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Self-Guided Tour

Jackson Hole - Red Lodge - Beartooth Highway Motorcycle Tour

5 days / 4 nights • Self-Guided • 470 mi / 752 km • 35 - 85 °F / 1.7 - 29.4 °C

Experience an unforgettable 5-day self-drive Harley-Davidson adventure from Jackson Hole, Wyoming. Roar through the stunning landscapes of Grand Teton and Yellowstone National Parks, then conquer the legendary Beartooth Highway, often hailed as “the most beautiful drive in America.” Twist through alpine meadows, past snow-capped peaks, and into the charming mountain town of Red Lodge, Montana, before looping back to Jackson Hole. This tour blends raw wilderness with epic high-altitude riding—a perfect getaway for motorcycle enthusiasts.
  • Jackson Hole

    day 1

    Jackson Hole - Arrival

    0 mi / 0 km

    Arrive in Jackson Hole, check into your hotel, and pick up your Harley at EagleRider. Stroll the lively town square, framed by elk-antler arches, and gear up for an epic ride through the Rockies.
  • Jackson Hole to West Yellowstone

    day 2

    Jackson Hole to West Yellowstone

    100 mi / 160 km

    Kick off your journey with a scenic ride north through Grand Teton National Park, snapping photos of the jagged Tetons. Enter Yellowstone, passing geysers and hot springs, and settle into a biker-friendly town just outside the park.
  • West Yellowstone to Red Lodge

    day 3

    West Yellowstone to Red Lodge

    150 mi / 240 km

    Ride through Yellowstone’s Lamar Valley, a hotspot for bison and wolves. Then, tackle the Beartooth Highway, a 68-mile masterpiece of switchbacks and vistas topping out at nearly 11,000 feet. Descend into Red Lodge, a vibrant mountain town with a rich mining history.
  • Red Lodge to Jackson Hole

    day 4

    Red Lodge to Jackson Hole

    220 mi / 352 km

    Take the Chief Joseph Scenic Byway (WY-296) south from Red Lodge, a stunning 60-mile ride through alpine forests and rugged canyons. Re-enter Yellowstone via the East Entrance, cruise past Yellowstone Lake, and return to Jackson Hole through Grand Teton on Highway 89/191. Drop off your bike at EagleRider.
  • Jackson Hole

    day 5

    Jackson Hole - Arrival

    0 mi / 0 km

    Spend your final morning in Jackson Hole, reflecting on an incredible ride through Yellowstone and the Beartooth Highway. Check out and head home with memories of some of the West’s wildest roads!

starting at $2,097

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$2,097 per person