Milwaukee's Best Old Fashioned [Updated 2025]

As I sipped my way through the heart of Brew City, I found myself on a mission—twelve of Milwaukee’s top spots beckoned with promises of the perfect old fashioned. Trust me, I’ve tasted every twist on this classic cocktail, from the smoky to the sweet, and I’ve come away with a treasure trove of favorites that’ll make your taste buds dance.

You know I take my cocktails seriously, and after countless hours in cozy bars and bustling taverns, I’ve honed in on the spots that truly elevate this iconic drink. Whether you're a lifelong fan or a curious newcomer, you're in for a treat as I unveil the ultimate contenders for the best old fashioned in Milwaukee.

Bryant's Cocktail Lounge

Highlights
Hidden gem atmosphere
Knowledgeable, interactive bartenders
No menu, personalized cocktails
Dim, romantic setting
Exceptional mixology skills

Bryant's Cocktail Lounge is a true hidden gem nestled in the heart of Milwaukee, exuding an old-school charm that's perfectly paired with their old-fashioned cocktails. From the moment I stepped inside, I was enveloped in the dim, romantic ambiance that sets the stage for an unforgettable evening.

What truly sets Bryant's apart is the experience—there's no cocktail menu here! Instead, the knowledgeable bartenders engage with patrons, asking questions to craft a personalized old fashioned tailored to your tastes. Mine arrived with a delightful twist, showcasing their exceptional mixology skills. Each sip resonated with rich flavors, accented by just the right amount of bitters and sweetness—the quintessential old fashioned experience.

These bartenders don’t just pour drinks; they create memories. They are interactive and eager to share their expertise, making you feel like a part of the cocktail-making process. The meticulous craftsmanship in my drink was evident, and I couldn’t help but appreciate the artistry that goes into each glass.

In a city known for its bar culture, Bryant's Cocktail Lounge stands tall. If you're in the mood for an old fashioned that combines tradition with a touch of personalized flair, this is the place to visit. Cheers!

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Boone & Crockett

Highlights
Lakeside seating
Chill, laid-back atmosphere
Perfectly mixed drinks
Dog friendly
Convenient online pickup

With an inviting lakeside ambiance, Boone & Crockett effortlessly marries relaxation with a top-notch cocktail experience. As I settled into the chill, laid-back atmosphere, I could feel my worries dissolve with each sip of their renowned old fashioned. This isn’t just any drink; it's a symphony of flavors, perfectly mixed to highlight the rich notes of bourbon while harmonizing with bitters and orange peel—a true work of art in a glass.

What truly sets Boone & Crockett apart—beyond just the drink—is their commitment to creating a welcoming environment. The dog-friendly policy means you can enjoy your evening with your furry friend by your side. To top it off, the convenience of online pickup allows you to take the magic home.

Every element at Boone & Crockett combines to create an experience that is both professional and playful, making it a must-visit for old fashioned aficionados in Milwaukee. So, whether you prefer to sip your cocktail while gazing at the shimmering lake or cozied up at the bar, you’re guaranteed to savor an old fashioned that’s been crafted with care. Cheers to that! 🍸

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The New Fashioned - A Bars & Recreation Experience

Highlights
Great for corporate events
Attentive and helpful staff
Fast food and drink service
Fun activities like Hyper Bowling
Cashless payment convenience

The New Fashioned in Milwaukee is an absolute gem where classic cocktails meet modern fun. As soon as I stepped in, I was greeted by an atmosphere that perfectly balances playfulness and sophistication. The lively vibe is accentuated by the delightfully attentive staff, who seemed genuinely invested in crafting the perfect drink for each guest.

Now, let's talk about their Old Fashioned. The blend of flavors was nothing short of transcendent. The bourbon was smooth, with just the right amount of sweetness from the muddled sugar and bitters. Each sip transported me to a nostalgic realm while still feeling refreshingly contemporary. The garnish—a bold orange twist—was a delightful touch, enhancing both fragrance and flavor.

What truly sets The New Fashioned apart is its commitment to fun. While waiting for my drink, I indulged in some entertaining activities like Hyper Bowling, which added a unique twist to my experience. The cashless payment system made it hassle-free, allowing me to focus on savoring that rapturous cocktail.

For anyone seeking the ultimate Old Fashioned experience in Milwaukee, I wholeheartedly recommend visiting The New Fashioned. Cheers!

