WinterNights: A Singer Songwriter Showcase (Day 1)

Lineup for February 25 (5 Talented Musicians in 3 Shows):

6:00 -- Ashton Naylor
7:00 -- Topo Chico Cowboys
8:15 – Kristi Grider & Tina Wilkins

6:00pm:  Ashton Naylor is a singer/songwriter from San Marcos, Texas. Growing up in a household full of music ranging from Willie Nelson to Pearl Jam, Ashton has a knack for music of all sorts. During his first semester of college, he began playing guitar and writing songs. A year later, he would attend South Plains College in Lubbock, to pursue a degree in music. Since then, Ashton has moved back to his hometown to continue honing his craft for songwriting, while also attending Texas State University. Ashton has a unique style of music, blending elements of country, blues, and Americana. Some of his biggest influences include Jerry Jeff Walker, Robert Earl Keen, and Tom Petty. Ashton’s focus moving forward is to continue developing as an independent songwriter and performer in the great state of Texas. For more info: ashtonnaylormusic.com

7:00pm:  Topo Chico Cowboys is the acoustic songwriting duo of celebrated Americana artists Drew Kennedy and Josh Grider, two longtime friends whose chemistry, humor, and deep musical connection have turned their shows into can’t-miss events. Born out of years of swapping songs on the road, late-night writing sessions, and shared love of storytelling, the Topo Chico Cowboys blend sharp lyricism with the easy camaraderie of two artists who know each other’s instincts inside and out.

Kennedy and Grider first crossed paths on the Texas songwriter circuit, quickly discovering a shared sensibility — warm melodies, lived-in narratives, and an appreciation for the small, human moments that make a song feel true. Individually, each has built a respected career with acclaimed solo albums, national tours, and songwriting credits across country and Americana. Together, they create an entirely different kind of magic: stripped-down performances full of wit, harmony, and the kind of effortless banter that can only come from genuine friendship.

A Topo Chico Cowboys show feels both intimate and expansive, shifting seamlessly between poignant ballads, character-driven stories, and the playful humor the duo has become known for. Their songs highlight the unique strengths of each artist — Drew’s literary detail and cinematic tone, Josh’s soulful phrasing and melodic warmth — while forging a sound that belongs wholly to the partnership.

Whether on festival stages, in listening rooms, or on their beloved “song swap” tours, the Topo Chico Cowboys exemplify the spirit of modern Americana: honest songwriting, exceptional musicianship, and a connection with audiences that runs deep. More than a side project, the duo represents a continuing creative conversation between two of the genre’s most compelling voices — one that’s still evolving, still inspiring, and still powered by friendship, craft, and a couple of cold Topo Chicos

Josh Grider is a deeply authentic voice in modern country and Americana, known for pairing heartfelt songwriting with a warm, lived-in baritone. Born and raised in Las Cruces, New Mexico, Grider discovered music early, growing up on his father’s country records and eventually finding his own place in choir and onstage. By his teens he was writing songs, and in college he studied classical voice, sharpening the technical foundation that would support his natural storytelling instincts.

After moving to Texas, Grider firmly planted himself within the state’s vibrant songwriter culture. Over the years, he has released a series of critically respected albums that showcase his gift for honest, unhurried narratives and melodies that feel at once familiar and fresh. Records like Good People and Long Way from Las Cruces highlight his ability to distill everyday moments—love, loss, hope, and the complicated beauty of home—into songs that connect deeply with listeners.

A steady presence on the touring circuit, Grider has earned a reputation not just as a compelling solo artist but as a generous collaborator. He performs alongside his longtime friend Drew Kennedy as one half of the Topo Chico Cowboys, contributes to the Red River Songwriters community, and often shares the stage with his wife, Kristi. His creative reach also extends behind the scenes, where he has emerged as a producer and mentor, helping shape the sound of rising artists while bringing the same thoughtful approach he applies to his own music.

