May in Tyler & East Texas: Events and Experiences

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Spring is in full swing in Tyler, and May brings an exciting calendar of events for visitorsRed brick two story house with white picket fence in the foreground. sign on fence says Rosevine Inn. and locals alike! From live music and wine festivals to shopping pop-ups and eco-fests, opportunities for fun and entertainment abound. Whether you’re here for a graduation, a special concert, or a relaxing weekend getaway, or an extended stay, make the most of your time — and don’t forget to stay at Rosevine Inn for a truly memorable experience. We offer a fabulous “home away from home’ in our fabulous extended stay rooms and suites.

Shopping Opportunities

Canton Trade Days — May 1–4, 2025
Entrance sign says main gate Canton Trade Days in red lettersPerfect spring weather makes it the ideal time to visit Canton First Monday Trade Days, the largest and oldest continually operating flea market in the United States. Stroll through thousands of vendors offering antiques, collectibles, home decor, and unique finds you won’t see anywhere else. It’s a shopper’s paradise, just a short drive from Tyler!

Mother’s Day Sip & Shop — May 10, 2025Flowery poster In green letters says Mother's Day Sip & Shop. under that in white letters says Come Join Us then in brown under that Saturday, May 10 11am-4pm then in white under that Pop's Wine Bar Parking Lot
Celebrate Mother’s Day a little early at this fun, festive event! Sip delicious wines at Pop’s Wine Bar while browsing unique, handmade gifts perfect for the special moms in your life. A portion of the proceeds benefits The Mourning Forecast, supporting families experiencing pregnancy and neonatal loss. Location: Pop’s Wine Bar parking lot (off Old Jacksonville), Tyler, TX. More info here.

Live Entertainment

Chris Tomlin Concert — May 1, 2025
Contemporary Christian music star Chris Tomlin brings his celebrated live worship experience to the Oil Palace in Tyler. Known for hits like “How Great Is Our God” and “Good Good Father,” Tomlin’s concerts are uplifting and unforgettable.

Moe Bandy at Blackhawk Creek — May 2, 2025
Classic country fans won’t want to miss Moe Bandy live at Blackhawk Creek. With a career spanning decades and beloved songs like “Bandy the Rodeo Clown,” this show promises a night of true country nostalgia.

black square with white letters in cursive says Moody Family WinesKim Ewing at Moody Winery — May 3, 2025
Relax with great wine and live music as local favorite Kim Ewing performs at Moody Family Wines. Her smooth vocals and acoustic set are the perfect pairing for a laid-back spring evening in the vineyard.

The SteelDrivers 20th Anniversary at Stanley’s BBQ — May 8, 2025
Celebrate 20 years of soulful bluegrass with the SteelDrivers at Stanley’s Famous Pit Bar-B-Q. Known for their rich harmonies and hard-driving sound, this Grammy-winning group promises an unforgettable night.Photo of Shinyribs playing guitar. in upper righthand corner the Date Friday May 16 is displayed. in the upper left hand corner the wording Stanleys + Colt

Shinyribs at Stanley’s BBQ — May 16, 2025
Get ready for a funky good time when Shinyribs takes the stage at Stanley’s BBQ. Blending soul, country, and swamp-funk, their energetic shows are always a crowd favorite in Tyler.

six sided poster in grey has a red spiked image at top and the words ROSE CITY COMEDY is super imposed across and Tyler, Tc is at the bottom rightDave Landau at Rose City Comedy — May 28, 2025
Catch nationally touring comedian Dave Landau at Rose City Comedy Club for a night full of sharp wit and laugh-out-loud humor. Known from appearances on “Louder with Crowder” and “The Anthony Cumia Show,” Landau brings his signature style to Tyler for one night only.

Festivals and Special Events

Spring Piney Woods Wine Festival — May 9–10, 2025
The Spring Piney Woods Wine Festival returns to Lindale, offering two days of Texas wine tastings, live music, artisan vendors, and small-town charm. Sample vintages from local wineries, stroll through craft booths, and enjoy the welcoming atmosphere in thisposter with a background of grapes, a wine bottle and a wine glass. At the top the words Piney Woods Wine Festival in maroon letters. under that in black says May 9-10. 2025 then Pickers Pavillion at Blackberry Square 205 Cannery row Lindale Tx historic East Texas town.

Festivalgoers can purchase a tasting ticket that includes a souvenir wine glass and tastings from dozens of vineyards across Texas. With beautiful spring weather, laid-back music performances, and plenty of small bites, it’s an ideal weekend event for couples, friends, or anyone who loves wine and local flavor.

sepia toned sign with an old building in the background in the middle are the words Red Dirt under that BBQ and Music under that festival Tyler, TxRed Dirt BBQ & Music Festival — May 10, 2025
The Red Dirt BBQ & Music Festival is one of Tyler’s signature annual events, blending Texas’ two biggest passions: barbecue and live music. Held in downtown Tyler, this all-day celebration features mouthwatering plates from some of the best barbecue joints in the state alongside performances by top Red Dirt and country musicians.

