Mississippi Blues Trail Itineraries – Mississippi Blues Trail

by Mauka · Published March 7, 2024 · Updated April 22, 2024

MISSISSIPPI BLUES TRAIL
ITINERARIES
As an extra…Experience the Magic of Mississippi’s Other Treasures

Mississippi Blues Trail Itineraries found below offer a variety of travel plans.
In addition to our main mission to capture the essence of where the blues music originated, we wanted to explore Mississippi’s other treasures. And that we did!
Furthermore, the following itineraries will take you places you probably did not know existed. I didn’t until I started researching the trip so sharing this with you hopefully will bring an added awareness to Mississippi’s phenomenal treasures.

It was towards the end of the Covid-19 pandemic when we visited
so we found a lot of blues venues with live music closed.
Unfortunately, there is not a lot to write about with regards to live music.

Mississippi Blues Trail Itineraries: DAY 1
Driving into Woodville is a little detour on Hwy 24 off Hwy 61. However, Woodville is a very sleepy little town with buildings and homes still occupied that were built in the 1800s and early 1900s.

In contrast, Natchez was a favorite stop. It is a beautiful, once very wealthy town sitting on the Mississippi River with rich histories from different time periods.

First of all, WOODVILLE, MS was our first stop on the southern end of the Blues Trail.
After a 2-2 ½ hour drive from New Orleans, this was a great place to stop and stretch your legs.
We spent maybe an hour walking and driving around the town looking at historic buildings and homes and reading the one Woodville Blues Trail Marker.
Additionally, Mammy’s Cupboard was to be our next stop for lunch before reaching Natchez. However, when we got there, it was closed. Make note that it’s only open Tuesday-Saturday from 11am – 2pm if interested.
Moreover, NATCHEZ, MS, our home for one night although Natchez is a town where you could spend several days.
The GRAND NATCHEZ HOTEL is where we stayed for the night, which was lovely. A sizable, clean room with a view overlooking the Mississippi River. Plus, a great location to take a walk along the river and catch a beautiful sunset.
Although, If staying more than 2 nights, a choice would have been one of the B&B’s in an older mansion converted into lodging.
In addition, Natchez has 4 Blues Markers located throughout the town.
First of all, Natchez Walking Trail is a self guided walking tour you can follow from the sidewalk signs around town leading you to some of the historic mansions and buildings that helped to build Natchez into what it is today. Additionally, plaques and signs are posted detailing info about the properties.
NATCHEZ POINTS OF INTEREST include the Historic Natchez City Cemetery, which was created in 1822. Come visit some of the very interesting characters that reside here and read about their unique stories.
Moreover, FORKS-OF-THE-ROAD is the site of a former slave market. Exhibits provide visitors with information about the second largest domestic slave market in the Deep South, where shackled remains still exist.
Moving on, ROSALIE MANSION was built in the 1820s as a private residence that also served as a Union Headquarters during the Civil War.
When it comes to Natchez, Under-The-Hill, it is located on the river at the bottom of the river’s bluff. In the past, Natchez-under-the-Hill was notorious for lawlessness and violence with brothels, gambling houses, and saloons. However, all of these have been converted to restaurants, bars, and shops.
Our choice for dinner was the Magnolia Grill and it was delicious! Additionally, across the street is where they dock a steamboat, which is pretty cool to see.

Mississippi Blues Trail Itinerary map for New Orleans to Natchez

Mississippi Blues Trail Itineraries: DAY 2
Before leaving Natchez to head for Vicksburg, we booked a tour of Natchez with REV’s NATCHEZ COUNTRY TOURS. Thankfully, the Rev suggested the OLD COUNTRY STORE on Hwy 61 for lunch so we pass on that suggestion to you!

Moreover, from here, we could have just continued north on Hwy 61 to Port Gibson,
but we decided to cruise a backroad (552) taking us to WINDSOR RUINS. Although there wasn’t much to see here, the drive was something different.

Unfortunately, KUDZO covered the plants and trees like a blanket being laid over the earth.
It was a remote lovely county drive that circled back to Hwy 61 in Port Gibson, that took all of 30 minutes.

Furthermore, PORT GIBSON was another drive through with quick stops to read markers and take pictures, as well as to reflect on what was.

Firstly, REV’s NATCHEZ COUNTRY TOURS has several options for different tours of the area and the Rev was like an encyclopedia of knowledge about the history of Natchez. Consequently, it was well worth every minute!
Additionally, the tour we booked was a 2-hour tour, which was all the time we had before heading to Vicksburg with the main focus being “Forks-of-the-Road”.
Moreover, FAYETTE, MS is 30 minutes north of Natchez where just off Hwy 61 is a Blues Marker for Charles Evers & the Blues.
Additionally, lunch at the Old Country Store, just 10 minutes north on Hwy 61 in Lorman, MS is advertised as having the best fried chicken in the world.
Even though the chicken was phenomenal so were the side dishes. Additionally, there is a full buffet lunch of Southern foods available.

