Generations Lounge

Generations Lounge Relax with friends at our full service bar with over 50 beer varieties to choose from.
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09/03/2026

Bobby Stillwell is bringing the music to Generations Lounge tomorrow night! If you’ve never caught Bobby live, this is a great night to come check him out — guitar, keyboard, saxophone and a whole lot of talent!
📅 September 4
⏰ 6–9 PM
📍 Leo’s Generations Lounge
Grab some friends and come spend your Friday night with us! 💜🎶

🏈 Football Saturdays just got an upgrade at Generations!We’ve been making a few changes upstairs, and the timing couldn’...
09/02/2026

🏈 Football Saturdays just got an upgrade at Generations!
We’ve been making a few changes upstairs, and the timing couldn’t be better. 👀📺
With 3 brand-new TVs joining our big-screen projector, there’ll be plenty of ways to keep an eye on the action all season long.
Football is back — come spend game day with us at Leo’s Generations Lounge! 🏈🙌

Bobby Stillwell is bringing a little bit of EVERYTHING to Generations Lounge this Friday, September 4th! From guitar and...
09/01/2026

Bobby Stillwell is bringing a little bit of EVERYTHING to Generations Lounge this Friday, September 4th! From guitar and keyboard to saxophone and vocals, Bobby knows how to keep the music going and the crowd entertained. 🎷🎸🎹
🎶 Bobby Stillwell LIVE
📅 Friday, September 4th
⏰ 6–9 PM
📍 Leo’s Generations Lounge
Grab your crew, find a table, and kick off the weekend with some great live music! 🙌

🍂 FALL CAME EARLY AT GENERATIONS! 🍂Samuel Adams OctoberFest has officially arrived! 🍁🧡Who says we have to wait for the l...
08/29/2026

🍂 FALL CAME EARLY AT GENERATIONS! 🍂

Samuel Adams OctoberFest has officially arrived! 🍁🧡

Who says we have to wait for the leaves to change to get into the fall spirit? 😉

📍 Generations Lounge | Oelwein
🔞 21+ • Please enjoy responsibly.

🍕 THURSDAY = PIZZA DAY! 🍕Grab a 12" 1-topping pizza for just $9.99 + tax! 🙌Choose thin crust or deep dish — dine in or c...
08/27/2026

🍕 THURSDAY = PIZZA DAY! 🍕

Grab a 12" 1-topping pizza for just $9.99 + tax! 🙌
Choose thin crust or deep dish — dine in or carry out!

🕓 Open at 4PM
🍕 Kitchen Closes at 9PM
⬆️ Elevator available to get upstairs

Come hungry! 💜
Leo’s Generations Lounge
Oelwein, Iowa

👀 LOOK what’s happening this September at Generations Lounge!You’re gonna want to save this one. 😉🎶🎤🧠
08/24/2026

👀 LOOK what’s happening this September at Generations Lounge!

You’re gonna want to save this one. 😉🎶🎤🧠

THIS WEEK AT GENERATIONS LOUNGE!🍕 WEDNESDAY & THURSDAY PIZZA SPECIAL12" 1-Topping Pizza — ONLY $9.99!✨ Deep Dish OR Thin...
08/19/2026

THIS WEEK AT GENERATIONS LOUNGE!

🍕 WEDNESDAY & THURSDAY PIZZA SPECIAL
12" 1-Topping Pizza — ONLY $9.99!
✨ Deep Dish OR Thin Crust
✨ Dine-In OR Carry-Out

Then Saturday night, it's time to grab the mic! 🎶

🎤 KARAOKE WITH B-RAD
📅 Saturday, August 22nd
⏰ 8 PM – Midnight

🍕 Pizza Wednesday & Thursday.
🎤 Karaoke Saturday.
Sounds like a pretty good week to us!

📍 Generations Lounge
Oelwein, Iowa

🧠✨ WHAT A NIGHT! ✨🧠A HUGE thank you to everyone who came out for Trivia Night last night at Generations Lounge! We loved...
08/13/2026

🧠✨ WHAT A NIGHT! ✨🧠

A HUGE thank you to everyone who came out for Trivia Night last night at Generations Lounge! We loved seeing everyone putting their knowledge to the test, having some laughs, and battling it out for the win. 💚💙

🏆 Congratulations to our August Winner — THE FANTASTIC FOUR! 🏆

Missed this one? Don't worry — you've got another chance!

📅 NEXT TRIVIA NIGHT
🧠 Wednesday, September 9th
⏰ 6:30–8:30 PM
📍 Generations Lounge
🎤 Hosted by the Trivial Dudes

Thank you again for making our first Trivia Night such a fun one. We can't wait to do it again! 💙

Whether you’re celebrating a birthday, anniversary, thank-you, or just because, a Leo’s gift card makes it easy to treat...
08/09/2026

Whether you’re celebrating a birthday, anniversary, thank-you, or just because, a Leo’s gift card makes it easy to treat someone special. 🖤
🍁 Available in any amount
🍁 Perfect for friends, family, teachers & coworkers
🍁 Great for upcoming fall celebrations — and it’s never too early to start thinking about the holidays!
Stop in and grab yours at Leo’s Italian Restaurant & Generations Lounge.
Good food. Good times. One easy gift. 🎁🍂

Address

29 Frederick Avenue S, Fl 2nd
Oelwein, IA
50662

Opening Hours

Wednesday 4pm - 10pm
Thursday 4pm - 10pm
Friday 4pm - 2am
Saturday 4pm - 2am

Telephone

+13192831655

Website

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