Escape to Nature

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(28)

From $39

Tiny towns and easy outdoor adventures lead into a cozy afternoon at a local cafe or brewery — with ice skating and snowshoeing added in during winter.!

When to Go Weds - Sun
ends near Orangeville, ON

Choose your format:

  • $8 Flat-Rate Shipping
  • Free Shipping on Orders $100+
  • 30-Day Returns & Exchanges

Trip Highlights

  • Easy hiking trails (snowshoeing and skating available in the winter)
  • A local brewery in a historic setting
  • Cozy cafes in the cutest towns
  • An outdoor sculpture garden for unique photo ops
  • Multiple recommendations included on every stop

How Long Is This Trip?

Please see the approximate driving distances below. Please note this just includes round-trip driving distances and not time spent at stops.

From Toronto:
2 hours and 40 minutes / 177 km

From Oshawa:
3 hours and 17 minutes / 260 km

From Burlington: 
2 hours and 48 minutes / 221 km

From Kitchener:
3 hours and 15 minutes / 228 km

From London:
4 hours and 57 minutes / 417 km

From Niagara Falls:
4 hours and 5 minutes / 358 km

From Barrie:
2 hours and 47 minutes / 205 km

From Collingwood:
3 hours 35 minutes / 236 km

When Can I Go?

Days of the week: Wednesday through Sunday

Seasons: Year-round

Not recommended: Mondays, Tuesdays, Holidays

Shipping & Returns

Shipping: $8 flat rate, free on orders over $100.

Standard shipping takes 4–10 business days. Need it faster? Choose the fastest option at checkout for 2–4 business day delivery.

Returns: Not the right fit? Reach out within 30 days of purchase to start a return. Products just need to be unopened, unused, and in their original packaging, return shipping is your responsibility. Digital trips, gift cards, and opened products can't be returned.

Exchanges: Want a different trip instead? Email us at questions@guesswheretrips.com within 30 days of your order, there's a small $8 reshipping fee to send your new pick out. Digital trips cannot be exchanged.

Read our full return policy →

FREQUENTLY BOUGHT TOGETHER

Detour Diaries: Ontario

500+ stops, 130+ maps, 300+ pages, plus a bonus interactive mobile map, all organized by highway for easy planning.

Escape to Nature

4.7 Physical Package

Here's How It Works

Browse by location and find a surprise trip that fits your day. Every route is road-tested by our team.

Your surprise destinations stay sealed until you're ready for them. One envelope at a time on the road, all day long.

Hidden gems, local favorites, and stories you won't find on Google. That's what's waiting for you.

Explore All Road Trips

Frequently Asked Questions

What's the difference between a physical and digital trip?

Both versions include the exact same trip itinerary - the only difference is how you receive and experience it.

A physical trip comes in the mail as 5 sealed envelopes: a "Before You Go" guide, plus 4 surprise stops you open one at a time as your day unfolds. Since it ships, it takes a few days to arrive. Please see our Shipping and Returns section above for shipping times.

A digital trip has the same 5 sections, sent instantly to your inbox after checkout. Since it's all one document, just go section by section and try not to peek ahead. Trips are received in a PDF format, so you can print this out at home but most trips are 50+ pages.

How do I know where I'm going?

Just below the trip description, you'll find the town/area where this trip ends. This will give you a good idea of how far you'll be from home at the end of the day.

You can also reference the trip map to view the ending locations here

Where do I start, and how do I find driving directions?

All recommendations include full addresses, so you can easily enter them into your GPS and hit the road. You’ll start from home and make your way to your first stop.

Because every trip can look a little different depending on where you’re starting from and which recommendations you choose to visit, turn-by-turn driving directions aren’t included in the itinerary. You’ll just need a GPS app such as Google Maps or Apple Maps to navigate along the way.

How far in advance should I order?

We recommend ordering the physical road trips 2-3 weeks in advance to allow enough time for it to arrive by mail.

Digital road trips can be purchased at any time, as the itinerary is sent to you via email once you checkout.

How many trips do I need to purchase?

You only need one itinerary per group.

For larger groups:

If more than 5 people are going, we recommend putting someone in charge of making reservations (they can peek at the trip by scanning the QR code in the Before You Go booklet).

This person can handle making any necessary reservations and reaching out to the local businesses along the way to confirm they can accommodate your group size, especially for groups of 10 or more. Many of the small local businesses we feature, such as cafés and farm markets, have limited space and appreciate a heads up so they can prepare for a larger group!

Are there additional costs during the trip?

Your purchase covers the itinerary itself. Any food, drinks, shopping, gas, parking or attraction fees are additional. We include plenty of free and budget-friendly options throughout our trips, so you can choose how much you'd like to spend.

How long does a road trip take?

Plan for a full day! Most trips include about 4–6 hours of stops and driving between them, plus your drive to and from home.

You don't have to do everything - we include multiple options so you can move at your own pace, skip things, or even finish another day. Please refer to the trip map here for all the ending locations. 

Can I bring my kids or dog? Are trips accessible?

Absolutely! Just keep in mind that you may not be able to experience 100% of the trip. We include a variety of options at each stop, so there will be plenty to choose from.

Travelling with kids?

If you're bringing kids, we recommend choosing a trip with less than two hours of round-trip driving. Another tip is to have the driver take a quick peek at the itinerary beforehand using the digital link included in your Before You Go guide. This way, you can choose the activities and stops that will be the best fit for your family. And while every road trip includes four stops, there's no pressure to do them all in one day - you can always save a stop for another adventure!

Bringing your dog?

We recommend choosing a trip with plenty of outdoor options and taking a quick look through the itinerary ahead of time to see which stops will work best for you and your dog. Warmer weather is best, when more patios, trails, and outdoor activities are available. There will be dog icons throughout the itinerary to help identify which stops are dog-friendly.

Keep in mind that no matter the season, some stops and activities may not allow dogs, so you may need to skip or adjust certain parts of the trip.

Is the trip wheelchair-accessible?

Some road trips are more accessible than others, and we do our best to include at least one accessible option at each stop. There will be accessible icons throughout the itinerary to identify which spots are accessible for wheelchairs, walkers and strollers.

You can view our most accessible road trips here.

Do I need to book anything in advance?

No advance planning needed for your road trip itself - since it's self-guided, you can pick any date. We do recommend the best days of the week and seasons for each trip, so it's worth checking those before you go. Very few stops recommend a reservation, and if they do we'll flag those in your "Before You Go" guide so you know ahead of time.

Can I make this an overnight trip?

Of course! After purchasing, you will find hotel recommendations in your confirmation email. You can also see a list of recommended accommodations here

The suggestions provided are generally in the area of the last stop location. 

Road Tested by Our Team

Our team spends 40+ hours researching, driving, and vetting every route: talking to locals, discovering hidden gems, and making sure every stop is worth your day.

We Remember Experiences, Not Things.

Research consistently shows that spending time together creates more lasting happiness than buying more stuff. Every Guess Where Trip is thoughtfully planned to help you reconnect, explore, and create memories that last long after the day is over.