Cozy Winter Date Night in Lake Geneva: Dinner at Brandy’s Old Fashioned
Winter Date Nights Just Got Better at Brandy’s Old Fashioned Supper Club in Lake Geneva!
Winter in Lake Geneva has a certain magic. The crisp air, glowing lights, and that unmistakable feeling that the best part of the night is waiting somewhere warm. If you’re planning a cozy winter date night in Lake Geneva, there’s one plan that never misses: a little stroll, a little sparkle, and a classic Wisconsin supper club dinner at Brandy’s Old Fashioned.
Because when it’s cold outside, your date night deserves the perfect mix of comfort food, candlelight vibes, and a brandy old fashioned that feels like a warm hug in a glass.
Start with a winter stroll in Lake Geneva
One of the best things about a Lake Geneva winter date is how easy it is to make the night feel special without over-planning it. Bundle up and take a short walk through downtown, admire the seasonal charm, and let the chilly air work up your appetite for a cozy dinner!
Pro tip: Winter dates are all about contrast. Cold outside, warm inside. That’s the recipe.
Step into a classic Wisconsin supper club
Brandy’s Old Fashioned brings the timeless supper club experience to Lake Geneva with all the details that make a night feel like an occasion. A welcoming bar, a cozy dining room, nostalgic touches, and the kind of hospitality that makes you want to linger.
Whether you’re celebrating something big or just craving a midwinter night out, this is the kind of place where “just dinner” turns into a memory.
The must-order for chilly nights: French onion soup
If you only order one thing to start your winter dinner at Brandy’s, make it the French onion soup.
It’s rich, savory, and deeply comforting. The kind of soup that instantly makes you feel like you chose the right restaurant on the right night. Perfect for sharing, perfect for warming up, and perfect for that first “mmm” moment that sets the tone for the whole date.
Pair it with a brandy old fashioned
A Lake Geneva supper club date night isn’t complete without the signature classic: a brandy old fashioned.
At Brandy’s, this isn’t just a cocktail, it’s part of the experience. There is a reason it became the Wisconsin State Drink in 2023! Whether you like it sweet or sour, it’s the ideal winter pairing for cozy conversation, slow dinners, and that “let’s order one more round” energy.
Make it a full supper club night
Depending on the day you visit, you can lean into the best of Wisconsin supper club tradition:
Friday Fish Fry for a classic end-of-week date ritual
Prime rib for the ultimate cozy, celebratory vibe of a Saturday night out
Your favorite supper club sides and comfort-food staples like Brandy's Broasted Chicken with loaded mashed potatoes!
This is the kind of menu built for winter: hearty, nostalgic, and ridiculously satisfying.
Save room for something sweet
A great date night ends with dessert (and maybe a final nightcap if you’re feeling it). The best winter dates aren’t rushed. They’re the kind where you look up and realize you’ve been talking for two hours without checking the time.
Your cozy winter date night plan (simple & perfect)
If you want an easy plan that feels thoughtful:
Dress warm and do a short stroll in town to check out the ice sculptures, lighted displays and markets.
Head to Brandy’s Old Fashioned for cocktails
Start with French onion soup
Choose fish fry or prime rib
End with dessert and one last toast
That’s it. That’s the winter date-night formula.
Reserve your table
Winter weekends in Lake Geneva can be bustling, and the coziest tables tend to go fast. If you’re planning a date night, reservations are always a good idea.
https://www.toasttab.com/local/order/brandys-old-fashioned-w3230-south-lake-shore-drive
Because the only thing better than a romantic supper club evening is knowing your seat is ready when you walk in from the cold.
FAQ: Cozy Winter Date Night at Brandy’s Old Fashioned
What is the best winter date night restaurant in Lake Geneva?
Brandy’s Old Fashioned is a go-to winter date night spot in Lake Geneva for classic Wisconsin supper club vibes, cozy cocktails, and comfort food that feels perfect on a cold night.
Where can I get French onion soup in Lake Geneva?
You can enjoy rich, cheesy French onion soup at Brandy’s Old Fashioned, a favorite starter for cozy winter dinners in Lake Geneva.
Is Brandy’s Old Fashioned a Wisconsin supper club?
Brandy’s Old Fashioned celebrates the classic Wisconsin supper club experience with brandy old fashioneds, comfort-forward dishes, and a warm, nostalgic atmosphere in Lake Geneva.
Do you serve fish fry every night?
Yes! Brandy’s Old Fashioned serves fish fry every night, making it an easy and delicious choice for a Lake Geneva dinner any day of the week.
When do you serve prime rib in the winter?
During winter, Brandy’s Old Fashioned serves prime rib on Saturdays, a perfect choice for a special, cozy weekend date night.
What should we order for a winter date night at Brandy’s?
Start with French onion soup, order a brandy old fashioned, and choose either our nightly fish fry or Saturday winter prime rib for a classic supper club dinner. Broasted chicken is also one of our customers' and staff's favorite dishes.
Should we make a reservation?
Reservations are recommended, especially for winter weekends and Saturday prime rib nights.
Is Brandy’s good for couples?
Yes. Brandy’s is ideal for couples looking for a relaxed, romantic dinner in Lake Geneva with classic cocktails and cozy supper club charm.
