6 days in Wisconsin Itinerary

6 days in Wisconsin Itinerary

Created using Inspirock Wisconsin itinerary planner

©
This plan was created by another user. Make it your plan

Route & dates

6 days in Wisconsin Itinerary

Start: Chicago
Train:  1​h 30​min
1
Milwaukee
— 2 nights
Drive:  3​h
2
Baileys Harbor
— 1 night
Drive:  3​h 30​min
3
Madison
— 2 nights
Drive:  2​h 45​min
End: Chicago

2
nights
Milwaukee

Milwaukee ©
Milwaukee boasts well-preserved historical districts with a rich European past and a strong beer-brewing tradition.
Your inner history buff will appreciate Basilica of St. Josaphat and Pabst Mansion. Venture out of the city with trips to Wind Point Lighthouse (in Racine), Holy Hill (in Hubertus) and Old World Wisconsin (in Eagle). Next up on the itinerary: see the interesting displays at Harley-Davidson Museum, contemplate in the serene atmosphere at St. Joan of Arc Chapel, get to know the fascinating history of Riverwalk, and admire the masterpieces at Milwaukee Art Museum.

Discover how to plan a Milwaukee trip in just a few steps with Inspirock's itinerary builder.

Chicago to Milwaukee is an approximately 1.5-hour train ride. You can also drive; or take a bus. In October in Milwaukee, expect temperatures between 62°F during the day and 46°F at night. Cap off your sightseeing on the 3rd (Thu) early enough to travel to Baileys Harbor.

Things to do in Milwaukee

Historic Sites Museums

Side Trips

Holy Hill, Wind Point Lighthouse, Ten Chimneys, Old World Wisconsin, Kneeland-Walker House
Highlights from your plan
Harley-Davidson Museum ©
Harley-Davidson Museum
Basilica of St. Josaphat ©
Basilica of St. Josaphat
Pabst Mansion ©
Pabst Mansion

1
night
Baileys Harbor

Baileys Harbor ©
Baileys Harbor is a town in Door County, Wisconsin, United States. Kick off your visit on the 4th (Fri): stroll around Cave Point County Park, admire the majestic nature at Peninsula State Park, then walk around Sunset Beach Park, and finally visit a coastal fixture at Cana Island Lighthouse.

For other places to visit, ratings, reviews, and other tourist information, you can read our Baileys Harbor sightseeing planner.

Traveling by car from Milwaukee to Baileys Harbor takes 3 hours. While traveling from Milwaukee, expect slightly colder days and about the same nights in Baileys Harbor, ranging from highs of 57°F to lows of 45°F. Wrap up your sightseeing on the 4th (Fri) to allow time to travel to Madison.

Things to do in Baileys Harbor

Parks Nature Historic Sites

Side Trips

Fish Creek, Cave Point County Park
Highlights from your plan
Peninsula State Park ©
Peninsula State Park
Cana Island Lighthouse ©
Cana Island Lighthouse
Sunset Beach Park ©
Sunset Beach Park

2
nights
Madison

Madison ©
Madison might be the capital of Wisconsin, but students rather than politicians give the city its identity.
Kick off your visit on the 5th (Sat): admire the striking features of The House on the Rock, admire the landmark architecture of First Unitarian Meeting House of Madison, then get a sense of history and politics at Wisconsin State Capitol, and finally take in nature's colorful creations at Olbrich Botanical Gardens. Here are some ideas for day two: admire the majestic nature at Devil's Lake State Park, then admire the landmark architecture of Taliesin Preservation: Frank Lloyd Wright Visitor Center , and then gain insight at Folklore Village.

To find photos, more things to do, traveler tips, and other tourist information, refer to the Madison online travel route planner .

Drive from Baileys Harbor to Madison in 3.5 hours. In October, daytime highs in Madison are 62°F, while nighttime lows are 43°F. Finish your sightseeing early on the 6th (Sun) so you can drive back home.

Things to do in Madison

Parks Historic Sites Nature

Side Trips

Spring Green, Folklore Village, Devil's Lake State Park
Highlights from your plan
Folklore Village ©
Folklore Village
Wisconsin State Capitol ©
Wisconsin State Capitol

Similar Plans

10 days in Wisconsin BY A USER FROM UNITED STATES July, culture, outdoors, relaxing, beaches, historic sites, museums, wildlife, slow & easy, popular sights PREFERENCES: July, culture, outdoors, relaxing, beaches, historic sites, museums, wildlife ATTRACTION STYLE: Popular sights PACE: Slow & easy 8 days in Wisconsin BY A USER FROM UNITED STATES September, culture, outdoors, relaxing, historic sites, museums, wildlife, popular & hidden gems PREFERENCES: September, culture, outdoors, relaxing, historic sites, museums, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 3 days in Wisconsin BY A USER FROM UNITED STATES September, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, slow & easy, hidden gems PREFERENCES: September, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Hidden gems PACE: Slow & easy 4 days in Wisconsin BY A USER FROM UNITED STATES October, kids, outdoors, relaxing, beaches, historic sites, wildlife, popular sights PREFERENCES: October, kids, outdoors, relaxing, beaches, historic sites, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 4 days in Wisconsin BY A USER FROM UNITED STATES August, culture, outdoors, relaxing, beaches, hidden gems PREFERENCES: August, culture, outdoors, relaxing, beaches ATTRACTION STYLE: Hidden gems PACE: Medium 13 days in Austin, Fort Collins & Wisconsin BY A USER FROM UNITED STATES September, culture, outdoors, relaxing, romantic, historic sites, museums, wildlife, popular sights PREFERENCES: September, culture, outdoors, relaxing, romantic, historic sites, museums, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 7 days in Wisconsin BY A USER FROM UNITED STATES November, historic sites, museums, popular sights PREFERENCES: November, historic sites, museums ATTRACTION STYLE: Popular sights PACE: Medium 5 days in Wisconsin BY A USER FROM UNITED STATES September, outdoors, relaxing, romantic, popular & hidden gems PREFERENCES: September, outdoors, relaxing, romantic ATTRACTION STYLE: Popular & hidden gems PACE: Medium 7 days in Wisconsin BY A USER FROM UNITED STATES September, popular sights PREFERENCES: September ATTRACTION STYLE: Popular sights PACE: Medium 8 days in Wisconsin BY A USER FROM NETHERLANDS September, popular sights PREFERENCES: September ATTRACTION STYLE: Popular sights PACE: Medium 8 days in Wisconsin BY A USER FROM UNITED STATES September, popular sights PREFERENCES: September ATTRACTION STYLE: Popular sights PACE: Medium 9 days in Wisconsin BY A USER FROM UNITED STATES September, popular sights PREFERENCES: September ATTRACTION STYLE: Popular sights PACE: Medium
View more plans