5 Weekend Trips in Ontario & What to Pack

Still Wondering What to Do This Summer?

Yep, us too. Somehow it’s already half over, and that trip we swore we’d plan? Still in draft mode. If you’re short on ideas (or just need a push), here are 5 Ontario destinations that feel like a proper getaway — and we’ve included outfit ideas from our Travel Edit to pack along for the ride.

We even made a free printable packing checklist so you can skip the overpacking spiral and actually remember your hairbrush.

 1. Prince Edward County – For Wine, Art & Boutique Vibes

Known for its boutique hotels, artisan markets, and stunning Sandbanks Beach, Prince Edward County is the perfect summer escape. Spend your days touring vineyards, browsing local makers, or lounging lakeside.

What to wear: Flowy linen sets, woven tote, and breezy layers from our Travel Edit.

  2. Niagara-on-the-Lake – Romance Meets Heritage

With cobblestone streets, heritage hotels, and horse-drawn carriages, this spot gives European getaway energy without crossing an ocean. Ideal for romantic weekends or wine-soaked girls' getaways.

What to wear: A floral dress, light sweater, and trench for twilight walks. Explore soft layers in our Travel Edit.

  3. Muskoka – Elevated Cottagecore

Lakeside cabins, cozy lodges, and dockside bonfires—Muskoka is cottage country at its best. Spend the day boating or exploring Port Carling, then settle in for s'mores under the stars.

What to wear: Soft sweatshirts, classic denim, and cozy-chic staples from our Travel Edit.

  4. Elora – Small Town with Big Character

Known for the stunning Elora Gorge and charming village shops, this one’s a dream for slow travel and nature lovers. Think riverside hikes and café hopping all in the same day.

What to wear: Relaxed pants, crisp white tops, and laid-back accessories. Shop easygoing looks in our Travel Edit.

 5. Stratford – Culture & Cafés

Home to the famous Stratford Festival, this town is a must for theatre lovers and cozy café crawlers. It’s walkable, welcoming, and full of little surprises.

What to wear: Wide-leg pants, neutral knits, and a polished tote from our Travel Edit.

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Final Thought

Ontario’s full of unexpected gems — and summer’s not over yet. So pack thoughtfully, dress with intention, and savour the adventure (even if it’s just a day trip).

And if you’re looking for outfit inspiration? Shop our Travel Edit online or visit us in-store in Aurora, ON.