6 Days Scenic Vermont to Wisconsin Road Trip (Complete Itinerary)

Introduction

A Vermont to Wisconsin road trip is more than a journey between two states — it’s a captivating adventure through charming towns, majestic forests, historic landmarks, and scenic highways that define the northeastern and midwestern United States. Whether you’re seeking cozy bed-and-breakfast stays, must-visit national parks, or vibrant city energy, this guide will walk you through a full-fledged itinerary from Vermont to Wisconsin.

Planning the Perfect Vermont to Wisconsin Road Trip

Before you set off, here are a few quick tips:

Estimated Distance: 1,000 miles
Ideal Trip Duration: 6–10 days
Best Travel Time: Late spring to early fall
Suggested Route: Burlington, VT → Albany, NY → Buffalo, NY → Cleveland, OH → Chicago, IL → Madison, WI

Day 1: Start Your Journey in Burlington, Vermont

Begin your adventure in Burlington, a picturesque city on the shores of Lake Champlain. Take a stroll along the Church Street Marketplace, and enjoy panoramic lake views from Waterfront Park.

Must-See Attractions:

ECHO Leahy Center for Lake Champlain
Shelburne Museum (just outside town)
Local breweries like Zero Gravity and Foam Brewers

Grab breakfast at Penny Cluse Café before hitting the road.

Day 2: Drive to Albany, New York – Capital City Charm

From Burlington, drive ~3.5 hours southwest to Albany, NY. This capital city blends colonial architecture with modern cultural vibes.

Top Stops in Albany:

New York State Museum
Empire State Plaza
Washington Park

Stay the night at The Morgan State House Inn, a boutique hotel near the park.

Day 3: Buffalo and Niagara Falls – Nature Meets History

Head west (~5 hours) to Buffalo, New York, with a detour to Niagara Falls.

Highlights in Buffalo:

Explore the revitalized Canalside district
Visit Frank Lloyd Wright’s Darwin D. Martin House
Sample wings at the Anchor Bar, the birthplace of Buffalo wings

Niagara Falls Tips:

Go for the Maid of the Mist boat tour
Visit Cave of the Winds for a close-up view
Stay at The Giacomo, a boutique hotel with views of the falls

Day 4: Cleveland, Ohio – The Rock & Roll Capital

From Buffalo, it’s a ~3.5-hour drive to Cleveland.

What to Do in Cleveland:

Rock & Roll Hall of Fame – a must for music lovers
Cleveland Museum of Art – world-class and free
Stroll through the Cleveland Metroparks Zoo
Visit the West Side Market for local eats

Dine in Ohio City at one of the trend-setting restaurants like The Black Pig or Larder.

Day 5: Chicago, Illinois – The Windy City Wonders

Next, make your way to Chicago (~5.5 hours). Break the drive up with a stop in Toledo or South Bend for quick sightseeing.

Chicago Must-Dos:

Snap a photo at Cloud Gate (The Bean) in Millennium Park
Admire views from Skydeck Chicago in Willis Tower
Tour The Art Institute of Chicago
Take a relaxing architecture boat tour along the Chicago River

Stay downtown or in the River North area for easy access to attractions. Don’t miss Chicago-style pizza from Giordano’s or Lou Malnati’s.

Day 6: Final Destination – Madison, Wisconsin

Wrap up your Vermont to Wisconsin road trip in Madison, the scenic capital of Wisconsin nestled between Lakes Mendota and Monona.

Must-Visit Places in Madison:

Wisconsin State Capitol – free guided tours available
Olbrich Botanical Gardens – lush greenery and tranquility
Shop and dine along State Street
Explore University of Wisconsin-Madison campus and lakeshore path

Try local cheese curds and craft beer at The Old Fashioned restaurant.

Optional Detours and Scenic Routes

Green Mountains, VT: Add a day to explore Stowe or Killington for mountain hikes.
Finger Lakes, NY: Wine tasting and lakeside beauty await.
Cuyahoga Valley National Park, OH: Stop for trails and waterfalls.
Lake Michigan Shoreline Drive: Between Indiana and Chicago for amazing views.

Road Trip Packing Essentials

Make your journey seamless with these travel items:

Printed itinerary and road map (GPS can fail in remote areas)
Snacks and water for long stretches
Phone mount and chargers
Travel pillow and blanket
Binoculars for scenic overlooks and wildlife sightings

Road Trip Tips to Remember

Start early each day to maximize daylight.
Fill up gas before remote stretches.
Book accommodations in advance, especially near national parks or major cities.
Keep your camera ready — especially for Vermont’s forests and Wisconsin’s lakes.

Experience the Best of America on the Road

The Vermont to Wisconsin road trip offers a beautiful blend of small-town charm, metropolitan culture, natural beauty, and hidden treasures. Whether you’re road-tripping solo, with family, or as a couple, this route promises an unforgettable journey through the heart of America. Embrace the scenic highways, discover local gems, and make memories on every mile of the trip.