If you grew up near a Great Lake you were likely drilled with the HOMES acronym in grade school to keep them straight: Huron, Ontario, Michigan, Erie, and Superior. Filled with folklore (hello, shipwrecks!) and rimmed with lighthouses, cultural landmarks, and resort towns, plus—in recent years—a thriving surfing culture and wine regions, these five freshwater lakes captivate first-time visitors. No, you cannot see across the lake and yes, these waters are deep. Ticking off five lakes in 14 days might seem ambitious, but hear us out. Using this carefully crafted route, all the Great Lakes are seamlessly woven into an easy-to-follow itinerary packed with signature regional eats, blissful hikes, and natural wonders.
Days 1 and 2: Chicago
Kick off your trip at the soaring heights of Skydeck Chicago at the Willis Tower for a grand view of the city and Lake Michigan. Then take a walking tour of downtown, visiting museums like the Art Institute of Chicago. Indulge in one of Chicago’s three famous culinary treats— deep-dish pizza, hot dogs, or Italian beef sandwiches. After dark? Sip a cocktail at a hidden speakeasy like the Drifter or catch a theater show.
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On your second day, catch an El train north to Wrigley Field for Cubs baseball; grab a dog at the seventh-inning stretch, and sing your heart out to “Take Me Out to the Ball Game.” Afterward, soak up a little beer and atmosphere on the patio at one of the local sports bars. Finish up with an outdoor concert in Grant or Millennium Park. Make sure to get your picture taken in the mirrored center of the Bean—the sculpture that’s formally known as Cloud Gate.
Day 3: Indiana Dunes National Park
This is one of your easiest driving days, a quick trip of around an hour, traveling south down Interstate 94 then Interstate 90 towards Indiana. No need to set your clocks forward one hour: northwest Indiana, including Indiana Dunes National Park, is on Central Standard Time. Hugging 15 miles of Lake Michigan shoreline, the national park’s 15,000 acres include 50 miles of trails. Into bicycling? Pack the bikes to explore the Calumet and Porter Brickyard Bike Trails. On the northern tip of the park, Old Lighthouse Museum in Michigan City (run by the local historical society) is the state’s oldest remaining lighthouse.
Day 4: Cleveland
Buckle up bright and early for your nearly five-hour ride to what many call the North Coast (tacking on an hour for Eastern Standard Time), following Interstate 90 East all the way. Few people know that Cleveland has beaches and—gasp!—islands (Lake Erie Islands: hop a ferry from Sandusky, an hour west of Cleveland, to the chain of 26 islands). Stroll Lake Erie’s shoreline or just chill on the sand at Edgewater Park Beach downtown. If you’re a hard-core music fan, don’t miss the Rock & Roll Hall of Fame in downtown Cleveland. Spend the night at Schofield Hotel.
Days 5 and 6: Niagara Falls
You can opt to stay in Buffalo for a day, or make the drive along Interstate 190 North (hop off at Exit 21) straight to Niagara Falls. You’ll need time to explore the falls, which straddles the United States and Canada, and where Lake Erie drains into Lake Ontario. Book a one-day tour with Gray Line. Two of the three falls are in the United States: Bridal Veil Falls and American Falls. The other (Horseshoe Falls, the largest) lies in Ontario, Canada. The Frederick Law Olmsted–designed Niagara Falls State Park—the country’s oldest state park—offers a mix of overlooks (viewing sites) as well as trails to hike.
Day 7: Detroit
In the morning, take the four-hour drive west to America’s Motor City, spending a day exploring sights such as the Detroit Motown Museum and Detroit Institute of Arts, or picnicking on Belle Isle before grabbing drinks in public-art-filled alley, the Belt. Stay in a cool hotel like the Siren before heading out bright and early.
Day 8: Traverse City
Next up, drive to Traverse City. If you love wine, Traverse City is your jam as it’s the state’s most developed (and revered) wine region with two AVAs: Old Mission Peninsula AVA and Leelanau Peninsula AVA. The town of 16,000 residents also hugs Lake Michigan along the shores of Grand Traverse Bay. Tasting rooms are akin to Napa and Sonoma with food-pairing packages, vineyards on-site, and grand tasting rooms. Green Bird Organic Cellars is a cute winery stop; it’s on a 67-acre farm, and the owners produce both estate wines and hard ciders.
Days 9 and 10: Mackinac Island
Leaving Traverse City, travel north on Interstate 75 North to Mackinaw City, driving through the Gaylord State Forest Area. You’ll hop the Star Line Mackinac Island Ferry ($29 round-trip) to car-free Mackinac Island. The ferry trip takes 18 minutes, and parking is available near the ferry’s departure point. Even if you aren’t staying at the Grand Hotel, pop over for a self-guided tour of the grand estate, one of Mackinac Island’s most photographed buildings. Two lighthouses are on the island: McGulpin Point Lighthouse and Old Mackinac Point Lighthouse. A horse-drawn carriage tour is a fun way to explore the island in less than a day—and don’t forget to buy some fudge as a souvenir.
Day 11: Pictured Rocks National Lakeshore
From Mackinaw City, drive two hours to Pictured Rocks National Lakeshore—named for the mineral stains on its cliffs—in Munising, which hugs the south shore of Lake Superior. Take a few days to explore the great outdoors of the region by kayaking through gorgeous sea cliffs, hiking, and camping.
Days 12 and 13: Green Bay and Door County
Pack up and head out early. U.S. 41 South traces the western shoreline of Green Bay through Wisconsin until you hit the city of Green Bay, before curling northeast to Sturgeon Bay. This is the largest city in Door County, a resort community popular with Chicagoans and Milwaukeeans and on the southern portion between Green Bay and Lake Michigan. Door County is home to five state parks with easy hikes and stunning water views. Closest to Sturgeon Bay are Whitefish Dunes State Park (on the Lake Michigan side) and Peninsula State Park (on the Green Bay side).
Day 14: Milwaukee
From Sturgeon Bay it’s 2½ hours to Milwaukee, where you should celebrate your road trip finish with a pint of the city’s finest beer or a visit to the Milwaukee Art Museum. Spend the night or leave in the evening to make your way back down to Chicago to fly out. Alternatively, you could tack on a few days to your itinerary and head west to Minnesota.