Hi, I’m Hannah - Product Manager at Guess Where Trips.
Winter is actually one of my favourite times to hit the road - quiet highways, cozy stops, and destinations that feel a little more magical this time of year.
Here are my top picks for winter road trips in Ontario, plus a few extra tips along the way, including cozy places to stay if you want to turn your day trip into an overnight getaway.
Take a look at the map below to get a general idea of where these winter road trips end.
My Favourite Winter Day Trips in Ontario...
Taking this trip in the winter? Here are my tips for 'The Small Town Charm Trail':
- Order a seasonal latte on stop 1: Our featured cafe has the BEST seasonal lattes that will warm you up from the inside out!
- Call the featured castle on stop 2 ahead of time: The castle has weather-dependent winter hours. Call ahead (519-634-8519) to confirm if inside tours are running -- otherwise, it’s still beautiful from the outside!
- Visit the "on-the-way" suggestion on stop 4: there, you'll be able to grab a hot beverage and cozy up on the comfy couch in front of the fireplace on the main level (my personal favourite spot!)
- Don't miss the self-guided trails: Our final stop on this trip offers a "Bacon & Ale Trail" or a "Chocolate Trail", both of which make great additions for a winter weekend getaway.
- Go on a tubing adventure: Kids and adults alike will love this epic winter tube slide just 10 minutes from your final stop.
- Enjoy free walking trails & winter activities: This cute small town museum has free walking trails which are great for snowshoeing, plus an outdoor skating rink on their front lawn (weather permitting)!
Recommended Winter Stays for 'The Small Town Charm Trail'
The Penrose Suites
The Country Nook (Air bnb)
Taking this trip in the winter? Here are my tips for 'Local Markets & Picturesque Towns':
- Travel on a Thursday or Saturday: We highly recommend travelling on a Thursday or Saturday so you can make the most of all of our recommendations.
- Order a cinnamon bun at stop 1: You absolutely HAVE to try a cinnamon bun or some of the mini donuts at the featured Farmer's Market on Stop 1.
- Don't miss out on fresh chocolate milk: You will absolutely fall in LOVE with the fresh chocolate milk at our stop 2 farm recommendation.
- Visit the lookout spot on stop 3: Even though the conservation area on stop 3 is closed in the winter months, you can still go to the Lookout Spot for incredible wintery photos!
- Visit a cozy winter winery on Stop 4: If you're a wine lover like me, you'll love the coziest winter winery stop 4 with outdoor fire pits! Reservations are recommended for the fire pits or for larger groups.
- Bring your snowshoes on Stop 4: If you're into outdoor winter activities, be sure to bring your snowshoes (or toboggans for little ones!) as our "On The Way" suggestion on stop 4 offers amazing winter trails and an iconic sledding hill.
- Take a detour to an Alpaca Farm: This Alpaca Farm is just 12 minutes from your final stop which offers visits year-round! Advance reservations are required.
- Enjoy delicious ice cream: Ice cream in the winter? You heard that right! This cute spot is open daily all year long and has amazing soft serve ice cream (and seasonal lattes if you need to warm up!). Just 30 minutes from your final stop.
- Visit the coolest local brewery: This cool local brewery is just 10 minutes from your second stop. The perfect spot to come back to at the end of the day, especially on their heated patio.
Recommended Winter Stays for 'Local Markets & Picturesque Towns'
Inner Joy Getaways
Luxury Tiny Home on Peaceful Country Estate (Air BnB)
Taking this trip in the winter? Here are my tips for 'Escape to Nature':
- Bring your snowshoes or cross-country skis: there are many great options for outdoor adventures on this trip!
- The featured cafe on stop #1: you've GOT to try their signature hot chocolate (or one of their maple-flavoured seasonal lattes if you're not a choco fan)
- Bring a toboggan for stop 2: Have kids with you? Bring a toboggan along for some sledding on stop #2!
- Don't forget your winter gear: Our featured conservation area on stop 4 offers ice fishing, skating, and snowshoeing so be sure to pack your gear before you leave home!