Drew Kennedy is a Texas-based singer-songwriter whose vivid imagery and easygoing charm have made him a respected voice in Americana and country music. Raised outside Philadelphia, he grew up with a love of books, baseball, and creativity. After playing college baseball in Virginia, he moved to New Braunfels, Texas, where he immersed himself in the region’s rich songwriting community.

Over two decades, Kennedy has released eleven studio albums and authored a novel, Fresh Water in the Salton Sea, reflecting the literary depth that defines his work. His songs blend road-worn wisdom with emotional subtlety, creating an intimate, cinematic atmosphere whether performed with a band or in a stripped-down acoustic setting.

His self-titled 2025 album marks a creative milestone. Written entirely on his own and produced with longtime collaborator Davis Naish, it stretches beyond traditional genre lines, mixing folk roots with modern textures while staying true to his storytelling center.

A dedicated supporter of the songwriting world, Kennedy co-founded the Red River Songwriters’ Festival and the Marathon Songwriters Festival, both championing collaboration and craft. As a writer, he has contributed songs to a wide range of country and pop artists.

Onstage, Kennedy is warm, thoughtful, and deeply engaging, connecting with audiences through sincerity and humor. Guided by curiosity and honesty, he continues to evolve as an artist and share stories that resonate long after the last note fades.

8:15pm: Kristi Grider & Tina Wilkins

Kristi Grider is a Texas-based singer-songwriter whose gentle strength, expressive vocals, and thoughtful songwriting have earned her a devoted following in the Americana and country music community. Originally from Kerrville, she developed a love for music early on, studying piano, singing in harmony whenever she could, and discovering an abiding passion for storytelling through song.

Over the years, Kristi has built a multifaceted musical life. She performs both as a solo artist and alongside her husband, Josh Grider, where her warm harmonies and intuitive musicality elevate every collaboration. Known for her clear, heartfelt voice and her ability to bring emotional honesty to each performance, she crafts songs that are reflective, uplifting, and deeply rooted in personal experience.

Her EP All Right showcases her melodic sensibility and her gift for turning life’s quiet moments into art. Kristi writes with a balance of vulnerability and confidence, blending introspection with a reassuring sense of hope. Her background in teaching further informs her work, adding patience, care, and clarity to her creative approach.

Beyond the stage, Kristi is dedicated to nurturing young musicians as a piano teacher, sharing her love of melody and encouraging students to find their own expressive voices. Her commitment to community, family, and authenticity is woven through everything she does—both in her music and in the relationships she builds along the way.

Onstage, Kristi carries a warm and calming presence. Whether leading a song or adding harmonies that glow from within, she creates a connection that feels genuine and grounded. As a singer, songwriter, educator, and collaborator, Kristi Grider continues to bring grace, heart, and quiet power to the modern Americana landscape.

Tina Wilkins is a soulful performer, writer, and creative force based in the Texas Hill Country. Whether she's singing solo, performing with her husband and musical partner, Walt Wilkins, or reimagining jazz standards with producers Ron Flynt, or Bart De Win, Tina brings warmth, grace, and authenticity to every stage she steps onto. 

Her musical journey began with chapters in Los Angeles and Nashville, where she was a sought-after session and stage singer. Over time, Tina developed a signature songwriting style -- honest, poetic, and deeply attuned to the beauty of everyday life. She has released six solo albums, including Moonflowers (2016) and Night Jasmine (2018), both of which offer lush interpretations of timeless classics alongside her own originals. 

Beyond her music, Tina is the visionary behind Spirit is Ageless -- a global movement and annual festival created to inspire women to embrace their soulful power and radiant authenticity at every age. What began with a song gifted to her in 2015 has blossomed into gatherings, retreats, art, and sisterhood. 

In May 2025, Tina completed her Master of Arts in Consciousness, Psychology, and Transformation, deepening her passion for helping others awaken to their intrinsic wholeness and timeless essence. 

Tina radiates joy, presence, and a love of life that's contagious. You'll find her performing in intimate venues, hosting Spirit is Ageless events, pondering poetry under the Texas skies, or singing jazz standards in romantic lounges around the world.