Skyline Drive, from Chester Bowl Park (1801 East Skyline Parkway) to Spirit Mountain
There are two ways to describe this route; one is short, one is a bit longer.
Short description: Stay on Skyline till Spirit Mountain.
But that's most helpful to folks who know that Skyline is occasionally and briefly interrupted by other roads.
From Chester Bowl's main front parking lot, head right (which is west) on East Skyline. Be careful on the inside of that snakey curve—auto traffic gets tight, and occasionally runners or dogs and their humans will pop from trails out onto the street.
See that lake vista that comes into view after climbing the gentle little rise? Get used to it, and enjoy it—revel in it, even—but also remember that Skyline is busy, and has narrow shoulders, and drivers are also gawking at the natural beauty, so bicycle-based sight-seeing is best done while stopped, pulled safely to the side, and not getting too complacent.
In less than a mile, there's a wide, busy, two-state intersection: First, 11th Avenue East (on the left) and Denney Drive (on the right) dump onto Skyline. A few meters farther, and East Skyline, meets Kenwood Avenue and Martha Street. Veer slightly left—head toward about 10 o'clock on an imaginary chronograph face, without going straight up Martha or straight down Kenwood.
For the next three-quarters of a mile, while approaching Mesaba Avenue, remain vigilant against traffic, and prepare to be even more so.
Where Skyline meets Mesaba, adopt the studious, aggressively protective instincts of a kindergarten teacher who's leading 20-odd squirrely five-year-olds in a tenuous single-file line. This is not a place to mess around.
After checking both left and right for traffic at least five or six times, move swiftly, but with control, across Mesaba to the right-most lane headed downhill. While making sure that no auto is creeping up behind and barreling into the right-turn lane, head toward the stop light that marks the intersection of Mesaba and Central Entrance.
Do not even think about running this light. Too many lanes of motor traffic come from too many directions, going too (illegally) fast—and drivers are far too distracted with keeping themselves safe and on course—for cyclists to get cocky.
Once the light is green, head straight through it, down the hill. Immediately after the light, start checking for traffic merging from the right. As soon as possible, get as far right as possible, and start signaling a right turn.
At Ninth Street, turn right and brake for an immediate stop sign. It's an easy one to unintentionally blow through.
Head straight up Ninth. Within a couple blocks, at the end of a nice climb, it merges back onto Skyline. Most traffic from here until Spirit Mountain is safer and more mellow, but roads are generally rough and almost comically full of potholes and crevasses in some points. Mind the gaps.
Stay on Skyline—it's now West Skyline Parkway, by the way—till two tiny bodies of water called Twin Ponds. (And don't believe high-school kids who claim the poinds were named for twin boys who died there in childhood.) After crossing the bridge between the ponds, head right, on a short bit of road called Enger Park Cutoff.
(Going left is also acceptable. The Cutoff and West Skyline meet at the same place, forming a short circle drive around the base of the huge rock on which Duluth landmark Enger Tower stands.)
For the next little bit, lake views will mostly disappear or be obscured.
At the intersection of the Cutoff and West Skyline, turn right, back onto West Skyline. More rotten road here, with the added hazard of negotiating golfers and their various carts heading back and forth between Enger Park Golf Course and its parking lot / driving range area.
Proceed on Skyline till the next busy, sort-of-complicated intersection. It seems like a confusing spot, because a lot is going on—traffic in all directions, up and down hills, around curves, and just kind of all over the place.
But to stay on Skyline, just go straight. Look both ways, many times. Obey signals and signs. Look both ways again. Then zip across the intersection.
This is a fun seciton. Be careful—still a narrow shoulder, still some bumps and cracks and holes, still the potential for auto traffic—but enjoy the view (there are some pull-off overlooks, often filled with teenagers who seem too wary to be up to much good), the twists, the trees, and the descent to Haines Road.
Haines comes up quickly, so be ready for it.
Check traffic up and down, cross to the right shoulder, and in just a few ticks, veer right and back onto Skyline.
This section is kind of pretty, with some decent climbing, but the roads are often ragged for a mile or two.
Nothing tricky till the intersection with Minnesota Highway 2. Just be careful there, because traffic is moving fast, exiting or entering Interstate 35, and this is not a spot where even most conscientious drivers would expect to see bicycles. Cross 2, find a comfortable climbing gear, and have at Thomson Hill.
The view from Thomson HIll Visitors Center is incredible, and getting to it adds more climbing, for folks who are into that sort of thing.
West Skyline acts as a frontage road for I-35 here, and the next intersection includes on-and-off-ramps, an overpass, a few gas stations and a McDonald's, and generally a fair amount of activity.
At the stop sign, turn left, onto the overpass, headed toward McDonald's. Ride defensively.
Immediately after the overpass, West Skyline takes a swooping right and flows past McDonald's, a gas station, and a hotel; it crosses a bridge over a railroad, and hits a stop sign at an intersection with West Mountain Drive. Hang a left, and follow the signs for Spirit Mountain.
That's it for the basic Chester-to-Spirit route.
Creative possibilities are nearly infinite. As an out-and-back it's a good, if utilitarian, ride. As a way to get from east to west rather quickly, it's quite effective. especially for riders looking to be out for many hours and miles, heading into Carlton County and beyond.
As always, consult online maps or a gazzetteer to come up with fun routes, then let us know about them.
Directions to parking
The front parking lot—immediate and unmistakable after pulling through the park's main gate—is almost never full, unless Fall Fest, May Fest, or Tuesday evening Music in the Park is happening. Make sure to get in a good walk around the park before or after riding. Walking trails go up and follow both sides of Chester Creek down to Fourth Street. Municipal ski trails wind through trees up and down the park's main hill—the one that includes a chair lift. Hike up far enough, then take the trail that dips into tall grass just past where the lift ends, and check out one of the best Lake Superior views in this end of town.
About 12 miles from Chester Bowl to Spirit Mountain, with many more or less possible.
Terrain range and difficulty
Moderately hilly, but no serious climbing. Amazing views. Nice way to reach one part of town from another. Not much shoulder. Roads are often bumpy, rutty, and in rough shape.
Got some? This is a popular route, but seldom mentioned as a favorite on its own merits.
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