Day 1 – Friday, October 23, 2026 Home Cities – Swift Current, SK – The Excitement Begins
Meals Included: None
The journey begins with a spirit of adventure as you set out together, gathering fellow travelers and sharing in the excitement of what’s to come. The open road stretches ahead, framed by wide prairie skies and rolling golden fields that seem to go on forever.
Along the way, enjoy the beauty of Alberta’s sunlit plains and take in the sight of the striking Saamis Tepee in Medicine Hat, a proud symbol of Indigenous heritage and the world’s tallest tepee. Crossing into Saskatchewan, the landscape welcomes you with its gentle charm and endless horizons—an inspiring start to your musical holiday.
Day 2 – Saturday, October 24, 2026 Swift Current, SK – Minot, ND – Across the Prairies to North Dakota
Meals Included: Breakfast
The vast prairie stretches endlessly in every direction, a patchwork of golden fields and big open skies. The journey carries you east to Moose Jaw, a city rich with character and prairie spirit, before continuing south through Weyburn and Estevan, where small-town charm and agricultural heritage shine through.
Crossing the border at Portal, you leave Canada behind and enter North Dakota, where new scenery and stories await. The day is filled with the quiet beauty of the plains and the growing anticipation of the adventures ahead on your Opry–Ozark holiday.
Day 3 – Sunday, October 25, 2026 Minot, ND – Sioux Falls, SD – From Buffalo Legends to Prairie Lakes
Meals Included: Breakfast
The adventure continues southeast to Jamestown, home to the world’s largest buffalo monument and a reminder of the prairies’ wild past. From there, the journey carries you to Fargo, North Dakota’s largest city, known for its welcoming spirit and lively heritage.
Crossing into South Dakota, the landscape transforms into the Prairie Pothole Region, a breathtaking stretch dotted with thousands of sparkling glacial lakes left behind from the last Ice Age. This remarkable scenery makes the day feel like a passage through both history and nature, as the open road leads ever closer to the heart of your musical holiday.
Day 4 – Monday, October 26, 2026 Sioux Falls, SD – St Joseph, MO – Legends of the Old West
Meals Included: Breakfast, Lunch, Evening Kickback
Journey south through the fertile farmlands of Iowa and into Missouri, where the stories of the Old West come alive. In St. Joseph, step back in time with a guided visit to the Pony Express Museum, where the thrilling but short-lived mail service is brought to life. Enjoy the charm of a restored one-room schoolhouse, a delicious catered lunch, and even a special surprise performance that adds a touch of fun to the day. Continue your exploration at the Patee House Museum and Jesse James Home. Here, you can wander Old Main Street, admire artifacts from a bygone era, climb aboard a vintage steam engine, and stand in the very place where the infamous Jesse James met his fate. This day is filled with history, legend, and the spirit of adventure that makes the West so unforgettable.
Day 5 – Tuesday, October 27, 2026 St Joseph, MO – Cape Girardeau, MO – River History and Cajun Flavors
Meals Included: Breakfast, Dinner
Begin the day at Missouri Western State University, where you can sit in Walter Cronkite’s chair, once used by the legendary newsman. Traveling southeast, the scenery shifts to Missouri’s rolling farmland and historic river towns, echoing the days of steamboats and traders.
Arrive in Cape Girardeau, a charming Mississippi River city filled with tree-lined streets, 19th-century architecture, and inspiring river views. The evening is capped with a lively dinner at Broussard’s Cajun Cuisine, where bold Louisiana flavors meet local hospitality, accompanied by the music and storytelling of Jerry Ford and his band.
Day 6 – Wednesday, October 28, 2026 Cape Girardeau, MO – Memphis, TN – From River Roads to Rhythm and Blues
Meals Included: Breakfast
The morning begins in Cape Girardeau’s historic downtown, where riverfront charm meets fascinating stories. A guided city tour reveals the area’s rich past, with stops at Riverside Pottery inside the restored 1937 B’nai Israel Synagogue, the elegant Glenn House with its Victorian décor, and Water & William Olive Oil Co. for tastings of premium olive oils and balsamic vinegars.
Following the Mississippi south, the scenery shifts as you cross into Tennessee and arrive in Memphis, the birthplace of the blues. Stroll the neon glow of Beale Street, where live music and the scent of Southern cooking fill the air. The evening brings you close to music history itself, as you stay just steps away from Graceland, the iconic home of Elvis Presley.
