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Press + news

The Watering Hole Podcast, Episode 209

This week on the podcast, we sit down with Hope MacGregor for a powerful conversation about music, resilience, and the unexpected paths that lead us back to our purpose.

Hope’s story is anything but ordinary—she went from growing up in the Midwest with a love for singing and songwriting, to serving as a U.S. Army helicopter pilot after graduating from West Point. Life took another turn when she transitioned out of the military, attended law school, and then found herself in the middle of personal loss and major life change. In that season, an old guitar resurfaced—and with it, a return to writing music that was honest, healing, and deeply personal.

MacGregor gives keynote address at the Women of Influence 2026 award ceremony

Singer-Songwriter Hope MacGregor served as the guest speaker for today’s event. Hope MacGregor is a songwriter, storyteller, artist, and Army Aviation Veteran. After eight years of active duty military service, Hope put down her uniform and found herself in law school. Then, in the middle of the global pandemic and the middle of school, her car broke down, her grandmother died, her dog got cancer, and her husband ran off with a blonde to Texas. With the encouragement of her father, MacGregor picked up her old guitar and pen – she started writing songs.

VetTunes Podcast Season 2, Episode 1

Host Mike Corrado sits down with Hope MacGregor,‬ an Army veteran and accomplished singer-songwriter. Discover Hope's inspiring journey from West Point graduate and Army helicopter pilot to a thriving music career. In this episode, Hope shares her experiences in the military, her passion for music, and the stories behind her albums, including the latest release, "Sloppy Seconds." Tune in for an engaging conversation filled with insights, personal stories, and Hope's unique musical journey.

How Hope MacGregor’s Entrepreneurial Journey Took Flight Through Music

Hope MacGregor never imagined her path would transition from flying helicopters over Afghanistan to standing on stage, guitar in hand. But if there’s one constant in her life, it’s embracing the pivot, and doing so with purpose.

Twenty-three hand-selected military veterans learned from Spears School of Business faculty and leading industry experts during an eight-day boot camp [at Oklahoma State University] as a part of the 15th annual National Veteran Entrepreneurship Program in Stillwater.

Hope MacGregor Awarded B. Curtis Hamm Dreamer and Doer Award

Earlier this month, KBEAR host Adam Smith had the opportunity to sit down with singer-songwriter Hope MacGregor at The MusicFest in Steamboat. During their conversation, MacGregor opened up about how her military background has influenced her music.

Military Experience Shapes Hope MacGregor

Eric Raines has a Texas Country Conversation with Hope MacGregor sharing stories about her diverse past - including time spent flying helicopters in the army, navigating through law school . . . and finding solace in country music. Find out why Hope MacGregor needs to be on your Country Music radar in 2025!

Texas Country Conversation with Eric Raines

On Stories, Music, and Place: an Interview with Hope MacGregor

Our Jackson Home: If you have lived in Jackson very long at all, chances are you have heard the name “Hope MacGregor” before. With her rich and powerful vocals, down-to-earth personality, and witty banter with her audience, it is no wonder that she has become a beloved figure in the music scene here in the Hub City. 

The MusicFest: From Open Mic to Official Slot at Dung Beetle Saloon

Hope MacGregor made her MusicFest debut with our open mic series this past Sunday. In a MusicFest first, we have invited an open mic performer to take the stage for a full set! Come check out this newfound talent at the Dung Beetle Saloon.

Professionally Offensive Podcast Ep. 110

Hope MacGregor, Country Music Artist has been on a long road back to where it all started... behind a guitar and microphone sharing what’s on her heart. This former Army Aviator and classically trained attorney has already lived several chapters of life and thanks to a conversation with her Dad, is back to her calling. Serving in the military and enduring personal hardship helped inspire her music.  Pain is not an easy thing to make sense of, but when we recognize that we are all enduring something, the right tune over the radio can make you feel a little less lonely.  

Elm City Radio Artist Spotlight March 2025: Hope MacGregor

Hope MacGregor is a Jackson, Tennessee-based artist who has taken a great journey with her music. From a theater and music kid at Rochester, Illinois High School to combat veteran to singer-songwriter; Hope's carrying the stories with her songs. 

About Hope . . .

Hope MacGregor is a Jackson, Tennessee-based artist (with musical homes in Memphis and Nashville) who walked a winding path to get back to music. She left her guitar and songwriting behind in her small, midwestern town to join the Army after high school. In 2011, she graduated from West Point and became an OH-58D Kiowa Warrior helicopter pilot. One tour to Afghanistan and eight years later, Hope decided to hang up her uniform to start law school.

Just a handful of months into the pandemic and her third semester of school, Hope’s (now ex-)husband ran off with a blonde to Texas . . . her grandmother died . . . her dog got cancer . . . and of course . . . her car broke down. She was, at that point, forced by the universe to pick up her old guitar to write a country song. What started as a way to endure a season of loss grew into a passion and a purpose. 

