Ashland, Wisconsin

It starts with the water.

Lake Superior, cold, wide, and wild, anchors Ashland, Wisconsin—Chequamegon Bay curves against the southern shore, its protected waters softening Superior’s edge. On many mornings, the bay is calm enough to hold a perfect reflection of the sky, broken only by the blade of a kayak paddle or the glide of a paddleboard. Even when still, there’s movement everywhere.

Ashland doesn’t push itself as a hub for runners, cyclists, paddlers, or skiers. It doesn’t have to. The lake, the woods, and the rhythm of the seasons speak for themselves. This is a working lakeside town, long tied to its forests and water, that also happens to be an exceptional place to explore under your power.

Where Water Leads

Chequamegon Bay is more than a view; it’s the center of Ashland’s outdoor life. ‘Find yourself next to the water’ is not just the tagline of the Chamber of Commerce; it’s a lived reality, woven into the city’s history, culture, and daily rhythm. For the Ojibwe, these waters have been a lifeline for generations, carrying birchbark canoes along the same sheltered shoreline a paddler can trace today. On calm mornings, when the bay lies flat and the sky doubles itself in the water, the rhythmic dip of a paddle can feel like a connection across time.

Public launch points at Maslowski Beach and Bayview Park offer easy access to the bay’s protected stretches. From here, a paddle might lead into quiet estuaries alive with red-winged blackbirds, or along tree-lined shores where the only sound is the whisper of water under the hull. To the west lies Whittlesey Creek National Wildlife Refuge, a rare slice of Lake Superior coastal wetland where herons stalk the shallows and native brook trout spawn. Moving slowly here is the best way to experience it; the habitat rewards patience and quiet.

Some experienced paddlers do venture beyond the bay toward Washburn, but most Apostle Islands trips begin farther north from Bayfield or Little Sand Bay, where the open-water crossings are shorter and safer. Even so, Ashland serves as a natural gateway — the Apostle Islands National Lakeshore headquarters is here, and Long Island’s sandspit lies within Ashland County. From shore, the sweep of Superior connects the city visually to the archipelago, even if the open lake demands respect.

Trails by the Shore

Ashland’s Waterfront Trail traces 11.5 asphalted miles along the shoreline past parks, beaches, public art displays, historic structures, and neighborhoods, connected to Main Street by the Ed Griffiths Pedestrian Pass, a tunnel beneath Lake Shore Drive lined with a 3,684-square-foot mosaic of native plants and animals, complete with a scavenger hunt on the mural wall.

It’s a trail for all seasons and all rhythms. At dawn, runners and dog walkers often have it to themselves. Midday brings cyclists cruising between lunch downtown and the sandy sweep of Maslowski Beach. In winter, fat bikes leave faint tracks on snow-covered sections that the city grooms for multi-use.

This modern path follows a historic line: freight trains once hauled iron ore from the Gogebic Range to ships waiting at the dock. Now, the air holds the softer rhythm of footfalls and tire hum. Along the way, you pass fishing piers, the family-friendly beach, and Bayview Park. Downtown, the trail skirts Ashland’s renowned Mural Walk, 21 large-scale works painted across historic brick buildings depicting people, places, industries, and the history of the area.

A small but beloved feature sits just steps from the beach: Maslowski’s artesian well. Cool, clear water flows from the spring, a welcome refill for anyone walking, cycling, or running along the trail, and a reminder that in Ashland, fresh water is part of daily life.

Inland to the Hills

A short drive inland changes the horizon. The Penokee Hills rise in ridges of Precambrian bedrock, rivers run faster, and forest touches the sky.

Copper Falls State Park offers two of northern Wisconsin’s most celebrated waterfalls, Copper and Brownstone, linked by the Doughboys Nature Trail. The loop crosses bridges built by the Civilian Conservation Corps in the 1930s and offers overlooks into gorges carved by the Bad River and Tyler Forks. Long before it became a park, these river corridors served as travel routes for Ojibwe families and later for logging crews.