Day 7 – Thursday, October 29, 2026 Memphis, TN – Nashville, TN – Elvis, Loretta, and Music City
Meals Included: Breakfast
Just steps away, the gates of Graceland open into the world of Elvis Presley. Tour the iconic mansion, from the playful Jungle Room to the glittering trophy hall of gold records, and even step aboard his private jets. Displays of stage costumes, rare photographs, and treasured artifacts paint an unforgettable picture of the King of Rock ’n’ Roll.
Continuing northeast, stop in Hurricane Mills, home of the Loretta Lynn Ranch. Here, exhibits honor the Coal Miner’s Daughter, showcasing memorabilia, awards, and recreated scenes from her Kentucky childhood. Loretta’s story unfolds with warmth, resilience, and authenticity—bringing her remarkable journey to life.
By evening, arrive in Nashville and check in for a four-night stay at the spectacular Gaylord Opryland Resort. With its lush indoor gardens, winding waterways, and festive atmosphere, this grand resort will be your home base as you experience the very best of Music City.
Day 8 – Friday, October 30, 2026 Nashville, TN – Nashville Highlights and Honky-Tonk Spirit
Meals Included: Breakfast
The day begins with a guided sightseeing tour showcasing the best of Nashville. Explore the colorful streets of downtown, pass through Bicentennial Mall Park, and admire the impressive Tennessee State Capitol. Stand on the steps of the full-scale Parthenon, a breathtaking replica of the ancient Greek landmark, and learn how this city earned its place as the recording capital of the country.
The afternoon is yours to enjoy at your own pace. Discover treasures at the Country Music Hall of Fame, step inside the Johnny Cash Museum, or soak up the lively energy of Broadway, where honky-tonk bars spill music into the street. As evening falls, return to the Gaylord Opryland Resort, where twinkling lights and festive décor create the perfect holiday backdrop.
Day 9 – Saturday, October 31, 2026 Nashville, TN – River Rhythms and Opry Nights
Meals Included: Breakfast, Lunch
Step aboard the majestic General Jackson Showboat for one of America’s most entertaining river cruises. Glide along the Cumberland River, savor a delicious meal, and enjoy dazzling live entertainment in the ship’s grand Victorian theatre. With Nashville’s skyline as your backdrop, the blend of scenery, music, and Southern hospitality creates an unforgettable experience.
After docking, take time to explore the shops at Opry Mills Mall, visit Madame Tussauds Wax Museum, or simply return to the Gaylord Opryland Resort to relax amid its festive beauty. This evening, the spotlight shines on the legendary Grand Ole Opry, where country music’s brightest stars and newest talents take the stage in a show that captures the heart of Music City.
Day 10 – Sunday, November 1, 2026 Nashville, TN – Backstage Legends and Free Time Fun
Meals Included: Breakfast
Begin the day with a rare insider’s look at two of Nashville’s most cherished landmarks. Go backstage at the Grand Ole Opry, where you’ll peek into dressing rooms, step onto historic performance stages, and stand in the famed wooden circle where country legends and rising stars have performed for generations. Continue to the Ryman Auditorium, the beloved “Mother Church of Country Music”, where exhibits and artifacts tell the story of its remarkable past.
The afternoon is yours to enjoy at leisure. Return to Broadway’s lively honky-tonks, visit more of Nashville’s world-class museums, or simply relax at the Gaylord Opryland Resort, where festive seasonal décor fills the air with holiday cheer. You might even take a peaceful float along the Delta River Flatboat, winding through the resort’s lush indoor gardens.
Day 11 – Monday, November 2, 2026 Nashville, TN – Branson, MO – From Country Classics to Branson’s Holiday Magic
Meals Included: Breakfast, Dinner
Leaving behind the sounds of Nashville, the journey carries you west through the scenic countryside of southwest Kentucky and into the foothills of the Missouri Ozarks, where another kind of musical magic awaits.
In Branson, your new home for the next three evenings, the holiday spirit comes alive. The city shimmers with millions of twinkling lights, carols fill the air, and the excitement of unforgettable shows sets the stage for the days ahead. A welcoming dinner and time to settle in mark the perfect beginning to your Branson adventure.
Day 12 – Tuesday, November 3, 2026 Branson, MO – From Ozark Charm to Celtic Song
Meals Included: Breakfast, Dinner
The day begins with a locally guided city tour, showcasing Branson’s musical heritage, iconic theatres, and the natural beauty of the Ozark Mountains. Learn how this once-small town grew into one of America’s top live entertainment destinations while taking in views of Table Rock Lake and the charming downtown district.