Brandy’s Old Fashioned: Lake Geneva Supper Club featured in At The Lake Magazine
Brandy’s Old Fashioned, a vintage-inspired Lake Geneva supper club on South Lakeshore Drive, was recently featured in At The Lake magazine. Discover our Wisconsin fish fry, broasted chicken, classic brandy old fashioneds, and timeless supper club atmosphere.
Brandy’s Old Fashioned: Lake Geneva’s “New Classic” Supper Club
There’s something special about walking into a true Wisconsin supper club. The lights are warm, the bar is buzzing, and dinner feels less like a meal and more like an evening you’ll talk about for years. That experience is exactly what Brandy’s Old Fashioned set out to create in Lake Geneva and it’s already getting noticed.
We’re honored that Brandy’s Old Fashioned was recently featured in At The Lake magazine’s Winter 2026 issue, highlighting our old-school atmosphere, classic supper club menu, and deep roots in Wisconsin tradition.
Located on South Lakeshore Drive, just minutes from downtown Lake Geneva, Brandy’s Old Fashioned is a cozy neighborhood spot for locals and lake lovers looking for a true Wisconsin night out (relish tray, old fashioned, and all)!
A Love Letter to Wisconsin Supper Clubs
Owner Brian Reynolds grew up visiting Wisconsin supper clubs across the state. Some of his favorite family memories are enjoying special supper club meals. Brandy’s Old Fashioned is his “love letter” to those memories and to the supper clubs that inspired them. When a space became available in Lake Geneva, Brian saw the opportunity to build a place where families, friends, and visitors could create their own traditions right here in Lake Geneva. A space to grab a Friday fish fry before the game, enjoy prime rib on date night, or sip on a Brandy Old Fashioned at the bar after a day on the lake.
Stepping Back in Time on South Lakeshore Drive
One of the first things At The Lake highlighted was the feeling you get when you walk through our front door: like stepping straight into the “good old days.”
To create that timeless look, the Reynolds family spent months driving around Wisconsin, hunting through antique stores and secondhand shops for just the right pieces. Both Brian and his wife Elizabeth have their favorites among the vintage finds: Elizabeth loves a 1940s family portrait for a sweet elderly couples’ 50th wedding anniversary. Brian can’t decide amongst the vintage beer signs which is his favorite! Adding to the design includes vintage fishing gear, old camping lanterns, framed historic photos, and classic beer and liquor memorabilia. Those finds now line the walls and shelves, giving the dining room and bar that “this place has been here forever” charm, even though Brandy’s is one of Lake Geneva’s newest supper clubs.
From the tin ceiling and cozy booths to the glow of the back bar, every detail is designed to make guests feel like they’ve slipped into a familiar, comforting spot that’s been part of the community for decades.
Classic Lake Geneva Supper Club Menu
At Brandy’s Old Fashioned, we keep the food as classic as the décor. Every meal begins with a complimentary relish tray because in Wisconsin, that’s just how supper clubs do it.
From there, our menu leans into the dishes guests expect from a Lake Geneva supper club, including:
Wisconsin Fish Fry served every night of the week
Hand-cut steaks like filet and ribeye
Bone-in pork chop, seasoned and grilled
Broasted chicken that quickly developed its own following after we opened
Bacon wrapped scallops cooked to perfection
We round things out with hearty sides and classic supper club staples, all meant to pair perfectly with an old fashioned or an ice-cold beer.
Save Room for Dessert (and an Ice Cream Drink)
No Wisconsin supper club experience is complete without something sweet. Brandy’s offers a rotating selection of homemade pies and desserts, plus the ice cream cocktails that so many guests remember from childhood trips “up north.”
One highlight from the At The Lake feature: our Grasshopper. The writer called it the best they’ve ever had! It is minty, creamy, and the perfect way to finish a classic Lake Geneva supper club meal.
Whether you’re sharing a slice of pie with the table or sipping an ice cream drink at the bar, dessert at Brandy’s is designed to be nostalgic, cozy, and a little bit indulgent. When in Wisconsin!
Old Fashioneds and New Memories in Lake Geneva
While Brandy’s Old Fashioned is one of Wisconsin’s newer supper clubs, many guests tell us it feels like we’ve been here for generations and that’s exactly the point. Between the vintage décor, the classic Lake Geneva fish fry, the broasted chicken, and the brandy old fashioneds, we want every visit to feel like a cherished ritual.
We’re grateful to At The Lake magazine for capturing that spirit in their feature and for helping share the story of Brandy’s with even more people who love this community as much as we do.
If you’re searching for a Lake Geneva supper club where you can unwind after a day on the water, celebrate a special occasion, or simply enjoy a classic Wisconsin dinner with family and friends, we’d love to welcome you.
Plan Your Visit to Brandy’s Old Fashioned
Join us at Brandy’s Old Fashioned for:
Classic Wisconsin Brandy Old Fashioneds
Complimentary relish trays
Nightly fish fry and broasted chicken
Homemade pies and ice cream cocktails
A warm, vintage supper club atmosphere on South Lakeshore Drive
Make your reservation, bring your favorite people, and come create old fashioneds and new memories in Lake Geneva, Wisconsin.
Check out the At The Lake article about Brandy’s Old Fashioned here: https://atthelakemagazine.com/brandys-old-fashioned-supper-club/