Miko

It was my First time,Food was really delicious steak 🥩 was really delicious and cooked even though we were at 8:30 pm but food and service was great a little bit pricey but worth it

Marisella Jauregui

Great atmosphere, friendly customer service. Delicious meal and cocktails. Along with even better company. Absolutely coming back!!! See yall very soon.

+15

Mia W

Sooooooo, whenever the man and I go to Temecula of course we either go or stay at one of the wineries, but this time we decided to do something different for his bday this. I wanted a good steak and good drinks and based off the reviews decided on The Gambling Cowboy, AND I’M SO GLAD WE DID. even though we had reservations we still had to wait a bit no biggie. The inside is spacious but loud so we opted to be seated on the patio (best spot ever). We dined, we drank then drank some more and had a fantabulous time. Food good, large portions, drinks good very tasty and pricing was reasonable. Our server, she was phonemail (forgot her name, too much to drink 😘) If you haven’t been give them a try. You won’t be disappointed. Everything was seasoned just right. 🧡

+4

Rachel Thomas

Do not show up without a full appetite. The food is so good. Blackened Ribeye steak medium well with garlic mash and corn. I legit want this every time I come to town.

Will Glenn

Located on the 3rd floor off the beaten path in Old Town Temecula is the Gambling Cowboy. An upscale chophouse with some rustic appeal, great service, and tasty vittles. We went on a Saturday night and were able to get in as an early dinner. Live music started at 630. I have had a lot of lobster Mac and cheese around SoCal. This place moves up to my number 2 spot with their rendition, having large chunks of sweet lobster, creamy cheese and perfectly cooked noodles. The only thing that knocked it out of the number 1 spot is price, which is on the high end at $35. Can't wait to revisit and find out how the aged steaks are.

Juan Padilla

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.

+21

Steven Wong

Good place for a nice steak with great ambience. Seems like a casual steak house but the food quality is significantly higher. I had the prime rib with mashed potatoes, and string beans. I think the food was a touch cold, but it makes sense because we had a large group of people. I warmed up the food the next day and it was fantastic. Would definitely recommend for date night or even just a nice family outing.

Megan

They have super cute decorations for far and Halloween which made the experience even better. If you don't have a reservation, you can walk into the bar section and there are plenty of high-top tables available in addition to bar sitting. We ordered the Cowgirl Kisses for the appetizer and the Queen of Hearts with a side of mac and cheese and mushrooms for the main dish. It was absolutely delicious! Nothing to complain about!

+14

First time at this place and the food was more than we expected. Food was amazing, Drinks were delicious, and the service was great. \n\nNext time I am in Temecula for dinner will be trying this spot!

First time at this place and the food was more than we expected. food was amazing, Drinks were delicious, and the service was great. \n\nNext time I am in Temecula for dinner will be trying this …

First time at this place and the food was more than we expected. Food was amazing, Drinks were delicious, and the service was great. \n\nNext time I am in Temecula for dinner will be trying this sp…

First time at this place and the food was more than we expected. Food was amazing, drinks were delicious, and the service was great. \n\nNext time I am in Temecula for dinner will be trying this sp…

From start to finish, this place exceeded expectations. The service was outstanding--our waiter was genuinely attentive, friendly, and made the whole experience feel special without being overbea…

Never disappoints! The food is delicious and the service great. Get the corn!! Reservations are recommended as it's always busy. If you're lucky you may get a spot in the bar but those are hard to …

Never disappoints! The food is delicious and the service great. Get the corn!! reservations are recommended as it's always busy. If you're lucky you may get a spot in the bar but those are hard to …

Everything went well! If you are looking for a melt in your mouth juicy prime rib, then this is the place! I love the bar section where you can actually dine and still enjoy your meal. It has a n…

Another delicious visit! Returned to celebrate for another life milestone and the Gambling Cowboy did not disappoint. Made reservations through Open Table for a brunch on the weekend and had no iss…

First time here.......it was such a great experience!!! We sat outdoors on the patio. Appetizers were delicious.......especially the calamari. The braised short rib with mushroom risotto was so a…

Every time wife and I go to the Gambling Cowboy for dinner, Sunday breakfast, or events, we continue to be amazed by quality of food, drinks, and entertainment. From the bartenders, specifically, T…

Great place to get an outstanding steak and wine. (Doffo Syrah was excellent) There was live music in the bar where we ordered drinks waiting for our table. \n We ordered scallops and the brussel…

