29 days in Wisconsin Itinerary

29 days in Wisconsin Itinerary

Created using Inspirock Wisconsin trip itinerary planner

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Route & dates

29 days in Wisconsin Itinerary

Start: Belleville
Drive:  5​h 30​min
1
Madison
— 3 nights
Drive:  1​h 15​min
2
Wisconsin Dells
— 4 nights
Train:  1​h 30​min
3
La Crosse
— 4 nights
Drive:  2​h 45​min
4
Wausau
— 3 nights
Drive:  2​h 45​min
5
Fish Creek
— 3 nights
Drive:  1​h 30​min
6
Green Bay
— 4 nights
Drive:  1​h 15​min
7
Sheboygan
— 3 nights
Drive:  1​h
8
Milwaukee
— 4 nights
Drive:  5​h 45​min
End: Belleville

3
nights
Madison

Madison ©
Madison might be the capital of Wisconsin, but students rather than politicians give the city its identity.
Venture out of the city with trips to Rotary Botanical Gardens (in Janesville) and Spring Green (The House on the Rock & Taliesin Preservation: Frank Lloyd Wright Visitor Center ). There's still lots to do: ponder the world of politics at Wisconsin State Capitol, examine the collection at National Mustard Museum, meet the residents at Henry Vilas Zoo, and get engrossed in the history at Livsreise.

To find reviews, more things to do, other places to visit, and other tourist information, read our Madison trip planner.

Belleville to Madison is an approximately 5.5-hour car ride. You can also fly. Traveling from Belleville in October, things will get little chillier in Madison: highs are around 62°F and lows about 43°F. Cap off your sightseeing on the 6th (Sun) early enough to go by car to Wisconsin Dells.

Things to do in Madison

Parks Museums Zoos & Aquariums

Side Trips

Spring Green, Matt Kenseth Museum, Rotary Botanical Gardens, Livsreise, National Mustard Museum
Highlights from your plan
Wisconsin State Capitol ©
Wisconsin State Capitol
Olbrich Botanical Gardens ©
Olbrich Botanical Gardens

4
nights
Wisconsin Dells

Wisconsin Dells ©
Named after a nearby scenic gorge famous for its steep sandstone formations, Wisconsin Dells features more than 20 water parks, making it one of the most popular vacation areas in this region.
When in Wisconsin Dells, make a side trip to see Wollersheim Winery & Distillery in Prairie du Sac, approximately 34 minutes away. There's much more to do: whizz through the canopy at some of the top local zipline courses and adventure parks, get in on the family fun at Mt. Olympus Resort, identify plant and animal life at International Crane Foundation, and cool off at Noah's Ark Water Park.

To see traveler tips, ratings, and more tourist information, use the Wisconsin Dells online holiday planner .

Traveling by car from Madison to Wisconsin Dells takes 1.5 hours. Alternatively, you can do a combination of bus and train. October in Wisconsin Dells sees daily highs of 60°F and lows of 41°F at night. Wrap up your sightseeing on the 10th (Thu) early enough to take a train to La Crosse.

Things to do in Wisconsin Dells

Theme Parks Parks Fun & Games

Side Trips

Baraboo, Wollersheim Winery & Distillery
Highlights from your plan
Elusive Escape Rooms ©
Elusive Escape Rooms
Devil's Lake State Park ©
Devil's Lake State Park
Zipline

4
nights
La Crosse

La Crosse ©
La Crosse is a city in the U.S. Explore La Crosse's surroundings by going to Chippewa Falls (Irvine Park & Jacob Leinenkugel Brewing Company), Elroy-Sparta State Trail (in Elroy) and World's Largest Bicyclist (in Sparta). Next up on the itinerary: take in the dramatic natural features at Grandad Bluff, stroll around Riverside Park, pause for some serene contemplation at Shrine of Our Lady of Guadalupe, and test your problem-solving skills at popular escape rooms.

For ratings, reviews, other places to visit, and other tourist information, you can read our La Crosse trip planner .

Traveling by train from Wisconsin Dells to La Crosse takes 1.5 hours. Alternatively, you can drive. Expect a daytime high around 63°F in October, and nighttime lows around 44°F. Finish up your sightseeing early on the 14th (Mon) so you can travel to Wausau.

Things to do in La Crosse

Parks Historic Sites Breweries & Distilleries

Side Trips

Chippewa Falls, Old Country Cheese, Elroy-Sparta State Trail, Treehouse Gift & Home, World's Largest Bicyclist
Highlights from your plan
Grandad Bluff ©
Grandad Bluff
Buena Vista Park ©
Buena Vista Park
Riverside Park ©
Riverside Park

3
nights
Wausau

Wausau ©
Wausau is a city in and the county seat of Marathon County, Wisconsin, United States. Venture out of the city with trips to 45 x 90 Geographical Marker (in Athens), Green Circle Trail (in Stevens Point) and Nueske's (in Wittenberg). Next up on the itinerary: admire the masterpieces at Leigh Yawkey Woodson Art Museum, sample the tasty concoctions at Bull Falls Brewery, admire the majestic nature at Rib Mountain State Park, and admire all the interesting features of Great River Road.

To see ratings, traveler tips, reviews, and other tourist information, read Wausau trip itinerary maker app .

Traveling by car from La Crosse to Wausau takes 3 hours. While traveling from La Crosse, expect slightly colder days and about the same nights in Wausau, ranging from highs of 58°F to lows of 40°F. Finish up your sightseeing early on the 17th (Thu) so you can travel to Fish Creek.

