Sipping Under the Stars
Saturday, December 5, 2026 · 4:00 PM
· Downtown Brownwood
About
Experience the magic of the holiday season in Historic Downtown Brownwood during Sipping Under the Stars, presented by Downtown Brownwood Inc. and Visit Brownwood! Stroll through our charming, illuminated downtown streets for an unforgettable evening of late-night shopping, local tastings, and festive cheer. Perfect for a cozy date night or a holiday outing with friends, this annual tradition invites visitors to sample delicious wines and seasonal craft beverages while exploring unique boutique shops, artisan markets, and local eateries. What to Expect: Exclusive Shopping & Dining: Local shops and boutiques open late with special holiday discounts, seasonal treats, and curated gifts. Tastings & Keepsakes: Enjoy curated sips from participating regional wineries and breweries as you stroll between stops. Festive Downtown Atmosphere: Take in the twinkling holiday light displays, festive music, and warm small-town hospitality. Full Day of Holiday Fun: Pair your evening with nearby festive happenings, including the Christmas Under the Stars Festival at the Brownwood Event Center, the Yuletide Express at the Lehnis Railroad Museum, and live holiday theater downtown. Whether you’re starting your holiday gift shopping, hunting for unique Texas finds, or simply soaking in the seasonal ambiance, Sipping Under the Stars is the ultimate winter evening getaway in the heart of Texas. Check back soon for ticket details, participating merchant lists, and tasting map check-in locations!
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Fri, Oct 16 · 12:00 PM
Becoming an Outdoors Woman
Downtown Brownwood
Ready to step outside your comfort zone and experience the great outdoors? Texas BOW (Becoming an Outdoors-Woman) invites women to an unforgettable, hands-on outdoor adventure designed to build confidence, learn new skills, and create lasting friendships. Whether you’re brand new to outdoor activities or looking to expand your skills, this supportive and encouraging retreat offers a welcoming environment where you can learn, explore, and have fun. Registration is required. Space is limited, so reserve your spot and get ready to discover a new adventure!
Sat, Oct 24 · 9:00 AM
Brownwood Fly in Fair
Brownwood Regional Airport
✈️ Brownwood Fly In Fair Take flight at the Brownwood Fly In Fair, a two-day celebration of aviation, history, classic cars, local art, and family fun at the Brownwood Regional Airport. Returning October 24 and 25, 2026, this exciting community event brings together aviation enthusiasts, families, and visitors for a weekend packed with unique attractions and hands-on experiences. Guests can explore impressive aircraft, enjoy helicopter rides, admire a classic car show, browse antiques and militaria displays, cheer on the vintage pinup contest, shop handcrafted goods and artwork, and grab a bite from a variety of food trucks. Whether you’re passionate about aviation or simply looking for a memorable weekend outing, there’s something for everyone to enjoy. 🛩️ Aviation Adventures & Community Celebration Hosted at Brownwood Regional Airport, the Fly In Fair showcases the rich spirit of aviation while celebrating local businesses, artists, collectors, and community organizations. The airport provides a unique backdrop where visitors can experience aircraft up close while also enjoying a wide variety of family-friendly entertainment throughout the grounds. From vintage displays and local vendors to delicious food and interactive activities, the event offers a welcoming atmosphere for guests of all ages. 🎟️ Admission & Event Info The Brownwood Fly In Fair takes place October 24 and 25, 2026, at Brownwood Regional Airport, located at 6251 Airport Road in Brownwood, Texas. Visitors are encouraged to wear comfortable shoes, bring the whole family, and plan to spend the day exploring everything the fair has to offer.
Tue, Dec 1 · 6:00 – 11:59 PM
Christmas Tree Lighting Ceremony
Downtown Brownwood
Brownwood will officially kick off the Christmas season with the annual Downtown Christmas Tree Lighting on Tuesday, December 1. The community is invited to gather downtown as the Christmas tree is illuminated and friends, families, and neighbors come together for an evening of holiday spirit and hometown cheer. A beloved Brownwood tradition, the celebration offers a festive way to welcome the holiday season. Past celebrations have included music, holiday treats, photo opportunities, and a special countdown to light the downtown Christmas tree. Additional details will be announced as they become available.