Woman holding four Guess Where Trips envelopes while on road trip

Cleveland Ohio

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
  • Can be done in winter
    Groves, Gardens & Grapevines

    Groves, Gardens & Grapevines

    $55 CAD Sale
    This incredibly picturesque road trip is full of whimsical gardens, lookout points, wineries, and easy strolls along forest paths. We think it's an area you'll want to come back to time and time again.
    • Kid-Friendly
    Sale
    Can depart from: Columbus Area, Cleveland Area, Toledo 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
Three women walking through tulip fields
Winding roads through mountains at sunrise

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