Additionally, Vicksburg is another favorite town
where we could have spent a couple of days at least
an extra night to take the haunted night tour at McRaven!
Moreover, downtown Vicksburg was a defined area
with museums, shops, and dining.
In addition, the Civil War Museum which
we just happened upon turned out to be a hidden jewel!
Likewise, within the same block is the Coca-Cola Museum
showcasing an elaborate collection of memorabilia.

First of all, VICKSBURG, MS is a must-visit destination.
Additionally, McRAVEN HAUNTED HOUSE is a fascinating stop along the way.
Moreover, the CIVIL WAR MUSEUM offers a unique perspective on the Civil War and likewise the COCA-COLA MUSEUM is a historical site not to be missed.
In addition, the Vicksburg Riverfront Murals provide a visual journey through the city’s past and afterward visit 10 SOUTH ROOFTOP BAR & GRILL for a casual dining experience at sunset.
Additionally, with 6 BLUES MARKERS scattered throughout the town, Vicksburg offers a rich cultural experience.
Finally, consider staying overnight in Vicksburg to fully immerse yourself in all it has to offer.

Mississippi Blues Trail Itinerary map for Natchez to Vicksburg Mississippi Blues Trail Itineraries: DAY 3

Another day of historical adventures driving from Vicksburg to Clarksdale.
However, plan on extra time when visiting the VICKSBURG NATIONAL MILITARY PARK to absorb the history of the battles that took place here and to learn about the USS Cairo, an ironclad boat.

In ROLLING FORK, a relatively small town that we stopped in to see the replica of Muddy Water’s cabin.
Here, we learned about the origin of the Teddy Bear. Additionally, we met Lee, an artist that creates figurines
out of cotton picking equipment parts. Sadly, in 2023 Rolling Fork was almost completely destroyed from a tornado.

MONT HELENA is a drive-by with a quick stop on the side of the road to take pictures.
Moving forward, we continued on to CLARKSDALE neglecting to visit many of the BLUES MARKERS along the way.

To help with your planning,
I’ve listed them for anyone wanting to seek them out.

First of all, VICKSBURG NATIONAL MILITARY PARK consists of a circular drive through a historic documentary of Civil War battles fought in Vicksburg. Additionally, make sure you stop and see the USS Cairo in the park. Furthermore, plan on 2 hours to explore the area.
Moving on to ROLLING FORK, which is 45 minutes north of Vicksburg Military Park, is where the birthplace of Muddy Waters is identified by a Blues Marker. A In addition, a replica of the shotgun shack is on display just behind the marker.
Another interesting tidbit is that the origination of the Teddy Bear came from Rolling Fork thanks to President Theodore Roosevelt.
Continuing the journey, MONT HELENA is about 6 minutes north on Hwy 61 from Rolling Fork. Moreover, the mansion sits atop an Indian mound built 1,000 years ago (which is part of the Mississippi Indian Mound Trail).
Lastly, currently Mont Helena is a private residence so there is no access other than stopping on the side of the road and taking a couple of pics.

Mont Helena to Clarksdale is approximately a
1 and 3/4-hour drive with no stops.
Additionally, the route offers picturesque views along the way.

Along the way, you will pass the following small towns with just one BLUES MARKER site:

Hollandale – Blues marker for Sam Chatmon (c. 1899-1983), a celebrated singer and guitarist.
Shaw – Blues marker for David “Honeyboy” Edwards, born in Shaw.
Peavine Railroad (west of Hwy 61 on 446) provided transportation for bluesmen of the Mississippi Delta. Notably, Charley Patton made it famous through his popular “Pea Vine Blues.”
Mound Bayou Blues – Blues markers for Charley Patton, fiddler Henry “Son” Simms, singers Nellie “Tiger” Travis and Sir Lattimore Brown, and guitarist Eddie El.
Winstonville – Blues markers for the Harlem Inn, “The Showplace of the South,” B. B. King, Little Milton, Bobby “Blue” Bland, Howlin’ Wolf, Tyrone Davis, T-Bone Walker, and Ike Turner and his Kings of Rhythm.
Shelby – Blues marker for Henry Townsend, born in Shelby, was the only blues artist to have recorded during every decade from the 1920s to the 2000s.
Duncan – Blues marker for Blues Legends of Duncan, Jimmy Reed, Eddie C. Campbell, Willie Love, Ernest Lane, Willie “Rip” Butler, and Anthony “Big A” Sherrod. It’s worth noting that Charley Patton’s daughter Rosetta Brown was also a longtime resident here.
Alligator – Blues markers for George “G. P.” Jackson and Robert “Bilbo” Walker, singer Johnny Drummer (Thessex Johns), and the gospel and R&B group the Kelly Brothers. Additionally Delta blues icon Robert Johnson also lived in this area in 1930.
Bobo – Little Junior Parker, one of the most outstanding blues singers of the 1950s and ‘60s, was born on a plantation near Bobo.

