Trail Boss Steak & Grill

Nestled in the heart of Kerrville, TX, Trail Boss Steak & Grill serves up a truly authentic American dining experience that steak lovers and casual diners alike will crave. This revamped gem at 416 Main St offers a warm, inviting atmosphere where you can choose between cozy booths or welcoming tables—perfect for everything from a relaxed lunch to a special anniversary celebration.

Trail Boss Steak & Grill masterfully showcases classic American cuisine with dishes that deliver both comfort and indulgence. Their signature ribeye steak, cooked to perfection and paired with golden mashed potatoes, is a true highlight. Each bite is a symphony of tender, juicy flavor balanced by rich, savory seasoning, complemented beautifully by crispy, golden onion rings. Not to be missed is their Fried Calamari, boasting a light, crispy coating and fresh, tender calamari inside—ideal for sharing as a starter.

The menu also offers a variety of fresh, vibrant salads that add a refreshing twist to your meal. Try the SIDE Seasonal Salad, a delightful mix of greens, seasonal fruit, feta cheese, and a candy-coated crunch of pecans and craisins, all lightly drizzled with honey balsamic vinaigrette—a harmonious blend of textures and flavors. Or indulge in the Wedge Salad, crowned with crispy bacon, blue cheese crumbles, and cherry tomatoes, delivering a rich, creamy punch with every forkful.

During lunch, Trail Boss offers lighter options like the Chicken Fried Steak served with whipped golden mashed potatoes and sautéed green beans—a dish described by many as "home-style comfort on a plate." The Parmesan Crusted BLT, featuring crisp bacon and fresh tomatoes nestled in parmesan-crusted Texas toast, is another standout that perfectly balances savory and fresh tastes.

Every meal at Trail Boss can be rounded out with one of their decadent desserts. The Chocolate Lava Cake is a gooey, molten masterpiece that oozes rich chocolate with every forkful. For those who prefer fruity sweetness, the Strawberry Shortcake and Pecan Praline Cheesecake offer a luscious, satisfying finish. Seasonal treats like Whole Peach Cobbler and Blueberry Cobbler Cheesecake showcase the best of Southern-inspired desserts that feel just like a comforting hug from home.

Trail Boss Steak & Grill has quickly earned praise from locals and visitors alike. Customers rave about the consistently tender, perfectly cooked steaks and the generous, shareable sides that complement every dish. One devoted guest, Melissa Martinez, calls it “one of the consistently best steaks for the money” and highlights the popular Key Lime Margarita as a must-try. Meanwhile, regulars like Debbie Ojeda feel right at home, praising both the food and the attentive, heartfelt service from familiar staff like Jennifer and Haleigh.

Whether you're marking a milestone like a 20th anniversary or simply searching for a satisfying meal bursting with rich flavors and comforting classics, Trail Boss Steak & Grill invites you to enjoy an unforgettable taste of Texas hospitality. The combination of expertly prepared steaks, fresh salads, and indulgent desserts sets the scene for moments worth savoring—and returning to time and again.