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Biking the Milwaukee Road

After a week of perfect sunny weather, I took off Saturday morning with high hopes of a smooth ride. Then the weekend came and with it 2 inches of snow. When we turned the corner to the trailhead and I pulled my bike out from the trunk it was a major gut check. But I took that first leap of faith and hit the trail pedaling on the Milwaukee Road.

Milwaukee Road Rail-Trail Quick Facts

States: MT

Counties: Silver Bow

Length: 4.5 Miles

Trailheads: Pipestone Pass (MT 2), Janney Road

Trail Surface: Grass, Sand, Gravel


The Milwaukee Road showcased modern engineering at its finest. At 2,300 miles long, the Chicago, Milwaukee, and Saint Paul Railroad connected central Montana to the Great Lakes! Finished in 1909 at an estimated cost of 560 million, it became one of the very first railroads to utilize electricity as a method to transport trains. Electricity made landscapes that had been near impossible to pass like the Continental Divide a breeze.
“Electricifaction has been such a tremendous success on the Milwaukee Road that…I think it quite within the fact to say that the Milwaukee Road has forgot that the Continental Divide exsits.”
—Charles A. Goodnow, Milwaukee Railroad Executive, 1915

Directions to the Trailhead

There are 2 ways to access the Milwaukee Road—Pipestone Pass (HWY 2) or Janney Road. To start on Janney Road you take HWY 2 off Harrison Avenue. Drive for 1.5 miles then turn right on to Janney Road. Stay on this road for 2.75 miles until you reach the gate above.

The advantage of starting from Janney Road is that finishing on HWY 2 makes being picked up much easier. The advantage of starting from HWY 2 is that the entire trail will be on a gentle downhill slope. I biked the trail starting at Janney Road ending at HWY 2.

The Trail

Take HWY 2 and turn on Janney Road. Follow Janney Road for 2.75 miles until you reach the trailhead. The trail begins at the black gate at the end of Janney Road.

In approximately .55 miles you will come across your first sign for Sagebrush Flats. Whatever you do stay on the trail. Don’t go towards Sagebrush flats if you want to finish the Milwaukee trail.

At 1.15 miles the trail cuts into the side of the mountain as it makes its way towards the first tunnel.

The trail from the start follows a gentle uphill path through gravel (and depending upon the time of the year, snow). At 1.35 miles you will reach the first tunnel of the day. This tunnel is 550 feet long. Men from 2 separate camps along the Milwaukee Road used ridiculous amounts of black powder and air-powered machine drills to shape these and other tunnels like it.

At 2.2 miles you will reach the second tunnel. At this point you are past the halfway point. The larger of the two tunnels, this beauty stretches for 1,110 feet. Tunnels along the Milwaukee Road were typically 16-24 feet wide and 20-24 feet tall to allow trains to pass through unscathed.

At 3 miles you will hit the first and only bridge that passes over Blacktail Creek. The view from center of this wooden bridge on a snowy day is picture perfect.

From the bridge the trail appears to end when you hit the Pipestone Pass Tunnel (2,300 feet long). Unfortunately the Pipestone Pass Tunnel is off limits to the public and outside of park boundaries. Turn right and head up the hill.

At 4.1 miles the trail ends right alongside HWY 2.

I hope you enjoyed this trail guide on biking the Milwaukee Road. Be sure to check out Biking the Copperway Regional Trail, another fantastic ride in beautiful Butte, Montana!


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