Event details

Melbourne Cup Lunch at Windsor Leagues Club hosted by Peter Paki.
Includes a two-course meal, free glass of bubbly on the day and lucky door prize ticket. 
11.30am- 3pm.

Address

Windsor Leagues Club, Rilfle Range Road, South Windsor NSW 2756

Phone

02 4577 6488

Event details

Soak up the sunshine while enjoying a delicious 2 course meal, a 3-hour beverage package, bubbles on arrival, live music from 11.30am till late, exciting sweepstakes, and dress to impress for our fashions on the field competition.
Upgrades available for additional cost,

Address

The Vineyard Hotel Sydney, 725 Windsor Road, Vineyard NSW 2765

Event details

Enjoy a carefully curated Luncheon menu.
There will also be sweeps and fashions on the field, so dress-up and celebrate the race that stops the nation. 12.00pm

Address

Bligh Park Hotel, 101 Ham St, South Windsor NSW 2756

Phone

02 4545 2540

Event details

Sip, Savour & Celebrate at our Melbourne Cup High Tea!

Celebrate Melbourne Cup Day with an afternoon of high tea in the courtyard. Join us on Tuesday 3 November from 1pm for a relaxed afternoon featuring a glass of bubbles or mimosa on arrival, followed by a delicious selection of savoury and sweet treats.

For just $40 per person enjoy a spread of smoked salmon and cream cheese sandwiches to mini quiches, gourmet pies, scones, macarons and more, there’s plenty to enjoy as you settle in and celebrate the race that stops the nation.

Take a sneak peek at the menu below and gather your friends for an afternoon of high tea, bubbles and Melbourne Cup celebrations.

Address

RG McGees 193 Windsor Street, Richmond NSW 2753

Phone

02 4578 1503

Event details

Showcasing the best of the Hawkesbury's local produce and food situated beside the central Richmond Park.

Every Saturday morning 8am-1pm

Address

Richmond Park, 118 March Street, Richmond NSW 2753

Phone

0427 892 960

Event details

Evicted Fairy Mushroom Company is an artist, based within the Hawkesbury. Having served in the military as a combat medic/nurse in various exotic locations, he was gifted with Complex Post Traumatic Stress Injury.

Just like the glass medium, sometimes you need to be broken to become something different.

Evicted Fairy Mushroom Company, will be exhibiting all new artwork, to raise money for Defence Community Dogs (DCD). Australia’s only independent program that trains rehomed dogs to Assistance Dog level and provides them free of charge to Australian Defence Force Veterans in need.

50% of all art sales, will go directly to DCD. With a raffle being held on the music and meal night in December (date to be announced), with 100% of raffle money, being donated.

Address

The Village Kitchen, 83 Old Bells Line of Road, Kurrajong NSW 2758

Phone

02 4573 0988

Event details

Local market featuring food,  local fruit and veges.

Every Saturday 10am-12pm

Address

Bilpin District Hall, Bells Line of Road, Bilpin NSW 2758

Phone

02 4567 1215

Event details

Hawkesbury Now is an annual exhibition celebrating the creativity of artists, makers and local art societies with a connection to the Hawkesbury. Bringing together emerging and established creatives working across traditional and contemporary art forms, the exhibition showcases the richness and diversity of the region’s creative community.

More than an exhibition, Hawkesbury Now provides artists with opportunities to exhibit and sell their work, build professional practice and connect with new audiences. It also offers visitors the chance to discover original artworks, meet local artists and experience the breadth of creative talent in the Hawkesbury.

All artworks are available for purchase, providing a unique opportunity to invest directly in local artists while supporting the region’s creative economy.

Address

Hawkesbury Regional Gallery, 300 George Street, Windsor NSW 2756

Phone

02 4560 4441

Event details

Hawkesbury's Ladies Day is here again!
Gather your family and friends and dress to impress this Ladies' Day.
Fashions on the field competition, live entertainment and food trucks. 
Gates open at 11am

Address

Hawkesbury Race Club, Racecourse Road, Clarendon NSW 2756

Event details

Join us to explore historic Howe House, built by John How nearly 200 years ago in the heart of Windsor!
11.30am-12.15pm.

