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Fall in Wimberley: Small-Town Charm Meets Hill Country Magic

When the air turns crisp and the oaks glow with autumn color, Wimberley, Texas becomes one of the Hill Country’s most inviting destinations. Just an hour from Austin or San Antonio, this peaceful town combines small-town warmth with big seasonal spirit.

Whether you’re sipping local wine, exploring artisan markets, or taking in Hill Country holiday events, Fall sets the stage for a festive and relaxing escape.

Wimberley Market Days & Boutique Shopping

Start your getaway with Wimberley Market Days, the Hill Country’s largest outdoor market, held the first Saturday of each month. Wander through hundreds of booths featuring handmade art, local foods, and unique holiday gifts. Downtown, Wimberley Square’s charming boutiques—like Rancho Deluxe, Shop the Tree House, and The Wild West Store—offer an afternoon of relaxed browsing just minutes from Messina Inn.

Wineries, Breweries & Live Music

Savor the season with a tasting at Wimberley Valley Winery or Driftwood Estate Winery, both offering weekend live music, fire pits, and panoramic views of the Hill Country. Beer lovers can head to Roughhouse Brewing or Middleton Brewing for craft pours and cozy vibes.

Outdoor Adventures in the Hill Country

Cooler weather means perfect hiking conditions. Explore Blue Hole Regional Park, where the walking trails wind beneath ancient cypress trees, or climb Old Baldy (Prayer Mountain) for breathtaking views of the Wimberley Valley. After your adventure, return to Messina Inn’s amenities—perhaps a dip in the hot tub or a quiet fireside chat under the stars.

Fall & Winter in Wimberley: A Celebration of Hill Country Holiday Events

October through January, Wimberley comes alive with festive cheer. From twinkling lights and parades to cozy community gatherings, Hill Country holiday events don’t get more charming than this.

2025 Hometown Holidays Lineup

• Boo! Hole at Blue Hole Park – October 18, 2025 | 4:00 PM–10:00 PM
  A family-friendly Halloween event with trick-or-treating, haunted trails, costume contests, and live music.
• Downtown Trick-or-Treating – October 31, 2025 | 4:00 PM until dark
  Local businesses welcome kids and families with safe trick-or-treating around the Wimberley Square.
• The River House Holiday Soirée – November 6, 2025 | 6:00 PM–9:00 PM
  A cozy evening of raffles, hors d’oeuvres, and early holiday shopping with festive cocktails and music.
• Kick-Off Party & Holiday Auction Preview – November 6, 2025 | 7:00 PM
  A community launch of the season with live music, drinks, and a preview of items supporting local education.
• Christmas Tree Lighting at Ace Hardware – November 13, 2025 | 6:00 PM (festivities begin at 4:00 PM)
  A festive tree lighting event with treats, samples, and music to kick off the holiday spirit.
• Holiday Sip ’N Shop – November 12, 2025 | 4:00 PM–8:00 PM
  Enjoy drinks and extended holiday shopping hours in downtown Wimberley with seasonal music and charm.
• Free Community Thanksgiving Meal – November 27, 2025 | 11:00 AM–2:00 PM
  All are welcome to enjoy a complimentary holiday meal at the Wimberley Community Center.
• Elf Fun Run – November 28, 2025 | 9:00 AM
  A festive 1- or 3-mile fun run to support the EmilyAnn Trail of Lights—holiday costumes encouraged!
• Main Stage Entertainment at Christmas Courtyard – Weekends from November 28–December 28 + NYE
  Live performances and holiday music scheduled on select dates at the Christmas Courtyard.
• Wishes 4 Wimberley Parade & Toy Drive – November 29, 2025 | 6:00 PM
  A festive nighttime parade followed by a toy collection and holiday celebration.
• Tree Lighting at Christmas Courtyard – November 29, 2025 | 7:00 PM
  Community tree lighting with cocoa, caroling, and a joyful gathering in the Square.
• EmilyAnn Trail of Lights – Nightly from November 29–December 27, 2025
  Walk or drive through a glowing trail of themed light displays—open every evening through the season.
• 19th Annual Holiday Bazaar – November 29, 2025 | 10:00 AM–4:00 PM
  Over 30 local vendors offering holiday gifts, baked goods, handmade crafts, and more.
• Photos with Buddy the Elf – November 29, 2025 | 2:00 PM–5:00 PM
  Take free photos with Buddy the Elf in the Christmas Courtyard—great for families and kids.
• Ace Hardware Stocking Stuffer Night – December 2, 2025 | 6:00 PM–9:00 PM
  Shop small gifts, enjoy hot cocoa, and grab a festive photo with Santa.
• Downtown Cup of Cheer – December 13, 2025 | 5:00 PM–8:00 PM
  Stroll the Square with a seasonal drink in hand while browsing holiday specials and live music.
• Santa Pub Crawl – December 13, 2025 | 6:00 PM–9:00 PM
  Dress up and join a holiday bar crawl through downtown Wimberley—fun for festive adults.
• Civic Club Breakfast with Santa – December 13, 2025 | Time TBD
  A cheerful breakfast for families to enjoy food and time with Santa at the Wimberley Community Center.
• Breakfast with Santa at Scudder – December 20, 2025 | 9:00 AM
  Another festive breakfast event hosted by the Wimberley Civic Club with holiday activities and photo ops.
• Mini Equine 2 U Appearance – December 21, 2025 | 11:00 AM–2:00 PM
  Visit with miniature horses and donkeys at Christmas Courtyard—a gentle experience for all ages.
• New Year’s Eve Ball Drop at Oak Park – December 31, 2025 | Evening (time TBD)
  A family-friendly NYE celebration with games, music, and an early ball drop under the stars.
• Polar Bear Plunge & 5K – January 3, 2026 | 9:00 AM–1:00 PM
  Start the new year with a brisk 5K and a plunge into Cypress Creek, followed by live music and warm drinks.