Hope and her band stand out not just as talented musicians, but as truly authentic artists with an honest story to tell. She writes the kind of music that finds humor in the heartbreak and helps the lonely feel less alone. In short, Hope’s music sounds like home.

Since 2020, Hope has released an EP and two studio albums. She has also joined the legendary roster of artists to perform at The MusicFest in Steamboat Springs, Colorado — most recently opening up for Zach Top and 49 Winchester with the National Anthem.

Hope and her band have played from Tennessee to Texas, Illinois to Oklahoma, and the Carolinas to Colorado. She has headlined a summer concert series of over 1,800 attendees, shared festival bills with three Grammy award winning artists, and amassed over 80k streams. Hope’s music has enjoyed airtime on 99.7 The Mix (AAC), 104.5 WFMB (Country), 92.3 KBEAR (NRRA), and 92.9 KVRE (Mix).

Hope was recently listed as a Rising Star in Music by the Tennessee Entertainment Commission and performed on the Opry Outdoor Stage at The Grand Ole Opry. She was also honored in 2025 as one of Jackson Tennessee’s Most Influential Women; Hope was the keynote speaker at the 2026 awards program. She was also awarded with the B. Curtis Hamm Dreamer and Doer Award at the Veteran Entrepreneurship Program hosted at Oklahoma State University.

If you really want to get to know Hope, though, just ask her about her beloved yellow lab, Lucy.

Photo credits:

Gray Photo Co. + Hannah Gore Photography

Past events + shows

  • July 2026: Opry Plaza Stage @ The Grand Ole Opry; Discovery Park @ Union City, TN; Selmer Freedom Fest @ Selmer, TN

  • June 2026: House show @ Concord, NC; Lamplighter Lounge @ Memphis, TN

  • May 2026: Freedom Sings Fest @ Shelbyville, TN; Exit 56 Blues Fest @ Brownsville, TN

  • April 2026: Block 34 @ Stillwater, OK; The Downtown Tavern @ Jackson, TN

  • March 2026: Carl Perkins Civic Center @ Jackson, TN; Hernando’s Hideaway @ Memphis, TN

  • February 2026: The Blue Canoe @ Tupelo, MS

  • January 2026: The MusicFest @ Steamboat Springs, CO

  • September 2025: The Amp @ Jackson, TN

  • August 2025: Album Release Show @ Jackson, TN

  • July 2025: National Tour

  • May 2025: Exit 56 Blues Fest @ Tina Turner Museum

  • April 2025: Central Station @ Memphis, TN; Tennessee Brew Works @ Nashville, TN

  • March 2025: Pizza Records @ Jacksonville, IL

  • January 2025: The MusicFest @ Steamboat Springs, CO; The Mercury Cafe @ Denver, CO

  • December 2024: For the Record Music Hall @ Florence, AL

  • November 2024: It’s All About Wine @ Springfield, IL

  • October 2024: Milan Fall Festival @ Milan, TN

  • September 2024: Smokin’ on the Beaver @ Atwood, KS

  • August 2024: The Amp @ Jackson, Tennessee; 7 Oaks Event Garden @ Beaumont, Texas; Neches Brewing Company @ Port Neches, Texas; Iron Horse Pub @ Wichita Falls, Texas

  • June 2024: Dancing Turtle Festival @ Stillwater, Oklahoma

  • May 2024: Vintage Makers Festival @ Jackson, Tennessee

  • March 2024: Hope MacGregor Live from Turntable

  • January 2024: The MusicFest @ Steamboat Springs, Colorado; Hub City Brewing @ Jackson, Tennessee

  • December 2023: EM w. Senior Veterans of Stillwater @ Stillwater, Oklahoma

  • November 2023: Doe’s Eat Place @ Jackson, Tennessee; Broadgauge @ Petersburg, Illinois; Door 4 Brewing @ Decatur, Illinois; It’s All About Wine @ Springfield, Illinois

  • October 2023: Central BBQ @ Memphis, Tennessee; Thirsty Goat @ Clarksville, Tennessee; Album Release Party @ Hub City Brewing @ Jackson, Tennessee

  • September 2023: Nashville Fair w. CreatiVets @ Nashville, Tennessee

  • August 2023: Nashville Grand Prix w. CreatiVets @ Nashville, Tennessee

  • July 2023: Recorded the Matriarch at Jaxon Records

  • June 2023: Old Country Store @ Jackson, Tennessee, CatBird Studios @ Jackson, Tennessee

  • May 2023: Writer’s Round @ Broadgauge, Show @ Fat Ass 5k, Writer’s Round @ E3 Chophouse

  • April 2023: The Pond @ Franklin, Tennessee, South Main Sounds @ Memphis, Tennessee, Memphis Farmers Market @ Memphis, Tennessee, Elwood’s Shack @ Memphis, Tennessee

  • March 2023: It’s All About Wine @ Springfield, Illinois

  • Final Fridays 2023: Monthly Residency @ Baker Bros BBQ @ Jackson, Tennessee