Festival of Mosman: Event Highlights

The Festival of Mosman is back—bigger, brighter, and more exciting than ever!

Over ten exciting days, Mosman will come alive with street parties, outdoor feasts, live music, cultural celebrations, and plenty of family fun – even the pets get their own special day! To help you plan your festival adventures, we’ve picked out some of the highlights you definitely won’t want to miss.

SpringFeast Night Market  

📅 Thursday 23 October, 4.30 - 9pm  

📍 Mosman Square and Village Green  

A vibrant, family-friendly event bursting with delicious food, live music and roving entertainment. Discover exciting new stalls, kids’ activities, plus artisanal goods galore. SpringFeast Night Market is proudly funded by the NSW Government’s Open Streets Program in association with Mosman Council.  

HMAS Penguin Freedom of Entry  

📅 Friday 24 October, 11am - 1:30pm  

📍 Prince Albert St to Mosman War Memorial  

Watch the officers and sailors of HMAS Penguin as they conduct a Freedom of Entry parade, a centuries-old tradition symbolising trust and respect between the Navy and community. The march is from Prince Albert Street, along Military Road into Gouldsbury Street, and along The Crescent to the Mosman War Memorial. Come along and be part of this special experience! 

Dinner on the Green 

📅 Friday, 24 October, 6:30pm - 9:30pm 

📍 Mosman Village Green 

An unmissable Italian-themed outdoor feast catered by Fourth Village Providore. Enjoy a three-course meal, served on 'a travolo lungo' (the long table), accompanied by traditional live music under the stars. BYO wine and beer. Tickets ($100pp) are essential for this unforgettable evening of delicious food, warm company and festive Mediterranean charm. 

Tickets: trybooking.com/DAEHY 

Festival Street Party  

📅 Saturday, 25 October, 5pm - 9pm

📍 Middle Head Rd, Mosman Junction 

Get ready for Middle Head Rd to come alive with tasty eats by The Buena, Four Frogs and other food vendors, live music from Bermuda Social and entertainment for all ages. Learn circus skills, get sparkling glitter tattoos, free hair styling and braiding for kids and much more. Festival Street Party is proudly funded by the NSW Government’s Open Streets Program in association with Mosman Council. 

Community Concert 

📅 Sunday, 26 October, 11am - 4pm

📍 Middle Head Rd, Mosman Junction 

The Festival Street Party continues, with local talent in the spotlight! Enjoy a full schedule of performances from local schools and community groups, with a show-stopping set by the Royal Australian Navy Band. With delicious food, kids’ entertainment and free face painting, it’s a fun day for everyone! 

The Heart of Mosman Film Screening

📅 Monday 27 October, 6pm - 8pm

📍 Mosman Art Gallery

Mosman Chamber presents a special film celebrating our vibrant local businesses and community. Join us for this free event to honour what makes Mosman a great place to live, work, and play. Everyone is welcome, and light refreshments will be served.

Sustainability Fashion Show and Swap

📅 Thursday 30 October, 6.30pm - 8pm

📍 Mosman Art Gallery

Join Nina Gabor, a sustainability advocate and fashion influencer for an inspiring evening featuring upcycled fashion, and conscious creativity. The event will showcase styles from one of our community’s most forward-thinking boutiques. Option to join the clothing swap. Light refreshments will be served.

Mega Mosman Trivia 

📅 Thursday, 30 October, 7pm

📍 Mosman Rowers Club

Celebrate Mosman’s history, landmarks and local legends. Enjoy a fun, nostalgic night filled with laughter and friendly rivalry, designed to bring the community together and celebrate everything Mosman. Hosted by trivia extraordinaires Yvonne & Jimmy from 7pm in the Rowers Bar with plenty of extra prizes and vouchers to win! Also, buy your tickets for the Mosman Mega Raffle on Friday, October 31. Tickets on sale from 6pm for a 7pm draw.

Sunset, Songs & Stories 

📅 Saturday,  1 November, 4pm - 8pm

📍 Headland Park

As the sun sets over Headland Park, stories come alive through art, music and culture. Celebrate the humpback whale migration with Whale Song, a magical interactive outdoor theatre procession. The event also features a live sand painting by First Nations’ artist Walangari Karntawarra, a Bush to Bowl cooking demonstration, live acoustic music and the chance to learn Wiradjuri weaving techniques by creating your own bracelet.  

Pets’ Day Out 

📅 Sunday,  2 November, 10am - 2pm

📍 Mosman Square and Village Green 

Get ready for a tail-wagging good time at Pets’ Day Out! Hosted by Farmer Dave, with entertainment from Dr Katrina Warren and the Wonderdogs, plus a DOGA class by Rancan Sisters Fitness. Enjoy competitions (with or without your furry friends), animal-themed market stalls, a petting zoo, reptile display - and maybe even a unicorn! It’s a paw-some day for pets and their people.