballero - Augusta Vin - Fredericksburg • Cibolo Farmers Market - Herff Farm - Boerne • Karaoke Night - Yee Haw Saloon - Fredericksburg
Sunday, September 6, 2026 • Ben Beckendorf Trio - Luckenbach • Ruben Pacheco - Arch Ray Resort - Fredericksburg • Fallon Franklin - Augusta Vin - Fredericksburg • Daniel Redcliff - Lincoln Street Wine Bar - Fredericksburg • Best Jazz Brunch in TX - The Dodging Duck - Boerne • Dillon Havins - Signor Vineyards - Fredericksburg Monday, September 7, 2026 • Trivia Night - Wilson’s Ice House - Kerrville • Ben Beckendorf - Silver Creek Beer Garden & Grille
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Sunday, September 13, 2026 • Texas Gun & Knife Show - Happy State Bank Expo Hall - Kerrville • Daniel Redcliff - Lincoln Street Wine Bar - Fredericksburg • Boerne Market Days - Main Plaza - Boerne • Javier Soliz - Signor Vineyards - Fredericksburg • Stoney LaRue - Gruene Hall - New Braunfels • Courtney Patton, Matt Hillyer & Wesley Hanna - Luckenbach Monday, September 14, 2026 • Ben Beckendorf - Silver Creek Beer Garden & Grille - Fredericksburg • Trivia Night - Wilson’s Ice House - Kerrville
• Curtis Lee - Hays City Store & Ice House - Driftwood Tuesday, September 15, 2026 • Shane Stumpf - Gravity Check Saloon & Arena - Bandera • Toddler Time - Cafe at the Ridge - Kerrville • Downtown Marble Falls Farmers Market - Marble Falls • Two Ton Tuesdays - Gruene Hall - New Braunfels Wednesday, September 16, 2026 • Karaoke Night - Gravity Check Saloon - Kerrville • Red Cliff - Hudson’s on Mercer Street - Dripping Springs • Blues Time Wednesdays with Johnny Nicholas - Hill Top Cafe - Fredericksburg • John Bardy Acoustic Pickers Circle - Luckenbach Thursday, September 17, 2026 • Trivia Every Third Thursday - Arcadia Live - Kerrville • Bandera Farmers Market - 415 Main St - Pipe Creek • Country Nights Open Mic - Gravity Check Saloon - Kerrville • Fun Friday - ArcoTex Cedar Park Friday, September 18, 2026 • Vanishing Bees - Pier 27 Bar & Grill - Kerrville • Fredericksburg Trade Days - 355 Sunday Farms - Fredericksburg • Sammy J - Round Mountain Cider Mill - Round Mountain • Michael Perez & Jennifer Lynn - Gin Mill Lounge - Fredericksburg • Mahjong Retreat - Tapatio Springs Hill Country Resort - Boerne • Keelan Donovan - The Hills Country Club - The Hills Chophouse - Austin • FBG Chamber Annual Golf Tournament - Fredericksburg Saturday, September 19, 2026 • Remo Fest 2026 - Hill Country Caribbean Vybez - Blanco • Muscadine Bloodline - Lonestar Premier Outdoors - Cibolo • Vanishing Bees Trio - Velvet Lounge Corner Bar - Fredericksburg • Live Music - The Dodging Duck Brewhaus - Boerne • Texas Flood - Rockbox Theater - Fredericksburg • RedCliff - Proof and Cooper - Johnson City • Dan Whitaker - Lost Draw - Johnson City • Jay Eric - Neon Armadillo - Wimberley Sunday, September 20, 2026 • Javier Soliz - Signor Vineyards - Fredericksburg • Daniel Redcliff - Lincoln Street Wine Bar - Fredericksburg • Radio Jouney - The Watering Hole Saloon - New Braunfels Monday, September 21, 2026 • 10th Annual Fredericksburg Classic Car & Truck Show - Pecan Grove Store • Ben Beckendorg - Silver Creek Beer Garden & Grille - Fredericksburg • Trivia Night - Wilson’s Ice House - Kerrville • David