The Midwest Road Trip Northeast/Midwest Loop

  • Starting in historic yet modern Boston head out through Western Mass into the rolling wine country of upstate New York’s Finger Lakes region.
  • Amish Country, The Baseball Hall of Fame and The Rock and Roll Hall of Fame welcome passing visitors in northern Ohio.
  • Spend some time in Michigan, with options of driving on to Wisconsin or take a car ferry across Lake Michigan. Wisconsin stop off cities may include Madison, Milwaukee, or Green Bay.
  • Start your turn around here or keep heading west into Minnesota.
  • Have a stay on the shores of one of the many lakes in the Northwoods of Wisconsin or take the ferry to car free Mackinac Island.
  • Looping back through one of the World’s Wonders, Niagara Falls, drop down into Vermont, where depending on the season, rafting, mountain biking, leaf peeping or skiing are the activities to stretch the legs.
  • Head back to Boston to complete the loop.

Other road trips we’ve done:

Naples, FL through Florida Keys to Key West Loop
Phoenix through Sedona to Grand Canyon returning to Phoenix
Phoenix through Moab and Arches to Snowmass/Aspen
San Francisco to LA one-way or loop
Salt Lake City through Yellowstone to Grand Tetons

Interested in having us help you plan a road trip? Email us at mmillerd@saltymountain.com.

trip planning specialists

More destinations

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