Skip to content Skip to main navigation Skip to footer

Fall Travel Itineraries

We know the Chequamegon Bay has so much to offer that we have put together some suggested Travel Itineraries to help you make the most of your visit.

Sample Itinerary #1: Designed for motorcycle riders, traveling in late summer/early fall

Day 1

• Continental breakfast at the hotel

• Stop at the Northern Great Lakes Visitor Center and ride to Iron River

Bag Lunch

• Ride the area

• Dinner

• Stop at Star Liquor and have drinks at the hotel

Day 2


Visit Bayfield

• Take the Madeline Island Ferry over to Madeline Island have lunch and tour Big Bay State Park or canoe at the County Park


• Evening at Big Top Chautauqua

Day 3

• Breakfast at Black Cat Coffeehouse

• Ride the “Horn” – Cornucopia

• Lunch

• Ride

• Dinner

• Watch the sun set over Chequamegon Bay


Sample Itinerary #2: Designed for single, active traveler, visiting in the fall

Day 1

• Stay at Bayview Motel

• Breakfast at Breakwater Café

• Shop and explore historic downtown/murals

• Lunch at the New China Restaurant

• Take a lakefront walk/5 mi plaques

• Dinner at Deep Water Grille

• Relax in room

Day 2

• Breakfast at the Black Cat Coffeehouse

• Hike at Morgan Falls and St. Peter’s Dome with a packed lunch from Tap Roots Coffee Shop

• Walk the waterfront at sunset

Dinner at Ashland Family Restaurant

Day 3

• Head to Madeline Island with a packed lunch from Sixth Street Market

• Bike to Big Bay State Park, use a rented kayak

• Dinner at Explorer’s Point


Sample Itinerary #3: Designed for two runners from Sheboygan traveling in the fall prior to the CenturyLink Whistleshop Marathon


• Stop at the Chamber office for course map

• Take the mural tour

• Check into the Super 8 Motel

• Shop on Main Street

• Visit the Benoit Cheese Factory

• Fish fry at the Avalon Bar


• Breakfast at hotel

• Run the 5th Street Corridor

• Orchard tour in Bayfield

• Have lunch on Madeline Island at Lotta’s Café

• Bike around the island

• Have dinner at the Deep Water Grille and hang out at the South Shore Brewery


• Stop at the Sixth Street Market for brats to take home

• Stop at Morgan Falls and St. Peter’s Dome before heading home

• Have lunch at The Green Lantern in Glidden


Sample Itinerary #4: Designed for four females from the Twin Cities, in their mid-30s, using their smartphones to plan trip in November for Chick-uamegon Race and shopping for food for Thanksgiving


• Check in at Hotel Chequamegon

• Dinner and drinks at Molly Cooper’s Lounge


• Breakfast at Delta Diner

• Shop in Ashland, then drive to Washburn

• Lunch at Dalou’s Bistro in Washburn

• Drive back to Ashland for spa treatments at Escape by the Lake

• Fish fry at The Platter

• Dine in room


• Run the Chick-uamegon Race wearing bling bought in town

• Main Street shopping following the race

• Lunch at Black Cat Coffeehouse

• Dinner at Second Street Bistro with music to follow



Ashland Area Chamber of Commerce

Strategic Planning Session Notes

February 7, 2014