Day tripping to the countryside of lush rolling green hills of Caledon Ontario is an easy escape for most that live in and around Toronto. Just an hour northwest you’ll find yourself in an unspoiled scenic rural landscape dotted with charming villages and beautiful conservation areas and trails. It’s a perfectly relaxing day spent in nature, with or without your dog. Me – I’m always looking for places that I can enjoy with my dog, Henry. Here are the best dog-friendly things to do in Caledon Ontario. 

What Brought me to Caledon Ontario

You might be wondering what brought me to explore Caledon in the first place. Sure, I’ve been here, well, technically I’ve driven through Caledon on these scenic roads to get to and from other destinations, but I’ve never really spent any time here. I owe it all to Guess Where Trips, a Canadian company that creates surprise itineraries bringing you to places that you’ve never heard of before, just like this one!

pond with greenery around it

Read More | Ultimate Day Trips in Ontario with Guess Where Trips 

Experience Guess Where Trips

If you’re bored with going to the same places over and over again, or simply don’t have the time to research and plan a really amazing day trip give Guess Where Trips a try. They will exceed your expectations. Even for an expert day-tripper like me who loves to plan, I will gladly relinquish all control and let Guess Where Trips lead the way. So what themed adventure did I try? 


The surprise itinerary I did was Vistas, Falls & Caves. And what an adventure it was! I’m not going to give away the entire trip, what fun would that be? Instead, I’m going to share all of the top things to do in Caledon and if it looks like fun to you, then choose the Vistas, Falls & Caves package from Guess Where Trips and let that surprise itinerary take you to some of the best hidden gems in Caledon.  

Best Things to Do in Caledon

The Caledon area is just so relaxing, likely because you’re surrounded by such beautiful nature. Surprisingly, there’s a lot to explore and discover here. Love tiny hamlets? Bit of a foodie? Interested in arts and culture? Looking for a sense of adventure? Yes, Caledon offers a little bit of everything for you to enjoy, even your dog. So let’s explore. 

girl and dog with waterfall

Best Villages in Caledon

There are so many quaint hamlets and villages to visit in Caledon. Each one offers something uniquely different. Without giving it away, Guess Where Trips does send you to an adorable hamlet as part of Vistas, Falls & Caves first stop. I won’t tell you which one, all I will say is – it’s my favourite on this list!

white historic building

Alton – settled in 1820, this historic village lies on the banks of Shaw’s Creek. Visiting here is like stepping back in time. One of the best things to do in Alton is to do your own historic walking tour. Almost every home was built pre-1900s and has loads of character. 

Belfountain – settled in 1825, this pretty little village lies on the Forks of the Credit Road. One of the draws to this picturesque hamlet is visiting the nearby conservation area. But stay a while, be sure to check out the swoon-worthy lifestyle boutique, Noinkees.  On the outskirts of this village, visit the Melville White Church and cemetery dating to 1837. 

historic building with porch

Caledon East – settled in 1820, lies at the crossroads of the busy Hwy 10 and Regional Road 24. Blink and you might miss it. A post office, in 1839, the first schoolhouse built from logs in 1828, and the first acetylene gas station to provide gas for street lamps are just some of the interesting facts you’ll find in this Caledon village. 

Cheltenham – settled in 1822, this rural hamlet lies in the southern part of Caledon. Visiting the dramatic landscape of the Cheltenham Badlands is a popular attraction. The historic Cheltenham General Store of 1887 is the only stone general store in Caledon. 

white church with stone wall

Inglewood – settled in 1883, this rural hamlet features the original general store and railway hotel. Most people stumble upon Inglewood as they come here for the premium golf courses that surround the scenic hills of Inglewood. Also fish stocked ponds and canoe rentals are another draw to this community. 

Terra Cotta – settled in 1855, is located on the banks of the Credit River. Grist mill and sawmill, along with brickworks from the local red clay were the biggest industries that caused this community to grow. Don’t miss visiting the Forge Park Picnic Shelter, a former blacksmith shop, Terra Cotta Inn, and Terra Cotta Country store. 

