A Fall Weekend in Wimberley

Events + Ideas for a Hill Country Getaway

Sometimes all you need is a reason to go.

Maybe it’s Market Days, an October event, the promise of cooler weather, or dinner somewhere you’ve been meaning to try. Maybe it’s simply the realization that you haven’t been to Wimberley in far too long.

Fall gives us plenty of excuses.

And that’s the nice thing about Wimberley: whatever gets you here doesn’t have to fill the whole trip. Spend part of the day exploring town, find something good to eat, head outside when the weather calls you—and leave plenty of time to be together back at The Gathering.

Because some of the best parts of a Wimberley weekend happen after you’ve stopped checking the itinerary.

So if you’re thinking about a fall getaway to Wimberley, Texas, here’s how we’d spend it.

Friday: Get Here

If you can, arrive while there’s still a little daylight left. There’s something nice about starting a weekend without immediately having somewhere else to be.

Unpack, claim bedrooms and take a look around. Someone will probably find the pickleball court. Someone else will spot the pool or hot tub. And if you arrive around dinnertime, don’t be surprised if everyone stops what they’re doing when the deer start wandering up for theirs.

Eventually, someone will remember that the humans need dinner, too.

Head into Wimberley or keep the first night easy and eat together at The Gathering. Either way, resist the urge to fill the evening.

Wimberley will still be there in the morning.

Sometimes the welcome committee arrives before you’ve finished unpacking.

Saturday Morning: See What’s Happening

If you’re visiting on the first Saturday of the month, Wimberley Market Days is an easy place to begin. With more than 490 booths spread beneath the oaks, it’s part treasure hunt, part people-watching and part Wimberley tradition. Add food, cold drinks and live music, and you can happily give it as much—or as little—of your Saturday as you’d like.

If Market Days weekend didn’t fit your schedule, no worries. There’s always plenty to do. Grab coffee or breakfast and wander the Square. Browse the shops and galleries, look for Wimberley’s larger-than-life painted boots, or take advantage of the morning and head outside.

And if you like having an actual excuse on the calendar, October has a few of those, too.

Happening in Wimberley - October 2026

OCT 3
Wimberley Market Days
More than 490 booths, food, cold drinks and live music beneath the oaks at Lions Field.
7 AM–4 PM · Event Details →
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OCT 10
Blue Hole Star Party
Bring a chair or blanket for live music followed by telescope viewing and a guided sky tour at Blue Hole Regional Park. Especially well timed with October's new moon.
7:30–9:30 PM · Event Details →
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OCT 24
BOO! Hole Halloween
A free, family-friendly evening at Blue Hole with trick-or-treating, carnival games, a hayride, live music, costume contest, cider and cocoa, plus a separately ticketed haunted trail after dark.
4–9 PM · Event Details →
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OCT 30
Downtown Wimberley Trick-or-Treat
Storefront trick-or-treating, family activities and plenty of small-town Halloween spirit around the Square.
4–7 PM · Event Details →
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Looking for more Halloween fun? Wimberley leans into the season with pumpkin patches, family-friendly festivities and more happening around town.

Explore Visit Wimberley's Halloween Guide →‍
Event dates and details can change. Check official event information before making plans.

Saturday Afternoon: Pick Your Kind of Wimberley

By Saturday afternoon, you’ll probably have a pretty good idea what kind of Wimberley day your group is having. Maybe nobody is finished wandering yet. Maybe the weather is calling you outside. Maybe you’re ready to find somewhere comfortable and hang out for a while.

Or maybe someone has already asked, “Can we go back to The Gathering?”

All valid choices.

Pick your fall fit.

The Wanderer

If wandering without much of a schedule sounds like a perfectly legitimate afternoon activity, stay around the Square and let one stop lead to another.

Wimberley is a designated Texas Cultural District, so art isn’t confined to a single gallery. You’ll find galleries and public art mixed right into town, including the giant painted cowboy boots that have become part of the Wimberley landscape. Browse the shops, stop for coffee or lunch, and see what you find that you didn’t know you needed.

When you’ve had enough shopping but aren’t quite ready to leave downtown, wander toward Cypress Creek Nature Preserve. It’s an easy way to trade shops and sidewalks for trees and creekside scenery without turning it into an entirely separate excursion.

The Get-Outside Crowd

If the weather is calling you outside, Wimberley gives you plenty of ways to answer.

If your group doesn’t mind a few stairs—and by “a few,” we mean quite a few. 218, to be exact.Old Baldy rewards the effort with sweeping views across the Wimberley Valley and Texas Hill Country.

For a more nature-focused outing, explore the trails and landscape atJacob’s Well Natural Area or Blue Hole Regional Park. And for groups with different ages and energy levels, EmilyAnn Theatre & Gardens offers gardens and outdoor spaces without requiring everyone to agree on what constitutes a “fun hike.”

The Hang-Out-Awhile Crowd

One thing Wimberley does particularly well is the family-friendly indoor/outdoor hangout—the kind of place where you can grab something to eat or drink, find a spot outside and let everyone settle in for a while.

Or make it a winery or brewery afternoon. The point isn’t really where you land so much as finding somewhere that fits your group and doesn’t make anyone feel rushed to move on.

And this is where Texas fall can be especially nice. We may not get a dramatic change of leaves, but eventually the season announces itself in other ways: a cooler morning, the first sweater pulled from the back of the closet, coffee that tastes better outside, or an evening when gathering around a fire suddenly sounds like exactly the right plan.

→ See Our Wimberley Favorites for some of our favorite places to eat, drink and hang out.

The “Let’s Go Back” Crowd

By this point, you may have shopped enough, climbed enough, or heard the kids ask approximately fourteen times when you’re going back to the pool.

Go back.

That’s part of the weekend, too. Change into swimsuits, start the pickleball rematch, settle under the pavilion, play bocce or take a nap while somebody else keeps going. The advantage of staying somewhere with plenty to do is that returning to the house doesn’t mean the day’s adventures are over.

You came to Wimberley for a getaway. You’re allowed to actually get away.

Saturday Night: Don’t Call It a Night Yet

Dinner may be over, but that doesn’t mean the day is.

Maybe there’s one more pickleball game under the lights while someone else starts a fire. A few people linger around the table. Somebody decides the hot tub sounds like an excellent idea. And eventually someone looks up.

Then everyone does.

Wimberley is an International Dark Sky Community, and on a clear Hill Country night there’s plenty of reason to stay outside. That’s why we created the Stargazing Stage at The Gathering—a place to stretch out, look up and see what the night decides to show you.

Come to Wimberley for the Dark Skies. Stay for everything that happens beneath them.

Sunday: One More Thing

Sunday morning doesn’t need much of an itinerary. Make coffee, see if the deer have wandered through, fit in one last game, and have breakfast together—or head back into Wimberley for it.

If you’re not quite ready to point the car toward home afterward, don’t. Stop somewhere you missed on Saturday, take a walk or make one last Wimberley stop before heading home.

There’s no rule that says checkout has to mean heading straight home.

Staying Longer? Even Better.

A weekend is a great introduction to Wimberley. An extra day gives you room for something that deserves more time—perhaps Wimberley Zipline Adventures, a winery afternoon, another outdoor excursion or a drive through the Texas Hill Country.

Or even better, don’t add another thing to the itinerary. Sleep later. Swim. Play. Cook something together. Give everyone enough time to enjoy being here instead of simply sleeping between outings.

Because that’s the trick with Wimberley. You may come for Market Days, a party, the weather, the art—or because somebody sent the group text that said, “We should go somewhere.”

Pick the thing that gets you here.

We’ll take it from there.