Day 1: From the Blue Ridge Mountains to the Mother Road

Every great road trip starts with a journey, and today ours began long before we turned the key.

We traded the mountains of Western North Carolina for the skyscrapers of Chicago, flying from Asheville to Midway and heading to the birthplace of Route 66. After landing, we skipped the rental car and rode the CTA Orange Line to downtown, watching Chicago's skyline emerge as we approached the Loop.

After settling in, we spent the afternoon exploring some of Chicago's most iconic landmarks. Our first stop was Millennium Park, where we admired the ever-changing faces projected on the Crown Fountain before making our way to Cloud Gate—better known as "The Bean." Its mirrored surface reflected the city skyline, the clouds overhead, and a growing crowd of visitors eager to capture the perfect photo.

From there, we walked through neighboring Grant Park to see Buckingham Fountain, one of the largest fountains in the world and one of Chicago's most recognizable symbols.

Before dinner, we stopped outside the Art Institute of Chicago to visit the famous bronze lion statues standing guard at the museum's entrance, a classic Chicago photo opportunity and a fitting reminder of the city's rich cultural heritage.

Our home for the night is the historic Palmer House Hilton, a Chicago landmark and the longest continuously operating hotel in North America. Originally opened in 1871 as a wedding gift from Potter Palmer to his wife, Bertha, the hotel blends history and elegance at every turn. The soaring painted ceiling, glittering chandeliers, and grand staircase make the lobby feel more like a European palace than a downtown hotel.

One of the hotel's most impressive features is its famous Peacock Doors. Designed by Louis Comfort Tiffany, the massive bronze doors showcase intricate peacock motifs and Art Nouveau craftsmanship. More than a century old, they feel as much like artwork as architecture.

For dinner, we visited The Berghoff, one of Chicago's oldest restaurants. Its old-world atmosphere, classic German fare, and rich history made it the perfect choice on the eve of our Route 66 adventure. Over a great meal of chicken schnitzel and spätzlel, we reflected on the day and looked ahead to the miles of highway, small towns, and roadside attractions waiting for us along the Mother Road.

After dinner, we returned to the Palmer House for a sweet piece of Chicago history: the original Bertha Palmer brownie. Created at the hotel for the 1893 World's Columbian Exposition at Bertha Palmer's request, the dessert is widely credited as the first brownie ever made. Rich, fudgy, and topped with a glossy apricot glaze and walnuts, it was the perfect ending to our first day in Chicago—and a delicious way to experience a recipe that has been delighting guests for well over a century.

Before heading back to the room for the night we made one final stop: the Route 66 Begin sign at Adams Street and Michigan Avenue. Standing beside the iconic marker was a surprisingly emotional moment. We had traveled nearly 700 miles from home, yet the real journey was just beginning. Tomorrow, we start driving the Mother Road.

Stay tuned. The adventure is officially underway.