Best Eateries in Caledon

Included in every Guess Where Trips package is some recommended places to eat and drink. Because their itineraries are action-packed, lasting a full day, keeping you hydrated and fueled for your adventure is important. It’s also a way that Guess Where Trips supports local communities. You won’t find any chain establishments as part of their itinerary, only passionate entrepreneurs. I’m not going to tell you which ones are part of the Vistas, Falls & Caves trip, but here are some recommended restaurants in Caledon to seek out while you are exploring this area. 

black barn door with canadian flag
  • Gather Café – 19793 Main St, Alton
  • Higher Ground Café – 17277 Old Main St, Belfountain
  • The Common Good – 10 Credit Park St, Belfountain
  • Rays 3rd Generation Bistro Bakery – 1475 Queen Street, Caledon
  • Terra Cotta Country Store – 119 King St, Terra Cotta 
green with metal sign saying country store
  • GoodLot Farmstead Brewing Co. – 18825 Shaws Creek Rd, Caledon
  • Badlands Brewing Company – 13926 Chinguacousy Rd, Caledon
  • Spirit Tree Estate Cidery – 1137 Boston Mills Road, Caledon
  • Caledon Hills – 17219 Highway 50, Palgrave

Best Arts & Culture in Caledon

I’m always on the hunt for those hidden gems. Luckily, Guess Where Trips specializes in taking you to places that are off the beaten path. It’s one of the reasons why I love their trip itineraries. You get to discover the undiscovered. Vistas, Falls & Caves will bring you to some pretty cool and interesting sites. I won’t give it away, but here are the top arts, culture, and heritage sites to see in Caledon. 

girl and dog in art gallery
  • Alton Mill Arts Centre – gaze upon art in an 1880s stone mill turned art gallery and an outside art amongst the trees Visit: 1402 Queen St. West, Alton
  • The Caledon TownHall Players – attend a community theatre in the old township hall built in 1875. Visit: 18365 Hurontario St, Caledon
  • Great War Flying Museum – learn more about WWI aviation through its collection of planes and artifacts. Visit: 13961 McLaughlin Rd, Cheltenham
  • Cory Trépanier – an art gallery featuring Cory’s paintings inspired by Wild Places. Visit: 16662 The Gore Rd, Caledon

Best Outdoor Adventures in Caledon

Now the real reason people are drawn to Caledon – is the amazing outdoor adventures. Nature lovers, hikers, photographers, and adventure enthusiasts know this area as offering some of the best outdoor activities in Ontario. It’s where the Niagara escarpment and the Oak Ridges Moraine collide producing rolling hills, vistas, waterfalls, and caves. It’s no wonder that Guess Where Trips created an itinerary called Vistas, Falls & Caves. Not that I want to give it away, but it’s safe to say that you’ll be blown away by where this surprise itinerary takes you. Here are the best outdoor activities in Caledon. 

yellow canola fields
  • Belfountain Conservation Area – easy, yet scenic hiking trails, a suspension bridge with a view of a beautiful waterfall, and an instagrammable “belle” fountain are all reasons to go! Tip: reservations are required to visit the park, book online, and all trails are dog-friendly.
  • Cheltenham Badlands – a top attraction in Caledon is the Cheltenham Badlands. It’s hands down the coolest thing you’ll ever see in southern Ontario. Considered to be the geological gem that was formed at the base of an ancient sea over 450 million years ago. Visit the dog-friendly trails and marvel at the rolling red rock that will make you feel as if you’ve landed on the moon. Tip: reservations are required to visit the park, book online. 
red rolling hills with trees
  • Forks of the Credit River – featuring Trans Canada Trails and the Bruce Trail, this is a must-visit for hikers. Biking and fishing and the beautiful Cataract Falls can be found here too. Tip: reserving your daily access guarantees you to the Provincial Park, book online, or take your chances it’s not full.
  • Terra Cotta Conservation Area – 485 acres of the Niagara Escarpment featuring mature forests, babbling brooks, wetlands, and ponds. Dog-friendly trails hiking and biking trails turn into cross-country ski trails in the winter. Tip: your pass to Belfountain Conversation allows you to visit here for free, book online

Best Farms and Orchards in Caledon

You can’t help yourself but stop along the scenic road at least one of the farms in Caledon. The on-farm markets are the best way to support local farmers but also know that you are getting the freshest produce in return. And, yes it’s a recommended stop on the Vistas, Falls & Caves itinerary, I just won’t tell you which one it is. 

red apple branch
  1. Albion Orchards – voted as one of the top 4 apple orchards in Canada by both the Food Network and Chatelaine Magazine how can you not visit here! This family-run farm offers you a pick your own apples experience, a pumpkin patch and Christmas tree farm, and a country store featuring all things apple. Open from September through to December only, and unfortunately, it’s not dog-friendly. Visit: 14800 Innis Lake Rd, Caledon East
  2. Dixie Orchards – along with apple picking and a pumpkin patch you’ll be able to experience one of the most unique things to do in Caledon. Nut picking. That’s right, learn how to pick your own nuts in their hazelnut orchard. Visit in August and you will be able to get one of those instagrammable photo ops in their sunflower fields. Visit: 14309 Dixie Rd, Inglewood

Bonus Insider Tip: Visit Plant Paradise Country Garden for their award-winning organic perennial nursery & botanical garden centre. Located at 16258 Humber Station Road. 

