Best Ontario Surprise Road Trips

Have you ever been on a surprise road trip? I love road trips and have been on hundreds across Ontario. While I love planning road trips, there’s something thrilling about surprise road trips where you have no idea where you’re going.

As many are people are busy with work, sometimes finding the time to do the planning is challenging. If this is you, you’re in luck! There are a number of businesses – like myself! – that have put in all the kilometres and done the work to give you everything you need to plan a spontaneous trip; all you need to do is fill the gas tank.

In this guide I’m sharing tips on how to choose where to go on a surprise trip and fun made for you surprise road trip itineraries in Ontario. Plus, you’ll learn how these trips make for unique gifts!

Disclaimer: This post contains affiliate links. By purchasing and booking through these links I may make a small commission at no extra cost to you.

How to choose where to go on a surprise trip

There are a few things to ask yourself when choosing a surprise trip.

• When are you hoping to travel? Are you looking for seasonal or festive places to visit?
• Who are you travelling with, kids or adults only?
• Are you looking for outdoor adventures?

The answers to these questions can help you narrow down the specific trip to choose. Many of the Guess Where Trips mention if it is family-friendly, if it’s seasonally focused and if it includes outdoor activities. On the other hand, my Memorable Route itineraries are mostly family-friendly and full of options to choose from whether you’re looking for hikes or more indoor options.

Another thing to ask yourself, is if you’re looking for a day trip or want to make it a surprise holiday. All of the Guess Where Trips as well as my trips are perfect for day trips. However, each offer suggestions on places to stay if you want to make it a surprise holiday weekend adventure.

Best Ontario Surprise Road Trips

Guess Where Trips

For many, the most popular business in Ontario offering surprise road trips is Guess Where Trips. Female owned and operated, Guess Where Trips started when the owner, Jessica, wanted to created a surprise trip for her parents.

Starting with surprise road trips in Ontario, Guess Where Trips offers road trips in other provinces across Canada and throughout the US too.

All of their trips are easy to choose from and based on where you are leaving from, whether it’s from Toronto, Barrie, or London. This means that if you choose a trip leaving from Toronto, it will likely be 1 to 2 hours away, making it an easy day trip.

What do Guess Where Trips look like?

If you’ve never done one, here’s a break down of what to expect.

• Order a Guess Where Trips – all are themed and offer a brief description of things you’ll see and do on the trip
• Package with road trip arrives – it usually takes a week to arrive
• Open the package – it includes a few envelopes, which include what to know before you go which you can open before day of departure.
• Pick a day and go – the box typically includes 4 to 5 envelops that you open at various points throughout the trip. For instance, the first stop envelope takes you to your first stop and area. After you’ve done those places, you open the second stop envelope.

It’s really that easy!

Use THEWORLDASISEEITTRAV10 when you purchase a Guess Where Trips to get 10% off!

Here are a few of my favourite Guess Where Trips;

Country Markets & Furry Friends – great if you’re leaving from Toronto or GTA area and includes country markets and farms with animals. I did it as a girls’ trip but it is perfect for families.

Beautifully Haunted – this trip can be done from Toronto or London area and has plenty of stops that are haunted. I did it as a weekend trip from Barrie and think it’s perfect for adults and families with teens.

All Things Merry & Bright – this trip is an easy day trip from Toronto, Kitchener or Barrie areas. It features festive small towns and is best done during the holidays for all the Christmasy vibes.

The Memorable Route

My surprise trips stemmed from my love of sharing hidden gems and local businesses. Even with all of my Ontario travel guides, I realized that many people wanted something easy and made for them. So, I launched The Memorable Route, surprise road trips in Ontario. Right now, they are available in a digital download.

So far, I have one itinerary, Muskoka Loop Adventure. But I’ll be launching new trips in 2026. All of my itineraries will be ideal as surprise road trips from Barrie or Toronto.

What do The Memorable Route trips look like:

Here’s what you can expect when you purchase one of my trips, from purchase to day of trip.

Purchase a Memorable Route – itineraries are available from my PayHip store.

Download the trip – download the digital road trip guide to your computer to print off or to your cell phone.

Open the digital guide – open the digital itinerary to the first page that gives tips for planning your trip, including where to stay if you want to make it a weekend getaway. (One of which I offer a promo code!)

Pick a day to go – once on the road, scroll to the second page for your first stops. And to keep it a surprise road trip don’t look ahead until you’re ready to go to the next stop. With so many stops available you can do them all over a weekend or pick and choose what fits your interest.

My digital itineraries:

Muskoka Loop Adventure – ideal day trip or surprise holiday weekend away from Toronto or Barrie area. The route includes +30 options for stop along the route through Muskoka. There’s everything from local cafes and shops to places to hike and hidden gems.

Giving a Surprise Road Trip as a Gift

I love giving experiential gifts instead of things – unless that thing is food! So, if you’re looking for unique Ontario gift ideas, then consider giving the gift of a surprise road trip. Whether it’s for someone’s birthday, and anniversary or for Christmas, these surprise trips make fun and unique gifts for all who love exploring.

FUN TIP: To make the gift more rounded, especially if you purchased a digital guide, make a little gift basket to go along with it. You can add some road trip snacks, a list of songs for them to create a playlist for the road and a pair of traveller mugs to grab coffee before you leave.

Looking for more road trip ideas?

31 Memorable Road Trips in Ontario

25 Stops on a Toronto to Thunder Bay Road Trip

Ultimate Lake Huron Road Trip Guide

Best Stops on a Toronto to Tobermory Road Trip

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