Custom Text


31 Things to Do in May

By  | 

Hello May! Discover what’s happening with Hello Woodlands’ “31 Things To Do” monthly guide featuring events, activities, locations, and ways to get involved in your community.

Join us this May by trying new activities and attending events in and around The Woodlands, Texas. Be sure to follow us on social media at @HelloWoodlands and subscribe to our email newsletter to stay updated for upcoming events, ticket giveaways, live videos, photos, and so much more!

31 THINGS TO DO – MAY 2019


May 1-5 – Insperity Invitational – Insperity Invitational presented by UnitedHealthcare. Where Legends Play. Free Grounds Admission courtesy of Insperity and Woodforest National Bank and Free Parking at Woodforest Stadium. Learn More

May 4 – Houston Ballet Mixed Repertory – The Pavilion welcomes an exquisitely beautiful Houston Ballet performance with both classic and modern elements. Lawn and Mezzanine seating is free. Gates open at 7:00 p.m. and show starts at 8:00 p.m. Learn More

May 4 – Building Hope Gala – The annual Building Hope Gala benefits Habitat for Humanity of Montgomery County. The 2019 Building Hope gala theme is “Making Dreams Come True.” The Building Hope Gala is a fun-filled evening that features silent and live auctions, an elegant dinner, a program that features a testimonial by a Habitat home owner, and dancing. This year’s entertainment will be provided by Tin Man Band. Learn More

May 8 – WORKSUITES Grand Opening & Ribbon Cutting Party – You’re invited to join WORKSUITES in celebrating the Grand Opening and Ribbon Cutting Ceremony for the newest flexible workspace location. Enjoy complimentary tacos & margaritas, win bottles of liquor & gift cards, meet other motivated businessmen & women, and tour this absolutely stunning space! And don’t forget to grab some WORKSUITES swag before you leave. There will be a ribbon-cutting ceremony with The Woodlands Chamber of Commerce at 4:15 pm and the reception continues until 6:30 pm. Learn More

Hello Woodlands WORKSUITES

May 9 – Shelter for Shelter – Join The Richmond Realty Group RE/MAX The Woodlands & Spring for an evening of fine food, wine, spirits, and entertainment hosted at the beautiful Mercedes-Benz of The Woodlands. You won’t want to miss being a part of the first class event “Shelter for Shelter” with community leaders, local businesses and restaurants, while raising funds for YES to YOUTH – Montgomery County Youth Services! All donations will be made to YES to YOUTH, which provides crisis counseling, shelter programs and prevention services to strengthen families, keep youth in school and prepare them to be productive citizens in Montgomery County. Purchase Tickets

May 22 – La BohèmeGet swept up in a romantic whirlwind. Set in the heart of the bohemian revolution, this romantic whirlwind from Houston Grand Opera brings opera’s greatest love story to The Pavilion’s Main Stage. Lawn and Mezzanine seating is free. Gates open at 7:00 p.m. and show starts at 8:00 p.m. Learn More.

May 23 – Go Red For Women – Dancing With the Stars icon Val Chmerkovskiy will make an appearance at The American Heart Association’s 15th annual Montgomery County Go Red for Women Sweet 15 Celebration from 1-4 p.m. at The Woodlands Waterway Marriott. Learn more

2019 Montgomery County Go Red for Women Celebration

May 30 – How to Train Your Dragon – in Concert – Fly into summer! DreamWorks’ How To Train Your Dragon is a captivating and original story about a young Viking named Hiccup, who defies tradition when he befriends one of his deadliest foes – a ferocious dragon he calls Toothless. Together, these unlikely heroes must fight against all odds to save both their worlds. Featuring John Powell’s Oscar-nominated score performed live by the Houston Symphony to the movie, How to Train Your Dragon – In Concert is a thrilling experience for all ages. Lawn and Mezzanine seating is free. Gates open at 6:30 p.m. and show starts at 8:00 p.m. Learn More

Visit the Hello Woodlands Calendar for MORE events, event information, details, directions, and links!



May 1 – Coffee with a Cop – Mark your calendars and come join The Montgomery County Sheriff’s Office for coffee and fellowship at Noe’s Crepes Coffee & Tea to enjoy Coffee with a Cop. Join Deputies from Montgomery County Sheriff’s Office to discuss local matters, build relationships, and drink coffee. Coffee with a Cop provides a unique opportunity for community members to ask questions and learn more about the Sheriff’s Office work in the community.

May 1 – Creekside Park Unplugged Free Concert Series – This family-friendly event in The Woodlands at Creekside Park Village Green will feature Troy Ita (rock, pop, and more) on May 1. Visitors are invited to bring their own lawn chairs and blankets to the concerts (no glass permitted).

