Bob's Trails End is more than just a dive bar on the corner of the street. Bob's Trails End represents the history of Oshkosh. This historic treasure was built in 1887 and is located right on Merritt Avenue and Broad Street. Bob Winkleman, who is the current owner, purchased the bar in 1985. When the bar was passed down to Bob, he inherited the legacy of the famous Trail’s End hot dogs. Before Bob had taken ownership of Trail’s End, the bar was formerly known as “Van’s” which was named after the previous owner Bill Vanderberg.
Van’s began their hot dog selling journey in 1926 and the bar has not looked back ever since. Randy Domer, an Oshkosh native and author, interviewed Bob Winkelman and asked him about the famous hot dogs. Bob told Randy that, “Van got the recipe for his hot dogs from a restaurant on Main Street that was going out of business….The secret is in the sauce.” That famous sauce that Bob is talking about is the chili sauce that gets drizzled on each dog along with a generous amount of fresh onions that will make you cry if your eyes get too close to them. When Bob became the owner he changed the name of the bar to what is known as “Bob's Trails End” today. Even though the name changed, the long lasting reputation of the hot dogs never left. In fact, these hot dogs were so popular, train passengers would call in advance to place an order when the train stopped by the bar. After hearing that, I had to see what Bob’s Trail’s End was all about!
As I walked into Bob's Trails End it’s like I traveled back in time. The barback was the same bar that was built in the late 1800s. It was cool to see how nothing in the bar had changed since Bob had bought it. The recipe that was used in the 1920s for the “secret sauce” is the same recipe they use today. The Bob's Trails End chili dog recipe is almost 100 years old! When I asked Bob more about Trials End, he told me that, “It has been a tradition that whenever older generations of Oshkosh families come to town, they meet at Bob's Trails End to hang out.” I then realized that this place is more than just a bar that serves chili dogs. Bob's Trails End is the epitome of Oshkosh tradition.
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