Selbo - Valeria Restaurant - Boerne Tuesday, September 22, 2026 • Night Owls - El Milagro Twenty Twelve • Mike Blakely - Western Edge Kitchen & Cocktails - Fredericksburg • Two Ton Tuesdays - Gruene Hall - Gruene • Shane Stumpf - Gravity Check Saloon - Kerrville Wednesday, September 23, 2026 • Red Cliff - Hudson’s on Mercer Street - Dripping Springs • Rawlyn Richter - Albert Ice House & Dancehall - Stonewall • Blues Wednesdays - Hill Top Cafe - Fredericksburg • Taste of Leander - Old Town Leander Thursday, September 24, 2026 • Open Mic Night - Gravity Check Saloon & Arena - Kerrville • Trivia at the Arcadia Live - Kerrville • Bo Show - Llano Music Fest - Robinson City Park - Llano Friday, September 25, 2026 • Llano Texas Music Fest - Robinson City Park - Llano • After Hours - Turtle Creek Vineyard - Kerrville • Fredericksburg Trade Days - 355 Sunday Farms Rd - Fredericksburg • Brock Stephen - Augusta Vin - Fredericksburg • Twin Sisters Dance Hall Fundraiser - Twin Sisters Dance Hall • Jamie Lin Wilson - Rockbox Theater - Fredericksburg • Karaoke Night - Velvet Lounge - Fredericksburg • Railcar Revival Music Festival - Buda City Park & Ampitheater - Buda Saturday, September 26, 2026 • Llano Texas Music Fest - Robinson City Park - Llano • Twin Sisters Dance Hall Fundraiser - Twin Sisters Dance Hall • All Hat No Cadillac - Contigo Ranch - Fredericksburg • DJ Big Worll - Fat Ass Ranch Winery - Fredericksburg • Heart of the Hills Farmers Market - Lot 741 Water St. - Kerrville • Railcar Revival Music Festival - Buda City Park & Ampitheater - Buda • Medina Lake Cajun Festival - Civic Center - Lakehills • Back to the Ranch: The LBJ BBQ Returns - LBJ Ranch - Stonewall • Menard River Rat Picnic - Low Water Crossing Park - Menard • TerraTX Art Festival - Concan Sunday, September 27, 2026 • Vanishing Bees - Slate Theory Winery - Fredericksburg • TerraTX Art Festival - Concan • Daniel Redcliff - Lincoln Street Wine Bar - Fredericksburg • Driftwood Run Solo Acoustic - Augusta Vin - Fredericksburg • The Walton’s Fan Experience 2026 - St. Joseph’s Halle - Fredericksburg • Fall Festival - Wildseed Farms - Fredericksburg Monday, September 28, 2026 • Trivia Night - Wilson’s Ice House - Kerrville • Ben Beckendorf - Silver Creek Beer Garden & Grille - Fredericksburg
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BEverages & Bites
• David Selbo - Valeria Restaurant - Boerne
• Parade of Homes - New Braunfels
Tuesday, September 29, 2026 • Two Ton Tuesdays - Gruene Hall - Gruene • Night Owls - El Milagro Twenty Twelve - Fredericksburg • Heartbreak Outlaws - Country Western Dance Night - Gravity Check Saloon - Kerrville
Monday, October 5, 2026 • Trivia Night - Wilson’s Ice House - Kerrville • Mindful Wellness Walk - Bear Moon Bakery Cafe - Boerne • Ben Beckendorf - Silver Creek Beer Garden & Grille - Fredericksburg
Wednesday, September 30, 2026 • Mindful Wellness Walk - Bear Moon Bakery Cafe - Boerne • Pollinator Picnic - Winding Branch Ranch - Bulverde • Red Cliff - Hudson’s on Mercer Street - Dripping Springs • David Harris - Pioneer Bar - Fredericksburg
Tuesday, October 6, 2026 • Trivia Night - Free Roam Brewing Company - Boerne • Two Ton Tuesday - Gruene Hall - Gruene • Jack White - Moody Ampitheater - Austin • Night Owls - El Milagro Twenty Twelve - Fredericksburg • Country Western Dance Night - Gravity Check Saloon - Kerrville
