Leave Rapid City around 7:30 a.m. and allow a full day for the drive to Jackson—roughly 8–9 hours of wheel time, before fuel, food, or photo stops. Follow I-90 W toward Sheridan, then take US-14 W through the Bighorn Mountains; continue toward Cody and pick up US-20/US-26 toward Jackson. US-14 is a beautiful but winding mountain road, so check Wyoming 511 for conditions and closures before setting out, and expect the trip to take longer if weather or road work slows you down. Build in breaks around Sheridan and Cody, and arrive with enough daylight to settle in.
After checking in, head to Jackson Town Square for a 30–45-minute leg stretch beneath its famous elk-antler arches. It’s right in the heart of downtown, with shops and cafés along the surrounding blocks if you want a quick wander. Then walk or make the short drive to Snake River Brewing for an easy dinner of pub fare and local beer; budget about $20–$40 per person. Sunday hours can vary, so check before you go, especially if the long drive puts you in late.
Finish with a brief look inside the Million Dollar Cowboy Bar, a longtime Western-style landmark on Jackson’s Town Square; give yourself about 30 minutes, and check the door policy or hours before heading over. Then call it a night rather than attempting the return drive: Jackson to Rapid City is another 8–9 hours without extended stops. Leave early tomorrow, retrace the US-26/US-20 and US-14 route east toward Sheridan, then continue on I-90 to Rapid City, with a planned rest stop along the way.
No packing list attached yet.