Day Trips from Caledon

The Village of Erin Ontario borders Caledon to the east and is definitely worth visiting while in Caledon. Founded in 1820, Erin has a charming main street lined with typical shops you expect to find in a small town. Start your tour of the downtown at Maddie Hatter Tea Shop Café – it’s quaint, cozy, and oozes charm. Now you’re ready to check out the boutique shops – antiques, books, home décor, fashion and end your shopping at Debora’s Chocolates

Other Ontario Day Trip Inspiration

If you love day trips as much as I do, you might enjoy these ones too!  


Best Time to Visit Caledon

As an easy day trip from Toronto, Caledon is a great destination in all seasons to visit! Caledon attractions are the most popular to visit during the summer. The hiking and biking trails are some of the biggest draws to this area. Come winter, snowshoeing and cross-country skiing take over and there’s a good chance you will see wildlife on those trails.

It’s late winter and early springtime which is the sweetest time of year to visit Caledon. I’m sure you know why too. Some of the best maple syrup harvestings happen here. In the fall, Caledon turns into a kaleidoscope of colours making this a must-see in the autumn. Take a drive on the scenic road, there are so many as you visit each hamlet. 

As a holidaymaker…

I hope you’ll enjoy this action-packed day(s) in Caledon Ontario as much as I did! Caledon is the perfect day trip for Torontonians, as it’s just outside the city and has so much to offer. My dog loved it too! Every shopkeeper or local we met was friendly and welcoming, especially Henry. There wasn’t a place we ventured that Henry wasn’t able to join too! 

This was inspired by Guess Where Trips itinerary called Vistas, Falls & Caves. I can assure you that I didn’t spoil anything by sharing this with you. In fact, only half of the day is spent in Caledon with the other half bringing you to another area about 45 minutes away. Curious, and want to take this surprise road trip yourself? You can, this by clicking here. Warning, they’re kind of addictive, don’t say I didn’t warn you! 

Thank you to Guess Where Trips for gifting me with a free trip. As always, the opinions expressed are my own and I only recommend it if I absolutely love it, and I did!

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  1. I’ve never seen an art gallery that let dog owners to bring their four legs companions inside. I guess gallery owners in Caledon know better. The villages around Caledon seems perfect for taking your dog around for a walking tour and ice cream stops. My dog will love it. And the outdoor of Caledon is just best to explore with your dog.

  2. How wonderful that Caledon is so dog- friendly. I used to live near Caledon and find the region full of wonderful outdoorsy things to do!

  3. I have never heard of Guess Where trips but I am totally going to recommend it to my friends in Toronto! Looks like you had a great time with all the different things to see and do in the Caledon area.

  4. It’s great that Caledon is such a dog friendly place. I sometimes look after a firned dog’s when they are away and I know it can be difficult to find places that will allow dogs inside, especially when it comes to cafes and restaurants. I would love to go to one of the apple orchards in autumn and pick up my own apples. That is such a cool activity!

  5. I love learning about cute little areas like this, they always have so much to offer to those who want to get off the beaten path to explore it.

  6. This looks like a really beautiful area to visit and I love the wooden houses from the time of the settlers. I have never heard of “Guess where trips” but it sounds like an interesting concept. It looks like there is a lot to do in the area and I would certainly like to see the outdoor parts, the cheltenham Badlands and the conservation areas too.

  7. This is awesome! As a furmom, I appreciate all these dog-friendly activities available that I can do with my little furball. We look forward to exploring the Belfountain Conservation Area and I am happy to know that all trails are dog-friendly.

  8. Another idyllic place and gorgeous pictures to capture its quaint essence! I’m loving all the hiking suggestions and that the art gallery is dog-friendly, too.

  9. I want to take a trip with Guess Where Trips! That sounds like so much fun to be totally surprised and not have to do the planning. (Do they do trips in the USA, too?) Caledon looks amazing, by the way. I’ve been to Toronto and probably drove right past Caledon as well. I love the charming neighborhoods and the waterfalls you explored.

