Ontario's Prettiest Town - Winter Edition

 After a couple of failed attempts, thanks to a pair of determined snowstorms, we finally made it to Elora to celebrate our 38th anniversary. It’s only about an hour’s drive for us, but winter had other plans the first two times we tried. The delay just made the anticipation grow and served to make the evening feel even more special once we actually arrived.

We started our evening with dinner at The Friendly Society, a quaint little restaurant tucked along the edge of the Grand River. The restaurant is on a lower level of  a historic limestone building near the Elora Mill. and is warm, cozy, and inviting - exactly what you want on a cold December night. The food was delicious and the atmosphere unhurried.  The whole experience set the perfect tone for the rest of the night.

After dinner, we wandered through the village, taking in the glow of Christmas lights strung across the streets and shop windows. Elora has a charm that’s hard to describe - historic stone buildings, narrow streets, and a quiet magic that seems to settle over the town during the holidays. We popped into a few shops for a bit of browsing and shopping. As it was a Friday night, the streets and shops were bustling with people, but somehow it added to the experience of a Christmas village.

One of the highlights was the small Christmas market set up in the village. We found ourselves drawn to the outdoor firepits, where Muskoka chairs were arranged in cozy circles. We sat for a while, warming our hands by the fire, breathing in the crisp night air, and soaking up the festive atmosphere around us. It was simple, but felt like we were part of a Hallmark movie.

 

After all the weather delays, our Elora anniversary finally happened, and it was worth every bit of the wait. Sometimes the most memorable times are the ones that aren’t planned at all - just a slow pace, lovely atmosphere, and time together.

Are you interested in visiting? Here's a quick guide to help you get started:

Location

Elora is a charming village in Southwestern Ontario, about an hour's drive from the Greater Toronto Area. It’s known for its historic stone buildings, scenic river views, and artsy small-town feel.

Best Time to Visit

Winter is surprisingly lovely, especially December, when the Christmas lights and markets are out.
But Elora is one of those towns that’s beautiful year-round.

What to Expect

• A slower, quieter pace

• Cozy restaurants and cafés

• Beautiful holiday lights and decorated storefronts

• Friendly locals and walkable streets

• A mix of nature, history, and small-town charm

Things to Do

• Enjoy a warm, intimate dinner at one of the many eateries around town.  I would highly recommend The Friendly Society

• Stroll through the decorated village streets

• Browse the local boutique shops

• Visit the seasonal Christmas market

• Sit around the outdoor firepits in Muskoka chairs

• Take in the Grand River views

Tips

• Parking can be limited during events so arrive a bit early.

• Winter weather can be unpredictable. Be sure to check road conditions before driving.

• Weeknights are quieter if you prefer fewer crowds.

• Make dinner reservations. Cozy spots fill up quickly.

What to Wear

• Warm layers (the village is very walkable, and you’ll want to explore)

• A winter coat, hat, and gloves, especially if you’re planning to sit by the firepits

• Comfortable, sturdy footwear for icy sidewalks

Additional Info

• Many shops are local and independently owned and great for unique holiday gifts.

• The village is compact, so everything is easily walkable.

• Elora often has seasonal events, markets, and pop-ups.  Check ahead to see what events are on.