Are you ready for an epic adventure? We're taking a road trip from the bustling streets of New York City to the vibrant city of Detroit! Along the way, we'll discover hidden gems, explore exciting cities, and create memories that will last a lifetime.
Our journey will take us through diverse landscapes, from sprawling farmlands to dense forests. We'll visit charming towns and bustling metropolises, each with its unique character and stories to tell. We'll embrace the vibrant culture, savor delicious local cuisine, and immerse ourselves in the rich history of the regions we pass through.
As we approach Detroit, the heart of the American automotive industry, we'll be greeted by a skyline dotted with iconic landmarks. We'll explore the city's rich musical heritage, visit its world-class museums, and discover the stories behind the innovations that have shaped our world. This road trip promises to be an unforgettable adventure, filled with discovery, laughter, and memories that will be cherished for years to come.

New York

New York to Detroit

Museums

Nature & Parks

Sights & Landmarks

Fun & Games

Tours

Nightlife

Food & Drink

Classes & Workshops

Outdoor Activities

Detroit

Hop aboard an unforgettable adventure as we embark on a journey through the heart of the Midwest, from the bustling metropolis of Chicago to the picturesque city of St. Paul. Along the way, we'll traverse rolling hills, glistening lakes, and charming towns, each with its own unique story to tell.
Our adventure begins in the vibrant city of Chicago, a hub of culture, architecture, and entertainment. From the iconic Willis Tower to the bustling Magnificent Mile, Chicago offers a captivating blend of urban excitement and historical charm. As we venture northward, we'll pass through the serene landscapes of Illinois and Wisconsin, where lush greenery and sparkling waterways create a tranquil backdrop. The gentle rhythm of train travel will allow us to soak in the beauty of our surroundings and connect with fellow travelers.
As we approach our destination, the Twin Cities of Minneapolis and St. Paul emerge on the horizon. St. Paul, the state capital of Minnesota, boasts a rich history, vibrant arts scene, and beautiful parks along the Mississippi River. Whether you're eager to explore its cultural treasures or simply relax amidst its natural beauty, St. Paul offers a warm and welcoming experience.

Chicago

Chicago to St. Paul

Shopping

Spas & Wellness

Other

St. Paul

Aboard the train, you'll have access to a variety of amenities to keep you comfortable and entertained during your journey. Each seat is equipped with a personal entertainment system, so you can watch movies, play games, or listen to music. There's also a dining car where you can purchase meals and snacks, as well as a lounge car where you can relax and socialize with other passengers.
The train will make several stops along the way, giving you the opportunity to stretch your legs and explore different cities. You'll have time to visit museums, historical sites, and other attractions. You can also take advantage of the train's Wi-Fi service to stay connected with friends and family back home.
At the end of your journey, you'll arrive in Enterprise, where you can continue your travels or simply relax and enjoy the scenery. The choice is yours!

Chicago to Enterprise

Concerts & Shows

Water & Amusement Parks

Enterprise

Prepare to embark on an epic journey through the heartland of America, from the bustling metropolis of Chicago to the picturesque city of Spokane. We'll traverse a vast expanse of rolling hills, shimmering lakes, and towering mountains, witnessing the country's rich diversity along the way.
As we depart from the Windy City, skyscrapers will give way to endless fields and charming small towns. The mighty Mississippi River will guide our path, its waters glistening in the sunlight. We'll explore hidden gems, encounter friendly locals, and soak up the vibrant culture of the Midwest.
Continuing westward, the landscape will transform into a breathtaking tapestry of towering mountains, ancient forests, and sparkling lakes. We'll marvel at the rugged beauty of the Rockies, hike amidst towering trees, and discover hidden waterfalls nestled within pristine wilderness. As we approach our destination, the Spokane River will welcome us into the city adorned with parks, museums, and vibrant nightlife, marking the end of our unforgettable adventure.

Chicago to Spokane

Traveler Resources

Spokane

Hop aboard and prepare yourself for an unforgettable adventure as we embark on an exciting journey from the bustling city of Chicago to the vibrant metropolis of Detroit. Along the way, you'll witness diverse landscapes, discover fascinating stories, and create memories that will last a lifetime.
Our journey begins in the heart of the Windy City, where towering skyscrapers pierce the sky and the energy of the city seeps into every corner. As we leave Chicago behind, we'll traverse vast stretches of verdant farmlands, rolling hills, and sparkling lakes. Along the way, you'll have the chance to delve into the rich history and culture of the Midwest, uncovering hidden gems and stories that have shaped the region.
As we approach Detroit, the landscape transforms into a bustling urban hub. Get ready to explore the Motor City, renowned for its automotive heritage and vibrant arts and culture scene. From iconic landmarks to hidden gems, Detroit offers a captivating blend of past and present, innovation and creativity. Prepare to be amazed as we uncover the many facets of this dynamic city, leaving you with a newfound appreciation for its spirit and charm.

