How do you see two tree lightings in one Wimberley evening? On Saturday, Nov. 28, the EmilyAnn Theatre & Gardens lights its hilltop tree at 5:15 p.m. Downtown, the Wishes for Wimberley Lighted Parade starts at 6 p.m., and the tree at the Downtown Christmas Courtyard is lit right after it. Getting to both takes a little planning and an early start.
This year the creeks are out of the holiday season. Hays County has canceled all swimming at Jacob's Well until further notice because the water is low, and Blue Hole's swim season ended in September. That leaves Wimberley's winter calendar on land: the Square, a few addresses on Ranch Road 12, and a short run of FM 2325 where Market Days and the EmilyAnn are close neighbors.
The Water Sets the Terms
Here is where things stand at the two swimming holes on the calendar's quietest weeks:
- Jacob's Well Natural Area is open 8 a.m. to 6 p.m., with no entry after 5:30 p.m. General entry is still free. All swimming is canceled until further notice because of low water, according to the Hays County Fiscal Year 2027 parks notice posted Sept. 18.
- Blue Hole Regional Park is open daily from 8 a.m. to sunset. The city lists swimming as seasonal, May 1 through Labor Day plus September weekends. The trails, playground and picnic areas are free and don't need a reservation.
The county notice also shows what Jacob's Well swimming will cost when it comes back. Under the FY 2027 schedule, adults 13 and older pay $12, up from $5 in FY 2026. Children 5 to 12, seniors 60 and older, service members and Hays County residents pay $9. Reservations will come in two-hour blocks, four a day, with no more than 40 people per block. So for now the walk to the well is free, and the swim will cost more than before.
Saturday, Nov. 28, Hour by Hour
Opening day of Hometown Holidays is busier than any other day of the season. The schedule runs from late morning to 10 p.m., and the two lit landmarks overlap around dinnertime.
| Time | What | Where |
|---|---|---|
| 11 a.m.–2 p.m. | Ryan Frenchak, live music | Downtown Christmas Courtyard |
| Noon–9 p.m. | WineBerley's 1st Annual Christmas Market | 13615 Ranch Rd 12 |
| 2–5 p.m. | Photos with Buddy the Elf | Downtown Courtyard, 101 Wimberley Square |
| 5 p.m. | Santa arrives, opening ceremonies begin | EmilyAnn Theatre & Gardens, 1101 FM 2325 |
| 5:15–6 p.m. | Tree lighting and singing at the hilltop | EmilyAnn Theatre & Gardens |
| 6 p.m. | Wishes for Wimberley Lighted Parade, with Jesse Stratton Band | Downtown |
| After the parade | Downtown tree lighting | Downtown Christmas Courtyard |
| 6–10 p.m. | Trail of Lights open | EmilyAnn Theatre & Gardens |
Look at the bottom of the table. The EmilyAnn trail stays open until 10 p.m. on opening night, so the parade and the downtown tree come first, and the trail on FM 2325 still has hours of light left after that. Anyone who wants the hilltop singing has to be at the EmilyAnn by 5:15 and leave before 6 to catch the parade. TX Atras is listed as opening-night entertainment at the EmilyAnn.
On Sunday, Nov. 29, the season moves to Henson Road. Jaclynn Renee Wine Collective, 107 Henson Rd, has a ticketed Santa storytime from 11:30 a.m. to 12:30 p.m., and then Santa is scheduled for public book sales and signing in Henson Square Courtyard from 1 to 2:30 p.m. The Hometown Holidays music schedule also has live sets on Friday, Nov. 27, and Sunday, Nov. 29.
Dinner Before the Parade
The Hays Free Press relayed the organizers' suggestion to arrive early, browse the Square and have dinner before the evening events. This year, one of the Square's best-known dining rooms is in the middle of a change.