Address

Hawkesbury Regional Museum, 8 Baker Street, Windsor NSW 2756

Phone

02 4560 4655

Event details

Meet Crias (babies and Hembras (females). Hand feed alpacas in the paddock, and learn interesting facts about the alpacas from knowledgeable staff.
Alpaca feeding 3pm daily.

Address

Madisons Mountain Retreat, 1880 Bells Line of Road, Kurrajong Heights, NSW 2758

Phone

0415 404 643

Event details

The Gin Joint takes a big swing sideways to welcome Bluegrass Royalty to our stage!

The Peel River Ramblers are that real deal - raw ,rootsy, bluegrass sounds that have been admired across NSW. Hailing from Tamworth where they are regular fixtures on the live music scene, The Ramblers -Travis, Chloe, Ethan, and Ben - are stitched together by a love of bluegrass, country, western, old-time, and everything-in-between music. Mixing sweet harmonies and spirited picking, their shows are lively and loose, their songs full of stories—occasionally true, usually decidedly tall.

They have performed at Tamworth Country Music Festival and Hats Off To Country, as well as support slots for Lady Lyon and Grand Pricks. They’ve already had an action-packed 2026, with a raft of performances at the Tamworth Country Music Festival, and many more across New South Wales.

The Gin Joint is part of Enniskillen Orchard. Tickets are very limited and so is the parking.

A food pre-order menu will be sent one week before Show Date, orders must be in 24hrs by latest.
Doors open at 6pm, showtime is 7.30pm.

Address

753 Grose Vale Road, Grose Vale NSW 2753

Event details

Celebrate five decades of classic Australian rock as the 50 Years of TMG Concert Series comes to The Regent Theatre.

Relive legendary hits including “Jump in My Car”, “Darktown Strutters’ Ball”, “Crazy”, “Jamaica Rum” and more in a special tribute to the music and legacy of Ted Mulry Gang.

Please note, this is an 18+ event.

Door open 7pm, show starts 7.50pm.

Address

The Regent Theatre, 145 Windsor Street, Richmond NSW 2753

Phone

02 4578 1800

Event details

Featuring International Performer Gemma Luxton & her Live Band.

Get ready for a sparkling celebration of the music, magic and unmistakable style of the one and only Dolly Parton!

Starring international performer and country queen Gemma Luxton*, backed by a sensational live band, this tribute brings Dolly’s legendary songbook to life in a night packed with huge hits, heartfelt classics and plenty of country charm. Sing along to favourites including Jolene, 9 to 5, Here You Come Again, Islands in the Stream and many more as Gemma celebrates the voice, stories and larger-than-life personality that made Dolly a global icon. From rhinestones and big hair to unforgettable songs, this is a feel-good night for lifelong Dolly fans and country music lovers alike.

Big songs. Big hair. Big heart. Grab your boots and get ready for a night of pure Dolly!

Doors open 8pm, show 8.30pm.
18+ only.

Address

Richmond Club, 6 East Market Street, Richmond NSW 2753

Phone

02 4578 1144

Event details

Evicted Fairy Mushroom Company is an artist, based within the Hawkesbury. Having served in the military as a combat medic/nurse in various exotic locations, he was gifted with Complex Post Traumatic Stress Injury.

Just like the glass medium, sometimes you need to be broken to become something different.

Evicted Fairy Mushroom Company, will be exhibiting all new artwork, to raise money for Defence Community Dogs (DCD). Australia’s only independent program that trains rehomed dogs to Assistance Dog level and provides them free of charge to Australian Defence Force Veterans in need.

50% of all art sales, will go directly to DCD. With a raffle being held on the music and meal night in December (date to be announced), with 100% of raffle money, being donated.

Address

The Village Kitchen, 83 Old Bells Line of Road, Kurrajong NSW 2758

Phone

02 4573 0988

Event details

Stroll through stalls bursting with handmade crafts, homewares, vintage finds, farm-fresh produce, and delicious street food. 
9-3pm.

