The 2026 ChiTown2Mississippi Heritage Blues Trail Tour
Travel the Mississippi Delta, see live music, explore the roots of chicago blues & Its Legends
This 5-day heritage blues trail bus tour, ChiTown2Mississippi, takes music and history lovers on a journey through the Mississippi Delta—widely regarded as the birthplace of American music and the heart of Chicago blues. Traveling by motor coach, participants dive into Mississippi's rich blues and civil rights history and its connection to Chicago, by visiting key landmarks, museums, juke joints, and community spaces that nurtured many iconic music legends. Among those celebrated are Chicago Blues founder Muddy Waters, as well as the King of the Blues, B.B. King, and other notable figures like Robert Johnson, Hubert Sumlin, Willie Dixon, James Cotton, Little Milton, David “Honeyboy” Edwards, Denise LaSalle, Sam Cooke, Elmore James, Ike Turner, and Dorothy Moore.
Travel dates
From Friday, October 16 through Tuesday, October 20, 2026.
Immerse yourself in the rich Mississippi Delta history, exploring iconic sites along the Mississippi Blues and Freedom Trails.
Trip Start & End:
Begins & ends in Memphis, Tennessee, a significant hub in blues & civil rights history.
You can also choose to return home from Jackson, MS.
Mississippi Destinations:
- Tunica
- Clarksdale
- Mound Bayou
- Indianola
- Cleveland
- Greenwood
- Jackson
These cities are all essential stops on the Mississippi Blues and Freedom Trails.
cost:
$1750 per person - single room occupancy
$1650 per person - double room occupancy
(This price does not include round-trip airfare to Memphis, TN, or optional return flight from Jackson, MS. Travel to and from Memphis must be purchased separately by tourists)
ways to pay
Debit/Credit Card/Apple or Google Pay/PayPal
Deadline:
Full payment due Tuesday, September 15, 2026
- Reserve your spot today with a $350 deposit.
Receive a full refund if canceled by Wednesday, September 16, 2026.
For more information on the cancellation/refund policy, visit the FAQ section below.
Don't miss your chance to explore the iconic Mississippi Delta tour that shaped the sounds of Chicago Blues.
At checkout, use the PROMO code: BLUE$5 for a 5% discount off the cost of your trip.
What's Included:
5-day guided bus tour along the Mississippi Blues & Freedom Trails, expertly led by Chicago-based cultural historians Dr. Traci Lombre, Sharon Davis, and local Mississippi historians, to explore the rich blues and civil rights history of the region.
- Admissions to museums and clubs, along with group gratuities.
- Comfortable transportation between destinations on an air-conditioned motor coach
- Round-trip airport transfers
- Hotel accommodations for 4 nights
- 4 breakfasts, 1 lunch, and 1 dinner
What's Extra:
- Your roundtrip airfare to Memphis, TN, or return flight from Jackson, MS
- Travel insurance (For more info, see the Frequently Asked Questions or FAQs)
- Some meals not included in package (We recommend budgeting $20-50 per day)
- Sales tax & booking fees (Use PROMO code: BLUE$5 at checkout, for a 5% discount off trip costs)
Tour Highlights
Day 1 Memphis - Clarksdale Friday, 10/16/2026
Day 3 Cleveland-Greenwood Sunday, 10/18/2026
Day 2 Clarksdale-Indianola Saturday, 10/17/2026
Tourists arrive in Memphis, TN, starting their journey with visits to iconic landmarks and monuments that highlight both Blues music history and civil rights. After enjoying lunch on Beale Street, visitors explore the nearby National Civil Rights Museum located at the historic Lorraine Motel. Next, we embark on a Mississippi Delta tour, t
Tourists arrive in Memphis, TN, starting their journey with visits to iconic landmarks and monuments that highlight both Blues music history and civil rights. After enjoying lunch on Beale Street, visitors explore the nearby National Civil Rights Museum located at the historic Lorraine Motel. Next, we embark on a Mississippi Delta tour, traveling down the Blues Highway to Clarksdale, MS, the cradle of Delta Blues. Here, we savor dinner at the famous Ground Zero Blues Club before wrapping up the night at Red's Lounge, a key stop on the heritage blues trail tour.
