This Historic Supper Club Near Hayward Has Been Serving Legendary Prime Rib For Generations

Some dinners are worth slowing down for. The kind where the room feels familiar, the plates arrive hearty, and nobody seems in a hurry to leave.

In Wisconsin, old-school supper club tradition still has plenty of pull. These are the places built around generous steaks, fresh fish, comforting sides, and desserts that make skipping the last course nearly impossible.

The atmosphere stays warm and relaxed. Regulars know their favorites, while first-time visitors quickly understand why people return year after year.

A good evening here can turn an ordinary drive into part of the experience. Arrive early, settle in, and enjoy the rhythm as tables begin to fill and familiar orders start making their way from the kitchen.

This particular stop has earned its following the old-fashioned way. Dependable food, a welcoming dining room, and the kind of experience that makes planning another visit feel almost automatic.

A Northwoods Landmark With Deep Roots

Long before the area became a vacation destination for anglers and cabin owners, roadside supper clubs like Trailways on 27 Supper Club were the social centers of small northern towns.

Dinner out meant driving a county highway, parking on gravel, and walking into a dining room where the host knew half the tables by name.

That tradition still shapes the experience here. The building sits away from any busy commercial strip, surrounded by pines, with landscaping and a small garden area near the entrance that regulars have appreciated for years.

You will notice the northwoods decor right away. Warm wood, cozy lighting, and a comfortable dining room give the space a settled feeling rather than a designed one.

What I find appealing is how the place has evolved without losing its character. Newer ownership has invested in the kitchen and menu while keeping the supper club rhythm intact.

If you are traveling through Sawyer County in Wisconsin, this is the kind of stop that anchors an evening. You come for dinner, but you also get a sense of how people up here have eaten out for generations.

Prime Rib That Regulars Plan Their Week Around

Ask around the northwoods about a proper cut of beef and the conversation turns quickly to prime rib. At Trailways on 27 Supper Club, the prime rib and ribeye come from Creekstone beef, a name the kitchen stands behind, and the prime rib and ribeye are made with Creekstone beef.

That matters more than you might think. Cutting on site lets the kitchen control thickness and trim, which is why people drive in specifically for the beef.

On Saturdays, you can order prime rib as a full dinner, and a prime rib sandwich also appears as a special at times. Both give you that slow roasted flavor with a savory crust on the outside.

My advice is simple. Decide your doneness before you sit down, since a thick cut cooks differently than a quick pan seared steak, and ask your server what sizes are available that evening.

Popular cuts can sell out on busy nights, especially during summer and holiday weekends in Wisconsin. Arriving close to opening gives you the best shot at getting exactly the cut you came for.

The Friday Fish Fry Everyone Talks About

Fish fry is close to a state holiday in Wisconsin, repeated every single week, and this dining room takes it seriously. The all-you-can-eat fish fry, offered on Wednesdays and Fridays at Trailways on 27 Supper Club, is the most talked-about item on the menu, and for good reason.

Battered pollock arrives light and crispy, served family style with thick steak fries, creamy coleslaw, and rolls. The portions are generous, and the servers keep an eye on your table so you can ask for another round of fillets.

Baked fish options are usually available too, which helps if someone at your table prefers something lighter than fried.

Here is my practical tip. Friday nights fill fast, and the dining room is not huge, so either call ahead for a reservation or plan to arrive right when doors open at 4 PM.

Coming early also means a calmer room, faster service, and first pick of tables. If you want the classic northern Wisconsin fish fry experience without a long wait, that early window is your best friend.

Walleye, Scallops, And Other Catches Worth Ordering

Beef gets the headlines, but the fish side of the menu deserves attention. Pan seared walleye shows up again and again as a favorite here, and it fits perfectly with a region built around lakes and fishing.

Walleye cheeks make an appearance as an appetizer, often paired with a cajun tartar sauce that gives the plate a gentle kick. Bacon wrapped scallops are another starter that regulars order without much debate.

