Dan Casey

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So you like to climb, eh? So do I. The steep roads of the Blue Ridge Mountains drew me to Roanoke, and every time I push myself to the top of one of them -- breathless, sweaty, heart pounding -- I feel like King of the Hill, even though my pace is more like a tortoise's.

With that in mind, I've come up with a short list of the toughest climbs in these parts, hatched with the help of a longtime Roanoke-area cyclist named Floyd. If you can handle all of these, you could handle any mountain in North America. So here they are, in order of difficulty. Click on the highlighted subtitles, and it'll take you to a loop ride that includes this climb.

1. Chestnut Mountain Road (from Roselawn Road)

With that, Manly Aylor stopped his bike, climbed off and dropped it in tall grass on the side of the road. He sat down with his head in his hands and complained that his stomach hurt. His face was pale as chalk.

It was early morning on Labor Day, and we were climbing the north slope of Chestnut Mountain. The narrow road corkscrews one mile up a brutally steep, grassy rise to Valhalla, one of Roanoke County's few vineyards.

"This is just great," I thought. "I drag one of my pals up the toughest climb in the whole region, and he's having a heart attack two-thirds of the way up. How am I going to explain this to his two sons?"

Thankfully, it never got that far. When I casually brought it up, Aylor hotly denied even the possibility his ticker might be quitting. But that didn't mean he could ride the rest of the way up the mountain. Instead, he finished it on foot, the chagrin mounting with each step.

Longtime cyclists in these parts agree: inch for inch, this is probably the hardest ascent in the Roanoke region. The length isn't bad, but there's never a break, and the average grade is something like 10 percent. The turns are evil and damn scary on the way down.

Getting there:

From Brambleton Avenue, follow Roselawn Road about 2.5 miles until it ends in a T-intersection. Take a left and you're on Chestnut Mountain Road. You reach the top just beyond the grape vines.

From Virginia 419, get on Sugarloaf Mountain Road over near Oak Grove Plaza, and follow it over Sugarloaf (a respectable climb in its own right). When you get to the bottom, stay straight and it turns into Chestnut Mountain Road.

If you stay on Chestnut Mountain Road after the climb, it'll bring you out on U.S. 221 about 4.5 miles south of the Virginia 419 intersection.

2. Starkey Wall

Ted Remandaban sails down "The Wall" on Merriman Road in southern Roanoke County. This 3/4-mile hill is the fastest descent around these parts. It's also one of the toughest climbs.

Starkey Wall, a.k.a. "The Wall," is a steep, mostly straight 3/4 of a mile on Merriman Road in southern Roanoke County near the Franklin County line. It has few redeeming features. The area isn't particularly scenic, and there's a fair amount of traffic. But among hardcore road bikers, this the most infamous descent in greater Roanoke. It's easy to reach 60 mph coming down. I once hit 48 -- and I was riding my brakes all the way.

But I thought: "What's it like to ride up that sucker?" To answer that, Ted Remandaban and I set out to conquer it early one Saturday morning. Ted had climbed it before, and his description was filled with expletives. This was my first time going up.

This is what I learned: The Wall is probably the most deceptive hill I've ever pedaled. It's smooth, fairly wide, and gently sweeping, and all those factors combine to trick your eyes into believing it's a piece of cake. It most definitely is not. As climbs go, this one is a total bitch.

Although I can take "The Old Road" up Mill Mountain (see below) at a pretty consistent 7 mph, The Wall slowed me to 4 or 5 mph, and even maintaining that pace was difficult. Its only redeeming feature is the ride back will put a bucketload of adrenaline in your veins.

Getting there:

From Virginia 419 near Tanglewood Mall, head south on Starkey Road to Buck Mountain Road, turn right and go across the railroad tracks to Merriman Road. Go left for a half-mile and take the first right (also on Merriman); follow for about 2 miles until you begin the hard climb.

3. Roanoke Mountain Loop Road

Here's the view hang gliders see at the top of Roanoke Mountain.

The Roanoke Mountain loop road is a 4-mile, one-way paved road that snakes up Roanoke Mountain at mile marker 120.5 along the Blue Ridge Parkway. It's a good thing it's one-way, because most of it is only about as wide as the average bike path.

It'll take you to about 2,200 feet above sea level, or 1,400 feet higher than Roanoke. It ends at one of only two approved hang-gliding launch sites along the Blue Ridge Parkway.

Along the way, you'll get to look down on Mill Mountain and Roanoke. From the top on a clear day, you can see dozens of miles, sometimes out to the twin Peaks of Otter, which are about 35 miles north on the parkway.

The books say the vertical gain on the loop road is 580 feet. But on a bike it feels more like 900. The climb is stepped in a series of four very steep sections; you get a brief breather at the top of each one before you're launched into the next. By the time you get to the first overlook, you're done with the hard climbing, but you've still got a ways to go.

The downhill dumps you out on the parkway about a half-mile north of the entrance. You have to be particularly careful coming down: The first one-way stretch is long and steep, with a tight, 180-degree switchback at the end. Heed the 15 mph cautionary sign. Be careful of potholes in the center of the road.