Travelling map for Vicksburg to Clarksdale

Mississippi Blues Trail Itineraries: DAY 4 – CLARKSDALE, MS
Moreover, we made the decision to spend three nights in Clarksdale, using it as a central point for our travels. This allowed us sufficient time to discover other exciting destinations along the Blues Trail. In addition, we had the opportunity to check out some fantastic music spots and savor delicious Southern dishes. Plus, we took advantage of a guided tour at the Delta Blues Museum to gain a deeper understanding of the origins of blues music. Clarksdale, Crossroads, Shack Up Inn

CLARKSDALE BLUES MARKERS
Firstly, SHACK UP INN on the Hopson Plantation is the place to stay. Additionally, with renovated sharecropper shacks and grain bins the lodging is most definitely unique. Furthermore, live music is periodically performed on site. If not staying here, stop by, walk around and read the Blues Marker found here. In conclusion, this is quite an extraordinary place.
Moreover, experience the CHARACTER OF CLARKSDALE. Walk around the town, drive the outskirts, read Blues Markers, see the painted murals, and unique displays. Additionally, meet and talk to the locals. Consequently, you will see it’s friendly and warm.
In addition, DELTA BLUES MUSEUM is well worth a visit. Notably, Mississippi’s oldest music museum (est. 1979) it is the place to explore the Blues of the past and to explore what is new.
Also, Blues Clubs to name just a few: Ground Zero, Reds, Hambones, Bluesberry Cafe, etc. Undoubtedly, these clubs are the reason you came to Clarksdale!
Lastly, CROSSROADS is at the intersection of Hwy 61 & Hwy 49. Furthermore, this is the place where Robert Johnson sold his soul to the devil. Be careful, currently this is a busy intersection.

Following the Blues Markers, visitors can venture on to other points of interest.
In the following Day Trip itineraries, they can explore more of the area.
Always arriving back in Clarksdale to catch the evening’s performers.

Mississippi Blues Trail Itineraries: SIDE TRIP 1
(short day)
Driving time to TUNICA, 30 minutes north of Clarksdale, not including stops along the way.

First of all, STOVALL FARMS is where Muddy Waters lived and worked as a tractor driver just 10 minutes out of town. Additionally, the Blues Marker is on the cabin site where he grew up.
Moving on to FRIAR’S POINT, MS which has a population of less than 1,000, so there isn’t much here. However, for us, it was a slow drive through with quick stops on the side of the road to read the Blues Marker for Robert Nighthawk, who called Friar’s Point his home.
Furthermore, other Friar’s Point interest are:
~ Its the birthplace of Conway Twitty.
~ Tennessee Williams and William Faulkner have written about Friar’s Point.
Transitioning to TUNICA, MS some points of interest are:
~ GATEWAY TO THE BLUES MUSEUM where exhibits tell the story of how the blues genre of music was born and the role Tunica and the Delta region played.
~ In addition, the Hollywood Café is a historical café that has merited a Blues Marker and is a great place to eat.
~ Also, there is a Veteran’s Memorial Park located at Rivergate Park and several casinos and resorts are located in Tunica
Next, in Lula there is a BLUES MARKER for Charley Patton, Son House, Frank Frost, and Sam Carr.
Lastly, in Lyon, MS is the site for BLUES MARKER ROCKET “88”, Jackie Brenston and his Delta Cats.
Additionally, Brenston and Raymond Hill, who played the saxophone, are buried in Heavenly Rest Cemetery on Highway 61 just north of the Lyon city limits.

Mississippi Blues Trail Itinerary map for Clarksdale to Tunica

Mississippi Blues Trail Itineraries: SIDE TRIP 2
(this is a very long day!) Whew… this day trip covers a lot of territory.
First of all, an early start worked to its advantage as we were able to do it all!

TUTWILER, MS is 20 minutes SE of Clarksdale. Additionally, a Blues Marker for W.C. Handy who reportedly discovered the blues on a train platform in Tutwiler is located here.
~ Moreover, Tutwiler Murals are several murals along Railroad Station Park painted on a brick wall depicting the first hearing of blues music on the station.
~ In addition, Tutwiler Funeral Home is the funeral home where EMMETT TILL’S body was embalmed.
~ Continue driving on Money Rd. to Money, MS, 30 minutes south of Tutwiler and just north of Greenwood.
~Furthermore, on Money Rd. in front of the dilapidated Bryant’s Grocery there is a marker on the “MISSISSIPPI FREEDOM TRAIL” documenting the murder of EMMETT TILL which led to the start of the Civil Rights movement.

