The Definitive Guide to Sydney's Best Road Cycling

Sydney is a world-class cycling destination, if you know where to look. From the rolling hills of the northern national parks to the iconic run down to La Perouse, our city offers a variety of terrain that tests both your legs and your kit. At Caffeine and Cranks, we spend most of our mornings on these exact roads, testing our designs in the real world.

Whether you are a local looking for a new loop or visiting from out of town, here is our tactical guide to the top 5 cycling routes in Sydney, including distances, difficulty, and highly rated coffee stops to reward your efforts.

1. The 'Lapa' Loop (La Perouse via Centennial Park)

This is the classic Eastern Suburbs run. Starting at the iconic Centennial Park, you head south through the back of Kingsford and Matraville until you reach the stunning views of Botany Bay at La Perouse.

The Stats: Approx 35km-40km return | Difficulty: Easy

Directions: Start at Centennial Park Grand Drive. Exit via the Musgrave Ave gates and head south via Anzac Parade and Gardeners Road. Follow the quiet backstreets through Maroubra and Matraville until you hit the coast at La Perouse.

Key Challenge: The wind. The run home along Anzac Parade is almost always into a stiff headwind that will test your formation riding skills.

The Gear: For the Lapa run, we recommend our Core Jerseys. It is a high-visibility social route, and the Core range offers the perfect balance of performance and style for those bunch laps.

The Coffee: Labara La Perouse. Highly rated for its great views and even better coffee, it is the perfect turnaround point before the headwind home.

2. Akuna Bay & West Head Masterpiece

Located in the Ku-ring-gai Chase National Park, this is arguably the most beautiful ride in Australia. It offers pristine bushland, winding descents into the bay, and a stunning coastal road leading to the West Head lookout.

The Stats: Approx 50km-70km (depending on start point) | Difficulty: Hard

Directions: Most riders start at Terrey Hills. Head into the National Park via McCarrs Creek Road. Descend into Akuna Bay, then tackle the climb back out toward West Head Road. Follow West Head Road all the way to the lookout and return the same way.

Key Challenge: The 'Akuna Wall'. It is a punchy climb out of the marina that will find any weakness in your legs after the technical descent.

The Gear: This route is for the climbers. We recommend our Pinnacle Bib Shorts for their elite-level compression and second-skin fit during technical national park efforts.

The Coffee: Cavallino Terrey Hills. A favorite among North Shore cyclists, it is highly rated for its authentic Italian coffee and cyclist-friendly vibe.

3. The Three Gorges Endurance Classic

If you want to test your climbing engine, the Three Gorges (Galston, Berowra, and Bobbin Head) is the Sydney gold standard. It is a long day in the saddle with constant elevation change.

The Stats: Approx 80km-100km | Difficulty: Hard to Extreme

Directions: Start at Hornsby or Turramurra. Head north to Galston Gorge, descend and climb out. Continue to Berowra Waters for the ferry crossing and climb out. Finish with the descent and climb through Bobbin Head before heading home.

Key Challenge: Accumulated fatigue. By the time you hit the third gorge at Bobbin Head, your legs will be feeling every meter of elevation.

The Gear: Hard efforts demand zero compromise. We recommend our elite Pinnacle Bib Shorts for the Three Gorges. Featuring the premium Elastic Interface® Paris HP chamois, they provide the essential support needed for 4+ hours of intense climbing.

The Coffee: Chasing Plates Turramurra. Known for its top-tier specialty coffee and cyclist-focused menu, it is the highest-rated spot to refuel after finishing the gorges.

4. The Waterfall Run (Royal National Park)

A legendary Saturday morning tradition. The road south from the city is wide and fast, leading you to the entrance of 'The Nasho'.

The Stats: Approx 60km-90km return | Difficulty: Moderate to Hard

Directions: Ride south from the CBD or Tempe via the Princes Highway. Follow the 'old highway' through Loftus and Engadine to Waterfall. From here, you can enter the Royal National Park and descend toward Audley or continue south.

Key Challenge: The fast bunch pace. The run to Waterfall is often a high-speed pace line where you need to stay focused and aerodynamic.

The Gear: The south coast wind can be unpredictable. Our Core Gilet is a must-have for the Waterfall run, providing essential wind protection on the fast, open sections.

The Coffee: 7th Heaven Sutherland. Consistently rated as one of the best in the Shire, this cafe is a prime post-ride destination for the Waterfall bunch to refuel before heading back into the city.

5. Mosman & Middle Head Harbour Vista

For those looking for maximum views with punchy intensity, the Mosman loops take you through some of the most beautiful harbour vistas in the world.

The Stats: Approx 25km-35km | Difficulty: Moderate

Directions: Ride over the Spit Bridge or from North Sydney. Head through Mosman to Balmoral Beach via the infamous Awaba Street. Continue out to Middle Head Road to reach the historic fortifications.

Key Challenge: Awaba Street. It is one of Sydney's steepest paved roads and will test your gearing and your grit.

The Gear: Short and sharp means high intensity. Our lightweight Core Baselayers are excellent here for managing moisture during the high-intensity climbs of the lower north shore.

The Coffee: Shot Mosman. Consistently one of the highest-rated coffee spots in the area, it is the perfect place to celebrate conquering the Mosman hills.

Ride Sydney with Confidence

Sydney's roads are best enjoyed in gear that is built for the challenge. Whether you are tackling your first Lapa loop or training for the Three Gorges, focus on kit that provides the technical support you need. We would love to see you out there - tag us in your ride photos on Instagram @caffeineandcranks.

Ready to upgrade your riding experience? Shop our full range of technical cycling apparel and build your perfect Sydney kit today.