Day 2 Clarksdale-Indianola Saturday, 10/17/2026
Day 3 Cleveland-Greenwood Sunday, 10/18/2026
Day 2 Clarksdale-Indianola Saturday, 10/17/2026
Explore the spaces that shaped Blues music history, featuring legends like Muddy Waters and B.B. King, as well as civil rights figures such as Fannie Lou Hamer and many others. We visit the Crossroads and various significant landmarks and cultural institutions throughout Clarksdale, Mound Bayou, and Indianola. The evening concludes at Clu
Explore the spaces that shaped Blues music history, featuring legends like Muddy Waters and B.B. King, as well as civil rights figures such as Fannie Lou Hamer and many others. We visit the Crossroads and various significant landmarks and cultural institutions throughout Clarksdale, Mound Bayou, and Indianola. The evening concludes at Club Ebony in Indianola, King's hometown, after a visit to the B.B. King Museum & Delta Interpretive Center, making this Mississippi Delta tour an unforgettable experience.
Day 3 Cleveland-Greenwood Sunday, 10/18/2026
Day 3 Cleveland-Greenwood Sunday, 10/18/2026
Day 3 Cleveland-Greenwood Sunday, 10/18/2026
Pay homage to the pioneers of Blues and Mississippi music by traveling to Cleveland, visiting the Grammy Museum and Dockery Farms. This plantation is closely tied to the birth of the Delta Blues and the legendary Charley Patton. We head to Greenwood to visit the gravesite of Robert Johnson, exploring more historical markers along the Mississippi Blues and Freedom Trails.
Day 4 All Day in Jackson Monday, 10/19/2026
Book the Tour! Deadline: Tuesday, 09/15/2026
Day 3 Cleveland-Greenwood Sunday, 10/18/2026
This day is dedicated to exploring Mississippi landmarks and institutions in Jackson, including the Smith-Robertson Museum, which preserves the crucial history of the civil rights movement and the Black experience in Mississippi, deeply connected to the roots of Blues music history. In the evening, we enjoy a Blues jam session presented b
This day is dedicated to exploring Mississippi landmarks and institutions in Jackson, including the Smith-Robertson Museum, which preserves the crucial history of the civil rights movement and the Black experience in Mississippi, deeply connected to the roots of Blues music history. In the evening, we enjoy a Blues jam session presented by the Central Mississippi Blues Society at Hal & Mal's Restaurant in downtown Jackson, a showcase of the rich Mississippi culture.
Day 5 Heading Home Tuesday, 10/20/2026
Book the Tour! Deadline: Tuesday, 09/15/2026
Book the Tour! Deadline: Tuesday, 09/15/2026
On the final day of the Mississippi Delta tour, if departing for home from Jackson, we first visit the Two Museums of Mississippi, which celebrate the state's history.
For those departing from Memphis, we explore the Stax Museum of American Soul and enjoy a delicious Memphis-style BBQ lunch at Central BBQ before heading to the airport.
Book the Tour! Deadline: Tuesday, 09/15/2026
Book the Tour! Deadline: Tuesday, 09/15/2026
Book the Tour! Deadline: Tuesday, 09/15/2026
Don't miss out on the deep blues music history that you'll enjoy on our heritage blues trail tour! If you are ready to take the first step to reserve your spot on this exciting Mississippi Delta tour, use the button below to pay with Credit/Debit Cards, Apple, or Google Pay.
At checkout, don't forget to use the PROMO code: BLUE$5 to recei
Don't miss out on the deep blues music history that you'll enjoy on our heritage blues trail tour! If you are ready to take the first step to reserve your spot on this exciting Mississippi Delta tour, use the button below to pay with Credit/Debit Cards, Apple, or Google Pay.
At checkout, don't forget to use the PROMO code: BLUE$5 to receive a 5% discount off the cost of your trip!
We look forward to traveling with you!