The Gambling Cowboy

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.

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

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. 🧡

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

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.

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.

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.

Delicious appetizers, nice outdoor balcony seating, fun decor and atmosphere. I really wanted to try the prime rib and baked potatoes but they don't those during lunch hour. Appetizers came out timely but the main dish took a little longer than expected. Food was good and service was great. Walking through Old Town Temecula on a sunny day after parking on the street was quitetpleasant.

We decided to try someplace new today for lunch. We're making the rounds through all the Temecula favorites. The Gambling Cowboy did not disappoint. We started with the Wedge Salad and the Famous Cowgirl Kisses. The wedge was crisp and fresh and a great ratio of ingredients and dressing. The cowgirl kisses are stuffed jalapenos wrapped in bacon, served with a raspberry chipotle sauce and fresh berries. Both were perfect. I'd order them every time we return and be completely happy! Our entrees were the Cowboy Steak Burger and the Prime Rib Dip. Both were very large portioned. The burger was cooked perfectly. The Prime Rib was sliced thin and piled high. Both were delicious and reason to return as well. We ended our meal with a slice of their 7 layer carrot cake. OMG it was delicious! So glad we stopped by other than the fact I now need to work off those calories! Service was attentive and timely. A great experience and one we will definitely look to repeat soon.

Ate here on 6.21.25 for our anniversary, we'd only been here once before for Thanksgiving Dinner in 2023, it was ok, but everyone we know raves about the steaks here so we decided to choose this place for dinner. Ambiance is pretty cool, staff is attentive and pleasant, cocktails were great, but the food was just rather disappointing. I ordered the Prime Rib, rare, also went with a cup of the clam chowder. Clam Chowder had great flavor but the potatoes seemed rather large and were a little too under done for me. Prime Rib was rather disappointing I'm afraid, the crust on it tasted great but I really had to work more than I ever have before to slice it, which I found rather odd for a rare prime rib. Husband had the ribeye and went with the wedge salad. Salad he definitely enjoyed and I equally took a bite and thought it was a pretty good wedge, not the same could be said for his Ribeye unfortunately. He ordered his medium and when he first sliced into it, it appeared to be medium, but as he cut more into the ribeye it looked seriously well done. He equally was disappointed and said it was rather dry and would definitely not recommend. I was hoping this place would have knocked it out of the park from all the people we personally know that have been here, but unfortunately it did not. We have family coming out who love steak and were hoping to bring them here during their stay, but yeah that definitely won't be happening. I don't know if it was just an off day in the kitchen or what but yeah I couldn't recommend this place.

I have been here twice now and both times were great! I love the vibe super cozy with cute decor and comfy booths. I think this is one of the best spots in Temecula for steak. The meat is flavorful and cooked just right (they nailed the medium, which a lot of places mess up!). Portions are big, and the service has always been nice and friendly. My only small complaint is the veggie sides, I wish they offered something a little more exciting with the steak. That part was a bit of a letdown. Overall though, I would definitely recommend this place if you're in the mood for a good steak and a chill atmosphere.

A wonderful place to dine, filled with exceptional service, uplifting music, and mouthwatering entrées. After a 45-minute wait at another restaurant, we reached out to GC and were welcomed in immediately. Just my wife and I, but it felt like a special occasion, reminding us of the joy found in great experiences.

STAR STUDDED ENTRANCE on the first walk in the place grabs you! From the walls to the music and one of a kind decor you are taken away! I couldn't get over the attention to details that were everywhere, this place is like an art museum. From the gold door arms, to the wood craved ceiling fans, you can just look around for days.! Now the food everything was awesome, we ordered the stuffed peppers, Mac n cheese, two filets one prime rib, all with loaded potatoes greens beans and more. But the standout for me and this might be strange, was the crab cake! Oh my goodness y'all soo rich with flavor and it was the first time someone mixed crab and shrimp which I thought was genius, aaaaand they gave me a lemon to squeeze on it! Say what! I know that may not sound like a big deal but it was, for someone who loves crab cakes this was the piece I had been missing.... I'm forever in debt!!! WE LOVE GAMBLING COWBOY!!!

