Part of the allure of West Yellowstone is its 400 miles of groomed trails that offer unlimited riding outside of Yellowstone National Park.
The most advanced riders will probably want to head right up the Big Sky Trail. It's the most challenging trail on the map and has more than its share of off-trail excitement. It eventually ends up at Taylor Creek, many miles north of town. A more moderate ride can be had on the Horse Butte Trail. This trail does offer about 400 feet of elevation change and some pretty good views. Hebgen Lake lies at the foot of the Horse Butte and Yellowstone National Park can be seen way off to the east.
If the altitude on Horse Butte tickled your fancy, try out the Lionhead Trail. It reaches up over 10,000 feet. Since the trail is only five miles long, this combination makes for some serious inclines. The trail is located on the east side of the Continental Divide and makes up for what it lacks in length by featuring what many consider to be the best off trail riding in West Yellowstone.
If you are into longer trail rides, you might try the Madison Arm Loop or Two Top Trails. Both of these trails head south of town and are long, wide and well groomed. The Two Top Trail showcases some of that award winning scenery and allows sledders to look over into Wyoming and Idaho.