Are you ready for another weekend escape in Caledon? This itinerary will bring you through our rolling hills on horseback, wheels, and your two feet! Next, we’ll throw a few beers, farm shops and a relaxing spa night into the mix. These activities are perfect for the upcoming summer to fall transition. The sun is out, the air is breezy, and you’re saying “Can we visit Caledon again?”

Friday Afternoon: Check in, Golf and Dinner

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Your home away from home this weekend is The Liberty Inn. This inn, newly opened in 2025 seamlessly blends historic charm and modern touches. Nestled in Caledon’s quiet countryside, it’s the perfect escape into nature for a relaxing stay. Featuring five suites to choose from, a private Nordic spa, stocked fridges and lush gardens, The Liberty Inn has carefully thought of every detail for their guests to experience pure luxury. Once you’ve checked in and feel settled, your first stop for the weekend is just a quick drive away.

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Five minutes straight down the road, you’ll find yourself landing at TPC Toronto at Osprey Valley. This pristine course offers you to play the Hoot, North or Heathlands. Each offers scenic views, a challenging game and impeccable course conditions. Ranked as one of the top courses in Canada, Osprey Valley is a must-play if you're in Caledon for the weekend. Hungry after your game? They offer three restaurants open to the public, ranging from casual burger bites all the way to elevated dining experiences. This evening, choose between Two Brothers, Fescue or The Kettle. Want a tip from a local? No matter what restaurant you go with, your taste buds will be thanking you.

Saturday Morning: Horseback Trail Ride

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We hope you slept well, because your Saturday is going to be packed with fun! Starting things off, let’s drive to the village of Palgrave to visit Rusty Jade Ranch. Get ready to learn the ropes of ranch life and western riding with a morning trail ride. Set on a scenic 100 acre farm, there’s no better way than to spend your morning in this rural haven. Owners Brad and Kelly are passionate about what they do at the farm, and put a heavy importance on wellness, and connecting with nature, ourselves and each other. During your guided trail ride, you’ll pass through wide open fields, lush pine forests, apple trees, growing oats and much more right on the property. You’ll learn about the holistic approach RJR takes to horse riding, growing their food and caring for the land and animals. When you arrive, your horse will be groomed, tacked up and ready to go, so you get the luxury of spending all your time in nature with your horse. This experience will leave you feeling refreshed, relaxed and wanting to book another ride! 

After you pack up your cowboy boots, we hope you’re hungry! Lunch today, Caledon Hills Brewing, is just a four minute drive from the ranch. This brewery offers a patio for sunny days, or you can opt for the historic church renovated into a German-themed beer hall with stained glass windows. Our secret? Wherever you choose to sit, you’ll be met with friendly staff and chill vibes. Grab a cold drink, and a meal from the changing chalkboard menu, then let your taste buds burst. You may even catch some live music, or see a few pups hanging out at this dog-friendly establishment. Did we already mention the good vibes???

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Saturday Afternoon: Cycling, Shopping and Exploring

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With happy hearts and a full belly, we’re venturing on to Caledon East. Ten minutes from Palgrave, there’s more to explore today. Home to gourmet food shops, heritage buildings and the Caledon Trailway, Caledon East is a walkable, friendly community in the heart of Caledon. Treat yourself at Gourmandissimo with decadent Belgian chocolates, wander through Glen Echo Nurseries for a dose of garden inspiration, and discover the many other shops on the main strip of Caledon East. There’s hidden gems on every corner. From here, there’s easy access right onto the Caledon Trailway. This 35 km trail follows an abandoned rail line built in 1877. Walk along the path for a leisurely stroll or pull out your bikes for a ride. You’ll be cruising along the path next to open fields, forested areas, the river and wildlife. Let us know if you spot a blue jay, turtle or beaver! 

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Ready for more? Dinner tonight is at the Villa Caledon Inn. This restaurant has been a Caledon favourite for more than 50 years. Take a seat on the patio surrounded by flourishing gardens on a sunny day, or choose the stone walls and rustic charm when you step inside. The menu has a wide range of cuisine, with mouth watering options for every taste bud. After your busy adventures, this is sure to hit the spot. When dinner is done, the last activity of the day is relaxing back at the Liberty Inn during your private Nordic spa booking. Melt away into the cedar hot tub, feel the benefits of the cold plunge and slow down in the Finnish sauna. This peaceful escape will let your mind and body slip into a serene state of relaxation, right before laying your head on the pillow in preparation for another exciting day on Sunday. 

Sunday: Farm Shop, Historic Conservation Park and Beers

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Have the energy in you for one more day? We’re starting the morning at Heatherlea Farm Shoppe. This farm has been raising pasture-fed Black Angus beef since 1975! (We recommend keeping a cooler in your car for the weekend so you can bring a treat back home). While they’re famous for their farm-fresh meats, you’ll also find unique pantry items and charming decor. In the summer, it’s a local favourite to watch the cows grazing in the fields from the fence line or the patio. Grab a coffee or sandwich from the cafe and take a moment to relax in the countryside before heading off to your next adventure. 

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A trip to Caledon is not complete without a stop to the iconic Belfountain Conservation Area-that is, if you’re visiting in summer or fall! This seasonal gem will remain open until October 26th, so make sure to plan accordingly. Why is this park iconic you ask? Many reasons! Filled with walking trails, beautiful forests and flowers, you’ll also pass by the waterfall and suspension bridge, which makes for awesome family photos, or just a beautiful site to see. Next, walk down the steps to enter the man-made caves. These caves were built in the early 1900s by Charles Mack, who drew inspiration from Yellowstone National Park. The main feature of the park is the historic “belle” fountain. Tucked beside the river, it’s a fairytale-like fountain that gives the park it’s charm and it’s name! 

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The grand finale to your Caledon road trip? A cold pour at Badlands Brewing. This on-farm brewery specializes in IPAs but will gladly serve farmhouse ales, crispy lagers and mixed fermentation sours. Taking a seat on the patio, you may find yourself enjoying live music on weekends or biting into a smash burger from the Badlands Kitchen food truck. When you’re ready for an activity, take a walk to the back to play a round of corn hole. The vibes at Badlands are everything you need to close out this memorable weekend.

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Caledon is calling, and all that’s left is for you to pack your bags and answer!