Longleaf Craft Kitchen + Bar at 314 Wimberley Square still lists its regular hours and takes reservations online. According to Wimberley Buzz, Longleaf announced on Facebook on Oct. 21 that it is handing the restaurant to co-chefs Sarai and Luis Felez for a new project called El Convit Longleaf. The announcement said familiar faces will stay involved and invited guests to come in before the handoff. In its Oct. 28 coverage, Local Eats reported that the outgoing team was still serving during the transition. A pre-parade dinner at Longleaf this season could be one of the last meals under its current team.
There's also a newer option a few steps off the Square. The Beer Ranch Project Tasty Room at 13510 RR 12 serves beer, wine, coffee and light bites, and Local Eats reported it open by mid-October. Wimberley Buzz lists The Forager Botanical Infusions at 13904 Ranch Road 12, Unit 3, as a fall 2026 arrival.
The EmilyAnn Trail, Night After Night
On opening night the EmilyAnn has to compete with the parade. After that, it has 28 nights to itself. The 2026 Trail of Lights runs Nov. 28 through Dec. 26. It's a walking trail through about 8 acres of lit exhibits, made by local businesses, organizations and families.
Entry is free. The EmilyAnn calls the trail its largest fundraiser and suggests a $20 donation per family, with donation stations at the entrance and along the grounds. Most nights have live entertainment on the stage by the yule log, free marshmallows and hot chocolate, and Santa in his house. Money from donations, concessions, the stores and special events all goes to the EmilyAnn. The theatre says hosts, entertainers and special-event nights will be added to its page as they're confirmed.
Local businesses and families can still get involved. Putting up a display costs nothing, and the people who build one don't have to staff it. The theatre takes inquiries about displays, sponsorships and performing at [email protected].
FM 2325 in December
The trail sits on the same road as Lions Field. The Wimberley Lions Club holds its December Market Days on Saturday, Dec. 5, from 7 a.m. to 4 p.m. at 601 FM 2325. The Santa Pub Crawl moves through downtown later that day. People are invited to dress as Santa or a favorite Christmas character, and donations are encouraged for Crisis Bread Basket. That puts holiday shopping on FM 2325, an evening downtown, and the EmilyAnn trail, a short way up FM 2325 from Lions Field, all in the same Saturday.
The rest of the calendar, in order:
- Thursday, Nov. 26: Free community Thanksgiving meal at Wimberley Community Center. Jacob's Well is closed that day.
- Every Friday, Saturday and Sunday through Jan. 3, 2027: Free live music at the Downtown Christmas Courtyard, 101 Wimberley Square, plus lights, decorations and photo spots.
- Saturday, Dec. 12, 8:30–11 a.m.: Civic Club Breakfast with Santa at Texan Academy.
- Saturday, Dec. 19: Photos with Texan Santa and Ben the Longhorn.
- Friday, Dec. 25: Jacob's Well Natural Area is closed for Christmas Day.
- Thursday, Dec. 31, 7 p.m.: Downtown New Year's Eve Ball Drop, an early-evening countdown downtown.
The Hometown Holidays calendar is the place to check for added events and final times. Organizers note that schedules and admission vary by event.
New Year's Day Is a New Opening
The county is making a small change as the season winds down. Starting in 2027, every Hays County park except Gay Ruby Dahlstrom Nature Preserve will be open on New Year's Day. That means Jacob's Well Natural Area, which closes on Thanksgiving and Christmas this year, will be open on Jan. 1. In the same notice, the county's education coordinator, Katherine Sturdivant, said the county plans a First Day Hike at Karst Canyon Preserve.
General entry to Jacob's Well is free, so a New Year's Day walk to the well costs nothing, whether or not swimming has resumed. The Downtown Christmas Courtyard stays open two more days, through Jan. 3.
If hosting Wimberley holidays has you picturing a place within walking distance of the Square or with room off FM 2325, Ivy Residential Group can talk through what's available, including homes that aren't publicly listed. Start a Confidential Consultation whenever you're ready, after the parade or on New Year's Day.