Family Brunch for 10 and we were there for 2 hours. Food was amazing and large portions. Some got breakfast some got lunch and we loved it all! prices were very reasonable. Service was outstanding.…

Our anniversary was May 6, and we were here May 7th to try a do-over after a disappointing dinner the night before. We were seated in an area apart from the noise on the other side of the partition …

We arrived on a busy Friday night without a reservation. Immediately met by friendly staff who provided a table in the bar area. Great Service. Interesting blue cheese bacon crust on filet mignon. …

We arrived on a busy Friday night without a reservation. Immediately met by friendly staff who provided a table in the bar area. Great service. Interesting blue cheese bacon crust on filet mignon…

We arrived on a busy Friday night without a reservation. Immediately met by friendly staff who provided a table in the bar area. Great Service. Interesting blue cheese bacon crust on filet mignon. …

excellent steak house! were there with our nephew and his wife, our niece by marriage to celebrate their 25th wedding vow ceremony and lunch, they took us to this restaurant, (along with large grou…

This a very kitschy restaurant with wild (west) decor... I had the rib eye that was cooked to perfection and so were the side dishes. My sister had the prime rib and was equally pleased wit…

We loved the decor and also was very happy you could dress casually, most nice restaurants do not allow shorts and sandals to be worn. The prime rib Dip was one of the best I have ever had. My Fi…

Arrived right at 5 and got a table near the bar, I ordered the ribeye steak and it was great. Live music was fun

We go to this restaurant once or twice a year. It is always busy. I made a reservation on a whim on Friday night. We got in with no wait and were seated promptly. We sat on the patio and had a fant…

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.

Meranda Garreaud

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.

David Rottblatt

This is such a fun place to have fun and dine in Old Town Temecula. The steak cobb salad was amazing as was the OG burger my son had. My wife had a sirloin with roasted corn, mashed potatoes and green beans which was amazing. My other son really enjoyed his Mac n Cheese. Service was fantastic The only thing I didnt like was that they called pest control to come while people were eating. Even though he was out on the patio, it just not something you want to see while you’re dining.

+3

Eddy Bretado

The portions match the price. Excellent value. The food was prepared as expected nothing lacking full of flavor fresh and also an excellent presentation. The decoration was nice everything was very clean and well-kept you definitely felt welcome and they also had a very huge bar

+6

I've been to themed restaurants before and the decor is laid on thick at Gambling Cowboy. Framed photos of horses, a saddle in the lobby, leather, wood, etc. Typically I just expect a fun ambiance fo…

Four of us came for dinner and were seated within minutes of our 6 o’clock reservation. Server came over immediately and was friendly, informative, and bubbly. Our orders were taken. This restaurant …

Four of us came for dinner and were seated within minutes of our 6 o’clock reservation. server came over immediately and was friendly, informative, and bubbly. Our orders were taken. This restauran…

Four of us came for dinner and were seated within minutes of our 6 o’clock reservation. Server came over immediately and was friendly, informative, and bubbly. Our orders were taken. This restauran…

The service was so bad. We had one drink and one appetizer in an hour. We ended up leaving and not even having dinner. They should pay attention to staffing and delegating service/bar tending. Our …

The service was so bad. We had one drink and one appetizer in an hour. We ended up leaving and not even having dinner. They should pay attention to staffing and delegating service/bar tending. Ou…

Yesterday evening we had a reservation made a few weeks ago, for 5:30 PM. we arrived at approx. 5:15 and were informed that it would most likely be 6:00 PM before we could be seated. At 6 PM we were seated in the main/Bar dining room and our server was "Ellen", a lovely lady! The person delivery our water handed the glass to the nearest guest and we had to pass them down. Ellen took our beverage order and all but one was delivered promptly. My son's beverage didn't make it to our table for several minutes after. We ordered our menu items and waited for approx. 15 minutes for them to arrive. Everyone's choice was almost perfect. I have to add here that the seat cushions were just awful! Needed to be repadded, making us sit in a "hole" throughout the evening. Not at all what was expected at this "high end" establishment! Overall experience was just "OK", nothing more considering the total cost of our dinners! We just cannot recommend this place because of our experience.

ForOurDog

All three of our entrees were ok, nothing amazing, but simply good. Our carne asada salad bowl was fresh, sadly the asada was overcooked. If you enjoy a burger the medium rare cook was perfect, flavor-wise it was a standard burger, adding bacon was a nice touch. Swap out the fries for the garlic mashed potatoes, it is a better compliment. As a breakfast item the Short Rib machaca was ok, but was missing all flavor. The meat was tender, but nothing else. Service is amazing, everyone was attentive and accommodated us with a dog-friendly outdoor seating.

