The Gambling Cowboy
A rustic-elegant steakhouse in Old Town Temecula, known for prime cuts of beef, lobster specialties, and a lively western ambiance.
Highlights
Must-see attractions
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The Gambling Cowboy
Highlights
Must-see attractions
A rustic-elegant steakhouse in Old Town Temecula, known for prime cuts of beef, lobster specialties, and a lively western ambiance.
"Experience exceptional service and delicious dishes in a fun, relaxing atmosphere with a western flair."
Reserve Ahead
Secure your preferred time and seating by making reservations in advance, especially for weekends.
Patience for Food
Consider ordering a drink or appetizer while waiting for your main course due to potential kitchen delays.
Quick Facts
Cuisine
Steakhouse
Price
$$$
Highlights
Discover the most iconic attractions and experiences
Melt-in-Your-Mouth Prime Rib
Indulge in generous portions of prime rib, often described as melt-in-your-mouth tender and richly flavored, served with classic sides.
Cowgirl Kisses & French Onion Soup
Savor the fan-favorite 'Cowgirl Kisses' - bacon-wrapped jalapeños - and the critically acclaimed French Onion Soup.
Rustic Elegance & Romantic Ambiance
Experience a charming blend of rustic western decor with an elegant touch, perfect for date nights and special occasions.
Plans like a pro.
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Menu
Most Popular Items
Insider Tips
from TikTok, Instagram & Reddit
Reserve Ahead
Secure your preferred time and seating by making reservations in advance, especially for weekends.
Patience for Food
Consider ordering a drink or appetizer while waiting for your main course due to potential kitchen delays.
Parking Strategy
Parking can be challenging; consider using nearby public parking structures, especially on weekends.
Celebrate with Staff
Inform staff of special occasions like birthdays for potential pleasant surprises and memorable moments.
Tips
from all over the internet
Reserve Ahead
Secure your preferred time and seating by making reservations in advance, especially for weekends.
Patience for Food
Consider ordering a drink or appetizer while waiting for your main course due to potential kitchen delays.
Parking Strategy
Parking can be challenging; consider using nearby public parking structures, especially on weekends.
Celebrate with Staff
Inform staff of special occasions like birthdays for potential pleasant surprises and memorable moments.
What Travellers Say
Reviews Summary
The Gambling Cowboy is celebrated for its rustic yet elegant ambiance, making it a popular choice for celebrations and date nights. Diners frequently praise the generous portions and the quality of the steaks, particularly the prime rib and the signature 'Gambler' ribeye. However, some reviews mention inconsistent food temperature or preparation, with a few instances of under or overcooked steaks, and service can occasionally be spotty.
"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."
Juan Padilla
"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"
Eddy Bretado
"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."
Steven Wong
What People Like
What People Dislike
Frequently Asked Questions
Signature dishes include the 24-ounce 'The Gambler' bone-in Ribeye, prime rib, and the popular 'Cowgirl Kisses' appetizer.
Yes, the restaurant's rustic-romantic ambiance makes it ideal for anniversaries and birthdays. Inform staff in advance for special arrangements.
Reservations are highly recommended, especially on weekends, to secure your preferred time and seating area.
The restaurant features an eclectic western-themed atmosphere that is both rustic and elegant, with a lively ambiance.
Yes, diners often mention that the portions are generous and provide excellent value for the price.
Yes, The Gambling Cowboy offers outdoor balcony seating with views of Front Street, which is a popular option.
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Situated in the heart of Old Town Temecula, The Gambling Cowboy serves up classic steakhouse items in an eclectic, western-themed atmosphere. Offering only the highest quality, aged, Midwestern corn-fed beef and a wine list that showcases many local wines, The Gambling Cowboy makes for a great place to dine out in Temecula. Insider Tip The Gambling Cowboy is all about prime cuts of beef hearty enough for the hungriest of cowboys, like the house favorite: a 24-ounce Certified Angus bone-in Ribeye known as The Gambler, served with homemade garlic mashed potatoes or Cowboy potatoes, signature roasted corn, and seasonal vegetables.
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For those who appreciate the finer things in life, The Gambling Cowboy Chophouse & Saloon is a culinary destination that promises to delight your palate. Located at 42072 5th St, this upscale steakhouse stands out as one of Temecula’s premier dining establishments, perfect for those looking to savor a sumptuous meal after a day of riding your Pan American through the scenic California countryside. As you pull up to this renowned chophouse, the rustic charm of the exterior invites you in, promising a warm and hearty dining experience.
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With its name, you may not be surprised that this is an amazing place for steaks in historic Temecula, but this spot does some great surf and turf too. In addition to their long list of beef cuts and preparations, this cowboy also offers Oscar-style lobster additions, lobster mac ‘n cheese, and lobster mashed potatoes too. Appetizers and entrees include a good number of other seafood options, and a surprising level of creativity for a place with “cowboy” in its name.
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The Gambling Cowboy is a steakhouse with an indulgent brunch menu that includes all things steak and short rib: Short Rib Hash Skillet, Bill’s Steak Burger & Eggs, Country Fried Ribeye, and Short Rib Benedict all made from high-quality, corn-fed beef. As the name implies, the dining room is cowboy-themed, and truthfully it can be a little dark in there. We love sitting the outdoor balcony with views of Front Street and the mountains.
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It’s your lucky day when you get confirmed for dinner reservations at The Gambling Cowboy for dinner. We recommend saving this one for when you’re starving because these hearty meals will instantly put you in a food coma. This is one of the best restaurants in town for quality meat with prime cuts and Choice Certified Angus Beef selections.
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The Gambling Cowboy Chophouse: For a more rustic yet romantic setting, the Gambling Cowboy Chophouse steakhouse combines a cozy atmosphere with mouthwatering dishes. Whether you're indulging in a perfectly cooked steak or sharing a plate of fresh seafood, the intimate vibe and dimly lit interiors set the stage for a memorable evening.
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The Gambling Cowboy is located right in the heart of Old Town Temecula and offers some amazing views looking over Old Town. They offer a classic steak and seafood menu as well as an impressive wine list from many local wineries in Temecula!. Enjoy the relaxed but romantic ambiance of this Old Town Temecula restaurant!
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For a Western-style steakhouse experience, The Gambling Cowboy serves up mouth-watering steaks and classic cowboy fare. The “Cowgirl Kisses” appetizer is a fan favorite, and their steaks are cooked to perfection. The rustic decor and friendly staff make it a fantastic spot for a hearty, satisfying meal.
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When it comes to steakhouses, The Gambling Cowboy is yet another top option for food in Old Town Temecula. This restaurant serves up classic western fares in an eclectic and fully western ambiance. The mashed potatoes and the iconic Gambler steak are some of the best items here.
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Located in the heart of Old Town, this eatery is a culinary fixture in Temecula, serving amazing seafood and steak plates for brunch and dinner, plus desserts and more.
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