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Small Town Christmas Trail Festive Surprise Road Trip - Toronto Area

By Guess Where Trips Inc.


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Sold and Shipped By: Guess Where Trips - This gift ships immediately via email. Redemption instructions are included in the email. All of our travel packages include free shipping Canadawide. Currently our travel packages are for Ontario and we are soon expanding to British Columbia.

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Why this makes a great gift

Get in the holiday spirit with this festive road trip through incredibly charming small towns. Within each surprise envelope we have included an extra suggestion that'll have you decking the halls and singing fa-la-la-la-la. No planning required, this gift comes with beautiful enveloped itineraries to open step by step so every destination is a fun surprise. Pack the car up and enjoy the fun!

Product Description

AVAILABLE NOVEMBER 20TH-DECEMBER 19TH. This trip is ideal for travellers who have not done our year-round Taste Trail trip. Some stops have stayed the same from last year's festive trip.

With this surprise road trip you’ll receive your package of destinations at least 10 days before your selected departure date. The package includes a ‘Before You Go’ guide and a series of envelopes that will lead you to several surprise destinations on your road trip.

On the morning of your trip, open up the first envelope and drive to your surprise destination. Along the way, we include a number of ‘roadside recommendations’ that will break up the driving time in between.

Location & Duration
This is a surprise road trip! While we can't tell you where exactly you will be going until you open your first envelope, below will give a rough idea as to where you will be going!

Stops are Located: Close to Toronto

Please see the approximate total round-trip driving distances/times below. These are driving distances only and do not factor in time spent at stops.
  • From Toronto: 3 hours and 30 minutes / 300 km
  • From Brampton: 2 hours and 55 minutes / 256 km
  • From Oakville: 2 hours and 55 minutes / 253 km
  • From Hamilton: 2 hours and 29 minutes / 214 km
  • From Kitchener: 1 hour and 24 minutes / 93 km
  • From London: 2 hours and 33 minutes / 185 km
  • From Niagara Falls: 4 hours and 10 minutes / 363 km
  • From Barrie: 4 hours and 30 minutes / 421 km
  • A ‘Before You Go’ guide with a packing list, approximate driving distances and more tips to plan for your day ahead.
  • A series of 4-5 envelopes that will make up your day’s itinerary with recommended roadside stops along the way.
  • Restaurant, attractions and activity recommendations based on your trip style.
  • Bring as many people as you want! 2-5 are recommended.
What's not included:
  • Transportation and gas
  • Entrance fees to any of the recommended attractions (we keep most of them free anyways)
  • Food, beverages and gratuities
  • Parking costs
What You Will Do:

This Trip is Great For: Families, couples, foodies, history buffs

Trip Highlights:
  • Bakeries, markets, and local shops for all your gift giving needs
  • A magical old-fashioned Christmas tree farm
  • Light displays that will leave a twinkle in your eye
  • Festive photo-worthy moments
  • Wintery adventures perfect for every activity level
Available to Depart: This itinerary can be used any time of the year from Wednesday - Saturday, with a few store closures on Sunday. Festive inclusions are available from November 20th - December 19th 2021.

What You'll Need to Bring:
  • Camera
  • Cash
  • An ice pack and cooler
  • Walking shoes
  • Road trip snacks
  • Reusable Shopping Bag
Additional Information:
  • Kid Friendly
  • Vegan
  • Wheelchair Accessible
Who Will Guide You
This trip is self-guided! Guess Where Trips will in advance provide envelopes with your surprise roadtrip destinations. You will pilot this trip throughout the journey.

Shipping and Return Policy