- Book a unique wine tasting: Make your weekend getaway extra special by booking a cozy outdoor igloo wine tasting experience at this beautiful estate winery.
- Enjoy maple treats: Open weekends from Family Day through early April, visit this adorable tree farm for their maple syrup experience.
- For those who want more winter activities: This nearby conservation area offers even more winter hiking, snowshoeing and cross-country skiing for all you outdoor adventurers!
Recommended Winter Stays for 'Escape to Nature'
Millcroft Inn & Spa
Character-Filled Farm Guest House on 8 Acres (Air BnB)
Taking this trip in the winter? Here are my tips for 'Markets to Mountains':
- Visit our on-the-way coffee shop: We love our featured farm market, BUT you don't want to miss our "on-the-way coffee stop" recommendation, especially for their breakfast bagel!
- Try this famous carrot cake: I'll admit, I'm not a carrot cake fan... but I had a slice of the famous carrot cake at our featured cafe on stop #2 and was forever changed.
- Avoid the third stop hike during heavy snowfall: The road to our third stop hike isn't always plowed if there's heavy snowfall, so I don't recommend heading there if you don't have snow tires on!
- Explore more cross-country skiing trails: While obviously there are tons of places in the area to do downhill skiing, there are also fabulous cross-country skiing trails if that's your thing! Check out this beautiful spot with 27km of trails!
- For those who love skating: you'll find a beautiful rink on this mountain top.
- Want a little R&R?: This iconic thermal spa is calling your name for a relaxing winter getaway.
- Enjoy a tasting in a cozy winter igloo: Reserve an igloo at this nearby cidery for a cozy winter tipple.
Recommended Winter Stays for 'Markets to Mountains'
Somewhere Inn
Blue Mountain Resort Village Suites
Taking this trip in the winter? Here are my tips for 'The Sweet & Scenic Route':
- Fritters galore: Don't skip the fritters at our featured farm market on stop #1!
- Winter wine tasting: Stop #2 features the most beautiful winery with outdoor fire pits and s'mores kits too!
- Sugar Bush Treks: On weekends in March you'll find Sugar Bush Treks running every 20 minutes at our maple farm suggestion on stop 3. (runs daily during March Break!)
- Don't miss this riesling: Wine lovers will adore the view s at our featured winery, plus their riesling is one of my personal favourite wines!
- Detour to Port Dalhousie: Just 20 minutes from your final stop is the cute waterfront town of Port Dalhousie, which has a cute main street to explore! Grab a seasonal beverage and book at the cutest bookshop here!
- Don't Miss this Hallmark town: Located just 30 minutes away, this is is the perfect location for an overnight getaway. Our favourite hotel in town even has a skating rink during the winter!
- Wine time: Enjoy more skating and local wines/whiskey at this well known winery.
Recommended Winter Stays for 'The Sweet & Scenic Route'
Private Cabin: Boar's Hollow (Air bnb)
Juniper Inn
Taking this trip in the winter? Here are my tips for 'Brews, Bites & Everything Nice':
- Enjoy tasty treats: Stock up on sticky cinnamon buns at our cafe option on stop #1.
- Tour the featured distillery on stop 3: it holds tours every 30 minutes on the weekends; highly recommend! Plus the town that it's in gives such Hallmark vibes - it's so cozy!
- End the day at the coziest British-style brewery & pub: it will warm you up as soon as you walk in the door.
- Visit a German bakery: Carb-o load and stay toasty warm at this adorable German bakery near your 4th stop.
- Take a detour on this trail: Stroll or snowshoe along the river at this beautiful riverwalk trail.
- Warm up indoors: If it's too chilly to be outside, head inside at this funky (and free!) museum on our 3rd stop; open Tuesday - Saturday.
- Visit this Hallmark town: Just 20 minutes from your fourth stop is another quaint small town that has all the Hallmark feels.
Recommended Winter Stays for Brews, Bites & Everything Nice
The Monte Inn
The Carriage House
Author: Hannah Elias
Hannah is the Product Manager at Guess Where Trips. From product launch strategy to research & development (and even writing our Detour Diaries book!), she continues to find new ways to improve our road trip products for customers.
