Jerry Jolly Overlook to the Jolly Long Connection Reopened

Ta da! Ted May, Gerry Miller, and Lindley Mattson take a rest after building 8 box steps. PHEW!!

Bayfield Area Trails volunteers opened a previously concealed footpath in the Jerry Jolly Trail network in mid-August. The reestablishes a connection between the Overlook and the Jolly Long Loop trails, creating opportunities for a new loop hike from the Overlook as well as a more direct link to ultimately travel to the Pileated Woodpecker Trail and Mt. Ashwabay.

Map of the project location.

Many thanks to volunteers John Ipsen, Nan Fey, Mark Filonowich, Ted May, Gerry Miller, Gene Lemmenes, Mark Peterson, and Kate Kitchell for their hard work on this very ambitious project! They were supervised by friendly dogs during the process.

This project would not have been possible without tremendous support from Lindley Mattson and Sara Hudson from Bayfield County Forestry and Parks, including providing pre-cut lumber and rebar for the steps, shuttling materials and tools to the site, and mowing all of the existing trails.
Kate Kitchell, BATs Committee Chair, noted that the footpath has been included in Bayfield County maps for at least 20 years—which explains the faded trailhead post at the Overlook. But beyond the post, there was overgrowth, eroded tread, a hazardous switchback down to a tributary, and a steep climb on the other side.

No More!

Using Rogue hoes and hard rakes to cut through soil and roots, John, Nan, and Kate restored the trail tread, widened the path, and reestablished side drainage.

Gene took the lead in creating a crossing at the tributary using stepping stones and rock armoring.

The new creek crossing, rock armoring, and box steps up from the creek.

A close up of the rock armoring and timber steps.

Ted, Gerry, Lindley, Kate, Mark, and Nan installed a total of 16 box steps on the steep ravine on the south side and cleared the trail leading to the Jolly Long.

The new path is a lovely, tree-lined trail along a steep ravine with views of a cedar stand and towering white pines.

A Favorite Fall and Winter Trail

The Jerry Jolly Trail is a scenic, non-motorized trail within the Pikes Creek and Mt. Ashwabay Trail Network in the Bayfield County Forest and the Nourse Sugarbush Natural Area. It’s maintained year-round for hiking, snowshoeing, and cross-country skiing (ungroomed).

Jerry Jay Jolly entrance sign.

SIgn showing the distances to four primary destinations.

Starting at the Star Route Trailhead, the 4-mile trail highlights the northern peninsula’s scenic glacial landscape: open grasslands, a meandering creek, hardwood forests, and deep ravines. It was made possible in 2006 by Jerry Jolly, who lived nearby and donated 72 acres of his land for public access in perpetuity.

Jerry's Meadow Loop
​One-third of a mile into the hike is Jerry’s Meadow Loop (.3 mi), followed by a forested trail that descends to Pikes Creek. At the base of the ravine, hikers can choose a shortcut to the creekside path or take a longer walk along the water.

Pike's Creek
​Pikes Creek is a high-quality trout stream, draining about 30 square miles and dropping 400 feet before entering Lake Superior’s Chequamegon Bay near the Les Voigt Fish Hatchery and the Salmo Trail. ​The creek usually runs clear and is especially stunning when reflecting the fall colors or flowing around snow-capped stones.

Overlook Loop Loop
​A bridge, built by volunteers in 2022, takes you across the creek and up to the Overlook Loop (.5 mi). To reach the ridge, hikers can continue along a creekside path and climb the ravine, or ascend via a ski hill.

The newly opened footpath can be accessed from the ridge. The improved switchback, new rock armoring, and hillside steps make this an easy and scenic walk to the Jolly Long Loop, a 3-mile classic ski trail through ravine and forest.

Mowing the ridge near the access point for the newly opened footpath.

Note: In 2023, BAT volunteers forged another trail along Pikes Creek. The Pileated Woodpecker Trail connects the hatchery to the Jerry Jolly Trail and continues on to Mt. Ashwabay. While the hatchery entrance is currently closed, the upper section of the Pileated Woodpecker Trail can be accessed at Ashwabay.

Additional Links

Ashland Daily Press: 
“Jolly Good Hike Near Bayfield”

Bayfield Area Trails: 
"Jerry Jolly Overlook Re-Opened​​ "
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