Cowboys Orlando is One of the Best Orlando Bars for Fun and Contests!

Get your boots knocking at Cowboys Orlando! Cowboys Orlando is a popular bar. So strap on your cowboy boots and get ready to party!

When you pull up you’ll see a private parking lot that is safe and well lit. If you go during an event then they even have event staff there to see that the parking is orderly. Plus the parking is always free.

1108 South Orange Blossom Trail

Orlando, Florida 32805-3742

sign at cowboys orlando

Website (opens a new window)


The parking lot may resemble a GM sales floor with large trucks lining the way. But it will also have a variety of other vehicles from Mercedes to Hondas.

The bar itself is just as diverse. It’s a place you can go and be yourself and still fit in. The Cowboys Orlando dress code is casual. Boots and hats are not required but add to the fun if you so desire.

front of cowboys orland

Once you walk up to the front of Cowboys Orlando you’ll see a happy looking place. It actually looks smaller than it really is. Once you go inside you’ll be surprised to see that it boasts over 20,000 square feet of fun and entertainment.

With eight bars and 30 hdtv there’s more to do than just dance. I especially like that they have pool tables and other fun things to do.

One cool thing about this place is people that are 18 and up can get in. It’s one of the few Orlando bars that allows anyone under 21.

The decor is old school country with pictures of famous country singers lining the walls.

Surprisingly it offers a great mix of country music as well as dance music. Making it a great place for everyone.

This Orlando bar also has a lot of fun promotions going on. Like Cowboys Orlando Thursday nights are ladies night.

Ladies get free admission and free wells, wines and drafts until 11pm. Plus get $2.00 “you call it” drinks all night long. And all import beers are only 3 bucks! Not a bad deal.

Wonder in on the second Thursday of the month and check out “boots and boxers” where the men of Cowboys strut their stuff in, you guessed it, boots and boxers.

They can win cash and prizes. If you feel up to it jump up on stage and show us what you’ve got!

I’m all about the men but for those of you that are into the ladies check out the Third Thursday of the month for “boots and bikinis” were the ladies strut their stuff for.

You will not see me up there though (sorry boys.) I’m a bit too modest (or scared.) Plus I don’t think I could compete with some of the girls that brave the stage.

There's also other fun contests every Thursday of the month. Be sure to check out the website to see what’s going on.

Cowboys Orlando Friday night offers Live country music all night long. Go early at 8pm (Thursday, Friday or Saturday) and get free dance lessons!

It’s always fun to be in group of people with two left feet. It’s sure to be a good time. Make sure to wear closed toe shoes so your feet are protected. Factor in $2.00 Bud Lights all night long and it’s sure to be an interesting night.

One complaint is sometimes people just stand there on the dance floor and take up space. I just try to get them involved and hope they start to move.

Cowboys Orlando is a great place for both singles and couples. It’s fun for singles because there are always plenty of people looking to have a good time. It’s fun for couples because you can watch all those singles trying to hook up.




Saturday Nights the cover to get into Cowboys Orlando is $7.00 if you go before 9pm. If you go after 9pm the cover is $12.00 but if you wait an hour (10 pm) you can have as many long neck beers as you want for FREE!

There’s also more contests and chances to win cash. It’s always fun to watch. As I said before it gets interesting once the booze starts to kick in.

Have a tattoo? Go to Cowboys on the fifth Saturday of the month and have a chance to win by showing it off.


crowd at cowboys orland

This is one of the Orlando bars that's always packed. Luckily there’s plenty of room to move around. I love the outdoor bar the best.

Mainly because they allow smoking at this Orlando bar. If you go outside it allows you to enjoy some Orlando, Florida weather. And gets you out of the smokey bar area.

outdoor bar at cowboys orland

Sit in the swings and enjoy the stars. Plus you can also play pool out there. I find that you can also get a drink a lot quicker because there are less people.



Cowboys Orlando is open Thursday, Friday and Saturday nights with doors opening at 8pm and closing at 2am. Sometimes they open on other nights during the week if they have special events.

We recently went on a Tuesday night to see a concert. It was a lot of fun. I especially enjoyed one of the songs that the man sang with the line “she had a honkey tonk badankadank.” Hilarious!

The club itself is not in the best part of town. So just be mindful of that and don’t leave valuables in your car. Plus if you decide to walk anywhere just make sure you do it in a group.

There’s plenty of police patrol so you don’t really have to worry about safety. Just don’t drink too much and wonder away and you’ll be fine.

I like to go to Cowboys Orlando for a fun, laid back time. Even if you’re not into country music you’ll have an enjoyable time.

The crowd just has friendly vibe. And you don’t have to dress up to not stick out. Jeans and a tee shirts are just fine. Just go as yourself and have fun!





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