Embark on a journey through time and across the American landscape! Route 66, affectionately known as the “Mother Road,” was established in 1926 and became a vital artery connecting Chicago to Los Angeles. It fueled dreams, facilitated westward migration, and became an enduring symbol of American freedom and adventure. Our curated road trip blends the nostalgia of this iconic highway with the luxurious comfort of Curator Hotel & Resort Collection properties, taking you from the Pacific Coast eastward, with a unique detour to Kansas City and a grand finale in the Great Lakes region.
Leg 1: Sunset Dreams in West Hollywood, California
West Hollywood, while not directly on the original alignment of Route 66, blossomed in the early 20th century alongside the burgeoning film industry in nearby Hollywood. It evolved from a small agricultural area to a glamorous entertainment hub, attracting artists, writers, and movie stars.
Here are your exceptional Curator Hotel & Resort Collection properties in West Hollywood:
- Chamberlain West Hollywood Hotel: Nestled on a quiet, tree-lined street, the Chamberlain exudes sophisticated tranquility. Imagine starting your day with a dip in their rooftop pool offering panoramic city views. The intimate atmosphere and personalized service make it feel like your own private retreat. Nearby, you’ll find the famed Sunset Strip with its legendary music venues, upscale boutiques, and vibrant nightlife. Explore the eclectic shops on Melrose Avenue or catch a show at the iconic Roxy Theatre.
- Hotel Ziggy: Embrace the rebellious spirit of rock ‘n’ roll at Hotel Ziggy. This vibrant hotel celebrates the music scene with its playful design and lively atmosphere. Dive into their saltwater pool, complete with a record-shaped hot tub, or grab a bite at their B-Side Pizza. Located just steps from the Sunset Strip, you’re in the epicenter of West Hollywood’s entertainment. Catch a live performance, explore the Comedy Store, or simply soak in the energetic vibe.
- Le Parc at Melrose: For those seeking a more residential feel, Le Parc at Melrose offers spacious, apartment-style suites with private balconies. Enjoy the convenience of a fully equipped kitchen and the luxury of a rooftop pool and tennis court. Situated in the trendy Melrose District, you’ll be surrounded by art galleries, design studios, and chic cafes. Take a stroll down Melrose Avenue and discover unique fashion finds and inspiring street art.
- Montrose at Beverly Hills: While technically in Beverly Hills, Montrose offers a stylish and centrally located option just a stone’s throw from West Hollywood. This boutique hotel boasts a rooftop pool with stunning views, a vibrant bar scene, and comfortable, well-appointed rooms. Explore the Golden Triangle of Beverly Hills with its high-end shopping on Rodeo Drive, or venture into West Hollywood for its lively nightlife and dining.
Beyond the iconic Sunset Strip, West Hollywood offers a vibrant tapestry of experiences. Explore the lively LGBTQ+ scene along Santa Monica Boulevard, visit the striking architecture of the Pacific Design Center, find fresh delights at the Original Farmers Market at The Grove, hike Runyon Canyon Park for panoramic city views, or browse the diverse art galleries on La Cienega Boulevard.
Embarking on the Mother Road & Journey to Los Angeles (Downtown)
As you drive towards Downtown Los Angeles, you’ll be tracing a path that, while modernized, echoes the early westward journeys. While the original Route 66 didn’t directly serve West Hollywood, it was a crucial artery into the greater Los Angeles area. Consider a slight detour to explore the Hollywood Walk of Fame and the Griffith Observatory for iconic LA experiences and stunning views. You might also consider a visit to Little Tokyo for a taste of Japanese culture.
Leg 2: Downtown History in Los Angeles, California
Downtown Los Angeles, the city’s historic core, experienced significant growth in the early 20th century, coinciding with the rise of Route 66. It was the western terminus of the Mother Road, a beacon for those seeking new opportunities in California.