Trailways on 27 Supper Club also runs steak and lobster combinations, which makes it a solid choice for anniversaries and milestone dinners when you want something a little more special.

If you are new to walleye, know that it is mild, flaky, and not fishy at all. It is one of the easiest ways to taste the northwoods on a plate.

I would suggest asking your server about the day’s specials before you decide. Kitchens up here work with what comes in fresh, and the specials board often holds the most interesting option of the night, especially during peak summer travel season.

Comfort Classics For Picky Eaters And Big Appetites

Not everyone at the table wants a giant steak, and that is where this menu quietly shines. Chicken parmesan comes in a generous portion with plenty of sauce over spaghetti, and chicken piccata brings a brighter, lemony option for anyone wanting something lighter.

Sandwiches hold their own too. A patty melt, a reuben, and burgers served with those thick steak fries give you a casual route through dinner without missing out on the supper club feel.

Deep fried chicken has long been a specialty of northern Wisconsin kitchens, and the version at Trailways on 27 Supper Club has earned praise for its crackly breading and juicy meat.

Kids meals are available, which makes this an easy pick when you are traveling with a mixed group of ages. Spaghetti with garlic bread tends to keep younger diners happy.

My honest take is that this flexibility is the reason large family groups do well here. You can seat nine adults and a couple of kids and everyone finds something they actually want to eat, which is harder to pull off than it sounds.

Desserts Worth Saving Room For

Save room. I mean it. The dessert lineup here surprises people who expect a standard roadside dinner ending.

Turtle cheesecake, grasshopper pie, key lime cake, and a tuxedo chocolate ganache cake have all built a following, and a tiramisu bomb shows up for anyone who likes coffee flavored desserts. Diners regularly say the sweets rival what you would find at a polished city restaurant.

Trailways on 27 Supper Club leans into this, and the owner has openly admitted a fondness for the dessert menu, which tells you it gets real attention rather than being an afterthought.

Here is a strategy I recommend. If you are ordering an all you can eat fish fry, pace yourself with the fillets so you still have room for a slice. Sharing works well too. Order two desserts for the table and pass forks around, which lets everyone try more than one flavor.

Dessert selections can rotate, so glance at what is available when you arrive. Ending a northwoods Wisconsin dinner with a rich slice of cheesecake is a fine way to close the evening.

Finding The Place And Planning Your Visit

Getting here is part of the fun, since the drive takes you along quiet county roads rather than a crowded main street. You will find Trailways on 27 Supper Club at 16021 County Hwy K, Hayward, WI 54843, a short drive from town and easy to reach with plenty of parking out front.

Hours are straightforward. The dining room serves Tuesday through Thursday from 4 PM to 8 PM, and Friday and Saturday from 4 PM to 9 PM.

Because seating is limited, reservations are a smart move, especially on weekends and holidays. You can call ahead, and the staff has a track record of fitting in last minute requests when they can.

Arriving at 4 or 4:30 has real advantages. You skip the rush, get seated quickly, and have the full menu in front of you before popular items run low.

If you are staying at a cabin or resort in the Hayward area, build the drive into your evening plan. Takeout orders are handled here as well, which helps on nights when you would rather eat by the lake.

Why This Supper Club Still Earns The Drive

Traditions last when they keep giving people a reason to return.

Between the in house cut Creekstone beef, the family style fish fry, and a dessert case that punches above its weight, Trailways on 27 Supper Club has built a menu that fits both a quick weeknight dinner and a special occasion.

The staff plays a big role in that. Servers here tend to be attentive and quick with recommendations, and the owner is often on the floor greeting guests and seating tables himself.

You get a genuine supper club experience without pretense. Comfortable seating, hearty plates, and a room where conversation flows easily.

My suggestion is to treat it as a destination rather than a stop. Book a table, arrive early, order the prime rib or the walleye, and let dinner stretch out.

Northern Wisconsin has plenty of places to eat, but few carry this much history along a single county highway. Next time you are near Hayward with an appetite and an open evening, point the car toward County Hwy K and see what generations of diners already figured out.