For a quieter escape, the trail to 70-foot-tall Morgan Falls and the breathtaking overlook at St. Peter’s Dome begins with a narrow cascade spilling through a granite cleft, then climbs to a rocky outcrop with sweeping views. On clear days, Chequamegon Bay shimmers in the distance. In midsummer, blueberry bushes fringe the path, inviting hikers to linger.

Nights Under the Pines

Ashland gives campers choices ranging from lakeside to deep forest. Prentice Park, on the city’s west side, offers wooded tent sites, a small campground, and direct access to the Waterfront Trail. Artesian wells here, like the one at Maslowski Beach, supply fresh drinking water. Outside the city, Copper Falls State Park maintains family and group sites within easy reach of its hiking loops and waterfalls. Nights carry the sound of rushing water through the dark.

For more solitude, the Chequamegon–Nicolet National Forest offers dispersed sites that feel far from anywhere. Backpackers can combine these with segments of the North Country Trail, while bikepackers can string together forest two-tracks and gravel roads into multi-day loops. Paddlers on inland lakes can haul gear to primitive sites, turning a day trip into an overnight under the stars.

The Long Paths

The North Country Trail, a 4,800-mile route stretching from North Dakota to Vermont, passes through Ashland County. South of the city, it runs along the Bad River and through Copper Falls State Park. Trailheads are often marked only by a blue blaze, a subtlety that adds to the sense of discovery.

Sections here follow old logging roads and river corridors used for centuries as natural travel routes. Hike them today and the forest feels intact, but each bend holds the layered marks of those who came before, from moccasin tracks to wagon ruts to modern boot prints.

Seasons in Motion

October brings the renowned WhistleStop Marathon and Half Marathon, when more than a thousand runners follow the crushed-limestone Tri-County Corridor from Iron River or Moquah to Ashland. The flat, fast route is framed by peak fall colors and lined with themed aid stations, volunteers, and music. What began in 1997 as a local wellness project has become one of the Midwest’s most beloved races — and one of Ashland’s proudest traditions.

Winter slows the pace but not the activity. Book Across the Bay, the upper Midwest’s most unique winter event, transforms the frozen surface of Chequamegon Bay into a 10-kilometer ski and snowshoe course lit by thousands of ice luminaries. The route varies each year with conditions, but the essentials—starlight, frost, and the glow of candles remain.

Just north of Bayfield, Mt. Ashwabay offers more than 40 kilometers of groomed ski trails in winter and over 20 miles of singletrack in summer. Athletes can ride or run its trails in the warmer months, then return to ski or snowshoe them under snow.

Cycling the Region

Cyclists find options ranging from shoreline spins to challenging inland climbs. Ashland’s flat lakefront is ideal for road rides and fat biking, while Mt. Ashwabay’s CAMBA-built trails deliver rolling climbs, flowy descents, and technical features for mountain bikers. Gravel riders can wander the surrounding countryside on quiet forest roads that pass old farmsteads and trout streams, sometimes tracing grades first cut for logging railways.

Layers of Land and Water

Ashland sits on Ojibwe land, with the Bad River Reservation to the east. The Kakagon–Bad River Sloughs, the largest remaining wild rice bed on the Great Lakes, are recognized as both a National Natural Landmark and a Ramsar Wetland of International Importance. They’re not open to public recreation without permission, but their cultural and ecological importance runs deep.

History is visible along the waterfront as well. The massive ore dock, once used to load iron ore onto freighters, now serves as a public walkway extending into the bay. Access is currently limited, with plans to expand in the future. Standing here, water and sky meet in every direction, and the curve of the bay hints at the scale of the lake beyond.

Why It Stands Out

Ashland is a place where a camping trip can double as a cycling weekend, where a hiking trail might follow the same line a logging crew once took to the river’s edge, and where the same shoreline that hosts a summer paddle can carry a ski trail across ice in February.

It doesn’t seek the spotlight. It waits for visitors who move quietly, notice deeply, and understand the way water, woods, and community fit together. Those who visit often leave with plans to return, drawn back to a place where the landscape tells its own story, and movement is the way to listen.