The Whipple Trail System begins right out of the river park in downtown Buena Vista. Begin by taking the bridge across the river, and then start climbing!
There are 3 different routes to the top: the Wipple Trail, North Whipple, and South Loop. Some are a bit steeper and rockier than others, but most of the climbs are quite manageable.
Once you finish the climb and hit the Midland Trail/old railroad grade, be sure to grab the Broken Boyfriend trail on the other side. The longest trail in this trail system, it climbs and dips along through the scrub pines and up and over rocks on dry sandy, soil. Be sure to stop every now and then when the trees open up and enjoy the fantastic views of Buena Vista and the Collegiate Peaks!
Next, either take the old railroad grade up/east-southeast to the Midland Hills trails, or grab one of the other trails in the Whipple trail system to drop back down to the Arkansas River.
 | Broken Boyfriend |   | 2 mi |
 | North Whipple | | 1 mi |
 | South Loop | | 1 mi |
| Whipple Trail | | 1 mi |
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A pretty fun, although somewhat short, trail system. Link it up with the Midland trails via the RR grade to extend your fun. There is a BLM campground and some dispersed camping available around the Midland Hills trailhead.
| ThankChallenging intermediate trail with some solid advanced moves sprinkled in. Some tight and twisty, some swoopy, but all fun. The map indicates the "preferred rider direction" is south to north, but it looked like it would be equally fun either way.
| ThankThis is a delightful trail system with super easy access. I thought the climb was challenging enough to be entertaining, but nicely doable. The Broken Boyfriend portion up top adds significantly to the tech level, not in a death defying way, but in a sort of tricky, lots-of-up-and-down-obstacles kind of way. It is great fun for a skilled intermediate or advanced rider who appreciates quick moves and low speed maneuvering as much as rippin' fast downhills. There is one short connector back down to the Barbara Whipple Trail that really ratchets up the gnar with big rock drops on really tight switchbacks.
| ThankI had fun on this trail system. Not too techie, but a few challenging features and some good steep sections
| ThankAgree with above that Broken Boyfriend is the highlight trail, and is easy enough to lap that section once you do the 1st moderate climb.
I do not get the doubletrack comment; wide, yes! But I actually like the climb up, you can pick your line to make it a bit more interesting or simply spin & weave on up. There is about a 1 mile span of gravel road (304), no biggie as the views to the west are stellar.
This is a nice ride in conjunction with a morning CT area segment. Or, the novice rider looking to step it up a bit.
| ThankShort but a great intermediate to int trail. Honest ride with a few challenging moves. The easy climb up gravel rd 304 gets you to the S end on the trail (recommended route). BB then tops out with very little climb, with a nice flow ride back down to rd 304. Trail = net descent. You can make laps if you want more.
| ThankWhile nice and flowy, this trail almost borders on doubletrack in spots.
| ThankShort and relatively steep, and pretty rocky, this is still quite climbable.
| Thank