Skip to content Skip to main navigation Skip to footer

Things to do while you are in Ashland
Take time during the day to check out the many unique Retail Stores in Ashland. Enjoy the historic Buildings on Main Street. Retail Business Owners are eager to welcome the many WhistleStop Racers, Families, Spectators and local Residents with WhistleStop in-store and sidewalk specials for the weekend. Ashland has gift stores, clothing, shoes, and even a chocolate shop with homemade German Chocolates! Solstice Outdoors specializes in outdoor and fitness gear with name brand clothing and will also carry plenty of supplements such as GU and Hammer products just one short block from the Civic Center… Also, check out Shoe Shack and Moore’s on Main where you will find name brand shoes, socks, and clothing for the outdoors.
While you are downtown, view the fascinating history of Ashland’s past heritage as painted on Murals from East to West in Ashland. Ashland’s Mural walk is in the 8-block Main Street business district and is listed on the National Register of Historic Places. In 2005, Ashland was designated the Historic Mural Capital of Wisconsin. Check out the murals at .
Chequamegon Bay on the South Shore of Lake Superior, Ashland promises to provide you with a breathtakingly serene, picturesque view of the largest body of fresh water in the world and fall color at its peak!

Plan a FUN weekend:

October 12:

  • Ashland Parks & Recreation “The Loose Caboose Kids’ Foot Race,” 1/2 or 1k foot race for children ages 4-11. Around Central Railyard Park behind the Bretting Community Center, 400 W. 4th Ave., at 5:30pm. Participants will receive a t-shirt and a train whistle. For more information, call 715-682-7059.
  • October 12 & 13:

  • Pumpkin Patch & Corn Maze at Northern Bounty Farm.  Open Fridays 3-6pm and Saturdays 10-6pm.  Take a hay ride out to our u-pick patch or shop our pre-picked carving pumpkins, pie pumpkins, gourds and more! Hay pyramid, corn bin play area, petting farm, games, and photo ops! There’s fun for all ages! Ages 2 and under are free. 3-6 are $5 and 7+ are $7 – that price includes all activities, maze, and a pumpkin of your choice! We accept cash, card or WIC! Porta-potties and picnic area available. We are a small family farm and would love the support of our wonderful community! Follow signs from Highway 13 and Bass Lake Rd. 38239 Bass Lake Rd, Highbridge.  Questions? 715-681-0022.
  • October 13:

  • Farmer’s Market, 6th Ave West and Main Street by the Burger Barn., 8am-12pm. Last Market Celebration.
  • Chequamegon Bay Golf Club presents ”Tough Man-Warmer by the Lake” Golf Tournament from 8am-5pm.
  • Ashland Bayfield County Sportsmen Banquet at 5pm, at Bad River Lodge and Casino, at 5pm. For more information or tickets, call 715-373-2088.
  • October 13-14:

  • WhistleStop weekend at HAUSER’S Superior View Farm,  86565 County Hwy J, Bayfield. Apple season will be in full swing this weekend and HAUSER’S will have hayrides through the orchards on Saturday and Sunday, October 13 & 14. Sample our apples, jams, and apple butter, check out the view, and enjoy the season at the farm!   While visiting check out the new APFELHAUS CIDERY – our very own handcrafted hard cider. From blossom to bottle – grown, pressed, fermented, and bottled right here at HAUSER’S Superior View Farm.  HAUSER’S is open every day through October 31 from 10am-5pm.
  • White River Ag presents the Hay Pyramid and A-Mazing Corn Maze Every Sat. & Sun 11am to Dark at 58330 Nelson Rd, Mason. Along with the Corn Maze there is Hay Pyramid, corn pit, games, corn launcher, photo ops, water races, food and pumpkin patch! Cost $8 (11 and up), $5 (4-10) and kids under 3 free. For more information call 715-765-4591.
  • October 14:

  • The Ashland Knights of Columbus will host an all you can eat pancake and sausage breakfast from 8am-12pm at Our Lady of the Lake Social Hall, 201 Lakeshore Drive East, Ashland. Cost: $6 for adults; $4 for children 6-11; free for children 5 and under. Proceeds will benefit Our Lady of the Lake School. For more information, call 715-682-9621.