Round Top September Calendar: Quilts, Culture, Galas and More
There's no shortage of things to do this month as the community transitions into fall.
Texas pride on display at the Round Top Film Festival Gala. (Photo by Jordan Geibel)
September is a busy month in greater Round Top. There is so much to explore as the community transitions into fall. From vineyard experiences and special dinners to live music performances and cultural activities, there is no shortage of things to do this month.
Now Through September 27
William Anzalone at 90 Pop-Up Exhibit at Red & White Gallery: Exhibition showcasing the storied painter’s recent work as he enters his 10th decade. Showcased will be nine new paintings, all in the OG artist’s signature and classic oil on canvas method. Arrange private showings by calling Jerry Herring at (713) 824-9433.
Sunday, September 7
11 am – 1 pm: Paint & Sip at Chapelton Vineyards. Led by the talented The Paint Lady. Create your own unique masterpiece with step-by-step guidance while sipping on a glass of one of Chapelton’s finest wines. No experience necessary. Tickets $105, here.
Saturday, September 13
11 am – 4 pm: Chappell Hill Annual Airing of the Quilts. Handmade quilts will be hung on display all over town for visitors to enjoy. Also view vintage quilts at the Chappell Hill Historical Museum. Quilts made by the Quilt Guild as gifts to veterans will be on display along with quilts for sale. Open to the public in downtown Chappell Hill.
5:30 – 9 pm: Round Top Family Library 2025 Wrangler’s Gala. Decadent dinner, live and silent auctions and more at The Barn at Windy Knoll. All in support of the Round Top Family Library. At Windy Knoll. Get tickets, here.
Sunday, September 14
6 – 9 pm: Cakebread Cellars + Royers Wine Dinner. Five course wine-paired dinner and experience featuring Cakebread wines. Text JB at 512-569-0013 to reserve your seat. Visit here to view the menu.
Thursday, September 18
6 – 9 pm: Community Keyholder Awards. The Greater Fayette Community Foundation hosts an elegant celebration of generosity, leadership, and lasting impact in the Greater Fayette region. The evening will recognize exceptional individuals, organizations, and nonprofits advancing positive change through community-driven powerful awards. More info and tickets, here.
Friday, September 19
6 – 10 pm: Oakbones Wedding Venue Ribbon Cutting Celebration. Live music by Black Cat Choir, small bites and cocktails by chef Victor Hugo. Gratis.
Sunday, September 21
3 – 6 pm: Meet the New Poet Laureate of Texas: Round Top Family Library and The Friends of Winedale invite you to meet Octavio Quintanilla, the new Poet Laureate of Texas. An afternoon of literature, art, and conversation with one of Texas’ leading voices in poetry. At the Meadows Building at the Winedale Historical Center. Reception to follow. Learn more, here.
Friday, September 26
9:30 am – 5:30 pm: Round Top Fall Art Show: The Round Top Fall Art Show is a dynamic celebration of creativity, showcasing a stunning array of artwork in various mediums. Learn more, here.
5 – 9 pm: Round Top Film Festival 2025 Gala. This premier event, held at Windy Knoll, brings together filmmakers, industry leaders, and passionate supporters to honor the power of film while raising crucial funds for independent cinema. With exquisite dining, exclusive screenings, and unparalleled networking opportunities, the gala offers a rare chance to align with creativity, community, and cinematic excellence in a setting unlike any other. Learn more, here.
Saturday, September 27
3 – 5 pm: Round Top Festival Institute presents Mariachi Aztlán. A celebration of National Hispanic Heritage Month with the nationally award-winning mariachi ensemble from University of Texas Rio Grande Valley. Lunch available with Reservations. Get tickets, here.
5 – 9 pm: Paul Michael Holiday House Preview Party. Be the first to experience the magic. Enjoy frozé, festive times and early shopping. Plus, enter to win a $100 Paul Michael gift cards and a $200 Duo (restaurant) gift card. Tickets $75, with $50 going to the Round Top Family Library.
Sunday, September 28
10 am – 5 pm: Wendish Fest. A day of celebrating Texas Wendish culture and history through delicious Wendish food, unique cultural activities, drinks, folklife exhibits, demonstrations, and live polka music by the Jodie Mikula Orchestra. Learn more, here.
Monday, September 29
9 am – 6 pm: Market Hill Fall Show. Shop premium dealers in antiques, the arts, contemporary furnishings, imports and more in air conditioned comfort. Restaurant and bar on site. Show runs through October 19. Learn more, here.