What a great experience! First off our server Maria was wonderful!!! She was charismatic and upbeat and kept our drinks full. Such a delight. Gambling Cowboy is a must go back and try something else kinda restaurant. I did a reservation for a birthday brunch and their food was so good! We ordered 8oz. Top sirloin, eggs & potatoes and a few other dishes along with an appetizer. Our entire party couldn't have been happier, great view sitting on the patio outside. Scenery is nice and you get to people watch. Half our party returned a few days later that's how good it was, looking forward to returning for lunch or dinner!

Cute place from the inside out, it's like you stepped into a filming of a western movie. So much to look at on their walls. The food was great and our waitress so so funny and charming.

Who is ready for a rootin tootin good time?! Well saddle up on your horse and head on over to the gambling cowboy! Take the elevators to the 3rd floor of the building and you will enter into a western country wonderland. This restaurant is perfect for Old town, definitely fits the theme. Had reservations and was seated immediately. Our waitress was attentive and polite. Alcoholic beverages are not to be messed with here! I ordered a high noon and blood orange margarita and I was ready to GIDDY UP! Well not so fast, we still gotta eat supper! The food here is incredible! I ordered a 8 oz filet mignon steak. It was cooked perfectly at medium rare. Juicy and tender. Along with mashed potatoes, corn and green beans. Buttery goodness! My husband ordered the Gambler which is the cowboy signature steak 24 oz bone in ribeye also with mashed potatoes, corn and green beans. He devoured it all! We also shared a creamy cowboy mac and cheese, I was in cheesy heaven. Be prepared to be in a food coma, food is heavy. Also be prepared for a pricey check! It's very exorbitant to dine here but it's worth every penny. I recommend giving the gambling cowboy a try! It's going to make your tastebuds go YEE-HAW!

Absolutely a delight. This little gem hidden off of the main drag tucked away behind several other buildings hidden in the 3rd floor is like getting the prize in your cracker Jax! The decor and ambiance is warm friendly, yet playful and fun. It can be romantic and whimsical. It felt like being in a hammock on a cool breezy day. Just plain relaxing. The food? From the pozole to the machaca with a nice warm tortilla, down to the giant 6 layer carrot cake absolutely delicious! My friend had the fish and chips / we shared ... it was fresh light and tasty , just as if ocean front fish. The staff was attentive without hovering. Glasses always full , anything we need there magically. So happy my friends suggested The Gambling Cowboy! It was like a short staycation with a 5 star chef! Check it out , old town Temecula!

The food was excellent. The steaks perfectly cooked. Loved the biscuits and gravy. Portions were nice and the price was good. Yelp really helped me find a hidden gem. The service was fantastic. Our server was friendly and attentive and made dining there fun. Loved the ambiance of the restaurant. Very cowboy saloon kitschy and I loved it!! Would definitely go back here and have already recommended to friends.

My husband made reservations for brunch here today. We were expecting the restaurant to be busy, but surprisingly it was fairly empty. Loved the ambiance and western themed decor, as well as the wonderful service. The food was fantastic, and I highly recommend the cowgirl bites as an appetizer. My son and I both opted for the Country Fried Ribeye Steak & Eggs which came with choice of fruit, tomatoes or "cowboy potatoes." My husband chose the filet mignon Benedict, which he said was very tender and delicious. Everyone enjoyed their meals, and we will definitely be back to try their bottomless mimosas and other dishes.

