Leave Missoula around 4:45 PM for the roughly 5½–6-hour drive east on I-90. This is a straightforward highway run, but it will be dark for much of the second half, so fill up before leaving and keep stops limited to fuel and a quick meal. Expect scenery through the Rocky Mountain Front and along the Yellowstone River corridor, with better rest and fuel choices around Butte, Bozeman, and Livingston. Since you are arriving late, confirm your hotel’s after-hours check-in and park immediately on arrival rather than trying to explore first.
If you reach downtown before the kitchen closes, make The Burger Dive your quick dinner stop; burgers, fries, and shakes generally run about $15–25 per person. Call or check same-day hours before committing, since late-night kitchen service can vary. Afterward, take a very short walk to Billings Depot, the restored historic railway landmark, then continue to Skypoint for its illuminated downtown sculpture. Both are easy evening photo stops and should take about 15 minutes each; use the nearby downtown garages or well-lit street parking, and avoid turning this into a longer walk after a full day on the road. Return to the hotel by roughly 11:15 PM for an early start the next morning.
This is an ambitious sightseeing-and-driving day, so leave Billings by about 7:30 AM with breakfast, water, and a full tank. Drive east on I-90 to Pompeys Pillar National Monument—roughly 30 minutes from town—where the visitor center and boardwalk generally open around 9:00 AM in summer. Allow about an hour for the interpretive exhibits and the climb to William Clark’s 1806 inscription; admission is typically around $7 per person, with a federal recreation pass accepted. Afterward, continue about 1½ hours southeast to Little Bighorn Battlefield National Monument in Crow Agency. Give yourself 1½–2 hours for the visitor center, memorials, and driving the battlefield road; summer hours are usually 8:00 AM–6:00 PM, with entrance fees commonly around $25 per vehicle.
From Little Bighorn, stay on I-90 toward Custer State Park, a long but scenic leg of roughly 2½–3 hours. Plan a quick lunch en route—Hardin or Sheridan are the most practical places to stop rather than detouring into town—and aim to spend about 90 minutes on the Wildlife Loop Road near Custer. Keep your speed down: bison, pronghorn, and burros can appear suddenly, and wildlife sightings are best in the late afternoon. The park charges a vehicle entrance fee, generally around $20 for a temporary pass; check the park’s current road conditions before committing, as construction or storms can affect the best loop access.
Continue toward Rapid City and, once in town, make Dinosaur Park your final quick stop before dinner. The free hillside park is open late and takes about 30 minutes, with broad views over the city alongside its 1930s concrete dinosaur figures; parking is available on-site, though the stairs and slope can be tiring after the drive. Finish at Tally’s Silver Spoon downtown, a polished but relaxed local favorite on West Boulevard, where dinner usually runs about $30–60 per person before drinks and tip. Because this schedule can put you in Rapid City anywhere from roughly 7:30 to 9:00 PM, confirm the restaurant’s reservation and kitchen hours that morning; if you are delayed, prioritize dinner over lingering at Dinosaur Park.
Leave Rapid City around 6:30 AM with coffee, water, and a full tank; this is a long interstate day, so treat the sightseeing stops as brief resets rather than trying to turn them into full visits. After roughly five hours on I-90, stop at Falls Park in Sioux Falls for about 45 minutes. The falls are right beside downtown, with paved paths, overlooks, restrooms, and easy parking; the park is open year-round and free, though the Falls Overlook Café and visitor facilities typically keep daytime hours. Allow extra time for construction or summer traffic before continuing onto I-29.
For lunch, use The Wheelhouse Bar & Grill in Sioux Falls, budgeting about $15–30 per person. It is a practical sit-down break rather than a major detour, but check the kitchen hours that morning, since weekday service can vary. Keep the stop to roughly 45–60 minutes, then continue south through Iowa; this stretch is mostly open highway, with fuel and rest areas spaced conveniently along I-29.
In the afternoon, make a short leg-stretch in Council Bluffs’ Historic Downtown, about 30 minutes. Park near Broadway and wander among the older commercial buildings before returning to the car; it is a useful break after the long run from Sioux Falls, but keep an eye on the clock because the remaining drive toward Farley still takes several hours via I-29 and I-70. Expect the final arrival window around 6:00–7:30 PM, depending on traffic, fuel stops, and roadwork.
After checking in, take an easy 20-minute stroll through Farley City Park. It is best viewed as a quiet arrival reset rather than a destination visit—stretch your legs, get some air, and then pick up dinner locally or near the Kansas City side if your overnight lodging is closer there. In late August, bring water and insect repellent for the evening walk, and confirm your rental-car drop-off instructions before settling in.