Sydney Flying Squadron Australia's oldest open boat sailing club, est. 1891

Jacaranda weekends on McDougall Street

The jacarandas of McDougall Street, Kirribilli, flower from late October, and on the busiest weekends North Sydney Council closes the street to cars so the crowds can walk it safely. The Sydney Flying Squadron is at the harbour end of the street. Walk down under the trees for coffee on the wharf, lunch at Foys over Careening Cove and, on Saturdays, the historic 18-footers being rigged in the park beside the club.

Closed
Saturdays and Sundays, 7am to 7pm, from Saturday 31 October to Sunday 6 December at the latest
Streets
McDougall Street between Clark Road and Willoughby Street, and Hipwood Street for 50 metres from McDougall Street
Cars
Only residents of the closed streets may drive in. Taxis, Uber and hire cars can't set down inside the closure, and council visitor parking permits don't apply in it.
The club
76 McDougall Street, at the Willoughby Street end, beside Milsons Park
Cafe
The Flying Bear, seven days, 7am to 2pm, walk in
Foys
Foys Kirribilli, Sunday to Thursday 12pm to 8pm, Friday and Saturday 12pm to 9pm. Book a table

Getting here without a car

  • Train: to Milsons Point Station, then walk down McDougall Street under the jacarandas to the water.
  • Ferry: the Neutral Bay service to North Sydney (High Street) wharf, then walk around the shore of Careening Cove.
  • Bus: the 263 to Clark Road or High Street, North Sydney.
  • Taxi or rideshare: ask to be set down in Willoughby Street, which stays open. The club is a short walk along McDougall Street from the corner.
  • Mobility Parking Permit: a car showing a state permit may drive in and park inside the closure with the permit holder aboard, at no more than 10 km/h.

Saturdays: the 18-footers in the park

Every Saturday of the closures is a race day. From late morning the club's historic 18-footers are rigged on the lawn of Milsons Park, beside the jacaranda crowds, then launched down the ramp below the deck. It is free to watch: ask the crews about each boat's history. Racing starts out on the harbour at about 2.15pm under the club's handicap start, and the boats come home to the clubhouse for the presentations.

Also at the club on jacaranda weekends

  • Cherub sprints, Saturday 21 November 2026 to Sunday 22 November 2026. The Cherubs race sprints from the club over the weekend of 21 and 22 November.

Breakfast, lunch and dinner on the water

The Flying Bear Cafe is on the lower deck over Careening Cove: breakfast, lunch and coffee, walk in, no bookings. Foys Kirribilli, the club's waterfront restaurant and bar, is open for lunch and dinner every day; jacaranda weekends are busy, so book a table. Every meal and every drink helps keep the historic 18-footers sailing on Sydney Harbour.

Look after the street

McDougall Street is home to the people who live on it, and residents may still drive in at no more than 10 km/h. Keep driveways clear and give their cars room. There are public toilets in Milsons Park.

The closure details are from North Sydney Council's announcement of 26 October 2026 and the council's letter to residents, with the closure map. The council closes the street for pedestrian safety while the crowds are large; it is not an organised event, and the council may end the closures sooner.