Thursday, October 1, 2026 • Pauline Reese - The Falls - Llano • Open Mic Night - Gravity Check Saloon & Arena - Kerrville • Bandera Farmers Market - 415 Main Street - Pipe Creek • Songwriters Night - The Red Bird Listening Room - New Braunfels Friday, October 2, 2026 • Oktoberfest - Markplatz - Fredericksburg • Susan Herndon - The Ridge Marketplace - Kerrville • Fallon Franklin - Augusta Vin - Fredericksburg • Stephen Wilson Jr. - Floore’s Country Store - Helotes • Fredericksburg Trade Days - 355 Sunday Farms - Fredericksburg • Live Music - 259 Bistro - Boerne • Live Music - Dodging Duck Brewhaus - Boerne Saturday, October 3, 2026 • Oktoberfest - Markplatz - Fredericksburg • Stephen Wilson Jr. - Floore’s Country Store - Helotes • Heart of the Hills Farmers Market - 741 Water Street 9a-1p - Kerrville • Spanish Colonial Heritage Day - Presidio de San Saba - Menard • Sacred Springs Powwow - Meadows Center - San Marcos • Cibolo Farmers Market - Herff Farm - Boerne • Ruben Pacheco - Arch Ray Resort - Fredericksburg • Josh Abbott Band - Carter Creek Winery Resort & Spa - Johnson City Sunday, October 4, 2026 • Oktoberfest - Markplatz - Fredericksburg • Daniel Redcliff - Lincoln Street Wine Bar - Fredericksburg • Sacred Springs Powwow - Meadows Center - San Marcos • Spicy Loops - William Chris Vineyards - Hye • Michael O’Connor and Libby Koch - The Redbird - New Braunfels
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Wednesday, October 7, 2026 • Red Cliff - Hudson’s on Mercer Street - Dripping Springs • Blues Wednesday - Hill Top Cafe - Fredericksburg • David Harris - Pioneer Bar - Fredericksburg Thursday, October 8, 2026 • Welcome Home Fest - Quiet Valley Ranch - Kerrville • Open Mic Night - Gravity Check Saloon & Arena - Kerrville • Jeremy Parsons Music - The First National Ice Haus - Bandera • Foreigner in Concert - HEB Center - Cedar Park • Tripping Daisy - Buck’s Backyard - Buda Friday, October 9, 2026 • Welcome Home Fest - Quiet Valley Ranch - Kerrville • Hill Country Honeys - Redbud Cafe - Blanco • Driftwood Run Solo Acoustic - Augusta Vin - Fredericksburg • Gruene Music & Wine Festival - Gruene Hall - Gruene • Texas Mesquite & Fine Art Festival - Marktplatz - Fredericksburg • Pickers Circle & Dance Lessons - Luckenbach Saturday, October 10, 2026 • Welcome Home Fest - Quiet Valley Ranch - Kerrville • Hill Country Heritage Farmers Market - 301 Junction Hwy - Kerrville • Gruene Music & Wine Festival - Gruene Hall - Gruene • Texas Mesquite & Fine Art Festival - Marktplatz - Fredericksburg • Cibolo Farmers Market - Herff Farm - Boerne • Texas Pumpkin Fest - VFW - Leander • Hill Country Revival - Cowboys & Cadillacs - New Braunfels • Fall 2026 Bison Field Harvest - ROAM Ranch - Fredericksburg
