This Wisconsin Downtown Is Made For Strolling
Most small towns in Wisconsin, or anywhere in the Great Lakes Region, for that matter, require a lengthy drive to get to. As such, a good leg-stretching stroll, complemented by charming attractions and an invigorating freshwater breeze, makes for a perfect counter-balance. Ashland, aka the "Historic Mural Capital of Wisconsin," is a casual lake town typically encountered by tourists en route to the Apostle Islands National Lakeshore. With a well-decorated and pedestrian-friendly Main Street, as well as a waterfront path on the opposite side of U.S. Route 2, Ashland's modest downtown is made for walking.
Welcome to Ashland

The seat of Ashland County is situated in the Lake Superior Lowland region of Northwestern Wisconsin. From this hub of Chequamegon Bay (i.e., a subsect of Lake Superior), it is a little over 200 miles to the closest major city: Minneapolis, Minnesota. Conversely, from Ashland, it is a mere 23-mile drive due north (after completing the traverse around the base of the bay) to the next point of interest: the aforementioned Apostle Islands National Lakeshore, as accessed from the city of Bayfield.
Originally incorporated in 1887, Ashland's population has settled at just below 8,000. Its downtown core reflects this modest figure in that it has just enough infrastructure and cultural expression to keep residents and visitors engaged, but it is still the type of place where jaywalking is an afterthought. Such low-key rule-breaking comes in handy when checking off the copious building-sized creations that constitute Ashland's Mural Walk.
Historic Murals

Of Ashland's 23 historic murals (all of which were designed by Kelly Meredith and Susan Prentice Martinsen), 16 are consolidated within the eight-block Main Street Business District, which is listed on the National Register of Historic Places. Two more can be found on East Main Street, while the last three hang out on the periphery, slightly beyond the scope of today's casual stroll.

The large and colorful works showcase Ashland's formative history (e.g., the Lumberjack Mural, Ore Dock Mural, Railroad Mural, and Voyageurs Mural), its Great Lakes beauty (e.g., Bayfront Mural, Apostle Islands Mural, and Lighthouse Mural), and its welcoming Wisconsonites (e.g. the Waitress Mural, Women of Ashland Mural, and Cabbies & Stagecoach Mural). The official Mural Walk begins on Ellis Avenue (i.e., the division of East and West Main Street) and heads west. While you're welcome to cruise around at your leisure (after all, these things aren't hard to spot), we'll assume this same flight plan while discussing other highlights of downtown Ashland.
Notable Downtown Destinations

If seeing all of these artistic depictions of Ashland's history piques your interest, then why not hit pause on the walk and take a tour of the Ashland Historical Museum? Here, you'll find a model railroad, wartime relics, everyday anachronisms such as rotary phones and a working jukebox, a well-equipped kids' area, and a passionate staff to boot. Admission is free, but donations are accepted (and I'm sure appreciated). Upon exiting, take note of the striking, red-bricked, circa-1915 Ashland County Courthouse across the street.

Next up is the Bay Theater. Now, this may not be the time to stop and see a whole movie, but I, for one, have always been a sucker for marquee cinemas. I love seeing independent theaters like this still up and running-especially this final era before straight-to-streaming releases. Perhaps a simple photo-op is enough for today, or perhaps when the stroll is complete, a movie night is in store.

A few blocks further down the line, Black Cat Coffeehouse offers a quirky community spot that is definitely worth popping into, even if it's just for a to-go coffee to fuel the second half of this walk. It was a particularly brisk morning when I strolled by, so the sight of hot coffee, chowder, and company coaxed me into an extended stay.

The 16th and final mural (of this part of town, anyway) can be found between 9th and 10th Avenue. But if you rejoin Lake Shore Drive and scoot down one more block, you'll be able to pose with Wisconsin's Largest Bass. As with many touristic novelties, this oversized ode to the Lake Superior angling scene will be entertaining for only a couple of minutes, but it will also segue nicely into Ashland's waterfront experience.
Walking the Waterfront

Between the highway and the waters of Chequamegon Bay, Ashland harbors an 11.5-mile Rails to Trails System. This multi-use asphalt path spans from Prentice Park all the way to Bayview Park, passing five other parks, plenty of beachfront, and some additional art installations along the way. Looping back to our downtown starting point, walk east into Memorial Park, past The Bandshell (where fair-weather concerts and screenings commence), take a peek at the Ashland Marina, and then head back up Ellis Avenue to Main Street. And just like that, you've completed a charming, engaging, and nature-infused walk in this overlooked Wisconsin city.
Similar Spots for Strolling
Bayfield

Since you're in the area, continuing on to the Apostle Islands National Lakeshore is practically mandatory. The base town for this stunning archipelago is Bayfield, the smallest city in Wisconsin. It too has a pedestrian-friendly main street (i.e., Rittenhouse Ave - a reduced-speed section of the Wisconsin Lake Superior Scenic Byway) with a gentle smattering of indie shops. At its eastern terminus, you'll find the cruise and ferry operators that will launch you into the Apostles.
Ephraim

Way over in eastern Wisconsin, hiding on the Eagle Harbor extension of Green Bay, the historic village of Ephraim overlaps with Ashland in a couple of regards. It too has a little artistic flair despite being a strictly preserved Moravian community, and it too has a paved path that passes parks and docks whilst paralleling its waterfront thoroughfare (Highway 42).
The beautiful state of Wisconsin is undeniably well-suited for the casual walker. Ashland, with its string of historic murals, unique downtown establishments, and lightly developed waterfront, invites a leisurely stroll that leaves a lasting impression. But as we have seen, towns such as Bayfield and far-off Ephraim further encourage this relaxing and healthy trend. With that in mind, be sure to check out these notable downtown areas.