Continue with a 15 minute drive to Greenwood, MS.

On the way into Greenwood on Money Rd. is Robert Johnson’s gravesite where a memorial has been established by fans.
Additionally, Greenwood is a larger town and the perfect place to take a break.
After Greenwood, head SW to the Sky Lake Preserve to enjoy the remote outdoors
and see one of Mother Natures wonders.

Notably, the movie “THE HELP”
was filmed at multiple places around Greenwood.

First of all, Greenwood, MS has 7 BLUES MARKERS in and around town. Additionally, there is a blues Marker & memorial site for ROBERT JOHNSON’S grave on Money Rd. Furthermore, just outside of Greenwood, at the Little Zion MB Church.
GREENWOOD, MS – POINTS OF INTEREST
~ Tallahatchie Flats on Money Rd. just north of Greenwood, has lodging similar to Shack Up Inn.
~ Moreover, Tallahatchie Bridge is the bridge mentioned in Bobbie Gentry’s song, “Ode to Billie Joe”.
~ Additionally, Grand Blvd. was once named as one of America’s “Most Beautiful Streets”. This mile long road is lined by century old oaks, estate size mansions, and cozy cottages.
~ Lastly, The Crystal Grill has been in business as a restaurant since 1932. It is a great place to drop in for lunch and a piece of pie for dessert.
Although, SKY LAKE PRESERVE is a 30 minute drive SW of Greenwood, and north of Belzoni, this remote preserve is worth a visit. You can walk the boardwalk where you will see Bald Cypress trees over 1,000 years old.

The following are BLUES MARKERS
that can seen on the drive from Greenwood to Sky Lake:

SW of Berclair is a blues marker for B.B.’s King Birthplace.
In Moorhead is the blues marker for “Where the Southern Cross the Dog” featuring W. C. Handy known as, “The Father of the Blues”

Heading back to Clarksdale (approximately an hour’s drive),
if there is still daylight and if you still have energy,
on the road between Moorhead and Clarksdale
are several small towns with only one BLUES MARKER site.

In Ruleville there is a Blues Marker for Jimmy Rogers a guitarist and vocalist, was a member of Muddy Water’s band.
Continuing on to Drew there is a Blues Marker for Roebuck “Pops” Staples of the Staple Singers.
Finally, there is the Parchman Mississippi State Penitentiary Blues Marker. The penitentiary was inspiration for many songs like “Parchman Farm Blues”.

Mississippi Blues Trail Itineraries: DAY 6
(leaving Clarksdale for Natchez)
Additionally, this can be another long day. Two museums to visit, two Indian mounds to explore, and several markers to visit.

In MERIGOLD, MS you can find the location of Po Monkey’s Juke Joint Blues Marker. This dilapidated building out in the middle of nowhere gives you an idea of how far people travelled for entertainment how small juke joints were.
In CLEVELAND, MS there are 5 BLUES MARKERS in and around town including Dockery Farms.
~ Furthermore, MISSISSIPPI’S GRAMMY MUSEUM celebrates all genres of music with a focused spotlight on the deep musical roots of Mississippi. Plan on spending a couple of hours here.
~ Lastly, DOCKERY FARMS, located just outside of Cleveland, is a historical site that pays homage to its musical heritage.
Shaw, MS simply has a BLUES MARKER for Honeyboy Edwards
In contrast, INDIANOLA, MS has 3 Blues Markers in town, a museum and several points of interest.
~ The B.B. King Museum shows how much this artist contributed to the music world. Plan on spending an hour maybe a little more here.
~ Additionally, the Blue Biscuit is across the street from the B.B. King Museum so stop in for a pulled pork sandwich and maybe a set of live music.
~ Moreover, Club Ebony is a well-known blues venue that was part of the Chitlin Circuit.
Moving on to LELAND, MS, it has 5 Blues Markers in town.
~ The Rainbow Connection Bridge is a local bridge whose name was changed in honor of Jim Henson who grew up here.
Interestingly enough, WINTERVILLE INDIAN MOUNDS is an ancient Indian mound where you can experience a creation from 1,000 years ago. It is located just outside Greenville.
Speaking of Greenville, it has 3 BLUES MARKERS in town.
Hollandale also has a BLUES MARKER for Sam Chatmon, a celebrated singer and guitarist who spent most of his life in Hollandale
Likewise, EMERALD INDIAN MOUND is another ancient Indian mound just outside Natchez that is a different creation than Winterville Mounds.

Overnight in Natchez, MS, finally rest and recuperation!

Traveling Clarksdale to Natchez

Mississippi Blues Trail Itineraries: DAY 7
Natchez to New Orleans – We added on to our trip staying two nights in New Orleans, in the quarter of course, before flying home.