As the warmer weather of spring fuels your wanderlust, you don’t need to venture far from Sydney to satisfy your urge to explore. And when there’s a food and wine festival, a celebration of cutting-edge country music or a sporting event waiting for you at your destination? Your weekend getaway is transformed into a springtime holiday to remember, all within a couple of hours’ drive of the harbour city. 

See a different side to the Hunter

Two very different events in the Hunter Valley provide equally compelling reasons to revisit Australia’s oldest wine region and discover a booming boutique winery scene. Prepare to get down and dirty (or look on in awe as participants alternate between grins and grimaces) during Tough Mudder, at Rydges Resort Hunter Valley in Lovedale on 6 September 2025. And return to watch top golfers compete for a big purse in the men’s Ford NSW Open Championship, at The Vintage Golf Club in Pokolbin from 13 to 16 November. 

Buckle in for the two-hour drive north from Sydney, or fly into Newcastle Airport and rent a car for the hour-long drive to the valley. Then check into your room at your event venue – the Rydges Resort for the Tough Mudder or The Vintage Golf Club’s Château Élan Hunter Valley – or book a stay at nearby accommodation such as Spicers Guesthouse in Pokolbin. 

Whether you’ve taken on the 5km or 15km Tough Mudder, where the personal challenge is actually completing the fiendish obstacle course, or you’ve engaged boss mode on the Infinity Tough Mudder, reward yourself for your outstanding efforts with a rejuvenating treatment at Château Élan’s day spa, Spa Anise at the Spicers Vineyards Estate or Elysia Wellness Retreat in Pokolbin.

Celebrate your Tough Mudder achievement, or a thrilling day of championship golf, with a memorable meal at one of Pokolbin’s many excellent restaurants, such as Circa 1876 at The Convent Hunter Valley, Muse Restaurant at Hungerford Hill Wines, Restaurant Botanica at Spicers Vineyards Estate, or the award-winning EXP Restaurant. 

And be inspired to extend your stay and seek out unexpected adventures and destination dining all across the valley, from Bistro Molines, a 20-minute drive away in Mount View, to famed farm-to-table fare at Margan Restaurant, at the Margan winery in Broke.

Be the first to experience an iconic event in Bowral

The Southern Highlands cool-climate wine region is set to heat up courtesy of the inaugural Horizontal Festival, at the Centennial Vineyards estate outside of Bowral, from 4 to 5 October 2025. 

An immersive celebration of art, music and culture as well as epicurean indulgences, this food and wine festival with a difference features a series of curated gourmet zones. Sip on sparkling wines and slurp down oysters in the serene Sparkling Bar, dip into NSW dairy delights in the Cheese Den, sample top regional pours in the white-wine-focussed Vineyard zone, the Rosé Room and the Barrel Room red wine specialty space, or enjoy interactive art, DJ tunes or live musical performances over craft beer at the Hops Garden & Concert Stage. 

After you’ve tasted your way through your chosen day or evening session, there’s plenty of time to work up an appetite before sampling more of the Southern Highlands’ incredible foodie experiences. Make a reservation and make room for exquisite paddock-to-plate fare sourced from local producers at the acclaimed Eschalot in Berrima. Enjoy a breakfast or lunch of ethically produced, expertly prepared goodness at Hearth, next to Bowral’s Ngununggula regional art gallery. Or tuck into a signature beef cheek pie at Briars Inn, less than a 10-minute drive from central Bowral in Burradoo. 

Continue your journey of discovery across this cool-climate wine region by sampling fine drops at wineries like PepperGreen Estate and Bendooley Estate, both in nearby Berrima. Book a luxe cottage at Bendooley Estate to continue your deep immersion in wine country, snaffle the three-bedroom Black Barn Bowral designed by Australian fashion legend Collette Dinnigan with your friends or family, or take a room at a boutique Bowral stay such as Berida Hotel or Links House.

Cheer on triathletes in Wollongong 

Watch some of the fittest and most dedicated athletes in the world compete at the World Triathlon Championship Finals in the laidback beachside city of Wollongong, a 90-minute drive south of Sydney, from 15 to 19 October 2025. 

The five-day event kicks off with an opening ceremony and parade of nations on Wednesday 15 October, with under-23s, junior and para triathletes competing in the following days and the elite men’s and women’s championships decided on the Sunday. Gather at Cove Beach between Wollongong’s two historic lighthouses to watch competitors swim out beyond the harbour breakwater, before they return to jump on their bicycles for a 40km circuit. Once the competitors have ditched the bikes for the 10km running race, head over to Wollongong City Beach to the south of the lighthouse to see who hits the finishing line first. 

Stay close to the action at the mid-century Palm Springs-style Surfside 22, mere steps from the finishing line, or Sage Hotel Wollongong, a five-minute walk down the beach. Or take your pick of eateries like the chic Italian bistro Restaurant Santino when you check into the minimalist Hotel TOTTO, near the Keira Street dining precinct in the city centre. 

Race heats start as early as 7.30am, but with local favourite café Diggies Wollongong serving breakfast from 6.30am at nearby North Wollongong Beach, you can fuel up and even savour a second coffee without missing a minute of the competition. Looking for something to do races? Venture north to check out beach towns like Austinmer and Thirroul, or slip down south to the beach-holiday hub of Kiama to see its famous blowhole. 

And after the last event has been decided on the Friday or Saturday, head over to South Coast Distillery’s bar for house-made sundowner cocktails and craft whiskies, or wash down a craft ale with a burger at Principle Brewing.

Sidle up to modern country music in Newcastle

Australia’s newest country music festival joins Newcastle’s packed events calendar when it debuts in the port city on 1 November 2025. Grab your ticket to Strummingbird to see edgy international country artists like the genre-bending Jelly Roll, Texas’s Treaty Oak Revival and Shaboozey (a guest vocalist on Beyoncé’s 2024 album Cowboy Carter) strut their stuff alongside homegrown stars such as indie-folk duo Dreggs. Away from the two live stages, steep in country culture as you ride a mechanical bull, learn how to line-dance or simply chill with smoky barbecue ribs and a cold beer. 

Make the most of Strummingbird’s handy location on Newcastle’s central Foreshore Park by staying at the nearby QT Newcastle, a 15-minute walk from the festival grounds, or the Crystalbrook Kingsley, a few blocks further inland. Either luxe boutique hotel makes a great base for exploring the hip bars, restaurants and creative spaces that have taken over former industrial buildings in the city centre. 

Looking to balance out the deliciously indulgent festival fare you wolfed down at Strummingbird with something a little more wholesome? Savour sustainable seafood paired with a glass of natural wine at Scottie’s, between Foreshore Park and Newcastle Beach, or nourish yourself with some of the creative Asian fusion dishes on offer at Signal Box, nestled in the Market Street Lawn precinct between the QT and the Hunter River. 

Linger in Newcastle to follow the Brewcastle craft brewery trail across town, cruise down the coast on an Adventure Tour with CoastXP, or get a better sense of the city and surrounding coastline on a guided tour with Newy Tour Co. Newy Tour Co. also offers absorbing guided day trips to the Hunter Valley wine region and nearby Port Stephens, home to thriving populations of wild koalas and dolphins.