Woman holding four Guess Where Trips envelopes while on road trip

Kellogg GWT

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

  • MOTHER'S DAY PICK
    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
  • MOTHER'S DAY PICK
    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
    The Small Town Charm Trail

    The Small Town Charm Trail

    $65 CAD
    You know those towns that are described as 'blink-and-you'll-miss-it'? They often have the most amazing hidden gems! Get to know a few small pockets of Ontario with this surprise road trip.
    • Accessible
    • Kid-Friendly
    Can depart from: Sarnia Area, London Area, Toronto Area, Kitchener-Waterloo Area
  • Add On: Gift Wrapping

    Add On: Gift Wrapping

    $14.00 CAD
    A reusable gift box with magnetic closure - perfect for presenting their surprise trip and storing souvenirs after the adventure.
  • 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
  • STAFF PICK
    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
  • MOTHER'S DAY PICK
    Woman sitting on a rocky shore overlooking a river.

    Riverside Roaming

    $65 CAD
    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
    Can depart from: Toronto Area, London Area, Kitchener-Waterloo Area
  • BEST DONE SPRING-FALL
    Hops, Hikes & History

    Hops, Hikes & History

    $65 CAD
    There is so much more to this trip than the name implies. From hidden local breweries to unique trails and scenic sights, this trip will take you to a few unknown areas that you’re sure to love!
    • Kid-Friendly
    • Dog-Friendly
    Can depart from: Sarnia Area, London Area, Kitchener-Waterloo Area, Toronto Area
  • MOTHER'S DAY PICK
    Secrets in the South

    Secrets in the South

    $65 CAD
    With funky markets, scenic roads and the most picturesque towns, you'll love all of the secrets you discover on the road. This trip is best enjoyed between June - September as there are a handful of fabulous seasonal suggestions.
    • Kid-Friendly
    Can depart from: Sarnia Area, London Area, Kitchener-Waterloo Area, Toronto Area
  • RETURNS THIS FALL
    Historic Haunts

    Historic Haunts

    CAD
    This haunted history route blends eerie legends and unusual attractions. Visit spots with documented haunted pasts — from towers and ruins to cemeteries — while uncovering the fascinating tales behind them. Please Note: This trip begins in Cambridge and takes place in the same area as Local Markets & Picturesque Towns.
    • Accessible
    • Dog-Friendly
    Sold out
    Can depart from: London Area, Toronto 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
  • MOTHER'S DAY PICK
    Woman holding hands with small child on the beach in front of the ocean.

    From Country to Coast

    $65 CAD
    Meander along country roads, explore waterfall wonders, & visit local breweries, farm shops, and beachside towns. This trip has something for everyone, from families to girlfriend getaways and seniors, you’ll find several hidden gems along the way.
    • Kid-Friendly
    • Dog-Friendly
    Sale
    Can depart from: Sarnia Area, London Area, Kitchener-Waterloo Area
  • MOTHER'S DAY PICK
    Sister and brother hugging on a boardwalk.

    Bridges to Beaches

    $65 CAD
    Picturesque bridges to sandy beaches and everything in between. This trip takes you off the beaten path to some of our favourite places in Ontario.
    • Accessible
    • Kid-Friendly
    • Dog-Friendly
    Sale
    Can depart from: Sarnia Area, London Area, Kitchener-Waterloo Area
  • Best done spring-fall
    A boardwalk leading to a beach with the sun shining brightly in the sky.

    Southern Express

    $65 CAD
    Think cozy bakeries, swim spots, easy hikes, and wine with a view, all wrapped up in one charming escape. You’ll wonder how this area stayed off your radar for so long!
    • Kid-Friendly
    • Dog-Friendly
    Can depart from: Windsor Area, Detroit Area, Sarnia Area, London Area
  • Road Trip Tote Bag

    Road Trip Tote Bag

    $20.00 $5.00 CAD
    Sale
    An essential locally made tote bag for your road trip ahead. Carry everything from your surprise package to all the snacks and goodies you'll pick up throughout your day.
    Sale
  • PERFECT OVERNIGHT GETAWAY
    Lighthouse overlooking the water

    Curiosities & Coastlines

    $65 CAD
    Wander through eerie ruins, stop at offbeat roadside finds, explore historic small towns, and relax by the shores of Lake Huron. This laid-back Bruce County adventure perfectly mixes local legends, great eats, and scenic spots!
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
    Sale
    Can depart from: Kitchener-Waterloo Area, Goderich Area, Collingwood Area
  • Road Trip Game Pack

    Road Trip Game Pack

    $12.00 CAD
    Keep the young ones busy with a fun game pack to play with on the road! Dozens of games and activities to keep kids of all ages entertained.
Three women walking through tulip fields
Winding roads through mountains at sunrise

CAN'T DECIDE?

Take Our Quiz to Find Out

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Woman on road trip leaning out window

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!