Gambling Cowboy: A Premier Steakhouse Experience in Temecula

Beautiful restaurant downtown Temecula off of front Street. We went there for early lunch on my husband's day off and I ordered fish and chips that were fantastic. My husband ordered a taco with a variety of meats. He enjoyed it very much. I ordered a virgin strawberry pina colada and my husband had a scope. We sat outside and had a beautiful day.

Got a recommendation to eat dinner here from a local winery tour guide and I am so grateful! First time to Temecula CA to tour local wineries (there’s close to 50 or so) and we had a great time. Pricing was what you would expect for a popular premium steakhouse. Super cool vibe in the historic downtown Temecula area - reminded me of what old California during gold rush times might have been like. My girlfriend’s steak was undercooked but flavorful, and the meatloaf was a huge slice but served rather lukewarm along with the homemade sides. Service was excellent considering the server was literally quadruple seated after us. Host stand was extremely accommodating as I had made a reservation for Sunday (we were there Saturday) and got us seated right after we enjoyed drinks at the bar. Highly recommend, allow time for parking it’s pretty scarce!

I was stressed out, chlosterphobic and wanted to run away. I went for a drive to Old Town and went for a walk. I saw the sign on the 3rd floor of an old building. Best damn choice I ever made. I went in with a hoodie and hat, ate in the bar area. Soroush is an awesome bartender, and has extensive high end food service experience. He was quick, visually attentive and took great care of me. Staff overall was kind, smiled and helpful. The food, omg, the FOOD! The bread came warm and seasoned butter melted right on. I ordered "The Cowboy" platter and ordered medium/rare. Cooked to perfection, it was juicy and delicious!!! The corn is to die for insane, and the mashed taters with bacon just sealed the deal. I had my Johnny Black double tall beverage with it and it went well. However, a smoked Old Fashioned I can imagine would make this meal tops! The decor is on point and very festive and gives the diner lots to enjoy and feels warm. The restrooms are super clean and roomy, although tricky to find at first...lol. They truely did make my evening, and made my entire crappy week worth it. I look forward to going again and enjoying another delicious steak. Thank you again Gambling Cowboy. I tip my hat to you.

The gambling cowboy was really good and cool vibes. The restaurant is on the third floor so you have to go up the elevator. The food was amazing and the service was on point. I had the 16oz rib eye with poblano chilli and it was amazing. Definitely will be coming back.

My wife and I celebrated our anniversary at The Gambling Cowboy, and it exceeded all expectations. The rustic charm, warm lighting, and cozy ambiance created a romantic atmosphere perfect for the occasion. We began our evening with two standout appetizers: the Brie Sachets—crispy, golden pastries filled with creamy brie and drizzled with a sweet glaze—and the Famous Cowgirl Kisses, which were smoky, bacon-wrapped jalapeños with just the right amount of heat. The bar staff was friendly and skilled; we both had handcrafted cocktails that were strong yet smooth and full of flavor. My wife’s drink had a floral finish with hints of citrus, while mine had a bourbon base that paired perfectly with the meal. For our entrées, my wife chose the Slow Braised Short Rib, which was melt-in-your-mouth tender, richly flavored, and served over a perfectly seasoned bed of mashed potatoes. I ordered the 72-Hour Blackened Ribeye, medium rare, and it was outstanding—juicy, flavorful, and seared with a perfect crust. The sides of mixed vegetables and loaded mashed potatoes balanced the dish well and were generously portioned. Service throughout the evening was attentive and sincere—our server made sure we were comfortable without being overbearing, and even wished us a happy anniversary with a complimentary dessert to cap off the evening. From start to finish, The Gambling Cowboy delivered a truly memorable dining experience. It’s the kind of place where food, atmosphere, and service come together beautifully. We’ll definitely be returning—and recommending it to friends and family.

Fun experience in the heart of downtown Temecula! Immerse yourself back to the Wild West! The ribeye and filetwere both on point! Friendly service. Ambiance is key!! Fun date night!! Hearty portions!!!

Heavily recommend making a reservation. Service was well attentive and refills were never an issue as I didn’t have to ask. Serving staff was not pushy on ordering alcoholic beverages. When it comes to the food it was amazingly well done. It came out to a perfect medium rare just like I asked and the juices and quality of the meet you could tell by just cutting into it. The pasta also came out better than expected. Well decorated interior.

My husband and I came about a week ago for a date night out, and this place is delicious! I highly recommend making a reservation. We came once as a walk-in, and they sat us right away. Another time I called later in the day, and our reservation wasn’t until about 9. Another time we came in, and it was about an hr wait for a walk-in. The food is delicious, and the main dishes have a lot of food on them. I was able to take my leftovers and eat them for another meal the next day. The steak was cooked perfectly, and when I cut into it, it was like cutting butter! The lobster was a bit dry in the lobster mashed potatoes but still good. The corn was super good. We ordered the cowgirl kisses for an appetizer. We did wish it came with four peppers instead of three, but still good. Service was a bit slow when we sat. It seemed the servers were more focused on bigger parties instead of smaller ones, so we did wait a little bit before we were served. But once we were served, everything was pretty quick. The atmosphere is very country, cozy, and cute. I love the food here, so I do recommend it.