Family of four sitting at a picnic table while opening up a Guess Where Trips package.

Kid-Approved Mystery Road Trips You’ll All Love

Summer may be winding down, but there’s still time for one last big adventure. Our Kid-Approved Mystery Road Trips are the perfect way to soak up those final carefree days before the school bell rings again. Think fresh air, curious minds, and family fun without the stress of planning. From charming hidden spots to easygoing trails, tasty treats, and even a chance to meet some furry friends at local farms, these trips give you a full day of excitement - and memories to carry into the school year. Pack the snacks, grab the envelopes, and make the last days of summer one to remember.

    Our Top Kid-Friendly Adventures in Canada

    Family of four walking through a grassy field while holding Guess Where Trips envelopes

    Toronto: The Whimsical Route

    London: Secrets in the South

    Ottawa: Quirky Adventures

    Victoria: West Coast Wonders

    Vancouver: Bowen Island Gems

    Calgary: Quirky Gems

    Halifax: Coastal Crawl

    Our Top Kid-Friendly Adventures in the U.S.

    Atlanta: Quaint Corners

    Austin: Cowboy Country Crawl

    Baltimore: Waterside Bliss

    Boston: Funky Farms & Storybook Tales

    Charlotte: A Little Bit of Everything

    Chicago: All Things Charming

    Cincinnati: Storybook Strolls

    Cleveland: Waterfall Wanderings

    Columbus: Cascades & Colors

    Dallas: Wonder & Whimsy

    Detroit: Sweet Sensations

    Indianapolis: Cozy Country Charm

    Los Angeles: South Bay Secrets

    Miami: Outback Oasis

    Minneapolis: Art Trails & River Tales

    New Haven/Hartford: Vibrant Vistas & Picturesque Towns

    New York City: Enchanted Adventures

    Orlando: Mysterious Gems

    Philadelphia: Whimsical Wonders

    Providence: Vintage Vibes & Views

    Raleigh: Timeless Towns & Scenic Sips

    San Diego: Country Treasures

    San Francisco: Coastal Jaunt

    Tampa: Offbeat Oddities

    Washington: Charming Curiosities

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