Cypress Creek Cottages is a property of twelve pet-friendly cottages in Wimberley, Texas. You get your own front door, a full kitchen, and a private hot tub on a private deck. Dogs of every breed and size are welcome. The Square is under a mile away; you can walk it or drive it.

Autumn is the season Wimberley is quietly best at. The heat breaks, the crowds that fill the swimming holes all summer thin out, and the cypress along the creek turns rust and gold. It is the easiest time of year to get a cottage, and the nicest time of year to sit outside in one.

Here is what there is to do around it in the fall.

What is there to do in Wimberley in the fall?

Festivals, wine, and long walks in weather that finally cooperates.

Wimberley Market Days runs the first Saturday of the month, March through December, 7am to 3pm at Lion’s Field on FM 2325. Around 490 booths under the oaks, free to get in, $10 to park, rain or shine. Dogs are welcome on a leash, which makes it one of the easiest things in town to do with the whole party.

Fall is harvest season at the Hill Country wineries, and two of the best are a short drive away. Driftwood Estate Winery pours seven days a week, 11am to 6pm. Note that it is adults only, 21 and over. Duchman Family Winery opens at noon daily, until 6pm Monday, 7pm Tuesday through Thursday and Sunday, and 8pm on Friday and Saturday.

Where can you see fall colour near Wimberley?

The Hill Country does not do New England, and pretending otherwise sets guests up for disappointment. What it does is subtler and, in its way, better: cypress along the creeks turning rust and gold, sumac going deep red on the hillsides, and clear light.

Old Baldy is the best vantage point in the valley. It sits 2.5 miles from Cypress Creek Cottages, under ten minutes’ drive, and it is 218 steps to the top of a 1,182-foot hill. From up there you can see the colour across the whole valley at once. We have written a full guide to the Old Baldy trail if you want the history and the practical detail before you go.

Blue Hole Regional Park has walking trails under mature cypress that are worth the visit in October whether or not you are swimming. The trails, playground and picnic areas are free, open to the public, and need no reservation. Dogs are welcome everywhere in the park except the swim lawn. Cypress Creek Nature Trail runs parallel to the creek and is flat enough for an easy morning walk.

What is there to do for Halloween near Wimberley?

The Devil’s Backbone is Ranch Road 32, which runs west from Wimberley toward Blanco. It is a spectacular drive along a limestone ridge, and locals will tell you it is the most haunted stretch of highway in Texas. Stories of Confederate soldiers, Spanish monks and a woman searching the ridgeline have followed it for over a century. Whether or not you believe any of it, the sunset from the overlook is worth the drive on its own.

Haunted Wimberley, a local Facebook group, is where residents trade ghost stories and mark the spots worth visiting after dark. It is a better source than any listicle, this one included.

For families, the neighbourhoods around the Square are safe and walkable for trick-or-treating on the 31st.

Is there anything worth driving to?

Two, both annual, both within about an hour:

• The Dripping Springs Songwriters Festival, 16–18 October 2026. Free, with more than fifty songwriters playing in the round across venues within walking distance of each other, about half an hour away.
• The Texas Clay Festival, 24–25 October 2026, in the Gruene Historical District of New Braunfels, with over eighty Texas potters and demonstrations running all weekend.

The Texas Marigold Festival in Blanco also runs every year, late October into the first days of November. Music, food, flowers and a Day of the Dead barn dance, less than half an hour away. Its dates are published differently in different places, so check the organiser before you plan a trip around it.

Can you bring the dog?

Yes, and autumn is the best season for it. All twelve cottages are pet-friendly. No “pet rooms”, no pet-free units, no breed restrictions and no weight limits. Around 3,000 dogs stay here every year.

Every dog is greeted with a VIP welcome package: a welcome letter, pet treats, a complimentary toy, a pet pillow, bowls, potty pick-up bags, and a “just in case” wee pad, waiting in the cottage on arrival. There is a fenced and lighted dog park by Cottages 2 and 3, with a scooper, bags, a trash can and covered seating provided. Cypress Creek runs along the south edge of the property by Cottages 9, 10 and 11 and is open to your dog for supervised splashing.

The pet fee is $15 per night per pet — no deposit, no breed restrictions, no weight limit. Most places around Wimberley do not take dogs at all; among those that do, $25 to $50 a night is the norm. Twenty-five percent of every pet fee goes directly to Wimberley Adoption Group & Rescue, the local Wimberley animal rescue that has been placing dogs since 2009.

Out in town, several Wimberley restaurants welcome dogs on the patio, among them The Shady Llama, Cypress Creek Café and Ino’z Brew & Chew. And if you want an afternoon at the wineries without the dog, in-house pet day care runs daily from 9 AM to 5 PM at $20 per hour, per pet.

Why the Hill Country is easier in autumn

Summer here is about water: Blue Hole, Jacob’s Well, Cypress Falls Swimming Hole, all of it booked out and full. Autumn is about everything else. The same drive that is punishing in August is pleasant in October. The wineries are working. And the cottages, which are hard to get on a July weekend, are considerably easier in the second week of November. A Hill Country cabin in October is a different trip from the same cabin in August.

Where to stay

Cypress Creek Cottages has twelve private cottages in Wimberley; four of them sit on Cypress Creek. Every one has a private hot tub on a private deck, a full kitchen, and a living room. A whole cottage, not a room in a building, with your own front door and no shared walls.

For a couple in autumn, Cottage 11 Jade is the one to ask about: a one-bedroom creek-facing cottage with a direct view of Cypress Creek from the deck, and the hot tub right there. For a family or two couples travelling together, Cottage 9 Amethyst and Cottage 10 Coral are the two-bedroom creek-facing cottages, sleeping up to six, and they book first.

A welcome basket is waiting when you arrive. Massages, in-cottage add-ons and swimming at our partner Cypress Falls Swimming Hole can be arranged through our experience packages when you book.

The advertised nightly price is the price. No resort fee, no cleaning fee, no booking fee — the only add-on is the $15 per night pet fee, and you see it before you pay. Cypress Creek Cottages is rated 4.8 on Google and is the #1 hotel in Wimberley on Tripadvisor.

Other Articles