5. Greenough, MT
Why go: Leaf peeping from the roads of New England is so predictable, but a road trip through Big Sky country feels new. Take the 49-mile Pioneer Mountains Scenic Byway in the Beaverhead-Deerlodge National Forest or the 68-mile Beartooth Highway through southwest Montana for a whole different take on fall foliage.
Where to stay: Post up at The Resort at Paws Up—a luxury ranch set on a 37,000-acre working cattle ranch in western Montana. Their six safari-style tented camps are open through mid-October (dedicated camping butler included). You can fly-fish on the Blackfoot River, ride horses through the Tamarack Trees, or float around in a hot air balloon when you’re not glamping.
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