Travel Itinerary


Explore Historic Downtown Ashland!!

Take time during the day to check out the many unique retail stores located in downtown Ashland and along Lake Shore Drive (U.S. Hwy. 2).  Retail business owners are excited to welcome the many WhistleStop racers and their families, as well as spectators and local residents with WhistleStop in-store specials and sidewalk sales for the weekend.

While you are visiting Ashland and Ashland County, check out any of these major assets or better yet plan a future trip to Ashland – the heart of Chequamegon Bay and the Historic Mural Capital of Wisconsin:

  • Beautiful location nestled along the south shore of Lake Superior
  • Friendly people who cordially welcome visitors and guests
  • Over a dozen vibrant outdoor murals located throughout the city, depicting the rich heritage and colorful history of Ashland
  • Pristine Chequamegon Bay, a world-class smallmouth bass fishery
  • Mouthwatering cuisine available at a wide variety of unique dining establishments
  • Numerous lodging establishments to fit your needs, from charming B&Bs and fine hotels to family-owned motels
  • Unique shops, galleries and specialty stores where you’ll find everything from local delicacies and gourmet delights, to outdoor gear, vintage clothing and fine art
  • Award-winning South Shore Brewery, home of Rhoades Scholar Stout, Nut Brown Ale, Maple Amber, and many other fine handcrafted beers
  • Scenic Waterfront Trail along Lake Superior connecting Maslowski Beach on the west and Bayview Park on the city’s east end
  • Two artesian wells offering pure, bubbling spring water located at Maslowski Beach and Prentice Park
  • Swimming beaches, parks, picnic areas, campgrounds, and an 18-hole golf course
  • Full-service, 140-slip municipal marina, conveniently located in the center of town

 Numerous points of local interest include:

  • Madeline Island, located in Ashland County, rich in natural beauty with a unique atmosphere everyone loves
  • Apostle Islands National Lakeshore, an archipelago of 22 islands located just one half-hour north
  • Whittlesey Creek National Wildlife Refuge
  • Northern Great Lakes Visitor Center, about 2 miles west of town just off U.S. Hwy. 2
  • Chequamegon-Nicolet National Forest
  • Historic Soo Line steam locomotive decapod (10-wheel) engine 950 located across from the Depot
  • Ashland Historical Society Museum, 216 Main Street West
  • Historic bandshell in Memorial Park on U.S. Hwy. 2 offering open-air summer concerts
  • Ashland Area Chamber of Commerce, 1716 W. Lake Shore Drive
  • Southern Ashland County featuring verdant hills teeming with wildlife and quaint towns
  • Copper Falls State Park, south of Ashland on State Hwy. 13
  • Breathtaking views of sunsets on tree-lined shores over the glistening water of Lake Superior

Winter, spring, summer and fall – Ashland is a year-round vacation destination for nature enthusiasts and silent sports fans.  No matter the season, the community welcomes visitors to enjoy and explore this shining jewel crowning the greatest of the Great Lakes.  Ashland – Find yourself next to the water!

Click here for a video on Ashland.