Address

Windsor Mall, George Street, Windsor NSW 2756

Event details

Hawkesbury Dog Festival & Dachshund Festival.
A huge day for dog lovers, families and the community!
Dog competitions, dog market stalls, market and community stalls, food vendors, free face painting. Dogs of all breeds, shapes and sizes are welcome. Two competition arenas : Arena 1 - All breeds, Arena 2 - Dachshund Festival. Extra cost to enter dog competitions.
10am-3pm

Address

Hawkesbury Showground, Racecourse Road, Clarendon NSW 2756

Event details

Hawkesbury Now is an annual exhibition celebrating the creativity of artists, makers and local art societies with a connection to the Hawkesbury. Bringing together emerging and established creatives working across traditional and contemporary art forms, the exhibition showcases the richness and diversity of the region’s creative community.

More than an exhibition, Hawkesbury Now provides artists with opportunities to exhibit and sell their work, build professional practice and connect with new audiences. It also offers visitors the chance to discover original artworks, meet local artists and experience the breadth of creative talent in the Hawkesbury.

All artworks are available for purchase, providing a unique opportunity to invest directly in local artists while supporting the region’s creative economy.

Address

Hawkesbury Regional Gallery, 300 George Street, Windsor NSW 2756

Phone

02 4560 4441

Event details

Experience the electrifying spirit of the 1940s with this live wartime swing concert featuring a stunning Tribute to The Andrews Sisters.

Harmonix Big Band teams up with the fabulous Starr Sisters vintage vocal trio for this high-energy show combining WW2-era harmonies, full big band arrangements and high-stepping performances to transport you back to the era of true grit and high hopes.

With nostalgic classics like Rum and Coca Cola, Sing Sing Sing and Boogie Woogie Bugle Boy, you'll be clapping and cheering as you get "In The Mood!

Two shows: 1pm & 4pm

Address

The Regent Theatre, 145 Windsor Street, Richmond NSW 2753

Phone

02 4578 1800

Event details

Meet Crias (babies and Hembras (females). Hand feed alpacas in the paddock, and learn interesting facts about the alpacas from knowledgeable staff.
Alpaca feeding 3pm daily.

Address

Madisons Mountain Retreat, 1880 Bells Line of Road, Kurrajong Heights, NSW 2758

Phone

0415 404 643

Event details

Award Winning Comedian at The Church Bar
Recommended age 16+
7-9.45pm.

Address

The Church Bar, 22 Kable Street, Windsor NSW 2756

Event details

Showcasing the best of the Hawkesbury's local produce and food situated beside the central Richmond Park.

Every Saturday morning 8am-1pm

Address

Richmond Park, 118 March Street, Richmond NSW 2753

Phone

0427 892 960

Event details

Evicted Fairy Mushroom Company is an artist, based within the Hawkesbury. Having served in the military as a combat medic/nurse in various exotic locations, he was gifted with Complex Post Traumatic Stress Injury.

Just like the glass medium, sometimes you need to be broken to become something different.

Evicted Fairy Mushroom Company, will be exhibiting all new artwork, to raise money for Defence Community Dogs (DCD). Australia’s only independent program that trains rehomed dogs to Assistance Dog level and provides them free of charge to Australian Defence Force Veterans in need.

50% of all art sales, will go directly to DCD. With a raffle being held on the music and meal night in December (date to be announced), with 100% of raffle money, being donated.

Address

The Village Kitchen, 83 Old Bells Line of Road, Kurrajong NSW 2758

Phone

02 4573 0988

Event details

The Professional Tattooing Association of Australia (PTTA) presents the Western Sydney Tattoo Show.
Live tattooing
Tattoo competitions and exhibitions
Traditional Samoan hand-tapped tattooing
Car and chopper show and competition
Live street art
Live music and entertainment
Food trucks
Market and industry vendors
Amusement rides
Free petting zoo
Free entry to the show for kids
10am-10pm.

Address

Hawkesbury Race Club, 1 Racecourse Road, Clarendon NSW 2756

Event details

Local market featuring food,  local fruit and veges.

Every Saturday 10am-12pm

Address

Bilpin District Hall, Bells Line of Road, Bilpin NSW 2758

Phone

02 4567 1215