A Trip Down Memory Lane: The Woodlands, 30 Years Later
It’s been 30 years since I last visited The Woodlands, Texas, and let me tell you, the place has undergone a complete transformation. It felt like stepping into a time machine, to emerge in what can only be described as Texas’ version of Rodeo Drive, complete with Chanel, Saint Laurent, Golden Goose, Breitling, Gucci, Louis Vuitton, and Tiffany’s—all within walking distance. Yes, I know what you’re thinking, “Is this really The Woodlands?” Trust me, I asked myself the same thing! But let me backtrack a little and tell you about my adventure, which was full of surprises and a lot more fun than I even anticipated.
A Fashionable Entrance: Rodeo Drive, Texas Style
As soon as I arrived in The Woodlands, I felt like I’d been transported to a shopping haven. It was as if Rodeo Drive had dropped down in the middle of Texas, and I was suddenly surrounded by luxury brands on every corner. Yet, despite the high-end labels, the atmosphere was refreshingly laid back. No stuffy suits or pretentious attitudes here, folks! If you’ve ever braved the crowds at The Galleria in Houston, you know how intense it can get. But The Woodlands? It was a breath of fresh air. I felt completely at ease, even in my simple sleeveless silk top, shorts, and Adidas Sambas. Oh, and did I mention the parking? Plentiful, with valet and even a free garage—when’s the last time you found a free parking garage at a luxury shopping center? Sorry if I sound like an ad, but seriously, FREE PARKING?!?!
Market Street Marvels: A Hidden Gem
My mini-shopping spree kicked off at right there in Market Street, when I stumbled on a hidden gem that quickly became one of the highlights of my trip. I was legit lost, in a sea of designer labels, when I suddenly found myself standing in front of the most charming little café, Sips and Sweets by Kendra Scott. Now, I had no idea Kendra Scott had ventured into the café business, but I was about to find out just how delightful it could be. With the typical Houston heat bearing down (we’re talking 168 degrees with 200% humidity, okay maybe not literally that hot, but it certainly felt that way), I was melting and in desperate need of something cold.
I came in for a water so you can imagine my surprise when the barista not only suggested a frozen beverage but had three options of frosés! And yes, they were as delicious as they sound—frozen sangria, frosé, and a swirled frozen sangria and frosé. She suggested the swirl, and she was right!
Check out my Instagram post to learn all about this fabulous spot!
Sweet Treats and Local Delights: A Culinary Surprise
As if the frosé wasn’t enough to cool me down, I also had the chance to taste-test a new signature coffee drink they were concocting. Enter the Caramel Apple Pie Coffee—it’s just as autumnal as it sounds, and I can’t wait for it to hit the menu this fall for everyone to try because it taste exactly like an apple pie. It hits all your senses, from the cinnamon on the nose to the caramel that wraps around the tongue to the taste of apple that remains in the mouth. It’s a well thought out concoction, and I want more! But really, let’s talk about the real star of the show: the baked goods.
Everything was sourced from local women-owned artisans, and each bite was a masterpiece. Don’t judge me when I say I ate. A lot. That might be kind of my thing these days. Between stunning chocolate bonbons, light and colorful macarons, and Kendra’s signature unicorn sparkle kringle—it was as if Willy Wonka had opened a high-end pastry shop right there in Market Street, and that’s only the treat I tried. There were so many other options! I left with a full belly, and a heart full of happiness.
The Trolley Chronicles: Navigating The Woodlands with Ease
Luckily, my hotel was just a short distance away, and I had multiple ways to get around—walking, the breezeway, or my personal favorite, the trolley. Imagine Mr. Rogers’ trolley from your childhood, but make it green and you’ve got The Woodlands Trolley. It makes a loop through The Woodlands Waterway, past hotels, The Cynthia Woods Mitchell Pavilion, and Market Street.
And here’s the best part: it runs every 15 minutes, and you can track it through the Ride Systems App! The app is totally free and available on both Apple (IOS) or Google Play (Android) stores. (After installing, just select “The Woodlands Township” from the menu to start using!)
As someone traveling with crutches, I found the trolley to be a lifesaver. The drivers were incredibly kind and patient, never making me feel like an inconvenience despite my slower pace. In addition to offering to help me up the stairs (I didn’t need that), they indulged my curiosity by answering questions about the sights we were passing. In case you’re wondering, the trolleys also come equipped with wheelchair lifts and have seats that lift out of the way to easily accommodate your chair. That’s the kind of service that turns a good trip into a great one!
