Music on the Mile brings a full day of live performances and Hill Country charm to Lost Oak Cellars on Saturday, May 2, 2026 from 12 pm to 10 pm at 111 Rosewood Ave, Boerne, TX. As part of the annual Music on the Mile celebration, the tasting room will host continuous live music, creating ... Read more
Saturday Live Music with Ralyn Gayle brings a relaxed afternoon of live entertainment to Free Roam Brewing Company. The performance will take place on Saturday, May 2, 2026 at 1 pm. Guests can enjoy Ralyn Gayle’s live performance while spending time in a casual brewery setting. The laid-back atmosphere makes it a great spot to ... Read more
Art in Bloom brings together art, wine, and nature for a relaxed afternoon in the heart of Boerne. The event will take place on Saturday, May 2 from 2 pm to 6 pm at The Carriage House Gallery. Guests can explore featured artwork, with a portion of sales benefiting The Cibolo Center for Conservation. The ... Read more
Cirque Ma’Ceo: The Year of the Horse brings a captivating blend of acrobatics, horsemanship, and theatrical storytelling to Boerne for a limited engagement. The show runs from May 1 through May 10 at the Kendall County Fairgrounds, located at 1307 River Road, Boerne, TX 78006. This live performance showcases the powerful connection between horse and ... Read more
3rd Annual Kentucky Derby Soirée brings a festive and stylish celebration inspired by Churchill Downs to The Oak of Boerne. The event will take place on May 2 at 4 pm. Guests can expect an afternoon filled with classic Derby flair, including seersucker suits, elegant hats, and springtime attire. The event will feature Derby squares, ... Read more
A lively community evening takes place during First Saturdays on Main every first Saturday of the month from 5 pm to 8 pm along the Hill Country Mile, 141 W Blanco Rd., Boerne, TX 78006. This monthly event is presented by The Boerne Life in partnership with the Boerne Retail & Restaurant Owners Association, bringing ... Read more
Evenings at The Dodging Duck Brewhaus feature live music every Sunday, Thursday, Friday, and Saturday from 5:30 pm to 8:30 pm in Boerne, TX. Set on the patio across from Cibolo Creek, the performances provide a relaxed soundtrack for dining and gathering in the heart of the Hill Country. Guests can order a favorite dish ... Read more
Live music fills the patio at Cibolo Creek Brewing Company every Friday and Saturday from 6 pm to 9 pm in Boerne, TX. The weekly performances create a lively setting where guests can gather with family and friends while enjoying an evening of local music. Visitors can pair the entertainment with cold craft beers and ... Read more
Live music sets the tone for the evening every Friday and Saturday from 6 pm to 9 pm at Pinchy’s Lobster & Raw Bar in Boerne, TX. Located in historic downtown Boerne, the restaurant offers a lively setting where guests can enjoy performances alongside New England-style seafood and drinks. The weekly lineup features a variety ... Read more
Live Music with Jorge Palomo offers a refined evening of live entertainment in a relaxed dining setting at Valeria Restaurant. Performances take place every Thursday, Friday and Saturday from 6 pm to 9 pm. Guests can enjoy guitarist and vocalist Jorge Palomo’s blend of classic favorites and contemporary hits while dining indoors or on the ... Read more
Saturday Live Music with Weston Ripps offers an evening of live entertainment in a laid-back brewery setting. The performance will take place on Saturday, May 2, 2026 at 6 pm at Free Roam Brewing Company. Guests can enjoy Weston Ripps’ live performance while relaxing with friends and taking in the welcoming atmosphere. The brewery’s selection ... Read more
Kentucky Derby Watch Party brings race day excitement to the Hill Country on May 2 at 6 pm at Lost Oak Cellars, 111 Rosewood Ave, Boerne, TX. Guests can watch the Kentucky Derby live while enjoying a selection of award-winning Texas wines, cocktails, and food offerings in a festive tasting room setting. Those who arrive ... Read more