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• RedCliff - Proof and Cooper - Johnson City • BestFest - MarktPlatz - Fredericksburg • Texas Wine Jam - Johnson City Sunday, October 18, 2026 • Texas Gun & Knife Shows - Abilene Convention Center - Abilene • Fallon Franklin - Augusta Vin - Fredericksburg • Daniel Redcliff - Lincoln Street Wine Bar - Fredericksburg • Barnyard Stompers - Poodies Hilltop Roadhouse - Spicewood • Jazz Brunch - The Dodging Duck - Boerne • Shakedown Live - Hays City Store - Driftwood Monday, October 19, 2026 • Trivia Night - Wilson’s Ice House - Kerrville • Ben Beckendorf - Silver Creek Beer Garden & Grille - Fredericksburg • Paint Kerrville 2026 - Kerr Arts & Cultural Center - Kerrville Tuesday, October 20, 2026 • Trivia Night - Free Roam Brewing Company - Boerne • The Night Owls - El Milagro Twenty Twelve - Fredericksburg • Heartbreak Outlaws - Gravity Check Saloon - Kerrville • Maplewood Brothers - Lincoln Street Wine Market - Fredericksburg Wednesday, October 21, 2026 • Blues Wednesday - Hill Top Cafe - Fredericksburg • Red Cliff - Hudson’s on Mercer Street - Dripping Springs • David Harris - Pioneer Bar - Fredericksburg • Scotty Alexander - Hays City Store & Ice House - Driftwoodx Thursday, October 22, 2026 • Fredericksburg Food & Wine Festival - 100 Block of Main St - Fredericksburg • Open Mic Night - Gravity Check Saloon & Arena - Kerrville • Not Your Granny’s Bingo - Arcadia Live - Kerrville Friday, October 23, 2026 • Vanishing Bees Trio - Firefly Resort - Fredericksburg • Fredericksburg Food & Wine Festival - 100 Block of Main St - Fredericksburg • Jake Martin - Hill Country Stories - Arch Ray Resort - Fredericksburg • Live Piano Bar by Andy Johnson - Cuvee Wine & Piano Bar - Fredericksburg • Karaoke Night - Velvet Lounge - Fredericksburg • Gary Allan - Floore’s Country Store - Helotes • Ella Reid - Liberty Hill Beer Market - Liberty Hill
Sunday, October 11, 2026 • Welcome Home Fest - Quiet Valley Ranch - Kerrville • Daniel Redcliff - Lincoln Street Wine Bar - Fredericksburg • Honey Creek Festival - St. Joseph Catholic Church - Spring Branch • Noah Peterson - The Dodging Duck - Boerne Monday, October 12, 2026 • Trivia Night - Wilson’s Ice House - Kerrville • Catch Curtis Lee - Hays City Store & Ice House - Driftwood • Ben Beckendorf - Silver Creek Beer Garden & Grille - Fredericksburg Tuesday, October 13, 2026 • Trivia Night - Free Roam Brewing Company - Boerne • Night Owls - Western Edge Kitchen & Cocktails - Fredericksburg • Two Ton Tuesdays - Gruene Hall - Gruene • Country Western Dance Hall - Gravity Check Saloon - Kerrville Wednesday, October 14, 2026 • David Harris - Pioneer Bar - Fredericksburg • Red Cliff - Hudson’s on Mercer Street - Dripping Springs • Rawlyn Richter - Albert Texas Ice House - Stonewall • Boerne Senior Expo - The Bevy Hotel - Boerne Thursday, October 15, 2026 • Open Mic Night - Gravity Check Saloon & Arena - Kerrville • Trivia Night - Third Thursday - Arcadia Live - Kerrville • Jake Bush - Gruene Hall - Gruene • Home Free - Brauntex Theater - New Braunfels • Astronox Festival 2026 - Valkyrie Ranch - Paige Friday, October 16, 2026 • Vanishing Bees - Becker Vineyards - Fredericksburg • James Keith & The Q-Tips - Roddy Tree Ranch - Ingram • Brock Stephen - Augusta Vin - Fredericksburg • The Merles - Luckenbach • Dylan Wheeler - Gruene Hall - New Bruanfels • Pecos & The Rooftops - Floore’s Country Store - Helotes • Songwriters Festival - Mercer Street - Dripping Springs Saturday, October 17, 2026 • Texas Gun & Knife Shows - Abilene Convention Center - Abilene • Baubles & Beads 2026 - Hill Country Youth Event Center - Kerrville • Songwriters Festival - Mercer Street - Dripping Springs • Dia De Los Muertos Festival - New Braunfels • Hill Country Heritage Farmers Market - Kerrville • DJ Big Worll - Fat Ass Ranch Winery - Fredericksburg • Boerne Barktoberfest - 6th Annual Pet Friendly Festival • Cibolo Farmers Market - Herff Farm - Boerne
