Local Markets & Picturesque Towns
Local Markets & Picturesque Towns
Bakery display with Pain au Chocolate and Cinnamon Rolls.
Woman sitting on a rocky shore overlooking a river.
Three people clinking their drinks together at a cafe indoors.
Local Markets & Picturesque Towns

Local Markets & Picturesque Towns

4.8 (189 reviews)

From $39

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.

When to Go Wed – Sat
ends near Elora, ON

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  • Free Shipping on Orders $100+
  • 30-Day Returns & Exchanges
  • No Booking Required

essentials for your trip

Detour Diaries: Ontario

Detour Diaries: Ontario

Packed with 500+ of our favourite road trip stops across Ontario, Detour Diaries features 130+...

$59
Lilac Road Trip Journal

Lilac Road Trip Journal

Track all your local adventures - big or small!

$25

Trip Highlights

  • The best chocolate milk you'll ever taste!
  • Historic towns with great local markets
  • Beautiful gorges, riverside walks, and a waterfall
  • A mini self-guided surprise route in the country
  • Tons of unique shops and cozy eateries
  • 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: 3 hours and 30 minutes / 265 km
  • From Oakville: 2 hours and 35 minutes / 216 km
  • From Hamilton: 2 hours and 29 minutes / 177 km
  • From Pickering: 3 hours and 40 minutes / 310 km
  • From Kitchener: 1 hour and 15 minutes / 70km
  • From Barrie: 3 hours 50 minutes / 335 km
  • From London: 3 hours 28 minutes / 297 km
  • From Collingwood: 3 hours and 46 minutes / 262 km
  • From Goderich: 3 hours and 40 minutes / 278 km

When Can I Go?

Days of the week: Wednesday through Saturday

Seasons: Year-round

Not recommended: Sunday through Tuesday, Holidays

Travel Tips

  • Best taken Thursdays or Saturdays.
  • This trip has some stops that overlap with Historic Haunts.
  • Note our "romantic landmark" covered bridge on stop #2 is currently closed for construction, but we've got two other great options on this stop instead!

Shipping & Returns

Shipping: Free shipping 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 →

Local Markets & Picturesque Towns

4.8 Physical Package

Finds you won't find on Google

Multiple options every stop

One package for your group

Every stop supports local

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.

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Frequently Asked Questions

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What People Love About Our Trips

Rated 4.9/5.0 stars

What an Amazing Day!

Our daughter gave us this for Christmas and we finally pulled it out this week, July now. We love a road trip and loved the mystery of each new step. Great things to see and experience. Great restaurants to enjoy. I’ve recommended it to all my friends. Amazing.

Donna S. 🇨🇦

First Time…There WILL be a second!

Knowing the area we went I was very pleasantly surprised. We saw things I did NOT know existed! One of the stops was closed however we were able to walk up to it for a photo.

Mary Y. 🇨🇦

Great day away!

Did this trip with my mom for Mother’s Day. Lots of quaint little stops and places to explore! They also gave a few options at each stop so you could choose your own adventure! Will definitely be doing this again, had a wonderful time!

Megan M. 🇨🇦

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.

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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.