Wimberley’s blend of community warmth, cheerful décor, and lively events makes it one of the most enchanting Hill Country holiday destinations.

Why Messina Inn Is the Perfect Hill Country Retreat

Just a three-minute drive—or a scenic stroll—from Wimberley Square, Messina Inn offers a peaceful yet convenient home base for your holiday getaway. Nestled along Cypress Creek, the inn combines boutique comfort with Hill Country charm, making it easy to enjoy both relaxation and celebration.

Seasonal Comforts & Amenities

• Cozy Suites & Private Cottages: Choose from 11 villa-style suites or two fully equipped cottages with kitchens, fireplaces, and private verandas. Explore our Rooms to find your perfect fit.
• Hot Tub & Fire Pits: Unwind after a day of holiday fun beneath starry skies or gathered around a glowing fire pit with cocoa or wine.
• Creekside Serenity: Sip your morning coffee overlooking the water or take a quiet walk along the Whitetail Trail.
• Complimentary Weekend Breakfast: Enjoy a hearty morning meal before heading out to your next Hill Country adventure.
• Relaxation All Around: From our sauna and pool to the tranquil courtyards, Messina Inn’s amenities make every stay restorative.

After a festive evening downtown, come “home” to the peace and comfort of Messina Inn. Whether you’re traveling as a couple, a group of friends, or a small family, the inn’s thoughtful touches make the holidays feel truly special. Ready to experience it? Book your stay now to secure your favorite suite before the season fills up.

Your 3-Night Hill Country Holiday Itinerary

Day 1: Arrival & Local Flavors

• Afternoon: Check into your suite or cottage at Messina Inn and take a stroll along Cypress Creek.
• Evening: Dine at The Leaning Pear or Community Pizza, then return to enjoy the hot tub or a fireside nightcap under the stars.

Day 2: Market Finds & Seasonal Sipping

• Morning: Start with breakfast at the Inn before heading to Wimberley Market Days or boutique shopping downtown.
• Afternoon: Visit Wimberley Valley Winery for tastings and live music beneath the oaks.
• Evening: Join the Holiday Sip ’N Shop or relax back at Messina Inn with wine by the creek.

Day 3: Holiday Magic & Creekside Calm

• Morning: Take a morning hike up Old Baldy for breathtaking Hill Country views.
• Afternoon: Visit the Wishes 4 Wimberley Parade or browse holiday shops around the Square.
• Evening: End the day at the EmilyAnn Trail of Lights, followed by hot cocoa around Messina’s fire pit.

Day 4 (Optional): One Last Slow Morning

• Morning: Enjoy a leisurely breakfast before checkout. Take one last walk along the creek and soak in the peace of the Hill Country.