May is one of our favourite months of the year.
Crisp mornings, crunchy leaves underfoot, gathering around the fire in the evening snuggled up with a glass of red or a hot toddy and of course, plenty of events in the Highlands to keep us busy and entertained.
Our Event Directory is bursting at the seams with over 280 events, workshops, performances, shows and loads more……check out our May Must Do’s for some event inspo!
1 :: LAUGH IT UP // Lawrence Mooney Dead Set Country Comedy Night at Bundanoon Hotel
Lawrence Mooney’s Dead Set Country is his latest stand-up show about a city bloke navigating rural life.
Expect plenty of lols as he tackles life in the sticks, chats with horses, line dances, and forms a strange bond with a tractor.
Tix include a 2 course meal so there’ll be both a belly full and belly laughs!
2 :: SAY THANKS // Mother’s Day in The Highlands
How amazing are our wonderful mums?
We love spoiling the special women in our life on Mother’s Day and that includes the gorgeous stepmamas, grandmas, aunties and godmothers out there too.
Check out our Guide to Mother’s Day In The Highlands for some fab ideas of where to go to treat Mum to a delicious meal out and bubbles!
Or head to our Shop Highlands Hub for some gift inspo, guides and quick links to loads of our local retailers – soooo good!
Plus, here’s a list of Mother’s Day activities on around the Highlands – there’s some amazing brekkies, lunches and high teas happening – totes got you covered!
3 :: YEAH THE GIRLS // 2025 Ladies Luncheon at Robertson Public House and Kitchen
Now in its fourth year, this is set to be an inspiring day filled with delicious food, music, and heartfelt connection.
Hosted by the always lovely Beth Macdonald and joined by our absolute idol Miriam Margolyes, with live tunes from Amber Kenny.
There’ll be food, raffles, a silent auction, and funds raised going to POP IN, supporting women and children facing domestic violence and abuse in the Wingecarribee Shire. So worth it.
4 :: ONE LOVE // Kangaroo Valley Reggae Fest 2025
Feel the rhythm! Feel the rhyme! Get on up, it’s Reggae Fest time!
Grab your tickets for this full day of tunes, tasty food and good times at The Friendly Inn Kangaroo Valley.
5 :: DEFYING GRAVITY // WICKED Sing-along Screening
For fans of the musical film Wicked, this one’s a must.
Channel your inner Elphaba or Glinda [or both…who says you have to pick sides?] and head to this fun movie screening and sing-along at The Empire Cinema on the 10th.
There’s even a prizes for best dressed, so it’s up to you whether you go all in with the green body paint.
6 :: MUSIC MAN // Conrad Sewell Firestone 10th Anniversary: Acoustic Sessions Tour at Bowral
Conrad Sewell is bringing his Firestone 10th Anniversary Acoustic Sessions to Bowral Bowling Club on 2 May as part of his biggest regional tour yet.
Celebrating a decade since the hit that launched him to global fame, Conrad will share stripped-back versions of his most-loved songs.
With heartfelt vocals and some new music thrown into the mix, it’s gonna be a special one.
7 :: JUST KEEP SWIMMING // FINDING NEMO JR. – The Musical
Support our talented Highlands youth by grabbing a ticket to this 60-minute musical adaptation of Disney/Pixar’s Finding Nemo.
All your fave characters will be there, like Marlin, Dory and of course the fish of the moment, Nemo.
Expect loads of energy, fun songs and an awesome underwater world brought to life on stage.
8 :: AVAST YE // Pirates Of The Caribbean: Murder Mystery Nights Dinner at The Robertson Hotel
Ooo we love a whodunnit – and with a pirate theme too? Shiver me timbers!
Pirate Captain William Kidd is calling a meeting of the Pirate Fraternity aboard The Angry Snail [aka The Robertson Hotel]. But when someone breaks the Pirate Code and Captain Kidd ends up overboard, it’s your job to uncover the traitor.
Tickets are $99 and include a 3-course meal. Aaargh!
9 :: SPORT FOR ALL // Wingecarribee Abilities Unleashed Sports Day
Breaking Barriers Wingecarribee is a new initiative from Wingecarribee Shire Council that’s all about making local sport more inclusive, accessible and welcoming for everyone in the community. Love it!!!
As part of the initiative they will be hosting an Abilities Unleashed Sports Day at Gillick Sports Complex in Mittagong on Thursday 15 May from 10am–1pm.
Both adults and children are invited to come on down and have some fun playing sports.
10 :: STREAM THE AUTHORS // Sydney Writers Festival Live and Local at CTC Robertson
No need to head to the big smoke to catch the best of the Sydney Writers’ Festival this year.
The fabulous crew at CTC Robertson will be screening select Festival sessions from Thursday 22 May to Sunday 25 May.
Grab individual session tickets or go all in with a pass to the lot. The CTC Café will be open 30 minutes before and after each session for tasty snacks and a cuppa.
11 :: OPEN MIND // 2025 Speaker Series: The Grey Zone by Professor Peter Greste
The Oxley College Centre for Ethics presents Journalist and author Peter Greste. Peter will be sharing his insights on something called the “Grey Zone”, the space between extreme opinions where open discussion and democracy can thrive.
He’ll look at how this space is changing around the world, and what it means for politics, the media, and free speech. Peter will also share stories from his time as a foreign reporter and what he’s seen over the years.
12 :: TUNE OUT // Daniel Champagne LIVE at Exeter Village Hall
Guitar virtuoso, singer and songwriter Daniel Champagne thinks live music should be for all ages.
That’s why he’s playing a family friendly concert at Exeter Village Hall on the 3rd.
It’s also a seated event so everyone can be comfortable as the bop and sway along to the beat.
13 :: COUNTRY COOL // Max Jackson at Robertson Public House
Boy oh boy, it’s a good time to be a music lover, right?
This one’s for the country fans. Max Jackson, Country Music Awards Australia Female Artist of the Year, is hitting the stage at Robbo Pub on the 10th.
Wear your comfiest boots because you’ll be dancing, singing, and soaking up every moment of this unforgettable night.
…
This blog features friends and advertisers of The Fold Southern Highlands and is fully endorsed by The Fold Southern Highlands. We strongly believe in the businesses and all the information we share with you on The Fold and we’re excited to share the amazing stories and adventures of our local businesses. We want to say a BIG thank you to you for supporting our sponsors who help make The Fold possible.