Greenwood MS Blues Trail – Points of Interest

by Mauka · Published March 6, 2024 · Updated April 24, 2024

GREENWOOD MS BLUES TRAIL
POINTS OF INTEREST
Greenwood MS Blues Trail points of interest
opens up a look into the past.
If you have never been to Greenwood, Mississippi,
let me tell you, there are plenty of things to do
and see in this charming town. Whether you’re a history buff,
a foodie, or a blues music lover, Greenwood has something for everyone.

Just before entering Greenwood, at the north end of town there is one of the must-see places for all blues lovers, the gravesite and memorial of Robert Johnson. As soon as arriving at his gravesite memorial, one could feel the weight of his legacy and contribution to American music. It is truly a surreal moment.
My recent visit to Greenwood was short but sweet. Although we only had a couple of hours to spare, we made the most of it by driving around and exploring the different historical markers scattered throughout the town. Notably, it was quite an experience.
Seeing multiple ads for these yummy pies we were enticed to eat lunch at the iconic Crystal Grill. This restaurant has been around since 1925 and serves delicious Southern food. From fried chicken to shrimp creole, everything on their menu is tempting.

Greenwood may be small in size but its rich history and culture
make it worth visiting for a couple of days or even just a few hours like we did.
So next time you’re passing through Mississippi, don’t forget to stop by
this hidden gem and explore all that it has to offer.

Greenwood MS Blues Trail: Historically speaking

Greenwood was originally known as Williams Landing and was founded in 1830 by John Williams as a trading post on the banks of the Yazoo River. In 1844, it was officially incorporated as Greenwood and named after Chief Greenwood Leflore.
The cotton market here was a very strong cotton market because of its strategic location in the heart of the Delta. It became a major shipping point to New Orleans, Memphis, and St. Louis, Missouri until the latter part of the Civil War.

Greenwood MS Blues Trail: Civil War Fort Pemberton (MS)

Greenwood MS Blues Trail: tour reveals Civil War history

Greenwood, Mississippi played a crucial role in the cotton industry and the Civil War.
Located in the heart of the Delta region, Greenwood was strategically positioned as a major shipping point for cotton. The rich soil and favorable climate made it an ideal place for growing this valuable crop. As a result, the cotton market in Greenwood was bustling and thriving.
However, things took a turn during the Civil War. In the latter part of the war, Greenwood became an important player in the Siege of Vicksburg. General Ulysses S. Grant attempted multiple frontal assaults on Vicksburg but failed each time.
So, he came up with a new plan – attack from the rear using the Tallahatchie and Yazoo Rivers since both rivers run through Greenwood. To make his plan successful, General Grant needed to pass through Fort Pemberton – a hastily built Confederate fort between the two rivers.
Ultimately, the Confederates were determined to defend their territory and put-up fierce resistance against Union forces. In fact, they even managed to sink one of their paddle wheelers – Star of The West – in Tallahatchie River’s channel, effectively stopping any advances by the Union flotilla.

Greenwood MS Blues Trail: A Civil War victory for the Confederates

This victory at Fort Pemberton forced General Grant to abandon his planned expedition and retreat north towards the Mississippi River before eventually launching another attack on Vicksburg from a different route.
The brave efforts of Confederate soldiers at Fort Pemberton proved that even hastily built fortifications could be effective in defending against enemy attacks if wielded by determined soldiers.
The end of the Civil War had a significant impact on the cotton industry, causing major damage to the once thriving economy of the city.
However, with the arrival of railroads in the 1880s and two lines running through downtown Greenwood near the Yazoo River, the city began to revive. It became a prominent shipping point for cotton and downtown’s Front Street was bustling with factories and businesses related to cotton production, earning it the nickname “Cotton Row.”
The city continued to prosper until the 1940s but has seen a decline in cotton planting in recent years.

Greenwood MS Blues Trail: Tallahatchie Flats
a property similar to Shack-Up Inn in Clarksdale

Located on Money Road between Money and Greenwood, Tallahatchie Flats is a row of sharecropper shacks that have been transformed into comfortable and cozy accommodations.
But what sets this place apart is its breathtaking location – right on the banks of the Tallahatchie River surrounded by cotton fields and filled with the sounds of Delta wildlife.
It’s just a stone’s throw away from Robert Johnson’s final resting place and only a few miles from Bryant’s Grocery in Money – where the tragic events surrounding Emmett Till took place. The historical significance of this area cannot be understated.
The renovated commissary at Tallahatchie Flats not only serves as a check-in spot but also features live music performances. Imagine sipping on your favorite drink while listening to some authentic Delta blues talk about an unforgettable evening!
Furthermore, the commissary can be rented out for special occasions! Whether it’s a birthday party or even a wedding, celebrating at Tallahatchie Flats will surely make it a one-of-a-kind event.

Greenwood MS Blues Trail: Bobbie Gentry’s best-known song,
“Ode To Billie Joe”

A song that tells the haunting tale of a young man (“Billie Joe McAllister jumped off the Tallahatchie Bridge”) who tragically jumps off the Tallahatchie Bridge. The iconic lyrics mention this bridge multiple times (“you and Billie Joe was throwing something off the Tallahatchie Bridge”), making it a significant location in the story.

In recognition of this cultural landmark, there is now a Mississippi Country Music Trail marker located at the entrance to the bridge in Greenwood. This serves as a reminder not only of Gentry’s powerful storytelling, but also of the enduring impact that this bridge holds in the hearts and minds of its visitors.”

Greenwood MS Blues Trail: GRAND BLVD

Interestingly a stunning mile long roadway lined with majestic oak trees
creating a picturesque scene of beautiful custom built
mansions and charming cottages.

Among them stands a neo-classical Revival house that was built in 1910 and still holds its grandeur today. It has been recognized for its historical significance and is listed on the National Register of Historic Places.
Originally owned by the Provine family, this house boasts an impressive two-story portico with a balustraded flat roof, bracketed cornice, and full entablature supported by fluted Ionic columns. A smaller version of this striking feature can also be seen over the entrance.
Not only does this house hold architectural importance, but it also played a role in pop culture history. In 1969, it was used as a filming location for the movie “The Reivers,” which takes place in Mississippi and stars legendary actor Steve McQueen.

Greenwood Grand Blvd Grand Blvd in Greenwood

Learn more about Greenwood’s Grand Boulevard.

Greenwood MS Blues Trail: THE CRYSTAL GRILL

Located in a building originally built in the early 1900s and opened as a restaurant in 1932, has undergone several renovations to become the modern 250-seat restaurant it is today.
The main attraction for many visitors is the delicious-looking pies advertised.
For those looking for a satisfying lunch with a delectable dessert, the Crystal Grill is the perfect place to go.

Greenwood MS Blues Trail: takes you to the Crystal Grill.

Greenwood MS Blues Trail: Keesler Bridge

Is a beautiful and historic Arch Bridge built in 1925, that graces the city of Greenwood with its detailed design.
The swing bridge is adorned with steel railings on the swing span and unique concrete railings on the approach spans.
As an important gateway to downtown Greenwood, its intricate features and rich history make it a must-see landmark for anyone exploring the city.

Greenwood featuring the Kessler historic bridge in downtown Greenwood