We were in Temecula after some wine tasting and wanted a bite before heading home. We picked this place, and figured since it was 5PM we would have no problem getting a table. Well, the place was packed! The bar area including high tops is first come first serve, and we got lucky to get a table. The service is great. Our server was very friendly and attentive. We started with a wedge salad and French onion soup. The salad was yummy with crispy onions on top. The soup had good flavor but had way too much cheese for my taste. My boyfriend had the prime rib dinner. I had the filet tips which is an appetizer but was plenty of meat with a yummy sauce. My boyfriend also likes his prime rib. The potatoes that came with it could be cooked a bit crispier for our likening, but overall the food was good. The space is fun and vibey, like a cowboy saloon.

We tried and loved their signature "the gambler" cooked medium to perfection. We upgraded to the lobster mash and it was soooo worth it. Usually restaurants cut up the lobster so tiny it doesn't make a difference but not here it was incredibly delicious plus a little squeeze of lemon on top. The asparagus, corn, and green beans were just as great. Well seasoned and our server was delightful. The decor is adorable definitely will recommend and come back. The fresh sourdough and garlic butter is also a must have.

Wow, what a meal! Excellent ingredients, tons of options, both land and sea, and a heavy handed bartender. Country western vibe. What's not to love!

Been here a few times and it's always delicious! Parking can be difficult due to limited amount of parking spots, so get there early. There are a couple handicap parking spots just outside the entrance if needed. You take the elevator up to 3rd floor. The restaurant is beautifully decorated for Christmas. So festive! The burger is the BEST! This time I had the Cowboy filet Benedict. I highly recommend. The waitstaff are so nice and helpful. We will be back!

A week ago we went on our date. Steak and lobster was amazing. I ordered a mezcal drink and it was perfect, but let me tell you our waitress Maria was amazing! The most helpful, knowledgeable and bubbly one yet, get this she has 3 kids including a 1 yr old and still makes it to work with great attitude!!! Yes I asked her since she was super nice to us. We are certainly going back! I can tell the people dining here are people who know good steaks! We have plenty here in SD but wanted to visit DT Temecula for a while.

SUMMARY: TOTAL DISAPPOINTMENT. We used to go here for special occasions - birthdays, anniversaries, etc. Expensive but the food USED to be awesome. After over a year's break, we went for dinner on 9/12/25 for my nephew's birthday. We ordered bacon-wrapped scallops as an appetizer, three ribeye steaks advertised to be "16oz hand cut with fantastic marbline unique to the ribeye" with loaded baked potatos, and the "Queen of Hearts", a surf-and-turf option, along with two bottles of wine. For $34 we got four 1" diameter scallops that were tasteless, wrapped in bacon that wasn't cooked enough to even render the fat. We used to order these and they were to die for - diver scallops exquisitely cooked wrapped in crispy bacon. Not any more. The ribeye steaks and their accompanying baked potatos were a total letdown. The ribeye's were all overcooked, medium-to-medium well when ordered medium rare. They did NOT exhibit "fantatic marbling" but were more akin to chuck steak - chewy, dry, flavorless. Not like any ribeye I've ever had. The baked potatos were obviously cooked far in advance, and not reheated. They were sightly undercooked, cold, no steam, no flakiness. We ate less than half our dinner. I didn't complain because I didn't want to place a pall over the birthday celebration, but I do intend to dispute the charges ($480 including tip) on my credit card - and we won't be back to the Gambling Cowboy. The saddest part - this place USED to be awesome. They had all 4- and 5-star reviews, and justly deserved. They're going downhill... ADDENDUM: My wife just said she's had better steaks at Sizzler...

A wonderful dining experience for a spontaneous date night. My husband is typically picky when it comes to going out to a steakhouse, but he was so happy we came in. We didn't have a reservation, but was still able to find a table in the open bar seating area for 2. Our server was extremely fun and easy to talk to. She offered some great options for drinks and dinner. Our steaks were both cooked perfectly! Too many times have been to steak houses and the lines between Medium and medium rare have too often been blurred. Gambling Cowboy did an AMAZING job. Both steaks were juicy, tender, and cooked to perfection. The Mac and cheese was piping hot, and of course I couldn't wait and burnt myself on it 85 was absolutely delicious, the perfect amount of creaminess and thickly coated pasta was more than enough to be a meal on its own. Highly recommend this place for a night out, especially with its ideal location in the heart of Front St!

