Gillette to Custer: Ultimate Road Trip Guide

Highway 14-16-85 is 214 miles of raw Western landscapes: Sheely’s Roadside Museum, Devils Tower, and the massive bends of the Black Hills. The route threads through Wyoming’s coal country—sheriff’s depots in Wright, thermals near Spotted Horse—before descending into South Dakota’s granite spires. Driving north from Gillette, the first 70 miles unfold across an ocean of sagebrush and exposed coal seams, a stark plateau carved by the Belle Fourche River.

The shift to alpine timberline happens abruptly around Beulah, WY, where lodgepole pines replace dust and the horizon tilts upward. Coal trucks yield to RV caravans near Devils Tower, whose 867-foot column has drawn climbers since 1893. Time-wise, expect 3½ to 4 hours of driving plus stops, but the scenery demands at least a full day.

Fuel stations cluster at Gillette, Sundance, Spearfish, and Custer—never let the gauge drop below half, as the 100-mile stretch between Beulah and Rapid City has zero services. Gas prices run 15-20% higher in tourist towns like Custer than in Gillette; fill up before crossing into South Dakota.

Most of the route is two-lane highway with occasional passing lanes. The pavement is well-maintained year-round, but watch for frost heaves in spring and gravel trucks on weekdays. Speed limits range 65-70 mph on open road, dropping to 25-45 mph through small towns.

• Wildlife crossings: mule deer, pronghorn, and elk most active at dawn/dusk.
• Winter: Interstate 90 is the reliable alternative; US 14/16 can be closed or icy.
• Full services (gas, food, lodging) only in Gillette, Moorcroft, Sundance, Spearfish, Custer.
• Cell signal: patchy; use downloaded offline maps.

For deeper route planning, see this guide on finding hidden gems. Always check the weather before leaving—snow can fall any month above 6,000 feet.

Rest zones appear every 30-40 miles; the most scenic are at Sundance Rest Area and the pull-outs at Bakerville. For families, the Vore Buffalo Jump (2014) has engaging archaeology exhibits, and Sundance’s town park has a vintage carousel. Many kids love the 'Bear Butte' rockslide near Sturgis—supervised climbing allowed.

Watch for deer and cattle on the highway, especially around dusk. Drive with headlights on even in daylight to increase visibility. If fatigue hits, pull into a paved rest area—cots are not provided, but picnic tables offer a safe nap spot.

Pet-friendly: most roadside diners allow leashed pets on patios; the Spearfish City Park offers off-leash hours from 6-9 AM.

• Best stops between Gillette and Custer include Devils Tower, Sundance, and Spearfish Canyon.
• The spearfishing falls and the granite-walled canyon are a top side-trip just 20 miles off US 14A.

The defining features are Devils Tower (America’s first national monument, 1906), the Black Hills’ granite escarpments, and the endless prairie. The Tower’s rock columns are phonolite porphyry, formed 50 million years ago; the site also holds sacred meaning for Lakota, Cheyenne, and Kiowa tribes.

But beyond the headline attraction, look for the deep river cuts at Keyhole State Park and the dry falls at Cement Ridge. Around Hulett, Wyoming, you’ll find the only working ranch still leasing grazing rights inside a national monument boundary—a working slice of history.