Chicago

Chicago to Hayward

Sights & Landmarks

Tours

Nature & Parks

Water & Amusement Parks

Museums

Fun & Games

Outdoor Activities

Nightlife

Concerts & Shows

Shopping

Spas & Wellness

Other

Hayward

Calling all road trip enthusiasts! Get ready for an epic adventure from the bustling metropolis of Los Angeles to the charming city of Madison. This cross-country journey will take you through diverse landscapes, from sun-drenched beaches to rolling hills and vibrant cities. Along the way, you'll discover hidden gems, create unforgettable memories, and witness the beauty of the American heartland.
Prepare to be amazed by the towering skyscrapers and iconic landmarks of Los Angeles, a city that embodies the glamour and excitement of Hollywood. As you drive eastward, the scenery gradually transforms into picturesque valleys, vast deserts, and rugged mountain ranges. Embrace the tranquility of nature as you traverse the awe-inspiring landscapes of the American West.
Your journey culminates in the vibrant city of Madison, known for its beautiful lakes, charming neighborhoods, and world-renowned university. Immerse yourself in the city's rich culture, explore its vibrant arts scene, and savor the delicious local cuisine. As you bid farewell to Madison, you'll carry with you the memories of an incredible road trip that will leave a lasting impression.

Los Angeles

Los Angeles to Madison

Traveler Resources

Madison

Chicago to Appleton

Classes & Workshops

Food & Drink

Appleton

This amazing road trip is full of beautiful scenery and one-of-a-kind places to see. You’ll pass by serene lakes, rolling green hills, and charming small towns. Along the way, there are plenty of opportunities to stop and take in the sights or grab a bite to eat at a local restaurant.
Once you reach your destination, you’ll have plenty to keep you entertained. You could explore the area's many museums, take a walk through the picturesque downtown, or catch a thrilling sporting event. No matter what you choose to do, you're sure to have an unforgettable adventure.
The drive itself is approximately 227 miles and takes about 3 hours and 30 minutes without stops. So, sit back, relax, and enjoy the ride. The journey is just as exciting as the destination!

Chicago to Green Bay

Green Bay

Get ready for an unforgettable adventure as we embark on a breathtaking journey from Columbus to Madison! This incredible road trip will take us through picturesque landscapes, charming towns, and fascinating historical sites. Along the way, we'll discover hidden gems, learn about the rich history of the region, and create memories that will last a lifetime.
As we make our way through the rolling hills and vibrant countryside, we'll encounter friendly locals, savor delicious local cuisine, and immerse ourselves in the unique culture of the area. Whether you're an avid history buff, a nature enthusiast, or simply seeking a fun-filled adventure, this road trip has something for everyone.
Get ready to embark on a journey that will ignite your imagination and leave you with a newfound appreciation for the beauty and diversity of the Midwest. So buckle up, pack your bags, and let's hit the open road for an unforgettable experience!

Columbus

Columbus to Madison

Events

Hop aboard an exciting adventure as we embark on a memorable journey from the bustling metropolis of Chicago to the charming city of Milwaukee. Along the way, we'll traverse a scenic landscape that unfolds like a vibrant tapestry, capturing the essence of the Midwest's natural beauty. Verdant fields dance in rhythm with the gentle breeze, while sparkling rivers meander through the countryside, creating a breathtaking panorama that will leave you mesmerized.
As we journey further along this captivating route, the urban sprawl gradually gives way to tranquil towns and quaint villages, each with its unique character and charm. Historic buildings whisper tales of the past, while modern marvels stand tall as testaments to progress. The air fills with the sweet scent of blooming flowers and the cheerful melodies of birdsong, creating a symphony that uplifts the spirits.
Our destination, Milwaukee, awaits us with open arms, promising an abundance of cultural and recreational treasures. From its renowned art museum to its vibrant culinary scene, Milwaukee offers a kaleidoscope of experiences that cater to every taste and preference. Immerse yourself in a world of discovery, where history intertwines with innovation, and where the spirit of the Midwest shines brightly.