Our accommodation in Downtown Los Angeles is:
- Los Angeles Athletic Club: Step back in time at this historic private club that also operates as a hotel. Founded in 1880, the LAAC boasts stunning architecture, a rich legacy, and an impressive array of amenities. Take a swim in their indoor pool, work out in their state-of-the-art fitness center, or simply admire the ornate details of this landmark building. Located in the heart of Downtown, you’re within walking distance of attractions like the Walt Disney Concert Hall, the Broad Museum, and the vibrant Grand Central Market. Catch a Lakers game at the Crypto.com Arena, or explore the historic Olvera Street.

Staying at the historic LAAC places you in the heart of this vibrant past. The club itself has witnessed much of the city’s evolution since 1880. As you explore Downtown, imagine the hopeful travelers arriving at the end of their long journey on Route 66. Savor diverse cuisines at Grand Central Market, admire the beauty of Union Station, or wander through the vibrant Arts District.
Places To See Along The Way
Before heading inland, consider a brief trip west to the Santa Monica Pier, the officially recognized western terminus of Route 66. As you head east, Barstow, CA was a crucial stop on Route 66. Visit the Route 66 Mother Road Museum to learn more. A short detour from the route will take you to Calico Ghost Town, a silver mining ghost town offering a glimpse into the region’s boom-and-bust history.
Experience the quirky former mining town of Oatman, Arizona, famous for its wild burros. Stop at the beautifully preserved Hackberry General Store, now a museum filled with Route 66 memorabilia. The towns of Seligman and Williams, AZ, proudly embrace their Route 66 heritage with vintage charm. Consider a visit to Meteor Crater near Winslow, AZ, for a stunning geological spectacle, and don’t miss the Standin’ on the Corner Park in Winslow, immortalized in the Eagles’ song.
Stop for a photo at the MidPoint Cafe in Adrian, TX, the official midpoint of Route 66. Don’t miss the iconic Cadillac Ranch in Amarillo, TX, and the beautifully restored U-Drop Inn in Shamrock, TX. Oklahoma City, OK has historical ties to the westward expansion, and a fun stop is the Blue Whale of Catoosa in Catoosa, OK. Finally, Joplin, MO, has a rich history tied to mining and Route 66.
Leg 3: Kansas City, Missouri
While the famed Route 66 did not directly traverse Kansas City, we are making it a deliberate detour on our journey, with its rich cultural offerings and vibrant spirit make it a worthwhile stop. This Missouri metropolis boasts a unique blend of history and modern attractions, offering something for every traveler.
Beyond its historical significance, Kansas City is renowned for its mouthwatering barbecue scene, passionate sports fans, and lively arts and culture. Whether you’re craving some world-famous KC-style ribs, want to catch a Kansas City Royals baseball game or a Kansas City Chiefs football game (depending on the season), or simply want to soak in the city’s energetic atmosphere, Kansas City promises a memorable experience on your cross-country adventure.
Our accommodation in Kansas City is:
- The Fontaine: This luxurious hotel in the Country Club Plaza exudes European elegance and modern sophistication. Admire the stunning fountains and Spanish-inspired architecture of the Plaza, then retreat to The Fontaine’s opulent rooms and suites. Indulge in a meal at their fine-dining restaurant, Nine Zero One, which offers a progressive take on new American classics with local soul, featuring seasonally driven cuisine and locally sourced ingredients. With floor-to-ceiling windows, Nine Zero One provides panoramic city views, offering a stylish setting for breakfast, lunch, and dinner, as well as handcrafted cocktails. For a more casual experience, enjoy the European-inspired pastries and coffee at the hotel’s Solarium café.

As you enjoy the elegance of The Fontaine, consider the historical context of Kansas City as a gateway to the West in its own right. Visit the moving National WWI Museum and Memorial, admire art at the Nelson-Atkins Museum of Art, explore the elegant Country Club Plaza, delve into music history in the 18th & Vine Historic Jazz District, discover unique finds in the West Bottoms, or enjoy a day at the Kansas City Zoo.