I've been here several times. 2 times my steaks were not edible. Chewy, grisly. One time I went for lunch. Didn't get steak so it was ok. A lot of people recommend but I haven't lucked out with a positive experience yet.

TLDR; started out great! Some things were really nice. Overall great service. Others hit or miss. Food was good. Drinks delish. Cowboy decor throughout was so cool. So much to look at! Made a reservation, surprisingly it was not busy for a Saturday evening, not a lot of people waiting, bar was empty and plenty of empty tables/booths on that side. Checked in for our reservation, but we were early so we grabbed a few cocktails at the bar (bartender was super attentive and friendly, got our drinks quick - Martini and Old Fashion, both delish). I told the hostess, and she then asked me if I was just going to dine there. I was like, no, just grabbing a cocktail until our table is ready. She said ok. We enjoyed our drinks, checked the time and it was like 10 minutes after our reservation time. Since no one came to get us, we aid and took our drinks to the little waiting area by the hostess stand. Also decorated very nicely. Now 20 minutes after our reservation time, so I checked again with the hostess. She casually said oh we can seat you now. As we walk pass empty tables and booths, she takes us outside to seat us. It was just too cold. So I went back in and asked if we could sit inside, she said well I can turn on the heat lamps for you. I was like, no I'd rather sit inside so the food doesn't get cold. So we come back & sit in the waiting area and she then escorts us to a super cute round booth. So I get over it (lol). And the server is super nice and friendly! No rush, lets us take our time ordering apps, drinks ... so great service and redeeming! Anyways, on to the food: Bread & butter - good!!! Artichoke - AMAZING! My favorite thing all night. Would go back for this. French Onion soup - delish! Cesar Salad - good, but had to ask for more dressing. Prime Rib - good! and comes with horseradish. Blackened rib-eye - the first one came out with A LOT of GRISTLE, a little cold, not charred. She kindly got me a new one, and while that one was not AS gristle-y. But this one was hot, & I could taste the blackened seasonings which was really yummy; not charred as I thought it would be or have seen in other pics. Baked Potato: The HUGEST potato I have ever seen! Veggies: so good. The corn - I would order on its own! Mashed potatoes: good. Too stuffed for dessert! Bar: Espresso Martini - really good, served really cold. Loved it $14. They do charge $4 extra for an Old Fashion! $14 + $4.

This was my fourth time dining here. The food was just okay, and the service was pretty average. It almost felt like our server wasn't too thrilled about taking our party. Honestly, the dessert ended up being the highlight of the meal.

Amazing Place! There is a TV in there as well to catch a game! The food was terrific, and the décor is fantastic and makes you feel like you're in a Western setting. The service was good--it could have been better, but we understand it was Mother's Day weekend, so they were swamped I had the ribeye with roasted poblano, and it was perfectly marbled. When laid right on top of the steak, the poblano added a delicious flavor. The sides--corn and greens--complemented the steak really well.Our favorite dish was the mac and cheese. It was creamy, flavorful, and delicious!

Hubby brought us here, a unique place that always reminds you Western Lifestyle:) We ordered three main course and one appetizer, kids also lyk the sweet corn as the side. Vibe is gd.

Definitely a higher end steakhouse to try at least once in the Temecula area. I came here for my mom's birthday and it did not disappoint. Their ribeyes are massive and juicy with loads of flavor. Their mashed potatoes and lobster mac and cheese are also super tasty!! Will come by again when I have the money LOL.

This was our first time and it was sooo good. I had the shrimp and crab Louie salad it was soooo good. Hubby had the ribeye, friends had the blacken sea base, and prime rib they all had doggie bags and everyone was so happy.

Outstanding Service and delicious food! The servers are very friendly, engaging and attentive! Very classy restaurant to go eat some delicious food with appetizers! Love the decor and the place is very clean!