Chicago to Milwaukee

Milwaukee

Prepare to embark on an awe-inspiring adventure across the heartland of America, from the vibrant shores of San Francisco to the bustling streets of Milwaukee. This epic journey will span vast landscapes, introducing you to the rich tapestry of the United States. You'll traverse towering mountains, meander through serene valleys, and witness the boundless beauty of nature's artistry. Along the way, you'll encounter charming towns and bustling cities, each with its unique character and captivating stories to share.
As you journey eastward, you'll delve into the untamed wilderness, where towering trees stand sentinel and crystal-clear rivers dance through verdant meadows. The air will fill with the sweet melody of birdsong, creating a symphony that will soothe your soul. You'll marvel at the grandeur of nature's creations, from majestic mountains reaching towards the heavens to delicate wildflowers that paint the ground in vibrant hues.
As you approach your destination, the landscape will gradually transform, giving way to rolling hills and fertile farmlands. You'll pass through vibrant cities where skyscrapers pierce the sky and the energy of commerce fills the streets. The aroma of freshly baked goods will waft through the air, tempting you with delectable treats that will delight your taste buds. As you arrive in Milwaukee, you'll be greeted by the shimmering waters of Lake Michigan, a breathtaking backdrop to the city's vibrant spirit.

San Francisco

San Francisco to Milwaukee

Get ready for an incredible adventure as we take a journey from the bustling hub of Houston to the vibrant city of Milwaukee. Along the way, we'll traverse vast landscapes, marvel at majestic sights, and explore hidden gems. From the vibrant streets filled with music and culture to the serene shores of shimmering lakes, each destination promises an unforgettable experience.
As we embark on this expedition, we'll encounter friendly locals who will captivate us with their stories and traditions. We'll immerse ourselves in the rich history and heritage that shaped these cities, discovering the tales of pioneers and dreamers who left their indelible mark. Along the way, we'll indulge in delectable cuisines, tantalizing our taste buds with flavors that reflect the diverse cultures we encounter.
But it's not just about the destinations; it's about the journey itself. We'll make memories that will last a lifetime, filled with laughter, adventure, and the spirit of discovery. Whether you're a seasoned traveler or embarking on your first great escapade, this expedition will ignite your imagination and leave you longing for more. Are you ready to embrace the call of the open road and create stories that will be cherished for years to come? Let's hit the road and embark on an extraordinary adventure!

Houston

Houston to Milwaukee

Get ready for an exciting adventure as we travel from the vibrant city of Detroit to the charming city of Milwaukee! Our journey will take us through picturesque landscapes, bustling towns, and along the sparkling waters of Lake Michigan. Along the way, we'll discover hidden gems, learn about the region's rich history, and create memories that will last a lifetime.
Our adventure begins in the heart of Detroit, where towering skyscrapers and bustling streets tell the story of a city on the rise. From here, we'll set out on our journey, winding our way through the rolling hills and lush forests of Michigan. As we cross the state line into Wisconsin, the scenery transforms into a tapestry of dairy farms and charming small towns. The vibrant colors of autumn leaves will paint the landscape in hues of gold, orange, and crimson, creating a breathtaking backdrop for our travels.
As we approach Milwaukee, the sparkling waters of Lake Michigan will come into view. The city's skyline, dotted with historic buildings and modern skyscrapers, will welcome us to our final destination. Milwaukee's rich German heritage is evident in its architecture, cuisine, and lively festivals, making it a perfect place to end our adventure and celebrate the journey we've shared.

Detroit

Detroit to Milwaukee

Get ready for an epic road trip from the sunny shores of San Jose to the vibrant city of Milwaukee! This adventure will take you across diverse landscapes, from towering mountains to rolling hills and shimmering lakes. Along the way, you'll discover hidden gems, explore bustling cities, and create memories that will last a lifetime.
Buckle up and prepare for a journey filled with endless possibilities. The open road awaits, promising new adventures at every turn. Embrace the freedom to explore at your own pace, stopping to soak in the beauty of nature or delve into the rich history and culture of each destination. From the vibrant streets of San Jose to the charm of Milwaukee, this road trip will ignite your imagination and leave you with a heart full of unforgettable experiences.
As you embark on this grand adventure, remember to savor every moment. The journey itself is just as important as the final destination. Embrace the unexpected detours, the spontaneous discoveries, and the countless stories you'll gather along the way. Let the open road guide you, and create memories that will warm your heart for years to come.

San Jose

San Jose to Milwaukee

Hop aboard and get ready to explore the vibrant landscapes and hidden gems that lie between the bustling city of Waukegan and the charming town of Waukesha. Embark on a journey that weaves through rolling hills, meandering rivers and picturesque countryside, where every turn promises a new adventure.
Discover the rich heritage and cultural tapestry that unfolds along the way. Immerse yourself in the captivating stories and traditions that have shaped this region, from the vibrant arts scene to the thriving culinary landscape. Meet the friendly locals who are eager to share their unique perspectives and create lasting memories.
Indulge in the natural beauty that surrounds you. Take a leisurely stroll through lush parks, marvel at breathtaking vistas from scenic lookouts, and uncover the secrets of hidden waterfalls. Whether you seek tranquility in nature or the excitement of urban exploration, this journey offers an unforgettable blend of experiences that will ignite your senses and leave you longing for more.

