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Ashland and Chequamegon Bay in the Fall means “Spectacular Color”, Fall Fishing, Waterfalls, Hiking, Biking, and Social Distancing “Naturally”!

Ashland is Wisconsin’s Historic Mural Capital with over 20 murals depicting our past and present! Click on the link for a Self-Guided Mural Walk and enjoy beautiful Art and Architecture as you browse the beautiful downtown and Ashland Area.

Shopping: Ashland’s Historic Downtown is an 8-block district and is listed on the National Register of Historic Places. 100% of the businesses in the district are locally owned and operated. Enjoy frozen yogurt at Kravin, to homemade Chocolates at Gabriele’s to fabulous whole foods at the Food Co-op, to yummy home bakery at the Ashland Baking Company and fun retail experiences from The Red Bicycle re-purposed goods to the New England Store, (the oldest retail store in Ashland) to Home Expressions where you’ll find a cool loft on the second floor. Our businesses love visitors and will welcome you with a smile! As you browse our many gift, clothing, sporting and specialty shops, you’ll find everything from local delicacies and gourmet delights, to outdoor gear, vintage clothing and fine art. Searching for that perfect gift for someone special? You’ll discover so many intriguing possibilities as you stroll through Ashland’s historic Main Street district.

Fall Events,  Red Clay Classic, Stock Car Races, AppleFest, in Bayfield and the Boston Qualifying Memorial Medical Center WhistleStop Marathon/Half-Marathon in Ashland.

Dining in Ashland:  Aside from the fast-food restaurants, our dining establishments in Ashland are all locally owned and operated, and each offer a unique venue! Find fresh Whitefish (our fish of choice on the bay) at River Rock Inn & Bait Shop and capture a selfie in front of the Smallmouth Bass! They also have delicious smoked fish from Chequamegon bay!

Ashland’s Waterfront is chock-full of parks and beaches. Maslowski on the west end marks the start of our waterfront trail that meanders throughout Ashland. The waterfront trail even includes a tunnel that connects the waterfront to the downtown. The tunnel is located at Pearson Plaza Park. The Waterfront trail is a 10-mile loop that is mostly paved.   Enjoy biking, walking, inline skating, running, or simply stroll through our city and enjoy the fabulous fall color and fall air. You can access the waterfront trail at Maslowski Beach, 6th Avenue Beach, Ashland Marina, Best Western/Hotel Chequamegon, Kreher Park, Bayview Park, and Culver’s on the waterfront. The 5th Street Corridor is the continuance of the trail on the cityside and has easy access all through the town.

The Oredock is located on the Waterfront near Kreher Park. The Dock jets out nearly ¼ of a mile to the “Diamonds”. The Oredock is a great place to walk, fish, or picnic. You can access the Oredock off the waterfront trail, or there is a very small parking lot located on St. Claire Street.

Prentice Park on the East end of Ashland is a great place to take the kids to play on the playground or simply walk through the trails in the park. Journey on the boardwalk that runs adjacent to the Fish Creek Slough. You are sure to see waterfowl and wildlife in this protected area of the bay. You’ll also find an Artesian well in Prentice Park continuously flowing with natural spring artesian water from Lake Superior. You may have to wait 6ft in line, because the locals “LOVE” the water from the wells in Ashland! Other wells are located at Maslowski Beach, the Blue Wave Inn, and behind Angler’s All.

Enjoy the Beautiful new pier at Bayview Park located on the east end of town. The Pier is handicapped accessible and a beautiful spot to enjoy the fall color and wave activity on Chequamegon Bay!

Central Railyard Park is in the center of town on the 5th street corridor. The corridor is an abandoned “rails to trails” project that continues the waterfront trail throughout the city of Ashland. Make sure to stop at the 950 Decapod located by the Railyard Park. When steam operations were concluded in 1954, the engine was retired and in 1956 the 950 was donated to the City of Ashland and was moved to its present location in 1987 at the time of the original Soo Line Depot restoration project.

There is no better place to watch a sunset over Chequamegon Bay than in Ashland. Ashland offers a diverse inventory of lodging properties from Chains to Mom & Pops to Cottages. Whether you want a pool or a patio, we have you covered!

Discover the fall charm of Wisconsin’s Northwoods with a visit to Ashland and the Chequamegon Bay as fall transforms the woods and terrain into a spectacular, warm, rustic, palette of striking beauty!

Ashland, the heart and soul of Chequamegon Bay, encourages visitors to enjoy and explore all that Lake Superior country has to offer. Click here to download the 2021 Ashland County Activity & Visitor Guide or here to have a Visitor Guide mailed to you. Find YOURSELF next to the water in Ashland!