Walk past the old Piccolina storefront on Main and Lincoln this month and you'll see butcher paper taped over the windows and a new sign going up. It reads Leroy's. That's notable because Leroy's Tex-Mex BBQ has spent years building its following out on Highway 290, next to Jenschke Orchards, a solid ten-minute drive from the tourists and the tasting rooms. Now it's opening a second location right in the middle of downtown, arriving this summer just ahead of the two biggest events Main Street hosts all year. That's not a coincidence worth glossing over. It's a bet on what kind of town Fredericksburg is becoming this October, and the answer turns out to be two different towns, roughly two and a half weeks apart, using the same city block.
Why A Highway BBQ Joint Is Betting On Downtown
Leroy's built its reputation the slow way. The original spot on US-290 does breakfast tacos, brisket, and a queso that has won the Fredericksburg Food & Wine Fest's Queso Competition two years running. That's a real credential in a town where the wine club crowd and the barbecue crowd don't always order off the same menu. The new location, opening this summer in the former Piccolina space at the corner of Main and Lincoln, puts that same menu a block from Marktplatz, the square where both of October's headline events happen.
A few things about the move are worth knowing if you're planning your own fall around it:
- The second location keeps the same fusion concept: Tex-Mex and barbecue on one menu, not two separate operations.
- It sits at Main and Lincoln, inside walking distance of Marktplatz.
- The opening window has been publicly stated as summer 2026, which means it should be running, or close to it, by the time both October festivals arrive.
A restaurant that already knows how to win a queso contest doesn't need downtown foot traffic to survive. Choosing to open there anyway signals something about what the owners think downtown demand actually looks like this fall.
Two Festivals, Eighteen Days Apart, Same Square
Here's the split. Fredericksburg Oktoberfest runs October 2 through 4, 2026, on Marktplatz. The Pedernales Creative Arts Alliance has organized it since 1981, and the proceeds fund the group's grants and scholarships for Gillespie County students and local arts organizations. It's built for families: kids six and under get in free, kids seven to twelve pay a dollar for a single day or two dollars for a multi-day pass, and there's a dedicated Kinderpark with bungee jumps and face painting. This is a community fundraiser wearing a beer tent.
Eighteen days later, on the same square, the Fredericksburg Food & Wine Festival takes over from October 22 through 25. The festival is more than three decades old but relaunched with a new look and schedule in 2024, and this year it's operating at a different scale entirely. The Grand Tasting on October 24 brings more than 35 Hill Country wineries to Marktplatz, part of a lineup of more than 75 culinary and beverage partners. Early Grand Tasting badges run $100 to $265. The Friday Street Dinner, presented by Waldorf Astoria, seats guests at a long communal table through downtown for a four-course meal prepared by chefs from Mesquite at the Warehouse and Boot Ranch, paired with Hill Country wine, and the ticket runs $275, or $400 if you add the late-night Après Garden Party. James Beard Award winning chef Jesse Griffiths of Austin's Dai Due headlines with a whole hog roast, and pitmaster Lance Eaker of Eaker Barbecue, which sits on Texas Monthly's Top 50 BBQ list, is part of the culinary lineup. Every winery, chef, brewery, and distillery in the festival has to be based in the Hill Country, and this year's event benefits the Hill Country Hospitality Workers Emergency Relief Fund.
One dollar to get a child into a bungee jump tent. Four hundred dollars for a seat at a street dinner two and a half weeks later. Same city block.
The Split Already Showed Up In May
This isn't a one-time October fluke. Fredericksburg ran its first-ever Restaurant Week back in May 2026, from the 4th through the 10th, and the same tension played out in miniature. Leroy's hosted a casual TexMex BBQ Fest called First Bite on May 9, priced and pitched like a neighborhood cookout. That same week, two venues that are normally reserved for wine club members, Stout's Signature at Grape Creek Vineyards and K Bistro at K Estate, opened their doors to the general public for the only time all year. Jim Mikula, president and CEO of the Fredericksburg Chamber of Commerce, called Restaurant Week a way to "celebrate the chefs, restaurants and hospitality that make our town a wine and culinary destination."
That's the pattern. Fredericksburg's food identity isn't drifting toward one direction, upscale or down-home. It's splitting into two parallel tracks that both use downtown as the stage, and local businesses are positioning themselves to catch either wave, or both.
What This Actually Means If You Live Here
If you're used to grabbing a table on Main Street without planning around it, the two bookend weekends in October are the ones to build around, not the ones to avoid entirely. Oktoberfest weekend, October 2 through 4, brings families and a beer tent crowd to Marktplatz, with parking tighter than usual but the vibe staying casual and kid-friendly. The Food & Wine Festival weekend, October 22 through 25, brings a different visitor entirely: ticketed events, a dressier crowd, and a Main Street that fills up around dinner reservations rather than walk-ins.
Between those two weekends sits a genuine window, roughly two and a half weeks in the middle of October, when downtown returns to its normal rhythm. That's the stretch to actually enjoy Main Street the way you do the rest of the year, without either the polka bands or the four-hundred-dollar dinners competing for sidewalk space.
And if Leroy's second location is open by then, it's worth watching what it actually becomes. A spot that can serve a family stopping in during Oktoberfest weekend and also hold its own for a Food & Wine Festival crowd looking for something less formal than a Street Dinner isn't choosing a side. It's betting that a queso good enough to win two competitions works just as well for both.
That's the part worth knowing before you make your own October plans. Main Street isn't one town in the fall. It's two, running on different budgets and different clocks, and the businesses opening there right now are the ones that figured that out first.
If you're weighing what any of this means for property on or near Main Street, or you're simply trying to time a move around a calendar that gets busy twice in one month, Shelley Herman knows this stretch of town block by block. Let's Connect.