What an amazing place. The bartender was very cool. We sat there before getting seated. The drinks were great. All of the food that we ordered was fantastic.

This place was an awesome find!! My husband and I have been to Temecula plenty of times and had never been here before. But now every time we visit Temecula this will be a must! My husband and I ordered their prime rib steak and it was perfectly seasoned and cooked. The steak came with three different sides which included corn, green beans and smash potatoes. Everything was so delicious. If you want to seat inside you should make reservations, because they are really busy. Luckily we were able to get a table outside, which was lovely. They have a nice set up, with lights, cute decor, cute ambiance! Our waitress was awesome! She was friendly, checked on us regularly and brought us a delicious chocolate mouse for our anniversary. If you're around the area make sure to stop here for lunch or dinner. I wish it was closer to home, so I could go back again sooner!

Erin was our waitress. She was AMAZING!! Attentive and polite. She really helped us have a great birthday lunch. We all got the Turkey BLT with avocado. I swapped the Swiss for pepper jack cheese and I Swapped out regular mayo for garlic aoli mayo. DELICIOUS! Hands down, will definitely be going back!!!

I really enjoyed this restaurant. It was packed the day we went and we had no reservations. Luckily, we were able to wait for bar side seating and we really didn't wait at all. We had a bowl of clam chowder and we shared an appetizer. I believe it was ahi tuna. It was a little too sweet for my taste. We each had a burger. The clam chowder was ok, but let me tell you about the burger... it was massive!! It was also very delicious. You need to have a huge appetite for it or maybe share it. It came with onion rings and those were delicious as well. My hubby had an espresso martini and he thought it was very tasty. Overall, we really enjoyed the ambiance of this restaurant, the service was great and I will definitely go to this restaurant when visiting Temecula.

I called to ask about happy hour. She told me $3 off drinks and they have food specials. I like to frequent happy hours, I get to gambling cowboy and there's no drinks on happy hour?? Just 5 food items. That's weird, a happy hour with no drinks. $20 cocktail with $10 tacos is ridiculous

Located in Old Town Temecula, while quaint, parking can be a challenge - plan accordingly (we parked nearby and walked over - far less stressful). As you can see my inside pics, it definitely has the cowboy theme going with a touch of splash. But that's not why you're coming here. We shared their Prime Rib (end cut - before you get too judgy, we like the bark. While it's a bit overcooked, quality beef will still be tender and juicy). And in this case, it was very tender and juicy (even though it was an end cut). What you see in my pic is an 8 ounce portion (there are 12 and 16 ounce options). The bark was great. It was seasoned just right, but perhaps too much salt. The garlic potatoes were quite fluffy - just as they look. But they were very weak on the garlic. The roasted corn was fresh and had the nice, roasted flavor. We ordered a side of Wild Mushroom Madeira Medley. It delivered as you would expect: plump mushrooms in a rich sauce. The 'shrooms and sauce went well with a bite of steak. Since we were there for an occasion, they provided us with a shared chocolate mousse. For being a freebie, it was refreshing, light way to end a hearty meal. We ordered red wine by the glass. I ordinarily don't discuss wines, since we all have such unique wine tastes. But we were impressed with our selections, both types had depth of body, a great bouquet, rich and very mild tannins.

1st TIMER HERE !!! FINALLY got to try the famous Gambling Cowboy! However, just for breakfast ! I cant wait to try lunch and dinner, as I have heard the food is amazing! Let's get to breakfast I ordered the country fried ribeye steak and eggs - and omg - I'd definitely order again! I do wish they had hash browns but the potatoes were delish and the eggs were good. Great prices for breakfast and the amount of food. Their brunch menu looks fabulous too! I definitely recommend sitting outside on the patio, the atmosphere is so fun and the decor is super cute. Staff is friendly and super attentive! Cant wait to go back and try their lunch sandwiches and dinner!!!!

