Small Town Charm Trail With Guess Where Trips

Everyone loves a good road trip. But who loves a great road trip? I know, what’s not to love about a great road trip right? What if I tell you that you can take your road trip to a whole new level? That’s exactly what you’ll get when booking the Small Town Charm Trail with Guess Where Trips!

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I hope that I’ve peaked your interest and you want to learn how you can up your road trip game. Let’s not waste anymore time, it’s time for me to fill you in on the latest trend in road trip adventures.

Who or What is Guess Where Trips?

The very first thing that you need to do in order to have an epic road trip adventure is to contact Guess Where Trips.

Guess Where Trips is a Canadian company which was established in 2020 and it has blossomed out of control ever since. Guess Where Trips provides various “mystery” road trip itineraries based on your specific interests and geographic location. All of the road trips aim to get you out of your comfort zone and to explore “in your own backyard”.

Read Next: Prepare yourself for the perfect road trip.

The beautiful grounds of Kilbride Castle in New Hamburg, Ontario
the gardens at one of the stops on the Small Town Charm road trip arranged by Guess Where Trips

How Guess Where Trips Work

To determine which road trip is best for you and caters to your interests, visit Guess Where Trips and complete the questionnaire. Once you have chosen the road trip itinerary suited best for you, you are ready to order your surprise package. Simply visit the Guess Where To website to place your order. You will be given the choice of receiving a downloadable itinerary or an old fashion “mailed” copy. I HIGHLY recommend getting the mailed copy, it’s a ton of fun!

Stop at the Wild Hog Market near Stratford when on a road trip for the freshest veggies and fruit around.  Browse through the gifts while there
Amazing market found on the Small Town Charm road trip
Releax with a cup of coffee while visiting the Wild Hog Market near Stratford, Ontario
2nd coffee stop on Small Town Charm road trip

Within a few days of ordering you will receive your package in the mail. Depending on the itinerary you’ve chosen, you will receive several envelopes. Do not open them until it’s time to begin your road trip, you don’t want to ruin the surprises.

One of the envelopes you’ll receive will be entitled Before You Go. It is important to open this envelope in advance of your departure. It will contain information needed to plan your trip properly, such as:

  • Best time to go
  • Best time to depart
  • How it works with the remaining envelopes
  • Any itinerary changes
  • COVID care
  • A complete list of what to pack, including any money you may need for parking, entry to attractions, etc.

When the times comes to hit the road on your mystery adventure, it’s time to open envelope number one. This envelope will provide an overview of your stop, tips on other great places to stop for coffee, drinks, food, etc. The guide will also provide a little bit of the history of each stop.

Read Next: Road Trip to Kincardine, Ontario on the rocky shores of Lake Huron

Stop at the Broken Rail, a craft beer brewery near St. Mary's when on your next Ontario road trip.
no road trip is complete without craft beer

When you have completed stop number one, it’s time to open envelope number two to see where your next stop will be. Repeat after each stop is completed, until all envelopes have been opened.

What Cities Do the Where To Road Trips Begin

As a starting point for your adventure, Guess Where Trips uses major Canadian cities:

  • Calgary Area Trips
  • Edmonton Area Trips
  • Halifax Area Trips
  • Toronto Area Trips
  • Ottawa Area Trips
  • London Area Trips
  • Windsor Area Trips
  • Vancouver Area Trips

When choosing the road trip itinerary best for you, choose the city closest to the area you want to explore.

NOTE: If at any time during the booking process you have questions, reach out to Guess Where Trips by email or Instagram. They are very quick to respond!



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It’s Time to Hit the Small Town Charm Trail

It’s important to me to keep the actual location and names of the stops along this trail “secret” so I don’t ruin your experience and disclose all of the surprises, but I will give a brief outline of the itinerary so you know what to expect.

Before You Go

It is important to open the Before You Go envelope in advance of your road trip. We had initially planned on taking this adventure on a Sunday, but the Before You Go let us know that some things on route might not be open on Sunday’s.

Take a selfie to document your mystery road trip with Guess Where Trips
Don’t forget the selfie before leaving on your Small Town Charm Road Trip With Guess Where Trips

My friends and I met at 8:30 a.m. on a Saturday morning full of excited anticipation for our road trip adventure. Before leaving, we obviously had to take the standard selfie to document our adventure and open our first envelope to see where our first stop would be.

First Envelope on the Small Town Charm Trail

While I won’t disclose the name or location of our first destination, suffice it to say that it was a 20 minute drive from our home. None of us had any idea that this spot existed, but it turned out to be our very favourite of all the stops along the Small Town Charm Trail.

We thoroughly enjoyed talking at length to the owners and learning about their personal history as well as the history of their business. It was our first time at this shop, but definitely not our last. We loved it!

Read Next: Take Yourself on a Road Trip to the Most Southern Point in Canada

Visit Mountain Oak Cheese in New Hamburg for some great cheese and learn a bit of history from the owners.
Our first and favourite stop on the Small Town Charm road trip

The next stop in envelope number one was a much needed coffee stop. Don’t expect your typical Timmie’s coffee at this stop. You will be treated to a cup of java made with freshly ground beans (which can be purchased) and the ideal country setting to relax with our first coffee of the day.

At this stop you can expect a line-up as this is where the locals frequent, so you know that they serve the best coffee around. The coffee is so good that this establishment supplies more than 300 businesses in Southern Ontario with their coffee.

Baden Coffee Company has the best freshly ground coffee , supplying over 3,000 Ontario businesses.
Best Coffee stop on the Small Town Charm road trip arranged by Guess Where Trips

The next and final stop of our first envelope was a visit to a National Historic Site. I don’t want to give anything away, so I’ll stop right there 🙂 .