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Tied House Milwaukee

Highlights
Crafty cocktails
Hidden gem
Warm, inviting service
Exciting seasonal menu
Great location in Third Ward

Tied House Milwaukee is truly a hidden gem nestled in the vibrant Third Ward, and my visit was an absolute delight. As I walked in, I was greeted by warm, inviting service that instantly made me feel at home. The ambiance is cozy yet stylish, perfect for unwinding after a long day.

Now, let’s talk about the star of the show: the Old Fashioned. This cocktail is a meticulous blend of flavors that showcases the bartenders' mastery. It's not just an ordinary old fashioned; it's elevated with a thoughtful spin that reflects the season's bounty. Whether it’s some aromatic bitters or house-made bitters, every sip offers a delightful surprise.

What I adore about Tied House is their commitment to crafty cocktails that keep the menu fresh and exciting—each visit offers something new to discover. They truly take pride in their craft, and it shines through in the complexities of their old fashioned.

If you’re wandering around Milwaukee, don’t miss the chance to stop by Tied House. Their Old Fashioned might just be your new favorite, proving that Milwaukee holds some of the finest old fashioneds out there. You’ll leave with a smile and a heart warmed by good company.

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At Random

Highlights
Exceptional bartending skills
Spectacular atmosphere
Charming and cute ambiance
Variety of unique drinks
Repeat visit favorite

At Random in Milwaukee is a delightful gem that deserves a spotlight in any exploration of the best old fashioned cocktails in the city. Upon stepping inside, I was immediately taken by the charming and cute ambiance that envelops you like a warm hug. It’s the kind of place that invites you to linger, sip, and enjoy.

The bartenders here possess exceptional skills that are evident the moment you observe their craft. They treat mixology as an art form, and their mastery shines through in every cocktail. I was particularly impressed with the variety of unique drinks available, each offering a twist on the classic while still holding true to its roots.

Now, the star of the show—the old fashioned. It was perfectly balanced, with just the right amount of bitterness and sweetness, making it an instant favorite of mine. I could easily envision returning for another round, and perhaps sharing a drink with friends in their inviting atmosphere. If you're on the hunt for a memorable old fashioned in Milwaukee, At Random is an absolute must-visit that will make your taste buds dance with joy!

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The Wicked Hop

Highlights
Great outdoor seating
Tasty fish fry options
Attentive wait staff
Awesome atmosphere
Fair prices & menu variety

When I walked into The Wicked Hop, I was immediately taken by the vibrant atmosphere that perfectly encapsulates the spirit of Milwaukee. With great outdoor seating that beckons patrons on sun-drenched days, it's a place where you can savor the season. The wait staff was incredibly attentive, making me feel welcomed and eager to offer recommendations.

Now, let's talk about the star of the show—the Old Fashioned. With a playful twist on the classic, it brought together the perfect balance of sweetness and bitterness. The rich flavors danced on my palate, entwining beautifully with the hint of orange. It was clear that their mixologists take pride in their craft, ensuring that every sip was a delight.

While indulging in this delightful cocktail, I couldn’t resist sampling their tasty fish fry options, which paired remarkably well. Fair pricing and an extensive menu make The Wicked Hop a hot spot for anyone looking to enjoy a well-rounded dining experience. If you’re on a quest for the best Old Fashioned in Milwaukee, this vibrant gem should certainly make your list!

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The Estate

Highlights
Great service
Amazing cocktails
Vibrant live music scene
Unique art decor
Cozy and inviting atmosphere

The Estate Review

Nestled in the heart of Milwaukee, The Estate is a gem that combines a captivating atmosphere with stellar cocktails. As I stepped inside, I was immediately struck by the unique art decor that vibrates with character, setting an inviting tone for the night ahead. The ambiance, enhanced by a vibrant live music scene, creates a delightful backdrop for sipping classic cocktails.

Now, onto the star of the night: the old fashioned. Expertly crafted, this drink was a true testament to the skill of the bartender. I loved how the balance of sweet and bitter flavors danced on my palate. The muddled cherries and fresh orange peel added an aromatic twist that transported me to cocktail heaven.

The service was impeccable; the staff was knowledgeable and infused a sense of warmth that made me feel like part of the The Estate family. This place truly nails that cozy yet lively vibe that Milwaukeeans crave. If you find yourself wandering the streets of Milwaukee, don’t miss out on their amazing cocktails, especially the old fashioned—it's a local treasure you won’t soon forget!

