May 1, 2026
May is the sweet spot of the year out here on the backroads. The weather is warm, the farmers markets are coming back to life, and there is something worth driving to just about every single weekend. This month we are covering events all across the six-county Blues Backroads region, from the Mississippi Delta to the Tennessee countryside and across the river into Arkansas. Mark your calendars and start planning your route.
Hightower Park and Amphitheater, 1323 E. Broadway Ave, West Memphis, AR | Every Thursday in May, 6 to 9 PM | Free
If you only put one thing on your May calendar, make it this. Every Thursday night in May, West Memphis turns on the blues at Hightower Park and Amphitheater with live music, food trucks, and free admission for all. Blues, brews, and an outdoor amphitheater setting right across the river — it is the kind of night that reminds you exactly why this region is special. Dates run May 1, 8, 15, 22, and 29.
Collierville Historic Town Square, Collierville, TN | May 2 and 3 | Free
The 50th Annual Fair on the Square is a full weekend celebration on Collierville’s beautiful historic Town Square. More than 170 vendors bring handmade goods, arts and crafts, fair food, and live entertainment all weekend long, and admission and parking are completely free. Presented by the Collierville Twentieth Century Club, this one has been a Mid-South tradition since 1976 and is a genuinely wonderful way to spend a May weekend.
Marion Recreational Complex, 3820 Complex Rd, Marion, AR | May 6 through 9
Cross the bridge and head to Marion for four days of community celebration right around Mother’s Day weekend. Esperanza Bonanza brings together a BBQ competition, carnival rides and games, live music, and family-friendly fun at the Marion Recreational Complex. All proceeds support local charities serving individuals with special needs in Crittenden County. It is a West Memphis staple that is well worth the short drive.
Silo Square, Southaven, MS | May 9
Live music, all-you-can-eat crawfish, and good company at Silo Square in Southaven, all in support of the Southaven Police Department’s First Responders Benevolence Fund and the DeSoto County Sheriff’s Office Blue Line Fund. Each wristband gets you the crawfish and four drink tickets. It is a great excuse to explore Silo Square and spend the afternoon in one of DeSoto County’s most happening spots.
Harrell Theatre, 440 West Powell Road, Collierville, TN | May 14 | Tickets $45
Tracing the sound from Clarksdale to Collierville to Chicago, this intimate performance at the Harrell Theatre is a must for anyone who loves the blues and the story behind them. Grab a friend, settle into this beautiful space, and let the music do the rest. Tickets are $45 through the Collierville Arts Council.
BankPlus Amphitheater at Snowden Grove, Southaven, MS | May 14, 7 PM | Tickets from $72
Treaty Oak Revival brings their West Texas Degenerate Tour to the BankPlus Amphitheater at Snowden Grove with special guests William Clark Green and Parker Ryan. If you like your country music with Texas grit and a whole lot of heart, this is the show. Doors at 7 PM at one of the Mid-South’s best outdoor venues.
Hernando Courthouse Square, Hernando, MS | May 16 | Free admission
Voted DeSoto County’s best festival, the A’Fair is back on the beautiful Hernando Courthouse Square for its annual showcase of handmade arts and crafts. All 300 vendors sell work they made themselves, and there is a free concert, a 5K, and a whole lot of Southern charm to enjoy. No admission, no parking fees — just a genuinely great Saturday in one of the prettiest little squares in North Mississippi. While you are in Hernando, the Hernando Farmers Market runs every Saturday on the Town Square from May through October.
Ruffin Theater, 113 W Pleasant Ave, Covington, TN | May 22 through 30 | Tickets $15
The Tipton Arts Council brings Stephen Sondheim’s beloved musical to the historic Ruffin Theater in downtown Covington. Cinderella, Little Red Riding Hood, Jack, and the Witch all collide in a story full of unexpected twists and unforgettable music. Performances run May 22 through 30, with tickets at just $15. Covington is the kind of town you want to wander around before or after a show — grab a bite downtown and make a night of it.
Veterans Plaza, 1483 Munford Ave, Munford, TN | May 26, 6:30 PM | Free
The Memphis Wind Symphony brings a free outdoor concert to Veterans Plaza in Munford on a Tuesday evening. Food vendors including Yummy Sourdough Pizza and Pour Palomino will be on site. It is the kind of small-town summer evening that feels like a gift — bring a lawn chair and enjoy it.
Germantown Performing Arts Center, 1801 Exeter Rd, Germantown, TN | May 28, 6:30 to 8 PM
GPAC kicks off summer with an outdoor concert in The Grove featuring Bailey Bigger. It is a free, family-friendly evening on the GPAC lawn in Germantown — bring a blanket, settle in, and enjoy live music under the open sky. Check gpacweb.com for full details.
Germantown Performing Arts Center, 1801 Exeter Rd, Germantown, TN | May 29, 7 to 8:30 PM
GPAC’s Jazz in the Box series brings the Denise Thimes Trio to the intimate Highland Capital Performance Hall for a sophisticated evening of soulful jazz. This is one of the best concert series in the region and a perfect way to close out the month. Check gpacweb.com for tickets and details.
17745 Hwy 64, Somerville, TN | May 30
The Somerville Farmers Market officially launches its every-Saturday season on May 30 with a big opening day celebration. Expect live music, kids crafts, a play area, and more than 30 vendors with fresh produce and artisan goods. A New Life Herbs Coffee Cafe will be open and serving frozen yogurt alongside their full menu, and Hex and Honey will be on site with Cajun-style food. This is one of the best farmers markets in West Tennessee, and May 30 is your first chance to make it a Saturday tradition.
Landers Center, 4560 Venture Dr, Southaven, MS | May 30, Doors 7 PM, Show 8 PM
Cap off the month in style with this stacked R&B lineup at the Landers Center in Southaven. October London, Lalah Hathaway, and Eric Benet share one stage for a special evening celebrating love, soul, and timeless music. Tickets on sale now at landerscenter.com.
Every Week in May
Beyond the one-time events, May is also when the weekly rhythms of backroads life come back to life. A few things worth putting on a repeating calendar:
The Hernando Farmers Market runs every Saturday on the Hernando Courthouse Square from May through October, with fresh local produce, live music, and free yoga classes some mornings. The Collierville Farmers Market opens Thursdays starting May 21 at Collierville United Methodist Church on West Poplar Avenue. And on the Collierville Town Square, there is a Bluegrass Jam every Friday evening at 6:30 PM, weather permitting — no ticket needed, just show up.
There is a lot of road to cover and a lot of good happening out here this May. Pick a direction and go.
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