Going from North to South: You can get water at Dickey Ridge (about 5 miles in after the first big climb), Elkwallow at Mile 25, Big Meadows at mile 52, and Lewis Mountain at mile ~62. South of there I am not totally familiar with but I know there is at least one place in the south end that has a park facility but it's name is escaping me at the moment.

Everyone's different, but if I leave on a summer morning (cooler), I can make it to the store at Elk Wallow / Mile 22 with 2 full bottles.

Not really on the way but at the southern end there is a great brewery/restaurant at the bottom of the mountain. It is called Blue Mountain Brewery and definitely worth a down-and-up detour. Take Afton Rd rather the 250 for the way down though.

Not sure the time of day you are planning to start. I was there yesterday and was informed by the park ranger that you are required, by law, to have front and rear lights on your bike if there is fog. He said something about giving out tickets or pulling you off the road if you do not have lights. I didn't encounter any fog when I rode but the park ranger said that there were fog earlier in the morning. I started my ride at noon.

And ... Thorton's Gap is at mile 32. It has bathrooms and water fountains, if you need fluids. If you need to purchase Gatorade, stop at the mile 25 station that was previously mentioned.

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My marathon PR is "under three, high twos. I had a two hour and fifty-something."

This. It will be 10 degrees cooler up there and 2 bottles gets you to each store. Usually....

I've done it twice the opposite direction, so I have to infer a bit to answer this question. You won't have trouble with water other than the last 35 miles, so ask the park rangers about where to get water before you get too far. Other than the finish part, which is mercifully mostly downhill, you won't have any problem. Just top off before then.

Thanks everyone - I knew the ST hive mind would come through! Sounds like 2 or 3 max bottles, cooler up higher, and mucho thanks for the advice on fog/lights.

The sig others will be driving the Drive later in the day, and meeting us at the end, so we'll try to stop at the brewery on the way back as a 4-some. Looking forward to the ride! I've raced the Shen 100 MTB race down there, and always wanted to do Skyline.

ride all the way to Wintergreen and reward yourself with cider from Hard Rock

We're definitely going the full distance to Afton (Rt 250), so we'll be looking for some "recovery" drink/food close by there :) Hoping Waynesboro has some place awesome to hang for a bit. Recommendations welcome!

very nice! should be enjoyable ride. also, you may want to follow SNP's facebook page in case of any road closures, etc. https://www.facebook.com/shenandoahnps/?fref=ts

good thing is that Bold Rock is at the foothills of Wintergreen, so you don't have to climb that beast. I'm going masochistic and slapping on a 34x36 combination to go up wintergreen this weekend.

Assuming someone is driving a car to put at the other end of your ride....Just hide some gallons of water along the way. Preferably near some trash cans so you can dispose of the empty jugs.