Home Away from Home: The Marriott Waterway Experience
Now, let’s talk about where I stayed. If you haven’t checked out The Woodlands Waterway Marriott , you’re seriously missing out. Let me tell you, it was an absolute treat! From the moment I walked into my room, I was impressed. The beds were nothing short of heavenly—so much so that I joked with my friend about sneaking the mattress into my suitcase because it was just that good. And here’s a little insider tip: you can actually buy these mattresses on the Marriott website! But beyond the blissful sleep, what really impressed me was how truly accessible the room was.
Check out my Instagram post to learn all about this fabulous spot!
As an older traveler with a disability, I’ve had my fair share of hotel mishaps, particularly in bathrooms. But not this time! The Woodlands Waterway Marriott, had thought of everything, from a flip-down shower chair to a handheld showerhead with a wall mounted switch valve that controlled the water temperature separate from the on/off. Many of you may be wondering why this is important but many of you already know about that miserable shower dance you must do while you attempt to get to the hot water. Well, the Marriott provided a thoughtful switch that allowed me to set the water temperature before turning it on —meaning I could get settled before turning on the water, no water dance required.
These little details might not seem like much, but they make all the difference when you’re traveling with a disability. It was clear that a lot of thought had gone into the design, and I left feeling not just well-rested, but also genuinely cared for. I’ve requested accessible rooms before only to find they didn’t really cater to my needs. But this room was different. It was clear that a lot of care went into the design and placement, making me feel genuinely cared for. So, a heartfelt THANK YOU to The Woodlands Waterway Marriott, and the ADA Design Team. Now, enough about the amazing accommodations—let’s get back to the adventures!
Dinner and a Show: Sixty Vines and the Stone Temple Pilots
After a restful afternoon, I headed back to Market Square for dinner at Sixty Vines before catching a concert at The Cynthia Woods Mitchell Pavilion.
It’s become something of a ritual for me to have a glass of bubbly whenever I’m exploring a new place, and Sixty Vines did not disappoint. I opted for the house-made, eco-friendly Sesenta Cava, paired with a pick-three board featuring house-made ricotta, Cabot clothbound cheddar, and Fra’ Mani Soppressata. Each bite was a revelation, especially when drizzled with honeycomb—who knew something so simple could elevate a meal to another level?
In addition, the boards have warm, sliced Pita bread, seasoned almonds, and honey served with the honeycomb. Now I’d never had honey or honeycomb on food before but at my servers behest I was definitely willing to give it a go, and let me tell you, she was not wrong! The lightly sweet flavor woke up the taste of each of the other items. Don’t get me wrong, everything was good by itself, but together? It was amazing and melded together perfectly with that simple drizzle of honey. I started with a simple schmear of ricotta and added crumbles of cheddar, a fold of Soppressata, and by the time I’d topped it off with thin slices of honeycomb oozing with sweet honey for a bit of sweet crunch, I realized this may be the most delicious sandwich ever.
The light food set off the crisp bubbly beverage perfectly, so much so that I had a second glass! With a satisfied stomach and a few bubbles in the brain, I made my way to The Pavilion, where I was about to relive my high school dreams. The lineup? Soul Asylum, Live, and Stone Temple Pilots—bands that may have defined my teenage years. And let me tell you, the venue was perfect. Despite the large crowd, it never felt overcrowded, not sure how they pulled off that magic trick but I’m definitely not complaining!
The multiple accessible seating options were a game-changer. They actually had seating set aside for people with limited mobility which was new to me. With the raised platform, I had a great view, even when everyone stood up, and the fans overhead kept the August heat at bay. Plus, there’s a super top secret second set of concession stands and restrooms on the opposite side from where you enter (It’s on the same side as the limited mobility accessible seating). It was the perfect setting for a trip down memory lane, only this time, I had the luxury of enjoying it with adult money!
The Post-Concert Indulgence: Late-Night Cravings Satisfied
The concert was everything I hoped it would be, but the night wasn’t over yet. After making my way back to the hotel via the convenient skyway, I found myself craving something indulgent. Luckily, the Marriott’s lobby had just what I needed—after-hours pizza and an ice-cold beverage. And because no great night ends without dessert, a tray of sweet treats magically appeared —the only magic spell needed was a simple call to room service! The delicious tray included an amazing variety of (pink) key lime pie, chocolate bonbons, macarons, and chocolate-covered strawberries. It was the perfect sweet ending to an unforgettable evening.
