Looking for family fun this May in The Woodlands, North Houston, Conroe, Magnolia, Montgomery, and Willis? We’ve got you covered! From festivals and markets to story times and splash pad openings, here’s your go-to guide for local events happening in May 2025
Big As Texas Festival
📅 May 9–11, 2025
📍 Montgomery County Fairgrounds, Conroe (77304)
Experience a weekend of country music featuring top artists. The Big As Texas Festival returns with an impressive lineup, promising three days of live performances, food, and fun. Past headliners have included Thomas Rhett, Billy Strings, and Dierks Bentley.
Monster Truck Wars
📅 May 17, 2025
📍 Lone Star Expo Center, Conroe (77303)
Get ready for high-octane excitement as Monster Truck Wars returns to Conroe. Featuring trucks like Outlaw and Shark Attack, enjoy thrilling performances, kids' Power Wheel races, and a pre-show Pit Party. Shows at noon and 6 p.m.; VIP and general admission tickets available.
Woodlands Symphony Orchestra: Fairy Tales LIVE
📅 May 4, 2025
📍 Christ Church Methodist, The Woodlands (77381)
Delight in a family-friendly concert featuring classics like "The Magic Flute" and "Peter and the Wolf." Children receive a free Young Artist Sketchbook and colored pencils to engage with the music creatively. The Courier of Montgomery County
"Little Shop of Horrors" at Owen Theatre
📅 May 9–25, 2025
📍 Owen Theatre, Downtown Conroe (77301)
Enjoy the quirky musical tale of a man-eating plant in this production by The Players Theatre Company. Performances run over three weekends in the heart of Conroe's historic district.
Antique & Unique Festival
📅 May 2–4, 2025
📍 14420 Liberty St, Montgomery (77356)
Browse a treasure trove of antiques, vintage collectibles, and handmade items in Montgomery's historic district. This free event is perfect for collectors and casual shoppers alike.
Insperity Invitational – PGA Tour Champions
📅 April 29 – May 5, 2025
📍 The Woodlands Country Club Tournament Course (77381)
Watch premier golfers aged 50 and older compete in this prestigious PGA Tour event. Admission is free, offering fans a chance to see legends like Ernie Els and Vijay Singh in action.
17th Annual Cultural Celebration & Kids Festival
📅 May 3, 2025 | ⏰ 11:00 AM – 2:30 PM
📍 Sterling Ridge Village, The Woodlands (77382)
Celebrate global cultures with food, games, bounce houses, and more. This family-friendly event supports local schools and offers fun for all ages.
Kentucky Derby Day Events
📅 May 4, 2025
- Conroe Symphony Orchestra Derby Day Gala
📍 Hyatt Regency, Conroe (77304)
Enjoy a live telecast of the Kentucky Derby, music, raffles, and more at this fundraiser event. - Bernhardt Winery Derby Day Festival
📍 Near Plantersville (77363)
Experience live music, wine tastings, and Derby festivities in a picturesque setting.
Mother's Day Brunch at Margaritaville Lake Resort
📅 May 12, 2025
📍 Margaritaville Lake Resort, Montgomery (77356)
Treat mom to a special brunch with scenic lake views, delicious food, and a relaxing atmosphere.
🇺🇸 Memorial Day Celebrations
📅 May 26, 2025
📍 Town Green Park, The Woodlands (77380)
Honor our heroes with a day of remembrance, featuring live music, children's activities, and a patriotic ceremony. A perfect way to spend the holiday with family and community.
May 2025 is packed with unforgettable events in The Woodlands, Montgomery and beyond! Whether you’re looking to experience live music, get active, support local artists, or enjoy time with family, there’s something for everyone. Check out our Events Calendar and mark your calendars so you don’t miss out! |
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Macaroni KID is a free local calendar, weekly newsletter and website focused on family-friendly events and information for The Woodlands - Montgomery areas. We gather all the local family-friendly events and activities we can find and add useful information about classes, family-focused businesses, book and product reviews, recipes, crafts, school and camp guides and more!
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