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Back from Bowral: the best sick day ever

3 November 2026 · Real People doing awesome stuff · longestday

Back from Bowral: the best sick day ever

A Monday start, two trains to Bowral and 144 kilometres back to the eastern beaches from the Southern Highlands. This Longest Day was also the reconnaissance for Chase the Sun in December.

This Longest Day broke a few of our habits. It was on a Monday, it started on a train, and it ran one way. The plan was to take the early train to Bowral and ride back to the eastern beaches: 144 kilometres and about 1,400 metres of climbing, starting 680 metres up and finishing at sea level.

The route got more study and discussion than usual, including a reconnaissance drive and a last minute suggestion from Frankie for the way across Razorback. It's the same road home we'll ride for Chase the Sun in December, so this was the real reconnaissance.

Ten riders said yes, a mix of regulars and new faces ready for an adventure. Elsie had asked a few weeks ago when the next long ride would be, and here it was. Jesse was looking at her longest ride ever. And bike-mad Maddie is never working if there's a ride on. Then Kev couldn't make it, and James didn't show (he has developed a habit of RSVPing and then forgetting he RSVP'd). That left eight of us.

Riders with lights on in the dark before the ride to Mascot station

To make the 5:37am from Mascot and the connection at Campbelltown, everyone had to be at the meet point ready to leave at 5:10am. Warwick's morning started with a costume change: he'd dressed in the dark, and had to unhook himself from his bibs and put them on again. A spirited ride to Mascot station followed, and we made the train. Once we sat down, one of us admitted to telling work they wouldn't be in that day.

A short delay on the first train put the Campbelltown change under pressure, until we found the next train three metres across the platform. From there a creaking train of two carriages took us up into the Highlands, past horses, cows, hot air balloons and open country. Dan found an unconventional way to stand his bike in the carriage, which probably had something to do with the stubborn front derailleur he was nursing when we got off.

Sunrise over farmland from the train window
A rider smiling between the bikes stacked in the train carriage

Stepping off the train in Bowral, Sydney's Hamptons, it felt a long way from home. The air had the cool of the Highlands, about 13 degrees under cloud. But we had nothing to do for the rest of the day except ride. Most of our Longest Days are loops out of Sydney, so a one-way ride home, with a few train stations on the way if things went wrong, felt like a proper adventure. On the platform a local asked Warwick where he was heading. He said he'd come off the Sydney train and was riding back to Sydney. The local didn't quite get it.

The group rolling out of the Highlands through the trees

Dan's derailleur settled down, and we rolled out through Mittagong and over Hill Top, then down to Picton for coffee before Razorback. Early on, Jeff acknowledged he'd earned a few demerits for sitting on the front and dropping the whole bunch without looking back. I let him know he'd lost all his points for the season.

A selfie on the descent with the bunch following behind
The group at the coffee stop in Picton
A rider at the Picton coffee stop, phone in hand

Over Razorback and on through Campbelltown and Liverpool, the Tonga and Samoa flags from the game the night before were flying from houses and cars.

The bunch on the road after Razorback
Following the bunch along an open road

We crossed plenty of bridges, but as a true engineer, Dan was only delighted once we rode across a real suspension bridge. According to Dan, the others didn't count. This follows his admiration for the roadworks during his recent Parramatta half marathon.

Crossing an old brick bridge, one of the bridges that didn't count
Another rider over the same brick bridge
Riding single file across the suspension bridge

By then the talk had turned to lunch. Steak sandwich? Would it come with caramelised onions? Warwick treated the onions as a test of how close we were to Sydney. The answer was the East Hills pub, with pensioners, steak sandwiches, caramelised onions and one glass of white wine. Lunch always makes the legs feel heavier, and it did on a few of the climbs that followed. The taste of chicken salt stayed with me all the way to Mascot.

We made good use of brand new cycling infrastructure across the day. Tim had kept us well swept from the back all day, and for the last stretch he suggested a bike path to get us out of the traffic. He led us from President Avenue at St George Private Hospital on a new path that took us straight back to Mascot.

Riding a new shared path lined with fresh plantings
A rider on a new bike path beside a painted pipeline

Each time I looked over at Dan and Elsie, they were smiling, well, most of the time. They're ready for Bondi2Berry next week.

Despite all the changed habits, it was still a Longest Day: a day off work, on the bike with friends, enjoying the road. One rider, nameless to protect the innocent, called it their best day at work ever.

Chase the Sun on Wednesday 16 December is a 350 kilometre loop in a single day, and it comes home on this same road from Bowral. The only difference is that we'll have 200 kilometres in our legs before we start it. You can follow it and support the riders at challenge.pathwayclub.org.

And it turns out Elsie has every second Monday off. More Monday Longest Days, anyone?

Elevation profile from Bowral to the eastern beaches, falling from 680 metres to sea level with the climb over Razorback near Picton

See the route we rode on Ride with GPS

By the numbers

  • 144 kms, 1,400 ^m ascending and 2,090 ^m descending
  • 5 hours 28 minutes riding
  • 2 trains
  • 8 riders, with 3 Longest Day newcomers
  • 0 punctures or mechanical problems
  • 1 glass of white wine at lunch
  • 1 sick day taken to ride all day
  • -25 demerits for Jeff

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