Kayaking Adventures
The morning after the concert, I woke up feeling completely refreshed, and I’ve got to say it again—those beds! The Woodlands Waterway Marriott knows how to pamper its guests, and I was proof of that. After waking up, I was feeling a little peckish and knowing I had a full day of activities ahead, I headed down to the Acqua Restaurant & Lounge in the lobby for their breakfast buffet. Let me just say, I felt no shame in loading up my plate with a biscuit smothered in gravy, scrambled eggs, crispy bacon, fresh fruit, golden potatoes, a glass of juice, and a strong cup of coffee. By the time I was done, I was convinced I’d never eat again—or at least not until lunch rolled around!
Feeling fueled and ready to take on the day, I took the trusty trolley over to the Riva Row Boat House for a little adventure on The Woodlands Waterway and exited a little early so I could enjoy all the large scale sculptures. Pro tip: there’s an actual wheelchair-accessible path that takes you from the parking lot to the boathouse. And here’s some exciting news—a little birdie told me that a wheelchair transfer assist is coming next year to help wheelchair users easily transfer into kayaks!
Now, here’s where things got interesting—or at least humorous… What possessed me to get into a kayak for the first time ever, while wearing Doc Martens and a dinosaur romper, is beyond me. But hey, when in The Woodlands, right? The helpful guy at the dock got me all suited up, gave me a quick lesson on how to work the paddle, and off I went.
They had other options like swan-shaped paddle boats and water pontoon bikes (which I’d never seen before), but with my newest injury, I didn’t trust my right leg enough to keep me from getting stranded in the middle of The Waterway. I could only imagine the embarrassment of calling for help, “Um, excuse me sir, I’m broken and stuck on a swan in the middle of The Waterway. Can you come rescue me?” So, a kayak it was, and I’m happy to report I didn’t tip over—not even once! Though getting into the kayak was pretty hilarious and I truly regret not recording my gracious, elegant entrance, NOT! Let’s just say I will forever be grateful evidence of that fail does not exist.
While kayaking I zigged and I zagged all over the place and was a bit of a directional disaster, but I made it quite a distance, turned around, and got back without any major mishaps. My arms were a little sore, but nothing too wild. And honestly, pre-kayaking I was a little concerned my old-lady arms would just give out on me, but shock upon shock, these suckers held up! More than the workout, what really caught me off guard was the sheer amount of public art around The Waterway. It seemed everywhere I turned, there were sculptures. I’d noticed it all around The Woodlands. There were sculptures, murals, and artistic installations—large and small—incorporated into the landscape. It added an unexpected layer of beauty and serenity to the whole experience.
A Taste of New Orleans in The Woodlands
After my kayaking adventure, I was ready for some serious refueling. I asked a few locals where I should go for lunch, and more than one person recommended Schilleci’s New Orleans Kitchen . With a name like that, how could I resist? While I was expecting good ol’ New Orleans comfort food, what I got was actually closer to Cajun fine dining. The venue is intimate, with limited seating (less than 20 tables), so on concert nights, it’s best to make a reservation because they have been known to turn people away—and no one wants that!
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The vibe is relaxed upscale and even those wandering over for an early dinner before their ’70s rock concert, ’80s hair band, or ’90s alternative rock show at The Cynthia Woods Mitchell Pavilion can feel comfortable sliding into a table and enjoying their extensive wine list. Some of the best parts about seeing bands when you’re older is having adult money and being able to order wine at dinner beforehand! And here’s a pro tip: Schilleci’s will knock $10 off the cost of any bottle of wine or champagne every Wednesday and Thursday night from 3 p.m. to close. Who doesn’t love $10 off a bottle of wine? Am I right?!
Don’t know much about wines, looking to learn something new, or want to expand your palate? Schilleci’s has you covered! They employ three sommeliers! Yes, you read that correctly—three sommeliers, which means there’s always one there when you are. Whether you’re a wine novice or a seasoned connoisseur, they’re ready to help you find the perfect pairing for your meal or introduce you to something new and exciting.
And in my opinion, getting voted “Best of The Woodlands” for Cajun & Creole in their opening year, 2010, was impressive, but winning that honor every year since? That’s nothing short of a Herculean effort! Schilleci’s is a family-owned gem and serves up authentic recipes passed down through generations, with Chef David at the helm.
An Evening Serenade and Sweet Surprises
After my late lunch, I found myself drawn back to the lawn in front of Sixty Vines, where a group of incredibly talented young musicians were performing, people congregated, and children played. The atmosphere was almost magical as they played a mix of piano and vocal tunes, ranging from jazz classics to top 40 hits and even a few country favorites. And somehow, despite it being August in Texas, the weather was perfect—not too hot, not too humid. It was as though The Woodlands had struck a deal with the weather gods just for this one evening, making everything feel just right. Or maybe that’s just how it always is here? I guess I’ll have to come back to find out!
