Circus Street Entertainment

03/14/2026

Unfortunately, we have to cancel Johnny’s show tonight so he can safely continue down the road. He had a blast last night and is very grateful—as are we!

We appreciate this journey and learning to navigate it!

Hopefully the weather doesn’t hit. Stay safe and as always, THANK YOU!

Make sure to keep an eye on Johnny, he’s going to be a hitter in the industry!

03/13/2026

JOHNNY SALAMI SHOW IS FREE TONIGHT AND TOMORROW! Please go have some fun and enjoy yourselves—as always, thank you for everything!!!

Circus Street presents: JOHNNY SALAMI

Get ready for two nights of laugh-out-loud stand-up with New York City’s own Johnny Salami — comedian, podcast host, and all-around crowd favorite. Johnny recently captured the nation's attention with his recent Don't Tell Comedy Showcase, which has garnered more than a million views.

📅 March 13 & 14
⏰ Music at 6pm • Comedy at 8pm
📍 Drake's Oak Hill

From his signature cadence and quick-fire jokes to hilarious takes on everyday life, Johnny always keeps the laughs coming. Don’t miss it!

03/11/2026

Come see the hilarious up and coming legend JOHNNY SALAMI this Friday and Saturday!!!

We thank you all so much for your support. This has been such a fun season and a dream come true to share with the community!

02/16/2026

When we launched Circus Street at Oak Hill Outdoor - 2188, it was built on a simple dream — to bring consistent, high-quality live comedy to our community and create a place where we could all gather and laugh together.

Oak Hill believed in that mission from the start. As our initial contract comes to an end, we are nothing but grateful for the way they got behind Circus Street and provided such a great venue to launch the cause!

Season One will officially conclude with Johnny Salami on March 13th & 14th — and we couldn’t think of a better way to celebrate this first chapter than packing the room one more time and saluting what we built together.

We’re also excited that Oak Hill plans to continue hosting comedy in their own way and keep the movement moving forward. That’s a win for everyone who loves live entertainment in Okoboji!

For me personally, building Circus Street has been a lifelong dream — sharing laughter with our community, creating moments people remember, and helping comedy grow here in a real way.

This is simply the end of Season One! We CHEERS and THANK YOU!

See you soon 🙏🏼 and please.. keep laughing!!! 🫶🏼

02/02/2026

Circus Street presents: JOHNNY SALAMI

Get ready for two nights of laugh-out-loud stand-up with New York City’s own Johnny Salami — comedian, podcast host, and all-around crowd favorite. Johnny recently captured the nation's attention with his recent Don't Tell Comedy Showcase, which has garnered more than a million views.

📅 March 13 & 14
⏰ Music at 6pm • Comedy at 8pm
📍 Drake's Oak Hill

From his signature cadence and quick-fire jokes to hilarious takes on everyday life, Johnny always keeps the laughs coming. Don’t miss it!

01/30/2026

Make this Valentine’s Day one to laugh about. 💕

Join us for two nights of music, comedy, and cocktails with Sara Manson (Sioux Falls Funniest Comedian of the Month for January) & Adam Goodge (recently voted FUNNIEST PERSON OF THE YEAR in South Dakota!!).

My Funny Valentine brings together sharp stand-up and a full night out of fun — perfect for date night, Galentine’s, or just falling in love with comedy.

We can’t wait to see you there!

📆 Friday, Feb 13 & Saturday, Feb 14
⏰ Music 6:00PM, Comedy 7:00PM
📍 Drake’s Oak Hill | 2188 Hwy 86, Milford, IA
🍽️ Food & drink specials available

Oak Hill Outdoor - 2188

Tickets available online 💌 https://square.link/u/RbDeAa7c

01/27/2026

Valentine's surprise! We are very excited to announce that Sara Manson and Adam Goodge will be bringing their yearly show MY FUNNY VALENTINE to Okoboji this year! We will be announcing our specials and more information in the next couple of days, but mark it down for FEB 13th and 14th!

This is an amazing show that involves everyone with hilarious interactions. Adam was just voted FUNNIEST PERSON OF THE YEAR in South Dakota and Koerner will be hosting!

We're thrilled and hope to see you! More information coming soon as well as our future lineup. THANK YOU FOR YOUR SUPPORT! Oak Hill Outdoor - 2188

01/15/2026

7 DAYS until Winter Games gets funny. 🎉 Grab your tickets today — we have two INCREDIBLE shows coming your way!

Winter Games Kickoff
• Thursday, Jan 22: https://square.link/u/EpAEOk17
• $50 Comedy/Music (Thursday only) | $75 All-Weekend Loakals Pass

Comedy Brunch
• Saturday, Jan 24: https://square.link/u/krDMr7eL
• $50 Comedy/Music (Saturday only) | $75 All-Weekend Loakals Pass

01/08/2026

We’re kicking off 2026 with a little gift for you — our upcoming shows with Nick Murphy are now FREE!

Same great laughs, zero ticket cost. Grab your friends and start the year the right way!

📆 Friday, January 9 and Saturday, January 10
⏰ Music starts @ 6:00 PM
⏰ Comedy starts @ 8:00 PM

🚨 Ticket purchasers: please check your email for refund options

01/08/2026

ANNOUNCEMENT! Nick Murphy's shows FRIDAY and SATURDAY are now going to be FREE! Those who purchased tickets will get their option of a refund or to sit up in the mezzanine (VIP)!

Nick is a MONSTROUS talent who recently shook the country with his set on THE TONIGHT SHOW! Please tell your friends and come support this comic who will soon be one of the heavies in the industry. Here's more about him from our previous post:

"We are thrilled to announce our 2nd booking for “COUNTRY’S RISING STARS!” Please welcome NICK MURPHY on Jan 9th & 10th! Nick recently had one of the biggest sets on THE TONIGHT SHOW and is highly regarded as one of the country’s top up-and-comers!

The best part about what we’re building is sharing comedy culture with our hometown. Not just the biggest names in comedy, but the ones who will soon be! It’s a great feeling watching and seeing someone great before the rest of the world does.

We’ll see you January 9th and 10th!

The Tonight Show: https://youtu.be/mZxujMzWwbU?si=7BHwIMf1aUY24nz9

More about Nick below:

Nick Murphy is a stand up comedian originally from Atlanta, Ga now based out of Austin, Tx. He is a regular performer at Atlanta's Punchline Comedy Club and Laughing Skull Lounge as well as Austin's Comedy Mothership, having worked with acts including Ron White, Jim Jeffries, and Sean Patton. In 2025, he was selected for the Netflix Is A Joke 'Introducing' Showcase after performing at the 2024 Netflix Is A Joke & Moontower comedy festivals. Nick credits his abilities onstage to years of observation, life experience and hard work while his beautiful, supportive mother prefers to take all the credit herself.”

01/08/2026

TWO. WEEKS. AWAY. 😮‍💨 Grab your tickets today!

Winter Games Kickoff | Thursday, Jan 22: https://square.link/u/EpAEOk17

Comedy Brunch | Saturday, Jan 24: https://square.link/u/krDMr7eL