Open the Second Envelope Please

With anticipation, we opened the next envelope which read “A Historic Photo Op“. During this stop, we strolled through a bit of Canadian history.

If you have worked up an appetite or thirst, you can visit a small town market that makes all of their food from scratch. All of the ingredients used are sourced from local farmers.

Travel back in time and learn a bit of history while visiting the Fryfogel Arboretun
A pit stop back in time with a ton of history

A Pit Stop Back in Time

The third stop will have you feeling like you’ve been transported back in time. We enjoyed the many delicious bakeries and local shops.

The real treat on this stop was learning about the history of this area from an elderly gentleman who was extremely welcoming and very knowledgeable about the area.

Stop at  the Chocolate Factory in St. Mary's to purchase some unique gifts when on the Small Town Charm road trip.
You will come across one of a kind shops on your Small Town Charm road trip

It is important to mention that all of us had driven by this spot a hundred times and yet we all were able to discover something new and unique during our visit at this stop.

Small Town Charm

We reached what we thought was our final stop which was full of country markets, breweries, restaurants, quaint shops, scenery and culture.

Guess Where Trips provides a plethora of recommendations as to what to see and do in order to make the most of your time in this small town. Guess Where Trips recommends allowing at least one hour to explore this small town. I recommend that you allow two to three hours for exploring, especially if you plan to eat and/or drink during this stop.

There will be plenty of restaurants to choose from at your last small town stop, but I suggest that you stop for a bite at the restaurant recommended by Guess Where Trips. The restaurant boasts great food, great drinks, and impeccable service.

Read Next: Small Towns of Ontario

Visit the Mercer Kitchen in Stratford for great food and drinks and superb service
yummy food and drinks at this small town restaurant.

Want to Keep Going on Your Adventure?

If time allows, Guess Where Trips gives you the option of exploring one more small town. Of course we were curious so we opted to keep going. Unfortunately by the time we arrived many of the shops had closed for the day, but none-the-less, we still enjoyed exploring this Ontario small town.

The Small Town Charm Trail – Know Before You Go

When choosing the Small Town Charm Trail itinerary, there are a few things you should know and some recommendations I can make:

  • 8:30 is a good time to start, but depending how long you are at your first couple of stops, you may arrive at a stop before opening.
  • budget your time at each stop if you want to experience everything. There were a couple of stops where we spent too much time which made us a little late to experience the final stop to the fullest.
  • bring lots of water with you, especially if it’s a hot day. This will save you some money.
  • Guess Where Trips will tell you how much money you need for specific things on the itinerary, but there are many shops, markets, etc. on this road trip that have one of a kind items that you will want to purchase.
  • to make the most of the Small Town Charm Trail, I recommended spending the night at the town in envelope number 4. I won’t tell you what the town is, but if you are taking the road trip during the off season, you should be able to find a room, or better yet, ask Guess Where Trips if they can reserve a room for you.
  • we left on our road trip at 8:30 a.m. on a Saturday and we arrived home at 6:00 p.m.
  • the road trip itineraries offered by Guess Where Trips are good to be done at any time of the year, unless you purchase a season specific itinerary.
  • 3 day itineraries are offered by Guess Where Trips
  • you will encounter other Guess Where Trips road trippers throughout your travels, which makes the experience fun and offers a great way to make new friends.
  • keep in mind that these are small towns that you are visiting and many shops close at 5:00 p.m. or earlier.

Ending The Small Town Charm Trail

All in all, we extremely enjoyed our Guess Where Trips experience and we all agreed that we’d do another one in a heartbeat. In fact, we decided we wanted to do all of them 🙂 .

Cheers to a Guess Where Trips for a fantastic road trip on the Small Town Charm Trail
Cheers to Guess Where Trips for arranging a fantastic road trip full of surprises!

To sum up what to expect when taking the Small Town Charm Trail, you will pass through the lovely countryside of the southern part of Ontario and through many small towns offering an abundance of cute markets, great foods a few historic sites and incredible scenery. Trust me when I tell you that it doesn’t matter if you’ve visited an area previously, you will still discover new and exciting things when road tripping the Small Town Charm Trail with Guess Where Trips!

Guess Where Next? 🙂

Kelly xoxo

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21 thoughts on “Small Town Charm Trail With Guess Where Trips

  1. Renee

    Once you try one, you’re hooked! GWT is such a brilliant company and I too enjoy their surprise day trips. I’ve done two, and counting! Happy to hear you enjoyed your surprise adventure too!

    Liked by 1 person

  2. Barry

    It’s a very interesting concept and one I’m sure many people will love.
    I had a few questions about more of how it worked, and the website answered those questions. Being a down to the minute advance planner it would be a challenge for me to let go and let someone lead me where to go. I would however definitely give it a go for the fun of the mystery.

    Liked by 1 person

  3. Emma

    What a brilliantly unique idea, I’d love to do this. Especially if in a different city visiting because it gets you out and about away from the usual places you might go. I’ll have to check this out near me in Vancouver

    Liked by 1 person

  4. thedctraveler9b7e4f7d4d

    That’s such a cool idea! Way to promote local tourism and support local businesses and communities. I’m a planner, but I think I would really enjoy the surprise aspect of it!

    Liked by 1 person

  5. JoJo Hall

    This is such a fun idea! It takes a lot of the stress and hassle of planning a road trip for you. Too bad it’s limited to cities or places in Canada, because I’d love to do this here in the states.

    Liked by 1 person

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