Woman holding four Guess Where Trips envelopes while on road trip

Hamilton-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

  • BEST SELLER
    Local Markets & Picturesque Towns

    Local Markets & Picturesque Towns

    $65 CAD
    One of our best-selling trips, and for a good reason. Stops include historic towns, local markets, eateries and hidden gems. This trip makes a great gift because of its versatility.
    • Accessible
    • Kid-Friendly
    Can depart from: London Area, Toronto Area
  • BEST SELLER
    Patio table filled with beers.

    An Adventure is Brewing

    $65 CAD
    This road trip takes you on the perfect summer adventure filled with lavender fields, funky hidden gems, beaches and unique wineries and breweries. This is our featured summer trip and is best taken mid-May to early-October!
    • Accessible
    • Dog-Friendly
    Can depart from: London Area, Kitchener-Waterloo Area, Toronto Area
  • Road Trip Gift Card

    Road Trip Gift Card

    $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
    Can depart from: London Area, Kitchener-Waterloo Area, Toronto Area, Barrie Area
  • GREAT FOR YOUNG FAMILIES
    Alpaca behind a fence, being fed a carrot.

    Country Farms & Furry Friends

    $65 CAD
    Alpacas, donkeys and goats - oh my! Start your day off at a funky country market, before hanging with the birds and ending the day with some furry friends.
    • Kid-Friendly
    • Accessible
    Sale
    Can depart from: London Area, Kitchener-Waterloo Area, Toronto Area
  • BEST SELLER
    Bikes parked in front of a flower shop.

    Funky Florals and Fine Wines

    $65 CAD
    This pretty little road trip offers quite a few hidden gems combined with a few iconic attractions. Must enjoy: wine, food and flowers.
    • Accessible
    Can depart from: London Area, Kitchener-Waterloo Area, Toronto Area
  • Detour Diaries: Ontario

    Detour Diaries: Ontario

    $59.00 CAD
    The ultimate travel companion that transforms Ontario's most-travelled highways into unforgettable adventures.
  • GREAT YEAR-ROUND TRIP
    Woman sitting on a rocky shore overlooking a river.

    Riverside Roaming

    $55 CAD Sale
    Start your day in a picture-perfect town by the river before strolling along boardwalks, dining at a funky distillery, indulging at farm shops and so much more. This trip is a nice distance from the city and can be done year-round!
    • Kid-Friendly
    • Accessible
    Sale
    Can depart from: Toronto Area, London Area, Kitchener-Waterloo Area
  • RETURNS THIS FALL
    Spooky Sights & Ghostly Tales

    Spooky Sights & Ghostly Tales

    $65 CAD
    Explore spooky ruins, abandoned buildings, and haunted mansions tied to eerie legends, with a mix of walkable trails, photo ops, and even a chance to dine in a haunted restaurant. Please note: some parts of this trip take place within the city of Hamilton, travellers may encounter some traffic.
    • Dog-Friendly
    Sale
    Can depart from: London Area, Kitchener-Waterloo Area, Toronto Area
  • 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
    Can depart from: Toronto Area, Kitchener-Waterloo Area, Barrie Area
  • HIDDEN GEMS IN THE NIAGARA REGION!
    The Sweet & Scenic Route

    The Sweet & Scenic Route

    $65 CAD
    A little sweet, a little scenic - this road trip blends cozy cafés, local wines, and maple treats with easy trails, waterfalls, and serene ponds. Perfect for a girls' getaway or a romantic day trip! *Note that this trip can be taken in the summer months; however, the waterfalls may slow to a trickle in the hot weather!
    • Accessible
    • Dog-Friendly
    Can depart from: Toronto Area, Kitchener-Waterloo Area
  • SCENIC ROUTE
    Spooky black and white photo of a road on a foggy day.

    Beautifully Haunted

    $65 CAD
    This outdoorsy, story-filled road trip blends spooky legends with beautiful scenery along a rural driving route. A few local eateries and trails are sprinkled throughout the day to keep your energy up while ghost hunting. Most haunted sites are best enjoyed from the outside, so bring your curiosity and imagination to make the ghost stories come alive.
    • Dog-Friendly
    • Kid-Friendly
    Sale
    Can depart from: Toronto Area, Kitchener-Waterloo Area, London Area
  • HIDDEN GEMS
    The Whimsical Route

    The Whimsical Route

    $65 CAD
    Get ready for a road trip where nature, history, hidden gems, and a touch of cinematic magic come together for a perfectly whimsical escape just outside the city!
    • Kid-Friendly
    • Accessible
    Can depart from: London Area, Kitchener-Waterloo Area, Toronto Area
Three women walking through tulip fields
Winding roads through mountains at sunrise

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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!