We tried this place for the first time last night. We dined outside, it was very warm for it being winter, they have heaters outside which is great. The view outside was soo pretty. Our food was delicious and huge portions! There was a large party dining near us over 20 in that party so the server was busy. Our server was good, but she did take a while to check on us after our meals and we had to wait a bit after finishing to ask for to go boxes because she was busy. Other than that it was great! We dined in on a Tuesday evening 7pm a party of 2, I can't imagine how busy they must get on the weekends! I recommend the crispy Brussel sprouts, and the cowgirl kisses for appetizers. Next time we go back we're gonna share an entrée because that's how huge the portions are, the Mac n Cheese was also very yummy! Our steaks were soo good too!
Jason
The food was excellent. I ordered the Steak Diane and it did not disappoint. The white cheddar mashed potatoes with chives was excellent too! I don't typically eat beans and won't touch corn, so I can't speak to those items. My wife ordered the meatloaf and said it was the best meatloaf she ever had! She loved all the food. If I had to give a critique, it would be that I would have preferred to be further away from the bar itself. There were some booths that were further away and it felt quieter and more intimate...something I would have preferred for our anniversary dinner. Server was so sweet and kind. She always had a smile on her face! The other staff there seemed to be very efficient in taking up plates when we were done (like the cowgirl kisses appetizer). Everyone seemed to be working together like a well oiled machine. The music was great too. The guy was a much better guitar player than singers but man he was a good guitar player!
Trisha
The service was excellent and the atmosphere warm and welcoming. Unfortunately, the hamburger was a letdown. The bun was soggy, and the meat was overly salty and fell apart, lacking the texture of a proper patty. While the staff was friendly and attentive, the food itself didn't live up to expectations.
Amy
This was our first time dining at the Gambling Cowboy . When we arrived, the place was packed and it seemed to be hectic . We had a reservation and we quickly were seated at one of the private circular booths towards the back of the restaurant. The decor alone spoke to me . We are from the south and avid hunters so we were please led with the attention to details . The Christmas decorations were still up so it added to the ambience as well. Our server was very pleasant and she gave us a few moments to settle in . We are not drinkers and we decided on just water . The menu is full of so many options , but we knew right away that we needed the French Onion soup . Bread was delivered after we order our soup . The bread is some of the best I have ever had . House made sourdough (warm) out of the oven served with herb butter . The soup arrived shortly after . Super hot, and the flavors were perfection . My partner order the Queen of hearts . A filet with lobster tail. He has eaten lobster tail for years and said this is definitely the best lobster EVER. The lobster is taken out of the shell and served with warm melted butter. I had the filet with the cowboy potatoes . The entrees come on all hand made pottery plates with a variety of colors . Wish I could have bought the plates . So uniques and beautiful. Our server was delightful and gave us time to enjoy our meal and each others company . We cannot wait to go back .. hopefully sooner than later . Thank you for a great experience . And shout out to the buser and food runner. The food runner taking time to take our picture .. and the bus boy for being on top of pulling our extra dishes when we were finished .
Susan
We enjoyed Sunday Brunch with our son and his partner. We were immediately seated and offered beverages. Our server brought them to our table end we ordered four fabulous entrees; Chilaquiles, Short Rib Hash Skillet, an Omelet mad your way and a Cowboy Breakfast Burrito. Not only was the food prepared perfectly, it was delicious. Lots of coffee refills and a surprise anniversary dessert for our 46th. A great meal.
Kevin
Unique steakhouse feel. Service was amazing. Everyone on staff made me feel like I was family. The portion sizes are really good. Had the artichoke appetizer, ribeye special with lobster mash potatoes. The amount of lobster was crazy. Most places give you a small amount, you get two full claws of meat. Ribeye was cooked to perfection. Came in for a birthday dinner. Made me love every second I was there.
Frank
Great food. Attentive staff. Missed this place. Haven't been in a couple years. Will be back again
Charles
I think the steak here is great. I've had their Steak and Wedge on 3 occasions and it was excellent every time. There is a jalapeño appetizer that was way too spicy for the table, but it wasn't enough to hinder the experience. Staff was very friendly and the place has a quiet setting for a busniness lunch. I'm certain we'll be back.
Michelle
We were sat immediately our waitress was so nice and not overbearing. The food was perfection. The restaurant was decorated so beautifully for Thanksgiving. It was such a great experience. I highly recommend The Gambling Cowboy for your next special evening!
Melinda
We were celebrating my husbands 94th birthday with his son and daughter- in-law. We were seated in a booth inside and from the hostess to the fellow who cleared our table, the service was excellent. We had varied entrees and each was well liked. Well prepared and tasty. The Cowboy is a wonderful place for celebrations.
We really enjoyed our dinner at The Gambling Cowboy. Everything was absolutely delicious. I got the prime rib and my fiancé had the gambler and we are still stuffed half a day later. Will definitely make this our “celebration restaurant.”
Martina Campbell
If you want the best steak ever this is the place to get it. They have the best steaks here. And their corn is the best corn that I have ever eaten. Their baked potatoes are huge. We've eaten here several times.
Atmosphere: 5
Food: 5
Service: 5
Lee
Delicious food! The citrus salad is amazing. This place is a main staple in Old Town Temecula. Decor is really pretty and I love the cowboy theme. Staff was incredibly friendly. Highly recommend. 
Danna Johnson
We decided to try this place for our anniversary. We had heard so many great things about this place. Our experience…..Our server was polite, just not attentive. Our steak wasn’t medium rare, but she never checked on us once the food came so we just ate it. It was delicious. When we ordered more drinks it took long enough to get them that we had finished dinner. Not horrible service. Just not what we expected for the quality that they portray.
Atmosphere: 5
Food: 5
Service: 2
Cynthia
Great restaurant all around! Next time, I want to dine there at sunset and enjoy the great views on their patio.