Attendees can sample brisket, ribs, sausage, and more while listening to a lineup of celebrated artists under the East Texas sky. This event sells out fast each year thanks to its unbeatable combination of food, music, and hometown pride — a can’t-miss for barbecue lovers and music fans alike.

Keep Tyler Green Eco Fest — May 17, 2025
Keep Tyler Green Eco Fest brings together local vendors, nonprofits, and communitynature background poster with the wording from top to bottom Keep Tyler Green Join the Movement ECO FESR Bergeld Park May 17 10am-4 pm organizations for a day focused on sustainability, green living, and environmental awareness. Held at Bergfeld Park, the event features shopping, hands-on activities, educational booths, and family-friendly entertainment.

Visitors can browse eco-friendly goods, attend workshops on composting and recycling, and enjoy activities like plant giveaways and kids’ crafts. Whether you’re looking to live a little greener or just enjoy a beautiful day outdoors, Eco Fest offers something fun and meaningful for all ages.

Family-Friendly Activities

Old Fashioned Run — May 4, 2025
The Old Fashioned Run takes place on May 4 at Bergfeld Park, offering a family-focused race experience for all ages. With 1K and 5K options, this event brings the community together to celebrate fitness in a fun, relaxed atmosphere.blue running show with a wing attached to the back

Participants are encouraged to dress in vintage athletic wear, and awards are given for both race winners and best costumes. Whether you’re a serious runner or just want a casual morning jog with the kids, the Old Fashioned Run is a charming way to enjoy the beauty of Tyler’s historic district.

Tree Talk at Tyler State Park — May 10, 2025

blue sky with several tall pine trees Head out to Tyler State Park on May 10 for Tree Talk, an engaging, kid-friendly event celebrating the importance of trees and conservation. This interactive program invites families to explore the park’s towering pines and hardwoods while learning about tree species, their roles in the environment, and how to protect them.

The program includes guided nature walks and hands-on activities perfect for children and adults alike. It’s a peaceful way to combine education and outdoor fun, just in time for the spring season.

Lindale Championship Rodeo — May 15–17, 2025
The Lindale Championship Rodeo rides into town from May 15 to 17, bringing classicbrown rectangualr sign in top left says Free to the public. in the middle is a cowboy on a horse under that says RODEO on a red background under that May 15-17., 2025 Crossbrand Cowboy Church rodeo excitement to Cross Brand Cowboy Church Arena. This multi-day event features barrel racing, bull riding, steer wrestling, and more, with plenty of action for kids and adults to enjoy.

With a family-friendly atmosphere, food vendors, and local entertainment, the rodeo offers a great evening out under the stars. Young rodeo fans can even participate in activities like the calf scramble, making it a memorable East Texas tradition for all ages.

poster with a home in the background in green at the top with red lettering says smith county master gardeners association 2025 Home Garden Tour. in the middle left in a green background in red letters says Join us for our 2025 tour featuring inspirational gardens Saturday May 17 9 am -3 pm Rain or Shine Tour tickets in advance are $15 online $20 per person day of the tour Home Garden Tour — May 17, 2025
Explore some of Tyler’s most beautiful private gardens during the Home Garden Tour, happening May 17. Hosted by the Smith County Master Gardeners, this self-guided tour showcases carefully tended gardens full of vibrant blooms, creative landscaping, and unique outdoor designs.

Garden enthusiasts, families, and anyone who appreciates beautiful spaces will enjoy wandering through a variety of home gardens, gathering ideas and inspiration for their own backyards. Expect to meet welcoming homeowners and master gardeners ready to share tips and insights.

On Point Ballet 5K — May 24, 2025
The On Point Ballet 5K hits Rose Rudman Trail on May 24, blending athletic fun withpink ballet slippers tied in a pink bow at the top arts support. This community race benefits On Point Ballet, a local dance organization, and welcomes participants of all ages and fitness levels.

Come run, jog, or walk to support the arts in Tyler while enjoying a beautiful spring morning on one of the city’s most beloved trails. With race medals, post-race treats, and a welcoming environment, it’s a family-friendly event that combines fitness and philanthropy.

Local Flavor and Dining Experiences

Vintner’s Dinner at Kiepersol — May 14, 2025
long table set elegantly with white table and red napkins. Lots of wine glasses. Three staff members are shown setting tableThe Vintner’s Dinner at Kiepersol offers an elegant night out on May 14, hosted at the renowned Kiepersol Estates in Tyler. This exclusive dining event pairs fine wines from Kiepersol’s own vineyard with a multi-course chef-prepared meal.

Guests can expect beautifully plated dishes, expert wine pairings, and an intimate setting surrounded by East Texas vineyard views. It’s a sophisticated experience perfect for food and wine lovers looking to savor local flavors in an unforgettable setting.

Plan Your May Getaway

With so many exciting events happening throughout May, it’s the perfect time tocrackling fire with a wine glass in the foreground-perfect evening at Rosevine Inn experience everything East Texas has to offer — from live music and local festivals to family fun and unforgettable dining. Whether you’re planning a quick weekend trip or an extended stay, there’s something here for everyone to enjoy. Ready to turn your visit into a relaxing getaway? Book your stay at Rosevine Inn and enjoy the perfect home base for all your adventures!

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