Getting there:

From downtown Roanoke, take Walnut Avenue east, which turns into Fishburn Parkway. Follow Fishburn to the end and make left. The entrance to the loop road is 100 yards up on the right.

4. Twelve O'Clock Knob

This sign, at the intersection of Twelve O'Clock Knob Road and Powell Drive, tells bikers to go back. Don't. The big climb starts here.

There's a good reason the pros chose this mountain between Salem and Southwest Roanoke County for a time trial on the now-defunct Tour Du Pont, the biggest-money bicycle road race in U.S. history. With curve after curve and a grade that reaches 10 percent, this 3-mile climb never lets up. Once you begin heading up the mountain from the Salem side, there are no breaks.

The climb is about 4 miles, if you count the low-grade ascent that begins right after you turn off Riverside Road in Salem onto Twelve O'Clock Knob Road. But the pitch of the road through this residential community is barely noticeable, especially in contrast to what's ahead.

The road twists up the mountain on sharp turns, steeply banked.You get to the hard part right after you see the green and white Bike Route sign that advises: "TURN AROUND." Keep going and you'll soon understand why some traffic engineer thought it was impractical for bikes.

You're near the top when you pass a natural gas line. From there, it's just a few hundred feet more. If you keep following the road, it'll bring you out to U.S. 221 about 5 miles south of the Virginia 419 intersection. (You can also climb from the 221 side, which is easier). Note: This is not a fun, rip roaring descent. You'll be riding your brakes all the way down this constantly curving road.

Getting there: Take Lee Highway/Apperson Road across Virginia 419 and make a right on Riverside Road. Follow it about 2.5 miles, Twelve O'Clock Knob Road will be on your left.

5. Apple Orchard Mountain

Fall's golden splendor is just beginning in this shot, taken on the way up Apple Orchard Mountain on the Blue Ridge Parkway. It's a 13-mile on the parkway from the James River (elev. 650) to the top of Apple Orchard Mountain, (elev. 3,950), the highest point on the parkway in Virginia.

It's not the pitch of this mountain on the Blue Ridge Parkway that puts it fifth on the list. The grade averages between 5 and 7 percent. But the astounding length makes it noteworthy. At 13 solid miles, it's the longest hill I've found in Southwest Virginia.

The fun starts at the bridge over the James River, which at 650 feet above sea level is the lowest point on the entire 469-mile parkway. Heading south, you'll climb 3,300 vertical feet before you top out near an old Air Force radar station on top of Apple Orchard Mountain. Note: Make sure you take plenty of food and water, and don't try this in the winter. The winds can get up to 100 mph, and the coldest recorded temperature in state history was taken up there.

Getting there:

The mountain is about 50 miles north of Roanoke. To get there, take Interstate 81 north to the Natural Bridge exit. Follow U.S. 11 north to Natural Bridge, where you'll pick up Virginia 130 north. Follow this to Glascow, and take Virginia 501 east. Where 501 bears right and crosses the James River, go straight on Virginia 130 instead. Follow it for about two miles to the parkway entrance and take a right (north on the parkway). You can park at the Otter Creek visitors center at mile marker 60 on the Blue Ridge Parkway. There is plenty of parking, food, water and bathrooms here.

Honorable mention: The Old Road up Mill Mountain

It seems hard to believe, but this shot was taken inside the city limits of Roanoke. Erin Garvin is riding along the Monument Trail, a killer, 1.75-mile run that leads from the monument at the saddle of Mill Mountian on Fishburn Parkway down to Sylvan/Prospect Road, aka "The Old Road" up Mill Mountain. A small band of hardy trailhounds have been quietly working on this gem for the past few months. It's not officially open yet, but people are riding it anyway.

Mill Mountain sits on Roanoke's eastern flank, and there are two ways to get to the top. The first is Fishburn Parkway, a wide, smooth, fairly sunny road that's a lot like the Blue Ridge Parkway (to which it ultimately connects).

The other way up is Sylvan/Prospect Road, a.k.a. "The Old Road," an engineering marvel cut into Mill Mountain's steep western face. Now closed to cars because of a fragile concrete bridge about three-quarters of the way up, this was the first road up the mountain. It opened as a toll road in the 1920s and quickly put out of business an incline railroad that went to Mill Mountain's peak.

This is my favorite climb of all time, and I do it at least 6 times a week. The road is open to pedestrians, bikes and the cars of the few people who live on the moutain. Through a series of four tight switchbacks, the Old Road zigzags 2 miles up through a thick forest that envelopes riders in deep shade. The grade is steady and averages about 8 percent. A few sections are steeper and there are some flat spots where you can catch your breath as well.

When you get to the parking lot near the Mill Mountain Discovery Center, follow the asphalt path up to the Mill Mountain Star.

Note: You don't want to descend on The Old Road, the turns are too tight to be any fun. Rather, come down on the new road, Fishburn Parkway. At the stop sign, turn left toward town. The curves are so well banked you don't even need your brakes.

Getting there:

From downtown, take Jefferson Street south to Walnut Avenue and make a left. Cross the bridge and follow Walnut up the hill. Make a right on Sylvan Road and follow it up the mountain.