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Saturday, October 24, 2026 • 150 Years ofd Kimble County - Kimble County Historical Museum - Junction • Texas Gun & Knife Shows - Fredericksburg Fair Grounds - Fredericksburg • Fredericksburg Food & Wine Festival - 100 Block of Main St - Fredericksburg • Barnyard Stompers - The Barrell House - Llano • Steven McClintock with Mark Piper - Lazy Days Cantina - Ingram • Llano River Pumpkin Float - Badu Park - Llano • Harvest Time Pull - AgriCultural Museum & Arts Center - Boerne • Water Street Festival - Kerrville Sunday, October 25, 2026 • Texas Gun & Knife Shows - Fredericksburg Fair Grounds - Fredericksburg • Fredericksburg Food & Wine Festival - 100 Block of Main St - Fredericksburg • Daniel Redcliff - Lincoln Street Wine Bar - Fredericksburg • Bronco Spooktacular - Guadalupe Brewing Company & Pizza - New Braunfels • Cela Harper - William Chris Vineyards - Hye Monday, October 26, 2026 • Texas Furniture Makers Show - Kerr Arts & Cultural Center - Kerrville • Ben Beckendorf - Silver Creek Beer Garden & Grille - Fredericksburg • Fredericksburg Food & Wine Festival - 100 Block of Main St - Fredericksburg • Trivia Night - Wilson’s Ice House - Kerrville Tuesday, October 27, 2026 • Trivia Night - Free Roam Brewing Company - Boerne • Night Owls - El Milagro Twenty Twelve - Fredericksburg • Country Western Dance Night - Gravity Check Saloon - Kerrville • Mike Blakely - Western Edge Kitchen & Cocktails - Fredericksburg Wednesday, October 28, 2026 • David Harris - Pioneer Bar - Fredericksburg • Red Cliff - Hudson’s on Mercer Street - Dripping Springs • Blues Wednesdays - Hill Top Cafe - Fredericksburg • Haunted Hallway - Greater San Marcos Youth Council - San Marcos Thursday, October 29, 2026 • Heart of Texas Honky Tonk Fest - Ed Davenport Civic Center - Brady • Open Mic Night - Gravity Check Saloon & Arena - Kerrville • Trivia Night - Third Thursday - Arcadia Live - Kerrville Friday, October 30, 2026 • Spirits of Blanco - Old Blanco County Courthouse grounds - Blanco • Texas Fleece & Fiber Festival - Happy State Bank Expo Hall - Kerrville • Michael Perez & Jennifer Lynn - Gin Mill Lounge - Fredericksburg • Karaoke - Velvet Lounge - Fredericksburg • After Hours - Turtle Creek Vineyard - Kerrville • Steven McClintock - Cafe At The Ridge - Kerrville • Texas Marigold Festival - Blanco Saturday, October 31, 2026 - Halloween • Fall Art & Wine Fest - downtown Mason Square - Mason • Moondance Outdoor Concert - Cibolo Center for Conservation - Boerne • Caroline Parker - Creekhouse Kitchen & Bar - Wimberley • Sheila Marshall - William Chris Vineyards - Hye • RedCliff - Altstadt Brewery - Fredericksburg • Ghosts of Hill Country - Gruene Hall - New Braunfels ______________________________ visit us at h i l l c o u n t r y h a p p e n i n g s . n e t
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