Food was amazing!!! We had a fun server that kept telling us stories. I had the prime sirloin steak and eggs cooked medium rare. Fantastic!!! Came with home potatoes and toast. The sad thing is I got no toast, my server forgot to bring it. Had the chocolate cake for dessert with two scoops of vanilla bean ice cream. We will be returning for sure.

We ordered the wedge salad, amazing! Prime rib, amazing! Filet mignon, amazing! Their garlic mash added to the selection made it all the more perfect! We paired them with a nice bottle of wine and called it a date! It was a Friday night so it was packed (reserve ahead of time to avoid long wait) so it's kinda understandable that our server was busy. Overall it was a great experience-food, ambiance and service. We will come back for the nth time

Food was fantastic best corn I have ever had and top 5 best steak I have ever had!!! Restaurant was beautiful and decorated for 4th of July in the Foyer. Love This Place We will definitely be back!!

I had a company work dinner here a week or so ago and three of the party ended up getting very sick from the food! When we called to see if they had any suggestions or could help us figure it out. They basically washed their hands of it and said they have no idea what happened and they're sorry, but there is nothing they can do? It's really too bad and very disappointing because the ambience was nice. The food looked good, but if you're making half of the dinner part very sick, and it's 100% related to the restaurant. (None of us were sick before) and some of us started feeling sick within an hour of eating,,,then it's off or not. I wasn't looking for a refund. I wasn't looking for compensation, I wasn't looking for anything except for sympathy and answers and was basically was told nothing to see here... very disappointing, I guarantee we won't be back!

We've eaten here once before, had an appetizer(burrata and cherry tomatoes)and French onion soup which were really good. On this occasion we had a full meal along with the same appetizers. The fish n chip special...DISGUSTING! With every bite I got a mouth full of old grease accompanied by mushy, smelly fish. My guests got hamburgers....tasteless meat in between a soggy old bun...REPULSIVE! The fries were saturated with fish n chips grease. ALL the food comes from a bag the heated up and put together by lazy, inept, careless kitchen staff. AVOID THIS PLACE!

I came for lunch and had the fish taco and Caesar salad. I was a fan of the dressing on the salad. Had a vinegar aftertaste. The taco was tasty 7/10. The chipotle sauce made it better The service was excellent! I sat at the bar and the server was so nice and friendly. Hate I forgot her name The ambiance is very cowboy themed. A lot of cute signage and props

First let me start by saying, Maria, our server was extremely knowledgeable and friendly. A breath of fresh air. Thank you Maria! We came in for lunch, started with the Angel kisses, delicious! Mains: wife ordered prime rib dip sandwich, tender and delicious, served with amazing onion rings. I decided on the BBQ Cowboy burger, 8 ounce ground sirloin patty, wonderful flavor, severed also with magnificent onion rings. Dessert: We shared the 6 layer Cowboy chocolate cake served with vanilla ice cream topped with hot fudge, complimented by a large sweet strawberry. Ambiance was relaxing as it was a lunch date during the week, noise level was very low making conversation easy. Strongly recommend Thank you and we will be returning!

Oldtown Temecula can be mind bogglingly busy. Initially, my family had tried to go to a restaurant next door but the wait would be an hour and a half! Fortunately, we walked over to The Gambling Cowboy and were seated within minutes. Had it been earlier in the day, it might have been bad, but from early evening into the night, our seats on the balcony were perfect with a nice breeze and decent view. We started off with the cowgirl kisses (essentially stuffed jalapeño) and cilantro shrimp. I would say that they're alright, but nothing mind blowing. My family decided to go with 2 ribeye steaks, a salmon, and braised short rib. The amount of food was substantial! I found my steak to be fine but as for the rest of my family, they found theirs to be too greasy. I will say that we appreciated the nice service. They ended up treating my parents with a complementary dessert for their anniversary. If I could give half a star, I would make this a 4.5 experience! We didn't have a long wait for seats, had good service, but some of our dishes were too heavy and greasy for our liking.

