Oakwood Is Back on the Hill, and This Time It's Built for a Regular Tuesday

Dallas Miller's description of Oakwood Public Market says nothing about the architecture or the sunset. He talks about a school-day loop. He and his wife Sarah stopped at the coffee shop after drop-off, went back for milk and a bottle of wine on the way home, let the kids get milkshakes at the soda shop, and came back again for dinner at the bar while the kids ran around with the Hill Country spread out below. "We were here all the time for multiple different reasons and that's why it just spoke to us," he told the Hays Free Press in August.

That loop is the business plan now. The Millers took over the hilltop market at 2500 Beverly Drive after it closed this summer, and they rebuilt it around the trips its neighbors already made. The Oakwood that opened in 2025 was a polished food-and-retail destination. The one on that hill this fall is closer to a corner store, a pizza counter and a family room that happen to share a very good view.

How a Hilltop Showpiece Went Dark

Oakwood opened in September 2025, and it had a lot of pieces from the start: a coffee shop, a patio bar, a soda shop, a pizza restaurant, a food market and retail shopping, as Community Impact laid out. Ahead of the ribbon cutting, the Dripping Springs Chamber of Commerce called it a "thoughtfully curated food and community hub" perched on a hilltop. Ryan Schibi, the director of operations at the time, said he hoped it would become "part of your daily rhythm."

Less than a year later, the operation announced it would close on July 3. Community Impact reported that the ownership team cited "numerous challenges," including staffing constraints, leadership turnover and rising costs.

Within weeks, two of its regulars had bid on it. The Millers had lived in Dripping Springs for about three years by then. Sarah works in events and hospitality, and Dallas is a director of operations. They signed a 10-year lease that keeps the building, the name and the concept. Local Eats reported that Oryx Development is still the landlord, and that Dallas grew up around The County Line, the restaurant his uncle Don "Skeeter" Miller runs.

"We live here in Headwaters, so we are part of the community and we really just want to make this a place where families can gather and … the community can make memories. The best part is we're one of them, as well." Sarah Miller, speaking to the Hays Free Press

Same Barn, Different Job

Four changes inside the same barn:

• The market became a Bodega. Local Eats describes the formerly upscale market as more of a neighborhood convenience stop now, with milk, cereal, paper plates and ice on the shelves.
• The event room became an arcade. The space once used for events now has Pac-Man, claw machines, basketball, racing games and a boxer game, all with tap-to-play.
• The outside vendors are gone. The earlier vendors did not stay. The Millers have talked about adding feature shelves for local makers in the future.
• The kitchen has a new chef. Charles Dowd, who previously ran kitchens at North Italia, Haymaker and Black Sheep Lodge, is behind the new restaurant menu.

Each of these changes points Oakwood toward an ordinary day instead of a special occasion. An event room waits for a booking, while an arcade and a shelf of milk and ice are there for any afternoon. In the Millers' words, they want the place to be "a one-stop shop for families."

The Loop, Counter by Counter

According to Local Eats, the reopening came in stages starting in August. The coffee shop came back first, and the rest followed about a week later. Here's how the counters line up with the day Dallas Miller described:

The table leaves out arcade and soda shop hours on purpose. Different pages of Oakwood's own website don't agree on them yet. As of mid-October, Local Eats said the soda shop was still finishing up, so call 512-368-4045 before promising anyone ice cream.

What to Order From the Pizza Window

The pizza kitchen sits inside the Bodega and makes 16-inch pies with a crispy semolina crust and a sauce of organic tomatoes and a little salt. These are the current menu items and prices as Local Eats listed them on October 15:

1. The Cheese, $16
2. The Standard, pepperoni and Parmesan, $18
3. The Oakwood, the house pie, with pepperoni, Italian sausage, roasted mushrooms and onions, $20
4. Sweet Heat, whipped ricotta, Calabrian chiles and hot honey, $20
5. Italian Sub, ham, capicola, soppressata and provolone, $15
6. Meatball Sub, $15

Pizza and subs are pickup only, ordered through the online order page. That's another sign of what the kitchen is set up to do. A $20 house pie you order from the car on the way home fits a Tuesday better than a Saturday outing.

The One Room That Is Strictly for Grown-Ups

Back in August, Dallas Miller described a plan to keep the coffee shop open late on Friday and Saturday nights, make it "a little bit more moody," and give the chef room to try a supper club with craft cocktails and draft beer. He called it a 21-and-up spot "because that's kind of lacking" on this side of town, and a date-night option for couples in the area.

That plan now has a name. Local Eats reports that the Jackalope Room, tucked inside the coffee shop, turns into a 21-and-up speakeasy on Friday and Saturday nights, with cocktails and small bites. So the room that sells breakfast tacos at 7 a.m. on a weekday is a cocktail bar by Friday night. Oakwood's website says new menu items and programming are being added every week, so the weekend lineup is still taking shape.

Why the Hill Matters More Before the Corner Fills In

Today Oakwood puts coffee, milk, pizza and a cocktail under one roof at the top of Headwaters. The commercial corner at the bottom of the hill is about two years from offering anything similar.

At the corner of Hwy. 290 and Canyonwood Drive, at the front of Headwaters, a Tacodeli spokesperson confirmed to Community Impact in September that a lease is signed. No opening date has been set. The Dripping Springs Sports Club says its flagship is "coming 2028" at the same commercial site. Community Impact reported that the plans include a wellness and recovery center, a cafe and childcare.

The state filing shows the scale. A Texas Department of Licensing and Regulation registration dated September 10, 2026, lists "Headwaters East Commercial" as 300,000 square feet of new retail space on East US 290. It estimates the cost at $20 million and the construction window at January 1, 2027, through August 1, 2028. Those dates are estimates, and the filing lists no assigned tenants.

Until those lots are built out, the hilltop's counters cover the coffee, pizza and milk-run parts of the day for this side of 290, and the couple running them live in Headwaters. For a look at how downtown Dripping Springs shuffled its own lineup this year, the summer roundup covers the Mercer Street side of town.

The Bodega opens at 10 a.m. daily, and the coffee shop opens at 6:45 on weekdays.

Two neighbors buying a place they already loved is the kind of Dripping Springs story we like most at Johnny Ronca. If you live off 290 and want to know what's going up on the Headwaters East lots or how that corner is changing your end of town, Let's Connect. And next time you're on the hill, try the Oakwood house pie.