Woman holding four Guess Where Trips envelopes while on road trip

Barrie-Area Road Trips

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

Browse all trips

  • Road Trip Gift Card

    Road Trip Gift Card

    Regular price $74.00 CAD
    Give the gift of a one-day surprise road trip with Guess Where Trips®! Valued at $74, this voucher covers the full cost of any of our mailed road trips, including tax and standard shipping. The recipient can choose any surprise road trip that suits them, and it will be shipped right to their door. These gift cards never expire.
  • STAFF PICK
    A person walking on a trail surrounded by tall trees

    Vistas & Caves

    $65 CAD
    This road trip is a quick jaunt north of Toronto and is perfect for the outdoor enthusiast. It really is the perfect mix of everything.
    • Accessible
    • Kid-Friendly
    • Dog-Friendly
  • BEST SELLER
    Weird & Wonderful Things

    Weird & Wonderful Things

    $65 CAD
    This road trip takes you north towards beautiful sights, unusual attractions and secluded waterfalls.
    • Kid-Friendly
    • Dog-Friendly
  • Detour Diaries: Ontario

    Detour Diaries: Ontario

    Regular price $59.00 CAD
    The ultimate travel companion that transforms Ontario's most-travelled highways into unforgettable adventures.
  • BEST SELLER
    Water reflecting forest and blue sky.

    Muskoka Meandering

    $65 CAD
    Muskoka Meandering is the perfect way to escape from the hustle and bustle of the city and immerse yourself in nature while enjoying delicious wines and beers, beautiful scenery and lookouts, and charming small towns.
    • Kid-Friendly
    • Dog-Friendly
  • GREAT OVERNIGHT GETAWAY
    Markets to Mountains

    Markets to Mountains

    $65 CAD
    From cute markets to mountainside hikes, Markets to Mountains provides you with all the stops for a cozy yet adventurous day trip in Ontario. We highly recommend booking a hotel at the finishing stop for the ultimate weekend getaway.
    • Kid-Friendly
    • Accessible
  • BEST DONE SPRING-FALL
    The Waterfall Route

    The Waterfall Route

    $65 CAD
    Explore a variety of waterfalls, charming towns, funky restaurants and several photo ops throughout the day! This trip is perfect for spring - fall travellers. Waterfalls may dry up in extreme heat.
    • Kid-Friendly
    • Dog-Friendly
  • BEST SELLER
    Taste of the Country

    Taste of the Country

    $65 CAD
    This trip is just a short jaunt from Toronto and is perfect for foodies and families! You'll explore incredible farmers markets, cute small towns, a few local spots to grab a drink and an easy wooded trail.
    • Accessible
    • Kid-Friendly
    Sale
  • GREAT YEAR ROUND TRIP!
    Man with rain jacket walking along a leaves-covered forest trail.

    Escape to Nature

    $65 CAD
    Explore tiny towns and easy outdoor adventures before cozying up at a local cafe or brewery. Optional wintery activities include ice skating and snowshoeing! Please note: this trip is similar to the Sport Chek Winter Trek for Toronto.
    • Kid-Friendly
  • MOTHER'S DAY PICK
    Two women on a beach looking out at the water

    Bayside Wonders

    $65 CAD
    The perfect blend of charming small towns, farmers markets, and wine tastings mixed with epic waterfalls and a couple unique trails. Bayside Wonders is a bit further, which makes for an incredible weekend getaway! Please note: A few recommendations have been moved from The Waterfall Route to this new trip. There are still tons of new spots to explore! 
    • Kid-Friendly
    • Dog-Friendly
    Sale
  • SCENIC ROUTE
    Historic white house underneath a vibrant blue sky.

    Hidden Gems of Huronia

    $65 CAD
    Discover the endless charm of a lesser-known area that is full of haunted history, picturesque trails, cute small towns and farm-fresh flavours. We're sure you'll want to keep coming back for years to come! 
    • Kid-Friendly
    • Accessible
    Sale
  • Digital Download Only
    Aerial view of Toronto cityscape during sunset, showcasing various buildings and the CN Tower.

    Toronto Gems

    Regular price $39.00 CAD
    Explore all of Toronto's downtown gems in a completely new way - ditch the car and walk or bike while you explore! This trip is best for anyone who isn't super familiar with the Toronto core, plus there's an optional “scavenger hunt" so there is something for you to find and decode at each stop!
Three women walking through tulip fields
Winding roads through mountains at sunrise

CAN'T DECIDE?

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Select your region and interests to find the best trip for you.

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Gift-a-Trip

The ultimate present for the avid traveller. Select a digital or mailed 'Gift-A-Trip' option that covers the full cost of one of our road trips. We promise you this will be one of the most memorable and unique gifts they'll ever receive!