  10. Guess Where Trips sounds like a great idea for a day trip. I’ve seen that kind of thing before for flights where you can get a surprise trip but not for local day trips. I love the look of the little villages, and of course all the delicious local food places. The Cheltenham Badlands sounds really interesting, the red rocks are so unique looking

  11. Caledon looks like a great place to explore especially with dogs! I am sure Henry enjoyed these trips. It is good you tried out Guess Where Trips and found out these hidden gems. Nothing more pleasurable than to find new places in the areas you have known earlier and enjoy them. I love the concept of landscapes, falls and caves. 🙂

  12. As a dog owner, this article is right up my alley! The dog-friendly hiking trails sound amazing! The whole area just looks gorgeous and I love that there’s so much to see and do with our little four legged friends!

  13. What a great itinerary! The locations are outstanding. For fans of the outdoors, this vacation package is ideal. Henry, your dog, appears to have liked the journey as well. For adventurers like me, Guess Where Trips is a must try—it looks fun! Thank you for sharing!

  14. I love the sound & look of this. Caledon looks like a beautiful place to explore, but even more appealing to me is the surprise of the itinerary. What a brilliant idea! Planning a trip back to Canada next year so saving this for then!

  15. Wow, there are lot of things to do with dogs here with great conservation areas. Caledon looks ideal for a weekend getaway to relax. Great article!

  16. This is a nice list of things to do in Caledon, whether you are with a dog or not! It’s a nice article and helps you to get a great time! thanks for sharing it!

  17. As a dog owner, I loved reading this, as I know how lovely it is to find great places to visit with my four legged friend. This vineyard sounds gorgeous and well organised. I think its lovely to get those food recommendations so you can really enjoy the wine at its best!

  18. I could not have read this at a better time! Myself, my partner, our daughter and our DOGGO are moving to Ontario later this year! we have lived there previously but are now returning with our daughter and puppy! This is so helpful

  19. This looks like such a cute village to visit in Ontario! We’re in the process of looking for places to visit this summer so I’ll add this to my list for sure.

  20. I love anywhere that I can travel with my dog, so I love that Caledon has lots of dog friendly activities. I think this is also a really cool idea where you give up the reins of planning and go on a suprise trip that allows you to discover new places that you might not have thought of on your own!

  21. What an interesting read! I love places that are not that well-known and that you don’t find in each and every guide or blog. Caledon seems to be a perfect place for a relaxed time-out. Especially the lush sceneries are truly intriguing.

  22. Wow, what gorgeous locations, scenic landscape and really cute towns to visit. I totally love the architecture here and the classic elements along with eateries, lodges and the art galleries that you can visit. But I’m definitely going to spend more time outdoors with some of the beautiful landscape, waterfalls and that colored rocky area that really is unique to visit in Caledon.

  23. What a wonderful concept Guess Where Trips has! These hidden gems in Caledon look just darling. I love that they also give you food recommendations that support the local community. And who doesn’t love a surprise adventure? I’m heading to Nova Scotia this fall and will definitely look into the Halifax Area Trips! Thanks for bringing this cool service to my attention. I’m so intrigued!

  24. You certainly teased me with the Vistas, Falls and Caves tease. I will have to check that out! We visited Cheltenham Badlands for the first time last year. But you shared a great selection of things to see and do in Caledon to keep us going back. We are always up for checking out the local bakeries in the small towns. And we sure would not pass on wine or beer stops! Good do know that you and your dog were welcomed warmly.

  25. Caledon looks like such a cute place to visit! I would love to see maple syrup being harvested! I love syrup and maple-flavored, well, everything! Haha

  26. I’ve been wondering about the Guess Where Trips. I was looking the other day and this specific trip intrigued me. I have been to Cheltenham Badlands, but other than that I haven’t explored the Caledon area at all. Maybe another road trip is in the future (like this weekend) 🙂

  27. The photos here give a real sense of a walkback to the1880 when most of these houses seem to be built from. There is clearly a lot to do around here and those tours sounds perfect. I have only done a few tours on my trips but each one was fabulous so I am tempted to do more in areas that are less accessible by public transport. Visiting an orchard is something new to me and sounds great in the Summer for a unique expereince. I’ve never seen maple syrup harvested so would certainly want to see how this is done.
    Lots of great tips here on what to visit and explore and those cute stores sound fab.

  28. I haven’t been to Caledon, Ontario yet, and don’t travel with a dog, but I would still like to visit all the places you write about. It’s good that you show pet-friendly places because I have many friends traveling with dogs, and it is always a problem for them to find trails or areas where they can actively spend time with their pet friends. Villages in Caledon seem charming. For sure, I would like to see Cheltenham Badlands and Albion Orchards.

    1. Caledon is a great place for dogs due to the natural conservation areas. My dog loved hitting those trails, and then to be greeted so warmly in the small towns was an added bonus!

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