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Hiking Mogan Ridge West Trail
(beehaw.org)
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There are a few nice trails in the southern part of the Hoosier National Forest, which is where this one is. Probably my favorite is German Ridge, which offers a variety of loops from 5 to 20 miles and a decent but not overwhelming number of hills. Tipsaw Lake is nice easy 6-miler which I hit when I want a quick couple hours with lake views. Two Lakes has some scenic parts, but a lot of that trail system has been logged in the past 2-3 years, so it really could use some time to recover before it'll be nice again.
Further out (2 or so hours from the Evansville area where I live), I like the Shawnee NF, the Deam Wilderness, the Adventure Hiking Trail, and the Mammoth Cave backcountry.
Oh, and the logo washed out, but that last additional arrow is because this trail segment is also part of the American Discovery Trail, so in theory at least you could follow it all the way to the Pacific.