Kansas City, Missouri Missouri boasts a well-preserved stretch of historic Route 66. Be sure to stop in Independence, MO, to visit the Harry S. Truman Presidential Library and Museum. Consider a short detour to see the Jesse James Bank Museum in Liberty, MO. In Cuba, MO, look for the historic Wagon Wheel Motel and the Giant Chair of Cuba. Explore the underground wonders of Meramec Caverns near Stanton. As you approach St. Louis, make a stop at the beloved Ted Drewes Frozen Custard, a St. Louis institution on a historic alignment of Route 66.
Off To Chicago
This leg takes us through regions with their own rich histories. From the early settlements to its industrial growth, Illinois played a crucial role in the development of the Midwest. Indiana is known for its agricultural heritage and the Indiana Dunes National Park. Michigan boasts a captivating history, from its early fur trading posts to its booming automotive industry and the natural beauty of the Great Lakes. The towns along Lake Michigan often have maritime and logging heritage. Consider stops in Springfield, IL, to explore Lincoln’s history, and a tour through historic Chicago.
This is where most Route 66 inspired road trips would end, but we recommend taking this opportunity to explore Lake Michigan and the surrounding areas.
As you travel along the western coast of Michigan, explore towns like Saugatuck/Douglas, Holland, Grand Haven, Muskegon, and Traverse City. Don’t miss the stunning Sleeping Bear Dunes National Lakeshore. Continue through Michigan’s Upper Peninsula, making time for the majestic Tahquamenon Falls State Park and the dramatic Pictured Rocks National Lakeshore before crossing the impressive Mackinac Bridge.
Leg 5: Mackinac Island, Michigan
Stepping onto Mackinac Island is like entering a different era. Perhaps the most unique aspect of this charming destination is the complete absence of cars. The clip-clop of horse hooves and the gentle whir of bicycles are the primary sounds, creating a remarkably peaceful and nostalgic atmosphere. Today, Mackinac Island thrives as a popular tourist destination, drawing visitors with its stunning natural beauty, including dramatic limestone cliffs, lush forests, and breathtaking views of Lake Huron.
The downtown area is a vibrant hub of activity, filled with quaint shops, fudge kitchens emitting irresistible aromas, and historic buildings meticulously preserved in their Victorian splendor. Horse-drawn carriages serve as taxis and tour vehicles, adding to the island’s old-world charm. It’s a place where time seems to slow down, offering a refreshing escape from the hustle and bustle of modern life.
Mackinac Island boasts a unique history, serving as a strategic military outpost during the American Revolutionary War and the War of 1812. It later became a popular summer resort destination in the late 19th century, leading to the preservation of its Victorian charm and the ban on automobiles.
Our grand finale awaits at:
- Grand Hotel: Step into a bygone era at the iconic Grand Hotel, a National Historic Landmark that exudes Victorian charm and grandeur. From its stunning white facade and the world’s longest porch to its meticulously maintained interiors and impeccable service, the Grand Hotel offers an unforgettable experience. Enjoy afternoon tea in the parlor, take a horse-drawn carriage tour of the island, play a round of golf on their historic course, or simply relax and soak in the breathtaking views of Lake Huron. Explore the charming shops and fudge kitchens in Mackinac Island’s downtown, visit Fort Mackinac, or hike or bike the scenic trails that crisscross the island.

The Grand Hotel itself is a testament to this gilded age, having welcomed guests since 1887. As you explore the island, you’ll be stepping back into a time of elegant leisure.
Conclusion:
Our Curator Hotel & Resort Collection road trip is a captivating journey through American history and iconic landscapes. From the legendary Route 66 and its nostalgic roadside attractions to the historical significance of our destination cities and the timeless charm of Mackinac Island, this adventure offers a unique blend of exploration and luxurious comfort. Enjoy the ride through the heart of America!