Woman holding four Guess Where Trips envelopes while on road trip

Cleveland Area

Select a trip that works with your driving and travel preferences. If it's hard to choose, take our road trip quiz instead.

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  • Can be done in winter
    Waterfall Wanderings

    Waterfall Wanderings

    $65 CAD
    The ultimate waterfall adventure not too far from home! Wander along historic paths, snap photos of four falls, enjoy a glass of local vino and explore a mysterious cave.
    • Kid-Friendly
    • Dog-Friendly
    Can depart from: Cleveland Area
  • TONS OF TASTY BITES & SHOPS
    A Taste of Amish Country

    A Taste of Amish Country

    $65 CAD
    Escape to quintessential Amish country for cheese tastings, sweet treats, craft shops, funky museums and some incredible historic photo ops.
    • Kid-Friendly
    • Accessible
    Can depart from: Cleveland Area, Columbus Area
  • A LEISURELY ROAD TRIP
    Woman hiking in a forest

    Woodland Walks & Wineries

    $65 CAD
    Funky forest finds are on every stop, which are perfect for the outdoor adventurer. Unique wineries, bakeries, and a museum celebrating a man we have a lot to thank for are sprinkled in for the more leisurely road tripper.
    • Kid-Friendly
    Can depart from: Cleveland Area, Toledo Area
  • SCENIC ROUTE
    Bridges & Beauty

    Bridges & Beauty

    $65 CAD
    Get ready to wind your way through scenic tree-lined roads, cross charming covered bridges, sip at cozy wineries, hike stunning trails, and maybe even get a chill from a ghostly tale or two.
    • Accessible
    • Kid-Friendly
    • Dog-Friendly
    Can depart from: Cleveland Area
Three women walking through tulip fields
Winding roads through mountains at sunrise

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