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Experts Only MKE

Highlights
Phenomenal atmosphere
Attentive and friendly bartenders
Exceeds bar food expectations
Great live music
Welcoming community vibe

Experts Only MKE is a hidden gem nestled in the heart of Milwaukee that understands what it means to craft the perfect Old Fashioned. From the moment I stepped inside, I was enveloped by the phenomenal atmosphere—an inviting blend of vintage charm and contemporary flair. The bartenders, attentive and friendly, offered a level of service that made me feel like a cherished guest rather than just another patron.

Now, let’s talk about the drink itself: their Old Fashioned is nothing short of spectacular. Made with a deft hand, the balance of flavors—bitters, muddled orange, and a hint of sweetness—danced on my palate, capturing the essence of a classic while adding their unique spin. Each sip was a delightful reminder of why this cocktail is timeless.

To top it off, the bar offers fantastic live music, enhancing the welcoming community vibe that makes you want to settle in and enjoy the night. And their bar food? It far exceeds expectations—it’s the perfect accompaniment to a stunning Old Fashioned. If you’re seeking an incredible cocktail experience in Milwaukee, look no further than Experts Only MKE!

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The Vanguard

Highlights
Unique Thai dog experience
Mixed drinks on tap
Disappointing portion sizes
High prices for limited food
Service could improve

I recently found myself in the cozy embrace of The Vanguard, a charming gem tucked away in Milwaukee. Known for its unique Thai dog experience, the ambiance struck me as both playful and sophisticated—perfect for sipping on an old fashioned. As I settled into a seat, the expert bartender greeted me with a smile and effortlessly began crafting my drink.

The old fashioned arrived with a flourish; it was a work of art. The balance of whiskey and bitters was impeccable. I appreciated the thoughtful twist on this classic cocktail, which made it stand out from the myriad of versions I've tasted throughout the city. Additionally, having mixed drinks on tap was an unexpected treat that invigorated the experience.

However, it’s worth noting that the portion sizes of the accompanying food left something to be desired, and the prices were on the higher side. This combined with service that could benefit from a splash more attentiveness slightly dimmed my overall impression.

Nevertheless, if you find yourself wandering the Milwaukee streets, I wholeheartedly recommend grabbing an old fashioned at The Vanguard. It’s a delightful spot that marries creativity with craftsmanship, making it a noteworthy contender for the best old fashioned in town!

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Oak Barrel Public House

Highlights
Attentive and friendly service
Delicious butter fat popcorn
Spacious and accommodating space
Great food and burger options
Convenient downtown location

Nestled conveniently in downtown Milwaukee, Oak Barrel Public House is a gem that effortlessly combines comfort with quality. As soon as I walked through the doors, I was greeted by attentive and friendly service, which set the perfect tone for what was to come. To kick off my tasting adventure, I couldn’t resist indulging in their delicious butter fat popcorn—a delightful start that pairs surprisingly well with cocktails!

Now, let's talk about their old fashioned. This classic cocktail was executed with precision. The balance of sweet and bitter was spot-on, showcasing the signature whiskey infused with a hint of cherry and orange. It was undeniably a standout.

The atmosphere was spacious and accommodating, making it an ideal spot for both casual outings and celebratory gatherings. As I sipped my drink, I couldn't help but admire their impressive food menu, featuring mouthwatering burgers that seemed to beckon to me.

If you're on the hunt for the ultimate old fashioned experience in Milwaukee, look no further than Oak Barrel Public House. With excellent cocktails, delicious bites, and a welcoming vibe, you’ll leave with both a satisfied palate and a great story to tell! 🍹

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Lost Whale

At Lost Whale, the old fashioned is not just a drink; it’s an experience. The moment I took my first sip, I was greeted by a delightful balance of bitters and sweetness, enhanced by a twist of fresh citrus. The bartender’s expert craftsmanship shines through in their use of local spirits, giving it a uniquely Milwaukeean flair. Served with a charming cherry and a delicate orange peel, this classic cocktail exudes character. The cozy atmosphere complements the expertly mixed drink, making Lost Whale a must-visit for anyone seeking the perfect old fashioned in the city. Cheers to that! 🍊🥃

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The Tin Widow

At The Tin Widow, the old fashioned is a delightful twist on tradition. This cozy spot showcases a balance of smooth bourbon and a dash of aromatic bitters, creating a drink that whispers elegance. The addition of a playful house-made cherry adds a unique touch that elevates the experience. Each sip takes you on a journey through rich flavors—perfectly crafted for both old-fashioned purists and adventurous palates. The ambiance is warm and inviting, making it a fantastic spot to sip and savor. If you're in search of an exceptional old fashioned, definitely stop by The Tin Widow—you won't regret it!

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