Note: This is the October guide. For the September guide, scroll to the bottom of this page.

Here are some of the best events across the North Shore in September.

Did we miss something? Let us know and we’ll update! Just email [email protected].

Crow Nest Street Festival 

Willoughby Road and Clarke Street will once again be cordoned off this year as the Crows Nest Festival returns, bringing music, food, stalls and roving entertainers. Thankfully the Crows Nest Metro will be open for the festival this year, easing travel times. 

When: October 18, 10am – 5pm

Where: Crows Nest main street

Mary’s House walk

Mary’s House Services is a local organisation supporting women and children impacted by domestic and family violence. Each year, they run a walk through North Sydney to raise funds for the services they provide. Begins with free sausage sizzle and performance from NSW Police brass band.

The walk runs from St Leonards Park down to Balls Head, over to Lavender Bay and back to the start. 

When: October 25, 8:30am

Where: St Leonards Park, Fig Tree Lane

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Orpheum Halloween screenings 

As October 31st approaches, the Cremorne Orpheum will be hosting a number of “Spooktober screenings” of vintage horror flicks. Screenings include Alien, The Fly, The Silence of the Lambs and will culminate with John Carpenter’s Halloween with a four piece ensemble playing the score live in the theatre.

When: October 16 – 31

Where: 380 Military Road, Cremorne

Wahroonga Food and Wine 

Celebrating twelve years since its inception, the Wahroonga Food and Wine will bring music, wine and global cuisines to Wahroonga Park once again this year. 

When: October 25, 11am – 5pm

Where: Wahroonga Park

North Shore Beer Festival 

Depot Brewery is hosting a North Shore Beer Festival at its Home HQ venue, featuring guest breweries including Akasha, Village Days Brewing and Moore Beer Brewing. The event will also have live music, games, prizes and taco trucks. Free entry. 

When: October 17, 12pm – 8pm

Where: Home HQ mall, Artarmon

Ceramic Art Festival 

North Sydney’s Rochfort Gallery is hosting the works of 13 local ceramicists this month. Free entry. See our full seasonal art guide here.

When: Thursday to Saturday, 10am – 6pm

Where: 317 Pacific Highway, North Sydney

Hunter Valley Uncorked at Balmoral

The Hunter Valley Wine & Tourism Association will be packing up their goods and travelling down to Mosman this month, serving Hunter Valley wines and artisan cheeses at the Balmoral Beach rotunda. Tickets $45, includes glass and 4 tasting vouchers (60ml pours). 

When: October 18, 11am – 5pm

Where: 63 The Esplanade, Mosman

What’s on the North Shore this September?

Wine, nature, theatre and paws: this month is festivals and fairs all the way through.

Lane Cove Festival

In partnership with the larger Sydney Fringe Festival, Lane Cove Council will be bringing live music, film screenings and theatre to the Pottery Lane Performance Space. Productions include All Things Must Pass (following the Beatles in the wake of Lennon’s death), Algorithm of Us (a satirical romantic comedy about AI) and Barnaby: A Country Musical from the creators of Gladys: A Musical Affair.

Ticket prices vary, see full program on the council website.

When: September 1 – 30

Where: Lane Cove

St Ives Food & Wine Festival

An annual festival bringing wine from across Australia to St Ives Village Green. Food from various cuisines — yum cha, goulash, empanadas, acai — is also available. Family friendly.

When: September 20, 10am – 4pm

Where: Village Green Parade, St Ives

Willoughby Fauna Fair

An event in Willoughby Park celebrating local wildlife. Features a presentation of local native animals by the Hills Wildlife Sanctuary, live music from Amelie Ecology, workshops and activities for kids. Free entry, reserve a spot online.

When: September 20, 10am – 3pm

Where: Willoughby Park, McClelland Street

Orpheum Father’s Day screenings

The Hayden Orpheum will be hosting special Father’s Day screenings of three dad-core flicks in 4K: Raiders of the Lost Ark, Master and Commander and The Deer Hunter.

Nothing screams “Father’s Day!” like a community of Pennsylvania steel-workers being torn apart by the Vietnam War. And Christopher Walken dance scenes.

Tickets $30, beer or cider upon arrival.

When: September 6

Where: 380 Military Road, Cremorne

Ku-ring-gai's Eco Festival

An environmental festival for all the upper North Shore green thumbs. Events include birdwatching, bushcare workshops, guided bushwalks and more. See full schedule on the council website.

When: August 30 – September 27

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Paws in the park

A community event at Willoughby Park for you and your furry friends. Events include educational sessions hosted by local veterinarians, dog agility demonstrations and a sausage sizzle. Free entry.

When: September 19, 10am – 1pm

Where: Willoughby Park, McClelland Street