Start in Tulsa with a classic breakfast or chicken and waffles at Dilly Diner, then spend the morning in Greenwood. Greenwood Rising gives you an immersive introduction to Black Wall Street and the 1921 Tulsa Race Massacre, while the nearby district lets you connect that history to the streets themselves.
After lunch at The Chowhouse, walk around the corner for the Woody Guthrie and Bob Dylan centers, then give yourself a couple of hours at the Gathering Place to get some fresh air. End the day with dinner at Mother Road Market, where you can choose from multiple food options ranging from burgers to world cuisine.
Stay: Cedar Rock Inn: This upscale bed and breakfast in the foothills just west of Tulsa is perfect for couples as well as families.
Day 2 - Claremore, Woolaroc, BartlesvilleHead north to Claremore to learn about "Oklahoma's Favorite Son" at the Will Rogers Memorial Museum. Enjoy lunch at the nearby Hammett House and save room for a slice of their famous pies. Make your way to the Woolaroc Museum & Wildlife Preserve for the afternoon. The ranch, Western and Native art, wildlife, and Osage Hills scenery deserve two to three hours. Continue to Bartlesville and admire the Frank Lloyd Wright-designed Price Tower. Grab dinner in downtown Bartlesville at Frank & Lola's, a local favorite.
Stay: Jewel Box Hotel Apartments: A unique stay in downtown Bartlesville, the Jewel Box Hotel Apartments have historic charm along with modern amenities.
Day 3 - Tallgrass Prairie Reserve, PawhuskaMake the landscape the star on your final day. Spend about two hours on the Tallgrass Prairie Preserve Bison drive before continuing to Pawhuska. Have lunch at The Pioneer Woman Mercantile, do a bit of shopping in the downtown shops, then shift into Osage culture at the Osage Nation Museum and cowboy history at the Ben Johnson Cowboy Museum. A short historic walk through the courthouse, church, and Constantine Theater ties the town together before dinner at a popular eatery like Buffalo Joe’s Drive-In.
Stay Frontier Hotel: Located in downtown Pawhuska, the Frontier Hotel is housed within the historic Triangle Building and features boutique touches and a refurbished marble staircase.
Planning note: Verify current hours, reservations, event calendars and lodging availability before traveling.