Waukegan

Waukegan to Waukesha

Boat Tours & Water Sports

Waukesha

Get ready for an unforgettable adventure as we embark on an epic journey from the vibrant city of San Antonio to the bustling metropolis of Milwaukee. Along the way, we'll traverse diverse landscapes, encounter fascinating cultures, and create memories that will last a lifetime.
Our journey begins in the heart of the Lone Star State, where the vibrant colors and rich history of San Antonio await us. From exploring the historic missions to strolling along the River Walk, there's no shortage of wonders to discover. As we venture north, the scenery transforms into rolling hills and lush forests, painting a breathtaking panorama as we journey through the heart of America.
As we approach Milwaukee, the shores of Lake Michigan emerge, inviting us to soak in the stunning views. The vibrant city awaits our arrival, where a mix of art, music, and culture awaits. Prepare to be captivated by the charm of the Midwest, where the warmth of its people and the allure of its attractions will leave you enchanted.

San Antonio

San Antonio to Milwaukee

Get ready for an unforgettable adventure as we embark on an epic journey from the bustling streets of Houston to the charming city of Madison. Along the way, we'll traverse vast landscapes, witness breathtaking natural wonders, and create memories to last a lifetime. From the vibrant cities to the serene countryside, this journey promises a kaleidoscope of experiences that will captivate and inspire.
Prepare to be swept away by the allure of hidden gems and iconic landmarks. Immerse yourself in the rich history, vibrant culture, and boundless beauty that unfolds before you. Whether you're seeking adventure, tranquility, or cultural enrichment, this journey has something for every traveler's heart. Let the open road guide you as you embark on a transformative experience that will leave an indelible mark on your soul.
As we journey from the vibrant heart of Houston to the picturesque charm of Madison, we'll encounter a captivating tapestry of diverse landscapes. From the bustling cityscapes to the serene countryside, each destination offers its own unique allure. Embrace the adventure, soak up the beauty, and create memories that will last a lifetime. This extraordinary journey promises to ignite your senses, broaden your horizons, and leave you forever enchanted by the wonders that await.

Houston to Madison

Take a journey through the heartland of America, where rolling hills and vast plains stretch as far as the eye can see. This epic adventure will transport you from the bustling streets of Philadelphia to the serene shores of Lake Mendota in Madison, Wisconsin. Along the way, you'll encounter vibrant cities, charming small towns, and breathtaking landscapes.
As you embark on this unforgettable journey, you'll witness the transformation of the countryside before your very eyes. Quaint villages nestled amidst lush greenery give way to sprawling metropolises, each with its unique character and allure. Whether you're exploring the historic landmarks of the East Coast or marveling at the architectural wonders of the Midwest, every stop along the way promises a new and enriching experience.
From the energetic vibe of urban centers to the tranquil beauty of rural landscapes, this journey offers a captivating blend of adventure and serenity. Whether you're seeking cultural immersion, outdoor escapades, or simply the joy of discovery, this epic trip from Philadelphia to Madison is sure to leave an everlasting impression.

Philadelphia

Philadelphia to Madison

Get ready for an exciting adventure as we embark on a journey from the bustling city of Dallas to the vibrant shores of Milwaukee. Our adventure begins in the heart of Texas, where we'll marvel at the towering skyline and explore the vibrant culture of Dallas. As we make our way north, we'll traverse vast plains, rolling hills, and sparkling rivers, each offering a glimpse into the diverse landscapes of our great nation. Along the way, we'll discover hidden gems, meet friendly locals, and create memories that will last a lifetime.
As we approach the Great Lakes region, the scenery transforms into a patchwork of lush forests, shimmering lakes, and charming towns. We'll immerse ourselves in the rich history and cultural heritage of the Midwest, visiting historic landmarks, exploring quaint shops, and savoring the flavors of local cuisine. As we reach the shores of Lake Michigan, we'll be greeted by the vibrant city of Milwaukee, a hub of industry, culture, and entertainment. From exploring its world-renowned museums to cheering on its beloved sports teams, there's something for everyone in this dynamic metropolis.
Throughout our journey, we'll embrace the spirit of adventure, embracing new experiences, and forging lasting connections. Whether you're a seasoned traveler or embarking on your first great adventure, this journey from Dallas to Milwaukee promises to be an unforgettable experience filled with discovery, wonder, and the joy of exploration.