After soaking in the music for a good half hour, I decided to explore a bit more. Just across the street at the cool vintage theatre that houses Reel Luxury Cinemas & The Audrey Restaurant , I saw the most amazing sight my eyes had ever beheld—a cupcake vending machine. Yes, you read that right, a vending machine that dispenses cupcakes! Have you ever seen one of these? I certainly hadn’t, and I probably looked a little crazy snapping about 20 photos and videos of this marvel of modern technology. But can you blame me? I mean, it’s a cupcake vending machine!
Once I got the perfect shot—okay, maybe not quite Ansel Adams level, but good enough—I rewarded myself with one of those made fresh daily Sprinkles Cupcakes. And let me tell you, it was delicious. Moist cake with just the right amount of frosting. The only challenge was juggling my bag, a cupcake, and a crutch, yet somehow, I managed.
I then wandered over to the other end of The Waterway, known as The Waterway Arts District, aptly named for its colorful art benches, large and small sculptures, and art installations scattered along the waterfront. A really stunning area for a stroll, jog, or roll.
Exploring the Waterway and Unexpected Finds
The Woodlands Mall, not to be confused with Market Street shopping center is just a hop, skip, and not even a jump away. This city is all about its shopping, and I love how convenient it is to stay at a fabulous hotel like The Woodlands Waterfront Marriott, catch a show, and then stroll around the Town Center area for some serious retail therapy. Honestly, I didn’t need my car the entire time I was here. The Trolley and the convenient paved pathways made getting around a breeze, even when walking is difficult.
As the sun set, The Waterway Arts District transformed from a laid-back, scenic spot to enjoy the artwork and gentle flowing water, into a lively party hub, teeming with bars and restaurants. Waterway Square, near The Westin Hotel , features a water wall and light show that makes for some epic photos at night. I wasn’t expecting such a vibrant nightlife scene, but maybe that’s the theme of this entire trip—expect the unexpected.
Baja Cantina: A Fiesta for All, Including the Pups
After snapping what felt like a million pictures at the water wall, I crossed the street to Baja Cantina for some delicious queso, margaritas, and a live DJ. The vibe was electric, the food hit the spot, and the music was on point. But the highlight?
The freaking adorable dog menu! That’s right, Baja Cantina offers a separate menu for your furry friends, with options ranging from chicken and scrambled eggs to steak. They even hand out free Milk Bone treats for all the good pups that visit. How cool is that? I sipped on my margarita (only half, since I still had to drive home) and soaked in the lively atmosphere.
The streets were lit up and bustling with pedestrians and outdoor diners, and I felt completely safe wandering around, enjoying the energy of the night. By the time I finally retrieved my car, it was well after 11 PM, and I thought my night of surprises was over.
But as I drove out of The Woodlands, I passed a Ferrari dealership.
For some reason, this sight struck me as the perfect final note to my short getaway—luxury, fun, and a little bit of unexpected charm, all wrapped up in one.
Planning Your Visit: Expect the Unexpected in The Woodlands
If you’re looking for a destination that combines luxury with laid-back charm, look no further than The Woodlands . My weekend here was full of surprises, from upscale shopping and fine dining to a vibrant arts scene and delightful discoveries like cupcake vending machines and dog-friendly menus. Whether you’re indulging in designer labels, savoring gourmet food, or catching a concert at The Cynthia Woods Mitchell Pavilion, The Woodlands caters to all your needs—and for those of us who need a little extra accessibility, they’ve thought of that too.
This is a place that defies expectations and offers something new around every corner. Whether you’re here for a quick getaway or a longer stay, one thing’s for sure: in The Woodlands, you should always expect the unexpected. Heck, the visitor center even offers a FREE Visitors Guide to help you plan your trip from where to stay, what to do, what to eat, and when to do it! So, what are you waiting for? Start planning your trip today and be prepared to rediscover a place that’s full of unexpected delights.
Now if you’ve made it this far, I want to include a little disclaimer: This trip was a hosted stay with The Woodlands tourism board, however this is not an ad. I legitimately had so much fun that I have since gone back 4 more times to see concerts (unhosted) and check out other parts of the city over the course of the last 2 months. Mind you, before this stay I hadn’t been to The Woodlands in nearly 30 years and now I’ve been a total of 5 times! So clearly, I had fun…
Mandi
MyTripABLE 
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