May 2 – Breakfast with Champions – The Breakfast with Champions is an opportunity to hear from champions of the game of golf in a unique environment at the Insperity Invitational. The breakfast is held on Thursday, May 2 from 8:00 a.m. to 9:30 a.m. in the Champions Club on the 18th hole with proceeds from the event benefiting Panther Creek Inspiration Ranch. The morning includes breakfast and a Q&A with World Golf Hall of Fame Member Nancy Lopez. Purchase Tickets

May 2 – North Houston Business Extravaganza – The North Houston Business Extravaganza is on Thursday, May 2, 2019 from 5 to 8 p.m at the Glade Arts Foundation. Attend the largest free Business Networking event in north Houston with over 450 local businesses. Admission is free with your business card! Build your sphere of influence and meet other businesses in your community. The focus is always on leadership, community, and the importance of business relationships. 

May 2, 9, 16, 23, 30 – Market Street’s Spring Concert Series – Market Street’s popular spring concert series, featuring artists in Top 40, Blues, Latin and more, returns to the shopping, dining and entertainment destination every Thursday, April 11 through June 6, from 6:00 – 8:30 p.m. Each concert in the series is free and open to the public. Guests are invited to bring blankets and lawn chairs and sit back, relax, and enjoy the performances.

May 2 – Cinco de Mayo Fiesta of Champions benefiting FAITH Fighting Cancer – The fiesta will honor the selflessness of FAITH’s Champions in their efforts to help others in our community. The Party Casual dinner will feature fiesta fajitas from El Bosque plus awesome silent and live auctions, featuring the famous Ray Burgess as the auctioneer this year. FAITH Fighting Cancer in Montgomery County is a 501©(3) non-profit organization, which is run entirely by volunteers, most of whom have dealt with cancer either personally or with close family members and friends.

May 3 – Fuzzy’s Ultra Premium Vodka Out Drive John Daly On Friday, May 3 join the Insperity Invitational for Fuzzy’s Ultra Premium Vodka Out Drive John Daly Competition! Come watch competitors try to out drive John Daly. End of play (around 5pm) on the driving range. Learn more

May 3 – Women of Distinction Luncheon – Join the community for the Montgomery County Women of Distinction’s 29th Annual Women of Distinction luncheon to honor the volunteers in our community! Brittney Bates has been chosen by the Montgomery County Women’s Center as its Woman of Distinction for 2019. Learn More

May 3 – The Woodlands Charities’ Chef Showdown – Six teams of chefs will compete for the coveted Golden Fork and Silver Spoon Award based on the funds they help us raise for a charitable focus. These wonderful Chefs are community leaders who will help prepare the fabulous Mexican food for all to enjoy. Come and spend an evening of food, entertainment, music, dancing and fellowship.

May 3 – Patsy Cline Tribute Concert – Enjoy a night filled with Patsy Cline’s favorite songs featuring Kelley Peters and Nobody’s Fool Band. Limited to 150 seats (40 VIP and 110 General admission). Cash Bar and light complimentary appetizers available throughout the show. Doors open at 6:30 p.m. Concert starts at 7:30 p.m. Purchase Tickets

May 4 – 3M Greats of Golf – Join Insperity Invitational on Saturday, May 4 for 3M Greats of Golf! Featuring Nicklaus – Player – Trevino – Sorenstam and more at The Woodlands Country Club Tournament Course. Greats will tee off following last official tee time! (approximately 12:30pm) Learn more

May 4 – Market Street’s Spring Fine Arts ShowFree and open to the public, the Fall Fine Arts Show at Market Street is one of the most popular gatherings for artists in The Woodlands where families can browse for great buys, enjoy live music and participate in artist demonstrations. Fun activities for aspiring artists of all ages also are scheduled.

May 4 – Texas Children’s Hospital The Woodlands Family Fun Run – Families with children of all abilities are invited to participate in a fun-filled morning. For years, the Family Fun Run has educated and encouraged families in Houston and the surrounding areas to adopt active, healthy lifestyles together. The Family Fun Run will include a 1K course. Following the race, participants are invited to enjoy the Family Fun Zone, presented by H-E-B, which will feature snacks and refreshments, interactive booths and inflatables, and special guests and mascots.

May 4 – Building Hope Gala – The annual Building Hope Gala benefits Habitat for Humanity of Montgomery County. The 2019 Building Hope gala theme is ‘Making Dreams Come True.’ The Building Hope Gala is a fun-filled evening that features silent and live auctions\, an elegant dinner, a program that features a testimonial by a Habitat home owner, and dancing. This year’s entertainment will be provided by Tin Man Band. Learn more

May 4 – June 29 – Waterway NightsEnjoy FREE, live music by local and regional performers in the picturesque setting of Waterway Square at Waterway Nights. Saturday nights starting on May 4 from 6:30 to 8:30 p.m.