We tried this place for the first time last night. We dined outside, it was very warm for it being winter, they have heaters outside which is great. The view outside was soo pretty. Our food was delicious and huge portions! There was a large party dining near us over 20 in that party so the server was busy. Our server was good, but she did take a while to check on us after our meals and we had to wait a bit after finishing to ask for to go boxes because she was busy. Other than that it was great! We dined in on a Tuesday evening 7pm a party of 2, I can't imagine how busy they must get on the weekends! I recommend the crispy Brussel sprouts, and the cowgirl kisses for appetizers. Next time we go back we're gonna share an entrée because that's how huge the portions are, the Mac n Cheese was also very yummy! Our steaks were soo good too!
The food was excellent. I ordered the Steak Diane and it did not disappoint. The white cheddar mashed potatoes with chives was excellent too! I don't typically eat beans and won't touch corn, so I can't speak to those items. My wife ordered the meatloaf and said it was the best meatloaf she ever had! She loved all the food. If I had to give a critique, it would be that I would have preferred to be further away from the bar itself. There were some booths that were further away and it felt quieter and more intimate...something I would have preferred for our anniversary dinner. Server was so sweet and kind. She always had a smile on her face! The other staff there seemed to be very efficient in taking up plates when we were done (like the cowgirl kisses appetizer). Everyone seemed to be working together like a well oiled machine. The music was great too. The guy was a much better guitar player than singers but man he was a good guitar player!
The service was excellent and the atmosphere warm and welcoming. Unfortunately, the hamburger was a letdown. The bun was soggy, and the meat was overly salty and fell apart, lacking the texture of a proper patty. While the staff was friendly and attentive, the food itself didn't live up to expectations.
This was our first time dining at the Gambling Cowboy . When we arrived, the place was packed and it seemed to be hectic . We had a reservation and we quickly were seated at one of the private circular booths towards the back of the restaurant. The decor alone spoke to me . We are from the south and avid hunters so we were please led with the attention to details . The Christmas decorations were still up so it added to the ambience as well. Our server was very pleasant and she gave us a few moments to settle in . We are not drinkers and we decided on just water . The menu is full of so many options , but we knew right away that we needed the French Onion soup . Bread was delivered after we order our soup . The bread is some of the best I have ever had . House made sourdough (warm) out of the oven served with herb butter . The soup arrived shortly after . Super hot, and the flavors were perfection . My partner order the Queen of hearts . A filet with lobster tail. He has eaten lobster tail for years and said this is definitely the best lobster EVER. The lobster is taken out of the shell and served with warm melted butter. I had the filet with the cowboy potatoes . The entrees come on all hand made pottery plates with a variety of colors . Wish I could have bought the plates . So uniques and beautiful. Our server was delightful and gave us time to enjoy our meal and each others company . We cannot wait to go back .. hopefully sooner than later . Thank you for a great experience . And shout out to the buser and food runner. The food runner taking time to take our picture .. and the bus boy for being on top of pulling our extra dishes when we were finished .
We enjoyed Sunday Brunch with our son and his partner. We were immediately seated and offered beverages. Our server brought them to our table end we ordered four fabulous entrees; Chilaquiles, Short Rib Hash Skillet, an Omelet mad your way and a Cowboy Breakfast Burrito. Not only was the food prepared perfectly, it was delicious. Lots of coffee refills and a surprise anniversary dessert for our 46th. A great meal.
Unique steakhouse feel. Service was amazing. Everyone on staff made me feel like I was family. The portion sizes are really good. Had the artichoke appetizer, ribeye special with lobster mash potatoes. The amount of lobster was crazy. Most places give you a small amount, you get two full claws of meat. Ribeye was cooked to perfection. Came in for a birthday dinner. Made me love every second I was there.
Great food. Attentive staff. Missed this place. Haven't been in a couple years. Will be back again
I think the steak here is great. I've had their Steak and Wedge on 3 occasions and it was excellent every time. There is a jalapeño appetizer that was way too spicy for the table, but it wasn't enough to hinder the experience. Staff was very friendly and the place has a quiet setting for a busniness lunch. I'm certain we'll be back.
We were sat immediately our waitress was so nice and not overbearing. The food was perfection. The restaurant was decorated so beautifully for Thanksgiving. It was such a great experience. I highly recommend The Gambling Cowboy for your next special evening!
We were celebrating my husbands 94th birthday with his son and daughter- in-law. We were seated in a booth inside and from the hostess to the fellow who cleared our table, the service was excellent. We had varied entrees and each was well liked. Well prepared and tasty. The Cowboy is a wonderful place for celebrations.
Restaurantji Recommends
We really enjoyed our dinner at The Gambling Cowboy. Everything was absolutely delicious. I got the prime rib and my fiancé had the gambler and we are still stuffed half a day later. Will definitely make this our “celebration restaurant.”
If you want the best steak ever this is the place to get it. They have the best steaks here. And their corn is the best corn that I have ever eaten. Their baked potatoes are huge. We've eaten here several times.
Atmosphere: 5
Food: 5
Service: 5
Delicious food! The citrus salad is amazing. This place is a main staple in Old Town Temecula. Decor is really pretty and I love the cowboy theme. Staff was incredibly friendly. Highly recommend. 
We decided to try this place for our anniversary. We had heard so many great things about this place. Our experience…..Our server was polite, just not attentive. Our steak wasn’t medium rare, but she never checked on us once the food came so we just ate it. It was delicious. When we ordered more drinks it took long enough to get them that we had finished dinner. Not horrible service. Just not what we expected for the quality that they portray.
Atmosphere: 5
Food: 5
Service: 2
Great restaurant all around! Next time, I want to dine there at sunset and enjoy the great views on their patio.
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