Originally Published August 19, 2022 1:18 pm CDT

Upon arrival in the Ashland area, it takes virtually no time to appreciate how people from the Ojibwe to loggers, trappers, and merchants fell in love with its picturesque landscapes, natural resources, and location at the end of Lake Superior’s Chequamegon Bay.

European settlers turned the region into a hub for transporting timber and iron ore by sea and later by rail. The massive and historic ore dock served countless freighters from 1916 to 1965 and became a symbol of the city until it was taken down in 20113.

The city that was once a major industrial port is now better known as a base for those who have no shortage of places to explore and enjoy during a visit—from sailing and other recreational boating to fishing, dining, and taking in some of that history in a place known as the “Historic Mural Capital of Wisconsin.”

Begin your trip to Ashland by stretching your legs downtown. There are some wonderful classic buildings to admire, both for their history and the work that has been done to preserve them. The stroll includes more than 12 murals spread along a route that depicts the town’s history in paint. The Storefront Mural shows 13 retail, entertaining, and banking establishments from the town’s past. Another favorite is the Shiller’s Shoe Store Mural, which shows a snippet of what Ashland looked like in the 1920’s Jazz era.

New murals are added to the walk so the town’s history is forever being remembered. 

“This is a fun thing to do if you find yourself in Ashland. The murals are beautiful and were created using historic photographs,” wrote a TripAdvisor reviewer named Catherine. “Many of them depict real people, including some of the founders of the town. My favorite is the mural that shows the old ore dock—very cool, and a great way to preserve the local history!”

The town’s chamber of commerce also throws a combination mural and classic car festival in the fall. This year the Mural Fest and Classic Car Show will be held on Saturday, Sept. 10. Attendees can look forward to sidewalk sales, music, face painting, balloon art, and dozens of classic cars—a little something for everyone in the family. 

While you’re meandering downtown don’t forget to pay a visit to Ashland’s scarecrows. They’re exactly as they sound—fun and creative scarecrows hanging out on the main streets. 

Ashland began its Scarecrow Festival in 2009, borrowing the idea from the neighboring town of Bayfield. You can find them sitting on hay bales, chatting on the phone on the street, and greeting visitors at the city hall—while Bayfield mostly placed their scarecrows in their natural habitat, the fields. 

So you spent all morning walking around Ashland to see the mural and scarecrows—that means you’re probably hungry. Stop by the Deep Water Grille for lunch,  it’s a fan-favorite restaurant right on Main Street. The menu includes local foods like Lake Superior fish, vegetarian and vegan options, and classic Wisconsin fare like beer-battered cheese curds. 

“The food was so good, we ate here all three nights of our stay!” wrote Jodi B. on TripAdvisor. “I highly recommend the Chicken Bacon Ranch Mac and Cheese. To die for!”

Deep Water Grille is part of a complex of dining options that actually also work in tandem. The LC Wilmarth Tap Room, which houses the South Shore Brewery located immediately adjacent to Deep Water, offers diners a step back in time with an old pub atmosphere. 

There are a couple of tables, but much of the seating is around an oval-shaped bar. You can order food from the Deep Water Grill menu or from The Alley—the third restaurant in this group. Or if you’re just feeling snacky, you can order a drink and munch on the free popcorn. 

The Alley is more of a sports bar and also offers pizza. 

Get a true Wisconsin experience and hit the lake with a guide service like Beyond the Catch. 

Ashland’s own Beyond the Catch offers fishing and lake excursions year-round. Owned and operated by Captain Tommy Hicks, the US Coast Guard-certified guide company will take attendees on full and half-day fishing excursions—including ice fishing, but don’t forget a very heavy coat to keep warm. 

Even in winter, attendees say this is a must-see experience. 

“We loved seeing the ice caves on the Sherp,” wrote Tara on TripAdvisor. “This is a must do experience whether you are ice fishing or just want to see the ice caves. Tommy was awesome! I don’t fish but I would come back and go fishing as I know it would also be a memorable experience. Thanks, Tommy!”

The fishing and boating experience is also suitable for children as young as 4, but no pets are allowed. 

There are also ways to get close to the lake without actually being on it or in it.

This shallow, sandy beach offers an opportunity to wade or even swim a little in the lake without having to commit to a half-day or full-day out on the water. The beach also offers a playground, changing rooms, and an artesian well.

The well, which is an attraction all of its own, can be found in a recently rebuilt shelter. The fresh and drinkable water is free—provided you FYOB (fill your own bottle)!

Elle Meyers Elle Meyers is a Congressional Reporter for COURIER where she covers national politics and lawmakers on Capitol Hill. Previously Elle was a beat reporter in Montgomery County, Maryland and she is a native of Portland.

travel Not a Regular Road Trip—Check Out These Quirky Badger State Attractions

travel Never Been to Wisconsin? Here Are Places to Visit Based on the Season.

Our Wisconsin Six Wisconsin Cities Earn a Spot in Livability’s “Top 100 Best Places to Live”

travel Day-Trippin’ Across Wisconsin: Mineral Point

Analysis POLL: WI ‘Very concerned’ over Sen. Johnson’s Role In ‘Fake Electors’ Plot

Get exclusive Wisconsin stories & news right in your inbox