Chicago to Detroit

Are you ready to embark on an epic adventure from the bustling streets of Chicago to the charming city of Stockton? This incredible journey will take you through diverse landscapes, from towering skyscrapers to rolling hills and picturesque countryside. Along the way, you'll discover hidden gems, encounter friendly locals, and create memories that will last a lifetime.
As you leave the Windy City behind, the urban sprawl gradually gives way to serene farmlands and tranquil towns. The gentle rhythm of the countryside will soothe your soul as you witness the beauty of nature unfolding all around you. Verdant fields stretch out before you, dotted with grazing cattle and wildflowers dancing in the breeze. Quaint villages beckon you to stop and explore their charming shops and cozy cafes.
As you approach Stockton, the landscape transforms once more. The rolling hills give way to a fertile valley, where agriculture thrives. Orchards laden with ripening fruit line the roads, promising a taste of the region's sweet bounty. Stockton itself welcomes you with open arms, its historic downtown and vibrant arts scene offering a delightful blend of past and present. Get ready to immerse yourself in the unique character of this captivating city and discover all that it has to offer.

Chicago to Stockton

Stockton

Embark on an epic journey that whisks you away from the bustling metropolis of Chicago to the charming city of Rochester. This adventure will lead you through diverse landscapes, immersing you in a tapestry of natural wonders and cultural treasures.
Your adventure begins in the heart of the Midwest, where Chicago unfolds before you with its towering skyscrapers and vibrant urban scene. As you leave the city behind, you'll traverse vast farmlands, the rolling hills dotted with quaint towns and picturesque countryside. This region, steeped in American agriculture, unveils the bounty of the heartland.
As you continue east, the landscape transforms into rolling hills and dense forests. The Midwest's rural charm gives way to the rugged beauty of the Appalachian Mountains. Winding roads lead you through lush valleys, past sparkling streams, and up to breathtaking vistas that showcase the region's natural splendor.

Chicago to Rochester

Casinos & Gambling

Rochester

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 to Milwaukee

Events

Milwaukee

Get ready for an epic adventure as we embark on an unforgettable road trip from the sunny shores of San Diego to the vibrant city of Milwaukee! Along the way, we'll traverse vast landscapes, discover hidden gems, and create memories that will last a lifetime.
Embrace the freedom of the open road as we wind through scenic mountain passes, roll across endless prairies, and admire breathtaking coastlines. Embrace the unknown as we venture off the beaten path, uncovering charming towns, quirky roadside attractions, and local treasures that will captivate your imagination.
Prepare to be amazed by the diverse cultures, flavors, and landscapes that unfold before our very eyes. From bustling metropolises to cozy hamlets, each destination promises a unique experience. Savor the vibrant flavors of authentic cuisine, delve into the rich history of historic landmarks, and immerse yourself in the vibrant arts and culture scenes that await us.

San Diego

San Diego to Milwaukee

Hey, I found a trip that will take you on a breathtaking adventure. We'll travel along the shimmering shores of Lake Michigan, where the gentle waves whisper secrets to the sandy beaches. As we journey inland, lush forests will envelop us, their emerald canopies reaching towards the heavens like a living tapestry. Along the way, we'll encounter quaint towns and bustling cities, each with its own unique charm and story to tell. Whether you're an avid explorer or simply seeking a memorable escape, this trip promises an unforgettable experience.
As we approach the midway point of our journey, the landscape transforms into a vibrant tapestry of rolling hills and sparkling rivers. Picturesque farmsteads dot the horizon, their fields a patchwork of vibrant hues. The air fills with the sweet scent of wildflowers and the cheerful chorus of birdsong. We'll have ample opportunities to stretch our legs, breathe in the fresh air, and capture the beauty of our surroundings with our cameras.
Prepare to be captivated as we reach our final destination: a bustling city where history, culture, and modern amenities converge. Here, we'll explore fascinating museums, savor delectable cuisine, and immerse ourselves in the vibrant arts scene. This metropolis offers something for everyone, whether you seek adventure, relaxation, or intellectual stimulation. It's the perfect culmination to our extraordinary journey, leaving us with cherished memories and a newfound appreciation for the beauty and diversity of our surroundings.

Chicago to Kalamazoo

Kalamazoo

Get ready for an unforgettable adventure from the bustling streets of Indianapolis to the vibrant shores of Milwaukee! Embark on a journey that weaves through picturesque landscapes, charming towns, and historic landmarks. Along the way, you'll uncover hidden gems, immerse yourself in local cultures, and create memories that will last a lifetime.
Witness the transformation of the scenery as you leave the urban sprawl behind and enter a realm of rolling hills, tranquil lakes, and verdant forests. Discover quaint villages nestled amidst towering trees, where time seems to stand still and the pace of life slows down. Marvel at architectural wonders that tell tales of the past and inspire awe in the present.
As you approach the shores of Lake Michigan, a vibrant metropolis awaits your arrival. Explore its vibrant arts scene, indulge in culinary delights, and revel in the lively atmosphere. From towering skyscrapers to charming neighborhoods, Milwaukee offers a captivating blend of urban excitement and Midwestern charm. Let the spirit of adventure guide you as you embark on this incredible journey from Indianapolis to Milwaukee, where every mile holds a promise of discovery and delight.

