October To-Do List Along the Backroads
Early October Fun
Songs n’ S’mores
8515 Cedar Crest Lane – October 3, 7–9 p.m.Kick off October around the fire with live music and toasted marshmallows under the stars. Bring a blanket, gather your friends, and soak in the crisp evening air while sharing a cozy autumn tradition.
MedleyFestOne
Memphis Street – Hernando, MS – October 4, 6:30 p.m.This lively community festival blends music, vendors, and local flavor into one big celebration.It’s a perfect way to discover Hernando’s charm and spend a Friday night supporting regional performers.
Oktoberfest
Mississippi Ale House & Brew Pub – Olive Branch, MS – October 4, 2–11 p.m.Raise a stein at this German-inspired bash featuring beer, food, and festive vibes. Expect hearty brews, pretzels, and a crowd ready to toast the season.
Crosspointe Church Country Fair
Crosspointe Olive Branch – October 5, 5–7 p.m.Games, food, and fellowship make this classic country fair a family favorite. Kids can enjoy activities while adults relax and connect with neighbors.
Free Family Pumpkin Palooza
Reach360 Church – October 5, 4:30–7:30 p.m.Celebrate fall with pumpkins, activities, and community spirit. It’s an easygoing afternoon where families can create crafts, snap photos, and welcome the season together.
Markets & Active Weekends (October 10–12)
Storytime in the Park
Tipton County Public Library – October 10, 10–11 a.m.Bring the little ones for an outdoor story hour surrounded by autumn color. It’s a gentle way tostart your weekend with books, fresh air, and community.
Hernando Water Tower 10k & Half Marathon
475 W. Commerce St. – Hernando, MS – October 11, 8 a.m.Lace up for a local race that winds through historic Hernando. Whether you’re running or cheering, it’s a tradition that gets everyone moving.
SxS Poker Run
Central Park – Ripley, TN – October 11, 2 p.m.Join an adventurous ride with stops along the route—best hand wins! This backroads poker runmixes fun, friendly competition, and beautiful scenery.
Kids Vendor Market
DeSoto Arts Council – October 11, 9 a.m.Support the next generation of makers at this youth-run market. Kids showcase and sell their creations while learning the ropes of small business.
Crittenden County October Market
Courthouse Square – October 11, 8–11 a.m.Fresh produce, baked goods, and artisan crafts await at this charming market. It’s a great stopfor stocking up on local favorites before your weekend adventures.
Fruitful Fall Market
808 East Broadway – West Memphis, AR – October 12, 1–4 p.m.Another chance to shop local and enjoy fall vibes. Meet makers, browse seasonal goods, and take home something special from the backroads.
Mid-Month Festivals (October 17–19)
Next Stop Comedy
Back Nine Grill & Bar – Brownsville, TN – October 17, 8 p.m.Get ready to laugh at this traveling comedy show featuring regional talent. Grab dinner, enjoy the show, and unwind with friends.
Celebrate Munford
Munford City Hall – October 18, 9 a.m.–5 p.m.Downtown streets come alive with vendors, food, and music for a full day of small-town fun. Shop handmade crafts, watch demonstrations, and soak up the community spirit.
Fall Festival
New Beginnings Methodist Church – West Memphis, AR – October 18, 9 a.m.This church-hosted festival blends games, treats, and fellowship. Families can expect bounce houses, food, and activities that feel like a warm hug from the community.
Storytime on the Square
Woolfolk Public Library – West Memphis, AR – October 18, 10 a.m.Bring the kids for a cozy morning of books and imagination in downtown West Memphis. It’s a sweet, low-key stop that connects children with stories and neighbors alike.
Hernando Fall Festival
Parkway Baptist Church – Hernando, MS – October 18, 4–7 p.m.Celebrate the season with crafts, food trucks, and live entertainment. The festival draws families and friends together for an afternoon of fun.
Prehistoric Halloween Party
Mississippi Ale House & Brew Pub – Olive Branch, MS – October 18, 6–11 p.m.This dino-themed Halloween bash turns a favorite local pub into a prehistoric playground. Expect themed cocktails, costumes, and live entertainment to keep the night roaring.
Pumpkins & Pilates
Cedar Hill Farm – Hernando, MS – October 19, 1 p.m.Pair your fall fitness goals with pumpkin patch vibes at this unique class. Enjoy a Pilates session surrounded by farm scenery, then stay to pick the perfect pumpkin or enjoy the petting zoo.
Huey’s Southaven 25th Anniversary Party
Huey’s Southaven – October 19, 2 p.m.Celebrate a quarter-century of burgers, blues, and good times at Huey’s Southaven. The anniversary bash features live music, giveaways, and plenty of local flavor.
Palmer Home Cornhole Benefit
10th Inning Sports – Hernando, MS – October 19, 2:30 p.m.Toss a few bags for a great cause at this cornhole tournament benefiting Palmer Home. Between the games, food, and community energy, it’s the perfect blend of fun and philanthropy.
Late October Highlights (October 21–25)
Superhero Fall Festival
Chick-fil-A Southaven – October 21, 4:30–7:30 p.m.Dress up your little heroes for an evening of games, crafts, and community spirit. This family-friendly festival includes themed activities, treats, and photo ops with favorite characters.
Boots, Brews & Bingo
Great Hall & Conference Center – Germantown, TN – October 22, 5 p.m.Put on your boots and get ready for an evening of bingo with a side of local beer and snacks. The prizes and atmosphere make it a can’t-miss stop on your October calendar.
Brighton Fall Festival
Brighton City Park – October 25, 10 a.m.–4 p.m.This park transforms into a family playground with games, food booths, and artisan vendors. From hayrides to handmade crafts, Brighton’s festival captures the best of fall in a relaxed, friendly setting.
Mason Jubilee Fall Festival
Front Street – Downtown Mason – October 25, 11 a.m.–4 p.m.Downtown Mason bursts with life during this annual festival, featuring food trucks, local artists, and plenty of entertainment. Walk the historic street while enjoying live music and classic fall activities.
Olive Branch Fall Festival
Olive Branch Family Medical Center – October 25, 2–5 p.m.Celebrate the season with games, crafts, and seasonal treats in Olive Branch. Local vendors and kid-friendly activities create a warm community atmosphere.
North Shelby County Music & Art Festival
Delta Blues Winery – October 25Spend a day immersed in local art and live performances at a stunning vineyard setting. Wander between exhibits, sip wine, and discover new talent from across the region.
Arctoberfest
Mississippi Ale House & Brew Pub – Olive Branch, MS – October 25, 7 p.m.Olive Branch’s favorite pub hosts an Oktoberfest-style bash with a regional twist. Enjoy craft beer, hearty food, and live music as you toast the season.
Ongoing Event
Landers Center – Southaven, MS – Through October 25Rides, food, exhibits, and entertainment for all ages—this regional tradition runs until October 25. Make it part of your fall memories before it’s gone for another year.
Take the Backroads This October
The beauty of the backroads is in the stories—music echoing through a town square, families gathering at a county fair, or neighbors meeting over pumpkins and Pilates. This October, let curiosity be your guide. Pack up the car, roll down the windows, and see where the road takes you.