Another GREAT dining experience, thank you staff, including wqit staff, chefs, hostess and more. Arrived early for a reservation, but we were warmly greeted and promptly seated (it rhymed too!) Our waitress, Natalya, was outstanding. Drink orders taken quickly along with appetizer order, drinks arrived fast (thank you for that) and the kitchen turned around the apps fast. So about the food (the best part). Try the shrimp! Large shrimp, perfectly battered and served with a spicy cilantro dressing, paired pefectly. Added the scallops, crispy bacon wrapped I must add. Delicious! Perfect combo of crunch and texture. Went all-in and added the roasted artichoke. Cant beat it. Rare to see it served perfectly, light garlic flavor complements the taste. Now steaks are where it's at! My party went with Filet Mignon, perfectly cooked, and prime rib, just right. Not too rare, but not too medium. If you want a GREAT steak, look no further. Ambience is great because it's fun but muted, you'll be just as comfy in a suit or slacks, or jeans (but wear a collared shirt, be dressy). Same as women, you wont feel over or under dressed. Arrive early because Old Town parking can get tricky, and no valet is anywhere around the area. Public parking, both free and paid, is available.

Called in to see how bad the wait was. We were told that no tables were open but the bar was available. After a search for parking (which is a nightmare in this area), we arrived only to be told that the bar was full. They estimated an almost 2 hour wait for a table or seat at the bar. We gave our number for a text and went to find another spot for dinner. As soon as we placed an order elsewhere (about 10 mins later), we received a text that they had a table ready. Disappointed at their inaccurate estimate, really wanted to try eating here.

Wonderful place fabulously decorated for the holidays western cowboy feel . We were greeted a taken care of by Tara wonderful host . I had the wedge salad with potatoes skin my Dad had the 3 tacos and my mom the cowboy burrito a meal for two .

Steak (ribeye) and potatoes are amazing! Staff is friendly. Can get busy call in advance

Loved the ambiance and service. The Blue Cheese Bacon Crusted Filet Mignon was so good! Can't wait to go back and try other delicious items on the menu.

This place just did not miss while we visited. We were greeted with smiles and a pleasant ambiance they said we love to serve and let's make this visit memorable. Our server was on it but not too on it... if you know you know... We weren't waiting too long for anything, including the food... the appetizers came out quickly and the food didn't come out before the appetizers were cleared. I love this attention to detail. Now for the food? Everything was cooked to perfection and that's why they get a 5.... Was this the best steakhouse I've ever been to? NO!!! Heck no!!!! For what they are and what they do they did it to perfection. The steak was tender and cooked perfectly... it wasn't bland but indeed could've had more flavor... same for the bass... but those Cowgirl kisses are to die for! this shrimp cocktail was on point too. If I could have give them a 4.6 but I can't so they get the round up. Happy eating!!!!

Wow! Loved this place! It's tucked away in the back near Mad Madeline's and is upstairs. You have to take an elevator to the 3rd floor to get to it. Food was amazing! Everything was flavorful and cooked well. Service was great! We made reservations through OpenTable and had no issues. We were seated right away when getting there. Our waitress was attentive. The ambiance was pleasant/smooth. Since my husband and I were celebrating our anniversary, we got a free chocolate mousse dessert! Busy place and I understand why! Cannot wait to come back to try different dishes.

While in town my husband and I were in the mood for a good steak. I heard many recommendations from locals that this was the place to come. The restaurant is in Old Town and on the second floor of a saloon esque type building. We were quickly sat and decided on the patio since the weather was so beautiful. My husband and I both opted for the steak and fries. I adored the flavor of the steak and it was cooked to perfection. I also decided on the spicy chophouse salad which probably was the best for me. I love the spicy goat cheese and the fresh berries. It was so full of flavor. I devoured it. As for a beverage I eventually decided on an espresso martini. So delicious and creamy. Service was quick and attentive. I would definitely recommend to anyone looking for a great meal for a great price.