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Oshkosh Waterfront Bar

A chair on a sidewalk by a body of water

From the Shores of Lake Winnebago

The Pioneer Inn & Marina stood for decades as an iconic Oshkosh location and the waterfront area has been reimagined to provide an incredible on-the-water experience for friends and family. Sometimes at Pioneer Island is a brand-new waterfront bar and a highlight of the beautiful Lake Winnebago waterfront that promises a one-of-a-kind experience for those who want to enjoy a cocktail on the water in the heart of the Fox Valley.

Featured Drinks

Cruise on into Sometimes at Pioneer Island this boating season, kick back and enjoy a refreshing summer cocktail, your favorite craft beer, or a glass of wine. Sometimes is a premier waterfront bar in Oshkosh, WI on the shores of Lake Winnebago and a short boat ride from the mouth of the Fox River. Sometimes, you just need to sit back, relax, kick your feet up, and enjoy a cold beer on a warm summer day right on the water – and Sometimes at Pioneer Island is the perfect place.

A glass with ice and a lime wedge
A glass with a straw filled with a red liquid

Food at Sometimes

Do you need a quick bite to eat after a long day on the water? Sometimes at Pioneer Island features a gourmet menu with food provided by our friends at Pilora’s Food Truck. A brilliant menu features Carne Asada Breakfast Burritos, the signature Pilora’s Lobster Roll, and much more to tantalize your taste buds. Take a break from your weekend boat ride and enjoy a Pilora’s Lobster Roll with a refreshing Spotted Cow – there is nothing better.


A white foodtruck with paint splatters on the side

Let’s Get Social

The Sometimes at Pioneer Island provides local residents with beautiful waterfront views, a fun atmosphere, a drink menu that includes all of your favorites, and gourmet food from a local food truck. Stop in at Sometimes at Pioneer Island – you do not want to miss out on this Oshkosh waterfront experience.
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