Indianapolis

Indianapolis to Milwaukee

Get ready for an unforgettable adventure as we embark on an epic road trip from the vibrant city of Austin to the charming town of Madison. Along the way, we'll traverse miles of breathtaking landscapes, discover hidden gems, and create memories that will last a lifetime. From the bustling streets of Austin to the serene shores of Lake Michigan, this journey will showcase the diverse beauty and rich history of the United States.
Our adventure begins in the heart of Texas, where Austin's vibrant culture and lively music scene set the tone for our journey. As we head north, we'll encounter rolling hills, lush forests, and charming towns that reveal the true essence of the Lone Star State. Leaving Texas behind, we'll cross the Red River into Oklahoma, where the vast prairies stretch out before us. The rich Native American heritage of this region is evident in the historic landmarks and cultural attractions that dot our path.
As we continue our journey through Kansas, we'll witness the iconic Flint Hills, a breathtaking landscape of rolling grasslands, and visit the Eisenhower Presidential Library and Museum in Abilene. Our adventure culminates in the charming town of Madison, nestled on the shores of Lake Michigan. Here, we'll soak in the beauty of the Midwest, explore the vibrant downtown area, and reflect on the incredible journey we've shared. Whether you're a seasoned traveler or embarking on your first road trip, this adventure promises to ignite your imagination and leave an everlasting impression.

Austin

Austin to Madison

Madison

Come along on an unforgettable adventure from the vibrant streets of Chicago to the sun-kissed shores of Gulfport. Our journey will traverse a tapestry of landscapes, from towering skyscrapers to rolling hills and tranquil waters. As we embark on this epic voyage, the rhythm of the rails will serenade us, connecting us to the heartland of America and the allure of the Gulf Coast.
Throughout our odyssey, history will unfold before our eyes. We'll delve into the bustling energy of Chicago, a city where dreams soar and innovation thrives. The charm of quaint towns will captivate us, inviting us to embrace their timeless stories and local flavors. As we journey southward, the landscape will transform, revealing the grandeur of nature's tapestry. Verdant forests will whisper secrets, while sparkling rivers and majestic mountains will ignite our sense of wonder.
Embracing the embrace of the Gulf Coast, we'll bask in the warmth of its sandy beaches and revel in the vibrant hues of its sunsets. The salty tang of the ocean breeze will invigorate our spirits, as we succumb to the allure of this coastal paradise. From bustling metropolises to serene coastal retreats, our journey from Chicago to Gulfport promises an extraordinary symphony of experiences, where the past, present, and future intertwine in a captivating tapestry of Americana.

Chicago to Gulfport

Gulfport

Get ready for an adventure on wheels as we embark on an exciting road trip from the bustling city of Chicago to the charming town of Lorain. Along the way, we'll discover hidden gems, see stunning landscapes, and make memories that will last a lifetime.
Our journey will take us through the rolling hills of Illinois and Indiana, where we'll pass by quaint towns and vibrant cities. We'll see towering skyscrapers and cozy cottages, all while enjoying the ever-changing scenery. As we approach Ohio, we'll drive alongside the sparkling shores of Lake Erie, where we can stop and admire the breathtaking views.
Finally, we'll arrive in Lorain, a delightful town located just west of Cleveland. With its historic downtown, beautiful parks, and friendly locals, Lorain is the perfect destination to end our adventure. Whether you're looking for a fun family getaway or a scenic escape, this road trip has something for everyone. So, pack your bags, buckle up, and let's hit the open road!

Chicago to Lorain

Lorain

Get ready for an exciting adventure as we embark on a journey from the bustling city of Chicago to the vibrant streets of Cleveland. Along the way, we'll discover hidden gems, marvel at breathtaking landscapes, and create memories that will last a lifetime. Buckle up and let's hit the open road!
As we leave Chicago behind, we'll traverse through rolling hills and lush greenery, passing by charming towns and quaint villages. The scenery will transform before our eyes, from towering skyscrapers to serene countryside vistas. We'll make pit stops at local eateries, savoring the flavors of each region and learning about the unique cultures that shape this diverse landscape.
As we approach Cleveland, the cityscape will gradually emerge, signaling our arrival in this thriving metropolis. The air will buzz with excitement as we explore its vibrant neighborhoods, discover its rich history, and immerse ourselves in the local arts and entertainment scene. Whether you're a seasoned traveler or embarking on your first road trip, this journey promises to be filled with unforgettable experiences and a newfound appreciation for the beauty and diversity of our surroundings. Let's roll!