Things to do in Wausau

Parks Outdoors Museums

Side Trips

Nueske's, 45 x 90 Geographical Marker, Great River Road, Mullins Cheese, Kovac Planetarium
Highlights from your plan
Rib Mountain State Park ©
Rib Mountain State Park
Leigh Yawkey Woodson Art Museum ©
Leigh Yawkey Woodson Art Museum
Woodson History Center ©
Woodson History Center

3
nights
Fish Creek

Fish Creek ©
Fish Creek is an unincorporated community located in Door County, Wisconsin, United States, within the town of Gibraltar and is located on Highway 42 along Green Bay.HistoryThe first settler of Fish Creek was Increase Claflin and his family circa 1844, but the village founder is considered to be entrepreneur Asa Thorp. Change things up with a short trip to Door County Historical Museum in Sturgeon Bay (about 32 minutes away). There's lots more to do: admire the majestic nature at Peninsula State Park, do a tasting at Door Peninsula Winery, take in nature's colorful creations at The Garden Door, and view the masterpieces at Edgewood Orchard Galleries.

To see traveler tips, reviews, maps, and tourist information, read Fish Creek travel route tool .

You can drive from Wausau to Fish Creek in 3 hours. In October, plan for daily highs up to 57°F, and evening lows to 42°F. Finish up your sightseeing early on the 20th (Sun) so you can go by car to Green Bay.

Things to do in Fish Creek

Parks Shopping Museums

Side Trips

Sturgeon Bay, Egg Harbor, Cana Island Lighthouse, George Burr Gallery
Highlights from your plan
Peninsula State Park ©
Peninsula State Park
Edgewood Orchard Galleries ©
Edgewood Orchard Galleries
The Farm ©
The Farm

4
nights
Green Bay

Green Bay ©
Home of the Green Bay Packers, the city of Green Bay centers around sports and is home to hundreds of notable football icons, including Brett Favre and Curly Lambeau.
Explore Green Bay's surroundings by going to Oshkosh (EAA Aviation Museum, Paine Art Center and Gardens, & more), Von Stiehl Winery (in Algoma) and Hearthstone Historic House Museum (in Appleton). There's much more to do: examine the collection at Green Bay Packer Hall of Fame, get in on the family fun at Bay Beach Amusement Park, take in nature's colorful creations at Green Bay Botanical Garden, and identify plant and animal life at Bay Beach Wildlife Sanctuary.

To see ratings, other places to visit, reviews, and tourist information, read Green Bay trip maker website .

Traveling by car from Fish Creek to Green Bay takes 1.5 hours. October in Green Bay sees daily highs of 60°F and lows of 42°F at night. Wrap up your sightseeing on the 24th (Thu) to allow time to drive to Sheboygan.

Things to do in Green Bay

Museums Parks Zoos & Aquariums

Side Trips

Oshkosh, Hearthstone Historic House Museum, Vern's Cheese Store, Von Stiehl Winery
Highlights from your plan
Green Bay Packer Hall of Fame ©
Green Bay Packer Hall of Fame
EAA Aviation Museum ©
EAA Aviation Museum
Green Bay Botanical Garden ©
Green Bay Botanical Garden

3
nights
Sheboygan

Sheboygan ©
Sheboygan is a city in and the county seat of Sheboygan County, Wisconsin, United States. Explore the numerous day-trip ideas around Sheboygan: Horicon Marsh (in Mayville), Belgium (Luxembourg American Cultural Society & Cedar Valley Cheese) and Shalom Wildlife Zoo (in West Bend). The adventure continues: take in nature's colorful creations at Bookworm Gardens, see the interesting displays at 1860 Light Station, pause for some photo ops at Acuity Flagpole, and admire the majestic nature at Kohler-Andrae State Park.

Ask Inspirock to suggest an itinerary and make planning a trip to Sheboygan fast, fun, and easy.

You can drive from Green Bay to Sheboygan in 1.5 hours. In October, plan for daily highs up to 60°F, and evening lows to 42°F. Finish your sightseeing early on the 27th (Sun) to allow enough time to drive to Milwaukee.

Things to do in Sheboygan

Parks Museums Zoos & Aquariums

Side Trips

Belgium, 1860 Light Station, Wisconsin Maritime Museum, Whistling Straits Golf Course - Straits and Irish, Horicon Marsh
Highlights from your plan
Bookworm Gardens ©
Bookworm Gardens
Shalom Wildlife Zoo ©
Shalom Wildlife Zoo
Horicon Marsh ©
Horicon Marsh

4
nights
Milwaukee

Milwaukee ©
Milwaukee boasts well-preserved historical districts with a rich European past and a strong beer-brewing tradition.
Venture out of the city with trips to Veterans Memorial Park (in Oconomowoc), SC Johnson Headquarters (in Racine) and Geneva Lake Shore Path (in Lake Geneva). There's lots more to do: examine the collection at Harley-Davidson Museum, get engrossed in the history at Mitchell Gallery of Flight, learn more about the world around you at Milwaukee Public Museum, and get to know the fascinating history of Riverwalk.

To find where to stay, other places to visit, more things to do, and tourist information, read Milwaukee travel itinerary planner .

Traveling by car from Sheboygan to Milwaukee takes an hour. In October, plan for daily highs up to 62°F, and evening lows to 46°F. Cap off your sightseeing on the 31st (Thu) early enough to travel back home.

Things to do in Milwaukee

Museums Historic Sites Parks

Side Trips

Veterans Memorial Park, The Cedarburg Chamber of Commerce and Visitor Center, Geneva Lake Shore Path, SC Johnson Headquarters
Highlights from your plan
Harley-Davidson Museum ©
Harley-Davidson Museum
Milwaukee Art Museum ©
Milwaukee Art Museum
Lakefront Brewery ©
Lakefront Brewery

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