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Great Western Loop Challenge

El Cajon, California , United States
41 mi




ft elev +


The Great Western Loop is a San Diego East County gem for road cyclists who want spectacular views, rural roads and climbs that seemingly never end. 

It isn’t that bad clocking in at 43 miles and just shy of 4000 feet of climbing, 3925 to be exact. So I told my girlfriend Jo about the Great Western Loop and how awesome it is to ride in such seclusion so close to Downtown, San Diego. As Jo is relatively new to the game, she agrees after some supportive persuasion, she decides to give it her best!. Regardless to say, this could have gone either way, really bad or really good. As an optimist, the later was, of course, my hope. As you come off Willow Glen drive, which is the only way to the first ascent, unfortunately, you have to deal with a wee bit of traffic as you head to Dehesa Road for first of a few extended climbs. Your first test will be at mile 8 when the road turns upward, and you climb a little over 6 miles with a grade between 5 and 7 percent. Then you get a small break to look around and take in the San Diego back county, which is quite remote without any development. Be on the lookout for wild turkeys crossing the road, and that’s no joke.

Next on tap is a ten miler heading to 2,528 feet with a grade between 6-9 percent grade. You will know when you have reached the top because on your left is a private dirt road call “Dead Dolly Lane.” Don’t ask me to explain. It is bizarre and macabre, and the owner either has a sick sense of humor or is trying to wart off some past demons. You should check it out, and I wouldn’t venture down that road with that kind of welcome I would recommend continuing on the second half of the GWL. 

At this point, Jo was hanging tough, and she was stoked to get to the top and wasn’t even that freaked out by the decapitated dolls at the top, so that was good news. From mile 20 to 28, you will be rambling up and down along private farms, livestock, and breathtaking views. At mile 30, you will get a much needed two-mile downhill, which you can get some high speed. If I forgot to mention, this is just a two-lane road with no shoulder. Don’t let that discourage you; generally, riders take the lane of the road because the traffic is almost nonexistent. 

At mile 32, you will get some serious, short, punchy climbs that can wind you if you’re not ready, so drink up and let that Go Macro bar kick in and keep it rolling! In reality, it’s just about three-miles of 400 feet of climbing. As you wind through Alpaca farms and open meadows with willow tree canopies that cool you off, you can feel like you’re getting to the end. 

There is a General Store where you can stop and get something or chat with the locals about whatever goes on up there. Now you have done all the work climbing, all that’s left is a funtastic five-mile downhill that takes you back to Willow Glen road. I would highly recommend this to check off the San Diego classic road ride. If you’re from San Diego or just visiting its one for the record books.

-Michael Trimble PEARL iZUMi Crew
From mile 20 to 28, you will be rambling up and down along private farms, livestock, and breathtaking views.
Just some dolls, right?

Challenge details

Start date

Sunday, July 12, 2020

End date

Sunday, July 26, 2020

Ride category