Was looking forward to trying this restaurant. Was disappointed in the high prices for mediocre food. The country fried steak was great, everything else was meh. They only gave 3 pieces of the jalape…

Was looking forward to trying this restaurant. Was disappointed in the high prices for mediocre food. The country fried steak was great, everything else was meh. They only gave 3 pieces of th…

Was looking forward to trying this restaurant. Was disappointed in the high prices for mediocre food. The country fried steak was great, everything else was meh. They only gave 3 pieces of the jala…

Was looking forward to trying this restaurant. Was disappointed in the high prices for mediocre food. The country fried steak was great, everything else was meh. They only gave 3 pieces of the …

IMO the food was just ok. Our order did not all come out at the same time. My sons orders the exact same thing..... steak and fries. They both ordered medium steaks but they were more well done. …

What happened?? Went there last Sunday we took out of towner. We've been raving about the cowboy for a long time and wanted them to experience it. We were a party of 4. Had reservations. We ordered…

Although the space is kind of old school cowboy steakhouse, the food does not match. I had a traditional ribeye that was quit chewy. And a bit overcooked. My wife's filet was very much undercooked…

Although the space is kind of old school cowboy steakhouse, the food does not match. I had a traditional ribeye that was quit chewy. And a bit overcooked. My wife's filet was very much underco…

Although the space is kind of old school cowboy steakhouse, the food does not match. I had a traditional ribeye that was quit chewy. And a bit overcooked. My wife's filet was very much undercook…

The food was okay. Tender steak, but nothing special about the rest of the meal. The garlic mashed potatoes were fine, but nothing outstanding. I had some kind of salad with some heat to it (perhap…

Don’t know why, but this place just didn’t hit me right. Food was okay but not great. Service was okay but not great. Felt a little crowed and tired for the prices. I know what they are going for i…

We had a reservation and were seated within minutes in a requested booth. Got drinks in a timely manner and ordered food. Waited 50 mins for food, server never came during that time to check on us or let us know why food was so delayed. I got the Beef Stoganoff, it sounded yummy but, for me it was awful. WAY to much Rosemary, it overwhelmed the meat and noodles. I found a big sprig if Rosemary , 3 inches, in the dish. This dish had great reviews on yelp. I dont mind rosemary but only a hint. Took 3/4 of my meal home, hoping it would taste better as a left over, it did not. For the price i would probably not come here again. I gave 2 stars for service because we were seated quickly, not for our server.

I went to gambling cowboy with a family member and I ordered a filet my mom ordered a ribeye. I ordered my steak medium rare. When I received my steak it was very underwhelming. No sear around …

I went to gambling cowboy with a family member and I ordered a filet my mom ordered a ribeye. I ordered my steak medium rare. When I received my steak it was very underwhelming. No sear around th…

I went to gambling cowboy with a family member and I ordered a filet my mom ordered a ribeye. I ordered my steak medium rare. When I received my steak it was very underwhelming. No sear around the …

We went here for new years and agreed to pay a cover charge, but were mislead as the cover charge was a money grab that did not include ringing in the new year at midnight. We had called over the p…

I have not attended this restaurant yet. I thought it would be a great place to go for a large group to sit outside on their veranda. I met with a manager who gave me all the information and I ex…

If you want to have a nice event DO NOT GO HERE. They discriminate and unless you want to pay a hefty price will not seat a large party of 10+ together unless you want to pay for a 'special event".…

Horrible service from our waiter , was visiting my mom and I was craving some lobster Mac and cheese and steak. My usual spot would be great oak steakhouse whenever I’m In Temecula, but always wanted to try this spot from all the good reviews. We realize that our waiter was not attentive at all to us, even forgetting to bring a condiment that we asked. Instead another waiter brought it to our table , did not offer us water. Did not check on us at all only until the end. And prior to this the food was taking long to show up and we understand that’s normal. We saw the other waiter tell the tables “food will be out shortly sorry for the wait” and our waiter nothing .. it definitely killed the energy and vibe for us. The food was delicious and the lobster Mac and cheese is a fav dish of mine. But makes me wonder if this is how the waiter is towards everyone or certain people. Work is work and sometimes bringing life emotions into work is not good. Hopefully the next table that is helped by her will feel welcomed. And I still tipped 20% + just because I’m a nice person 😜