May 5 – Celebrate Cinco de Mayo at Caffé di Fiore! Visit this local favorite at 10110 Woodlands Pkwy and view the menu and learn more about this local favorite with Authentic Mexican Cuisine – open for breakfast, lunch, happy hour and dinner – at


May 8 – Dermalinfusion Day at Seychelles Med & Laser Spa – Celebrate Dermal Infusion Day with one-day only special pricing and visit with Seychelles’s experts to learn all about DERMALINFUSION®, a patented, non-invasive, 3-in-1 dermatological treatment that simultaneously exfoliates, extracts, and infuses skin with condition specific serums for an all-inclusive treatment in one step – with no downtime! Call Seychelles Med & Laser Spa at (832)813-8086 to schedule your appointment while spots last and to purchase this special offer. Learn More


May 10 – Inspirational Series Featuring Author Becky KiserLocal Author, Motivational & Inspirational Speaker Becky Kiser will be leading women in reigniting the passion for their dreams during this luncheon at Black Walnut Cafe in The Woodlands. This inspiring event designed to give women the practical tools they need to live their best lives. Motivation & inspiration require regular maintenance! Becky Kiser often says the only thing that differentiates her from those who want to achieve their goals is that she never quit on her goal of writing a book and found ways to maintain her motivation. She will be sharing her tips to keep that passion & motivation. You CAN do anything! Learn More

May 10 – May 12 – “30 Years! One Day in Our Lives” PerformanceMiddle and Upper School dance students at The John Cooper School will honor the school’s 30th anniversary as they perform” 30 Years! One Day In Our Lives” on May 10-12 on the main stage of the school’s Glenn Performing Arts Center. Through jazz, hip hop, ballet, lyrical, contemporary and apparatus dancing\, dance students will highlight a typical day at The John Cooper School. Tickets are $15 for adults and $10 for student and senior reserved seating and will be on sale online. Purchase Tickets

May 11 – Woodforest Bank Triathlon The 16th annual Woodforest Bank TRI – The Woodlands will take place Saturday, May 11 at Northshore Park from 7:00 to 11:30 a.m. The event culminates with a festive awards party featuring music, great food and beverages.

May 12 – Mother’s Day Recital and BrunchMake this Mother’s Day a special celebration brunch with the world renowned pianist Matthew Kent! Enjoy the emotional depth and power of Matthew Kent’s piano recital in the unique museum setting at Glade Arts Foundation. Light brunch will be served along with two complementary drinks of your choice from the bar. Learn More

May 16 – Fiesta at CanopyCome dressed and ready to party at Canopy’s Fiesta! Light lunch & drinks will be served. RSVP to Canopy Cancer Survivorship Center at 713.897.5939. Learn more about Canopy

May 18 – Bike The Woodlands Day – Every year, The Woodlands Township celebrates National Bike Month in May. Bike The Woodlands Coalition, with the support of The Woodlands Township, has planned a myriad of fun events for cyclists of all ages and abilities to enjoy during the entire month of May. Events include Bike Shop Week, Bike-In Movies, Bike to Work Day, The Woodlands Cycling Club Rides, Bike Maintenance Workshops, Bike The Woodlands Day and so much more! Learn More

May 18 – Health, Wellness & Fitness Expo – The expo will feature free fitness classes in Market Street that will begin on the hour. This event is open to the public, free of charge. From 9 a.m. to 2 p.m., visit vendor booths who are showcasing their healthcare and wellness-related services available to all Montgomery County residents. This event will take place rain or shine. Learn More

May 26 – Memorial Day FestivalCelebrate the official start to summer at the annual Memorial Day Festival in The Woodlands! The Sunday event pays tribute to all military service men and women who lost their lives while serving the United States, and also honors all veterans who serve as a symbol for those who paid the ultimate sacrifice of life to protect our freedom. The festival features live music, children’s activities, strolling entertainers and more at Town Green Park. The evening concludes with a dazzling fireworks display choreographed to a patriotic soundtrack. Concessions will be available for purchase. Learn More

May 28 – Nest for Newbies Breast Cancer Support GroupThe Nest for Newbies, a breast cancer support group, is a safe haven for women who have been newly diagnosed with breast cancer. This is a five month program\, held once a month at 12pm with a different topic each time. We will cover different topics\, learn from one another and give encouragement. Please RSVP to the Canopy front desk by calling 713-897-5939. Learn more about Canopy Cancer Survivorship Center located at 1120 Medical Plaza Dr, Suite 250, The Woodlands, Texas, and the group here.nest newbies breast cancer support group

Summer Camps are coming soon! Learn more and sign up for Sunny Dayz Camps by The Woodlands Township starting this June. Learn more

Plan ahead for June! Visit our online calendar, subscribe to our Email Newsletter, follow us on social media at @HelloWoodlands, and check back for a list of 31 things to do in June 2019! Contact us at to tell us events, activities, locations, businesses, and non-profits we should feature and visit in June!