This evening, gather for dinner and dessert at the Pickin’ Porch Grill, where hearty Ozark comfort food is paired with warm Southern hospitality. The night sparkles with a performance by The Dublin Irish Tenors & The Celtic Ladies, an acclaimed show of rich harmonies, soaring vocals, and the timeless charm of Irish and Celtic traditions.
Day 13 – Wednesday, November 4, 2026 Branson, MO – From Holiday Sparkle to the Miracle of Christmas
Meals Included: Breakfast, Dinner
The curtain rises on Christmas Wonderland, a dazzling holiday spectacular filled with glittering costumes, festive choreography, and timeless seasonal songs that capture the joy of the season.
Later, gather for a hearty Southern-style dinner at Paula Deen’s Family Kitchen, where comfort food is served family-style with true Southern warmth and hospitality.
The evening builds to a grand finale at the magnificent Sight & Sound Theatre with The Miracle of Christmas. Elaborate sets, breathtaking special effects, and a talented cast bring the Nativity story to life in a way that is both awe-inspiring and deeply moving. With live animals, sweeping music, and moments of quiet reverence, this unforgettable production is truly a highlight of your Branson stay.
Day 14 – Thursday, November 5, 2026 Branson, MO – Kansas City, MO – Underground Wonders & City Lights
Meals Included: Breakfast
Leaving behind Branson’s holiday sparkle, the journey winds through the scenic Ozark Mountains to Springfield, home to one of America’s most unique natural wonders—Fantastic Caverns. Board a comfortable tram and venture underground, where ancient formations, cathedral-like chambers, and the soft drip of mineral-rich water reveal a story written over thousands of years. This rare ride-through cave offers a fascinating experience without the need for extensive walking.
After this remarkable underground adventure, continue north to Kansas City, a vibrant Midwestern hub filled with jazz heritage, fountains, and warm hospitality, where the day comes to a close.
Day 15 – Friday, November 6, 2026 Kansas City, MO – Watertown, SD – Through the Heartland
Meals Included: Breakfast
The journey carries you north through Missouri’s rolling farmland and into the open countryside of Iowa, before crossing the Missouri River into South Dakota. The scenery shifts from gently tilled fields to broad stretches of prairie, dotted with shimmering glacial lakes—ancient remnants of the last Ice Age.
As the road unwinds, the horizon stretches endlessly, offering a peaceful reminder of the vastness and quiet beauty of the Great Plains. By day’s end, you’ll reach Watertown, carrying with you the calm and charm of the countryside vistas experienced along the way.
Day 16 – Saturday, November 7, 2026 Watertown, SD – Minot, ND – Prairie Horizons and the Magic City
Meals Included: Breakfast
The route winds through the heart of the prairie, where wide-open skies and golden stubble fields stretch endlessly to the horizon. Crossing into North Dakota, the journey passes through towns born along the old rail lines, each carrying its own unique story of settlement and growth.
By day’s end, you’ll arrive in Minot, fondly known as the “Magic City” for its rapid boom during the railroad era of the early 1900s. It’s a place where history and prairie charm meet, marking another memorable step on your homeward path.
Day 17 – Sunday, November 8, 2026 Minot, ND – Swift Current SK – Across the Plains and Towards Home
Meals Included: Breakfast, Farewell Dinner
Crossing the border back into Canada, the road stretches across the quiet beauty of southern Saskatchewan’s plains, where farming communities and wind-swept fields paint a timeless prairie scene. The journey follows the course of the South Saskatchewan River, a lifeline for generations of settlers and traders.
Arriving in Swift Current, you’ll learn the city takes its name from the swift-flowing creek once noted by Hudson’s Bay Company explorers. It’s a fitting stop on the homeward path—rich in history, shaped by the land, and wrapped in the enduring spirit of the prairies.
Day 18 – Monday, November 9, 2026 Swift Current SK – Drop Offs – Memories to Last a Lifetime
Meals Included: Breakfast
The final stretch carries you across Alberta’s wide-open prairies, where familiar towns slowly come into view. Onboard, the spirit of the trip lingers—lively conversation and toe-tapping holiday tunes from Branson fill the air, wrapping the journey in cheer.
As you reach your drop-off points, fond farewells are shared with new friends who now feel like family. You return home carrying not just souvenirs, but a collection of memories—of music and laughter, twinkling lights and timeless songs, and the warmth of a holiday journey well spent.
