Sometimes at Pioneer Island

Sometimes at Pioneer Island 🌴 Island vibes on Pioneer Island
🍹 Cold drinks | 🛥️ Waterfront views
🎶 Live music every weekend
📍1000 Pioneer Dr, Oshkosh, WI
⏰ Open Thurs–Sun, 11 AM–11 PM

We're more than just a bar; we're an experience. Nestled on the picturesque Pioneer Island, we offer a unique blend of chilled drinks, fresh air, and an unforgettable marina vibe. Kick back with a cold beer in hand as you watch boats drift by on the serene waters. With panoramic sunset views, you're in for a visual treat! Whether you're a boating enthusiast, a cocktail aficionado, or just someone looking to escape the hustle and bustle of daily life, we've got a seat with your name on it!

08/07/2026

POV: You just entered the Main Gate at XRoads41 and are looking for the Sometimes Stage! Stop by and say Hi! It’s always good vibes at Sometimes 🎶🍺

Happy hour starts soon, the Brewers are on, and the weather is perfect!!! Come spend your pre-weekend with us at Sometim...
08/06/2026

Happy hour starts soon, the Brewers are on, and the weather is perfect!!! Come spend your pre-weekend with us at Sometimes!

🕚11-11
🥨12-8
♟️Yard games
📍1000 Pioneer Dr Oshkosh, WI

08/06/2026

James Anderson is our first winner!!!
Good news, contest round two coming up! We have two XRoads41 Rock Detour tickets to give away!

🎟️ WIN 2 ROCK DETOUR TICKETS! 🎟️

We all have that one friend who’s always down for live music…

Tag them below and tell us why they’re your ultimate concert buddy!

❤️ Like this post
🌴 Follow Sometimes
👥 Tag your concert buddy
🎸 Tell us why you’re bringing them

We’ll pick one lucky pair Saturday by Noon!

Good times start at Sometimes and XRoads! 🍻🎶

Consider your plans, planned!! Check out what we have going on at Sometimes this week!🕚Thursday through Sunday 11-11🥨Thu...
08/05/2026

Consider your plans, planned!! Check out what we have going on at Sometimes this week!

🕚Thursday through Sunday 11-11
🥨Thursday through Sunday 12-8
🐟Friday Fish Fry Friday 12-8
🧘🏽‍♀️Yoga with Simply Yoga, LLC Saturday 8:30 am
🎶Joe & Jannis Saturday 3-6
🎶Kevin’s KO Band Sunday 2-5
🎶On site at XRoads41 Tonight-Sunday (Two bars, stop and say hi if you’re there!!)
📍1000 Pioneer Dr Oshkosh, WI

It’s XRoads41 time!!! We will be on site in TWO locations this year!! Come see us in the campground and inside on the gr...
08/04/2026

It’s XRoads41 time!!! We will be on site in TWO locations this year!! Come see us in the campground and inside on the grounds!
(Don’t worry, our hours are still normal for the week at Pioneer Dr!)

Now, who’s ready for some fun!?

🎟️ WIN 2 GA TICKETS! 🎟️

We all have that one friend who’s always down for live music…

Tag them below and tell us why they’re your ultimate concert buddy!

❤️ Like this post
🌴 Follow Sometimes
👥 Tag your concert buddy
🎸 Tell us why you’re bringing them

We’ll pick one lucky pair Thursday by 10 am!

Good times start at Sometimes and XRoads! 🍻🎶

Helping people is what it is all about!! Thank you Service League of Oshkosh for being awesome!
08/04/2026

Helping people is what it is all about!! Thank you Service League of Oshkosh for being awesome!

Update to our previous post from our celebrity bartending event-
Sometimes at Pioneer Island graciously matched our tip total! Because of their amazing gift, we will be donating $3360 to those in need of assistance in Menasha.
Thank you again to all those who joined us and tipped for great cause!!

Who had a great weekend!? We sure did!!Thank you to everyone who stopped by and spent part of your week/weekend with us!...
08/03/2026

Who had a great weekend!? We sure did!!

Thank you to everyone who stopped by and spent part of your week/weekend with us! Here are your weekly winners! Remember to stop in this coming week, let the staff know your photo was featured, and your first cold one is on us!!

📸 Reminder for our weekly feature!

Every Monday, we’ll pick 4 photos from customers who tagged us in their photos at Sometimes and share them on our page.

If your photo is selected, stop in starting Thursday of that week and we’ll have a Sometimes koozie filled with your favorite cold beverage waiting for you—on us!

Tag us in your posts, stories, and photos. We love seeing Sometimes out in the wild.

08/01/2026

We had to cancel the music for today, but we’re still OPEN!! Saturdays at Sometimes is the place to be 🚤

🕚11-11
🍔12-8
🍹Cocktails and mocktails
📍1000 Pioneer Dr Oshkosh, WI

Address

1000 Pioneer Drive
Oshkosh, WI
54902

Opening Hours

Thursday 11am - 11pm
Friday 11am - 11pm
Saturday 11am - 11pm
Sunday 11am - 11pm

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