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Roam Around

undefined Itinerary

Last updated: 2024 Jun 14

Morning

Start your day early and head north to the charming town of Lake Geneva, Wisconsin. Take a stroll around the historic town and then head out to explore the beautiful fall foliage along the lake. Take a boat tour to see the colors from the water or hike around the shoreline.

Afternoon

Enjoy a late lunch at Popeye's on Lake Geneva, a local favorite for burgers and brews. Then, head back to Chicago in time for a sunset stroll along the Chicago Riverwalk.

Evening

End your day with dinner at River Roast, which offers stunning views of the Chicago River and delicious American cuisine.

Bedtime

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Morning

Drive west to the town of Galena, Illinois, known for its charming Main Street and historic homes. Take a walk through Grant Park to see the beautiful foliage before heading to the Galena Cellars Vineyard and Winery for a wine tasting and picnic lunch.

Afternoon

Enjoy a scenic drive along the Great River Road, which follows the Mississippi River. Stop at Apple River Canyon State Park to see the fall colors and hike through the park's trails.

Evening

Head back to Galena for dinner at Fried Green Tomatoes, a cozy restaurant serving up delicious Southern fare.

Bedtime

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Morning

Head south to Starved Rock State Park, one of Illinois' most popular parks. Take a hike through the park's canyons and along the Illinois River to see the stunning fall foliage.

Afternoon

After your hike, head to nearby Matthiessen State Park for more hiking and beautiful views of the changing leaves.

Evening

Enjoy dinner at Uptown Grill, a local favorite for American cuisine and craft beer.

Bedtime

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Morning

Drive north to the town of Lake Forest, known for its stunning estates and beautiful gardens. Take a tour of the Lake Forest Historic District to see the stunning architecture and fall foliage.

Afternoon

Visit the Chicago Botanic Garden, located in nearby Glencoe, to see the beautiful fall colors and take a walk through the picturesque gardens.

Evening

Head back to Lake Forest for dinner at Market House on the Square, a farm-to-table restaurant serving up delicious American dishes.

Bedtime

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Morning

Drive southwest to the town of Starved Rock, Illinois, and take a hike through the stunning Matthiessen State Park.

Afternoon

Visit the nearby town of Ottawa and explore the charming downtown area. Take a walk along the Illinois and Michigan Canal and see the beautiful fall foliage.

Evening

Enjoy dinner at the Lone Buffalo, a local brewery and restaurant serving up delicious pub fare and craft beer.

Bedtime

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Morning

Head north to the town of Lake Geneva, Wisconsin, and take a boat tour of the beautiful fall foliage along the lake.

Afternoon

After your boat tour, head to the nearby town of Fontana-on-Geneva Lake and explore the charming downtown area. Take a walk around the lake to see the beautiful fall colors.

Evening

Enjoy dinner at Pier 290, a lakeside restaurant serving up delicious American cuisine.

Bedtime

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Morning

Drive west to the town of Galena, Illinois, and take a stroll through the charming Main Street area.

Afternoon

Visit nearby Apple River Canyon State Park to see the beautiful fall foliage and hike through the park's trails.

Evening

Enjoy dinner at Fritz and Frites, a cozy French restaurant serving up delicious cuisine in a charming setting.

Bedtime

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