Quirky Gems

4.6 (24 reviews)

From $39

Our best-selling Calgary road trip! Hit the road and visit some quintessential Alberta towns, eat at funky restaurants, support local businesses, and explore picturesque hikes and natural attractions. All without venturing too far from the city!

When to Go Thurs - Sun, Spring - Fall
ends near Bragg Creek, AB

Choose your format:

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

essentials for your trip

Mint Road Trip Journal

Mint Road Trip Journal

Track all your local adventures - big or small - in one place. With space...

Road Trip Tote Bag

Road Trip Tote Bag

An essential tote bag for your road trip ahead. Carry everything from your surprise package...

Trip Highlights

  • A few country Western towns
  • Distilleries, Wineries and Breweries (alternative options available)
  • Hiking options that are great for everyone
  • Waterfalls and mountain views
  • Unique photo ops throughout the day
  • 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 Calgary: 2 hours and 10 minutes / 170 km
  • From Okotoks: 2 hours / 169 km
  • From Cochrane: 2 hours and 45 minutes / 223 km
  • From Airdrie: 3 hours  / 259 km
  • From Red Deer: 5 hours and 15 minutes / 484 km

When Can I Go?

Days of the week: Wednesday through Sunday

Seasons: Spring, Summer, Fall

Not recommended: Mondays, Tuesdays, Winter, Holidays

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 →

Quirky Gems

4.6 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

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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.