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If there is one road trip Romeo & I return to again and again, it is the Southern Highlands and Kangaroo Valley.

This part of NSW was practically made for Autumn adventures with your dog — gorgeous country towns, open fires, cosy cafés, rolling green hills, beautiful gardens and winding country roads that make you want to keep driving just to see what is around the next corner.

The best part? It is surprisingly dog friendly.

So, if you are looking for the perfect weekend escape with your furry best friend, here is one of our favourite itineraries.

Stop 1: Bowral 🌷

Bowral is one of those towns where you can easily lose hours simply wandering. Between the unique boutiques, antique stores, cafés, bookstores and beautiful gardens, it is the perfect first stop on your Highlands adventure.

Of course, Bowral is perhaps best known for the legendary Tulip Time, when the gardens burst into spectacular colour and visitors flock from everywhere to experience the display. It truly is beautiful — but if you are planning on visiting with your furry bestie, I highly recommend avoiding weekends if possible.

During Tulip Time, busloads of tourists and day trippers head down from Sydney, and the gardens can become incredibly crowded and overwhelming for dogs (and honestly, humans too!). If you can, plan a midweek escape instead. You will still get all the beauty of the tulips and gardens, but with a far more relaxed atmosphere and much more space to enjoy it all with your dog beside you. Tulip Time in 2026 will be running from 11 September – 5 October 2026, Dogs Day Out, Monday, 21 September 2026.

Dog-Friendly Things to Do:

 

Here are some of Romeo’s favourite eating places:

Dog-Friendly Accommodation:

  • The Fitzroy Inn – established in 1836  so you are sleeping in history has a gorgeous parlour with an open fire , a wonderful library, lots of open fires, a billiards and games room with beautiful gardens and surroundings  https://www.fitzroyinn.com.au
  • Peppers at Cragieburn – a gorgeous heritage resort with log fires, spectacular grounds,  licensed bar and restaurant  and alfresco dining  complete with a nine hole golf course, billiards room and tennis court https://www.pepperscraigieburn.com.au/rooms/

Stop 2: Berrima 🍁

Just a short drive away is historic Berrima — one of the prettiest villages in NSW. Think sandstone buildings, old pubs, quirky stores and tree-lined streets that become even more magical during Autumn.

If you can, try to time your visit around The Schoolyard Markets which bring the village to life with local makers, artisan stalls and country charm.

Must-Do Experiences:

Where to Eat:

A stop at Surveyor General Inn is almost compulsory. It is one of the oldest continuously licensed inns in Australia and has the perfect country atmosphere for a cosy lunch with your dog beside you. https://surveyorgeneralinn.com.au

Other Places Worth Exploring Nearby:

Final Thoughts 🍂✨

What makes this trip so special is not just the destinations — it is the feeling of slowing down. Long walks in crisp air, coffee beside a fire, winding country roads, discovering hidden little stores and having your dog beside you for all of it.

For Romeo & I, these Southern Highlands and Kangaroo Valley escapes are some of our favourite memories together — and honestly, Autumn is the perfect time to experience them.

So pack the lead, grab a jacket and hit the road. Your next great dog-friendly adventure is waiting. 🐶🚗

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