Martinsdale (52 miles round-trip)
Take an extra couple hours and maybe even a night to continue west from Harlowton on US to Martinsdale. For a community with all of 64 residents, it's a happening place. And before you even arrive, you'll be able to say you've been in famous Two Dot, home of the famous Two Dot Bar and geographic center of Montana.
To reach Martinsdale, turn left on MT 294 off US 12 and be sure to take a tour of the Charles M. Bair Family Museum just across the Musselshell River.
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The museum is actually the family ranch, and it positively sparkles with its bleach-white buildings and red roofs. Bair was an Ohio man who was said to have come west with fourteen cents and seven green apples in his pockets. ? After making a fortune during the Alaska gold rush by investing in a ground-thawing device, he put his money into coal, oil, mining, and an assortment of other endeavors that made him even wealthier. Along the way he built friendships with Teddy Roosevelt, Charlie Russell, Chief Plenty Coups, Will Rogers, and a handful of U.S. presidents. A guided tour of the elegant home with its eclectic collection of Native American, western and European art, along with a wide variety of antiques is not to be missed. Hours vary from Memorial Day through the end of October; admission is $5 for adults.
After visiting the Bair complex, you'll want to have dinner at the Crazy Mountain Inn and perhaps even spend the night. The frontier-style rooms are priced from $47-65. Bathrooms with shower and tub are in the hallway. The restaurant, open May through November, is renowned for its chicken-fried steak, thanks to kudos from both Esquire magazine and frequent visitor Jim Harrison, a part-time Livingston resident and author of Legends of the Fall. If you're a fisherman, Martinsdale Reservoir is a productive playground unless the winds headed for Judith Gap are howling, in which case the lake is turned over to windsurfers.
Harlowton: You can't stay yet at the visually arresting Graves Hotel, but Whistle Stop Cafe ($/$$, 406-632-5798, B/L) is the place to go for a bite to eat if you're passing through Harlow. ? In an old railroad town, naturally a menu highlight is the Engineer Burger. Breakfast and lunch already are served, and plans for a dinner menu were in the works in 2015. Four new owners opened the restaurant and have big dreams of restoring the 1909 three-story sandstone structure to its former glory. The Graves was the fulcrum of the community until the Milwaukee Road left town four decades ago. Snowy Mountain Coffee ($, 406-632-6838, B/L/D Mon.-Sat. ) is a breath-of-fresh-air spot for fresh-roasted coffees, muffins, scones, smoothies, soups, and sandwiches. And if you're passing through Thursday, Friday, or Saturday night don't miss their pizza.
Hobson: You've got to venture just off the beaten backroad for this one, but Tall Boys Tavern merits veering left at Moore on US 87 for the short drive to this bright little street corner in Hobson, an agricultural community with twin grain elevators. Opened in the spring of 2015 in Hobson's 1910 brick Murray Block Building, Tall Boys isn't your classic Montana tavern. In fact, they toss around the words gourmet and gluten-free here when they talk about their versatile food menu. They also serve everything from traditional whiskeys, bourbons, beers, and wines to margaritas, Murray mules, cosmopolitans, and a concoction called the Icelandic Trashcan that tosses in everything sweet-ish but the kitchen sink. As expected with a new endeavor in a rural setting, their menu which highlights chicken salad, Philly cheesesteak sandwiches, burgers, prime rib, and steaks is a work in progress. Something must be working, though: Tall Boys has become a magnet for folks from Lewistown to Great Falls, and points between.