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Date ideas in the Southern Highlands
11 date ideas around the Southern Highlands, from dinner at Leo's by Night and whisky in Joadja's ghost town to the Bradman Museum, the maze at Harper's Mansion and Fitzroy Falls from the East Rim. Swipe through them above, or browse every one below. Each was checked on the place's own website: what it is, when it's on and what it costs. 2 are free.
Every date idea in the Southern Highlands, by kind
11
ideas
2
free
4
kinds
Oct 2026
last checked
Food and drink: 5 date ideas in the Southern Highlands
BOWRAL
A guided tasting in Centennial's Barrel Room
Centennial grows cool-climate grapes just outside Bowral, where the fruit ripens slowly in the cold. A guide pours up to eight wines in the Barrel Room. Stay on the terrace with a glass and a small plate, or spread a blanket on the lawn.
When Cellar door daily 10am to 5pm, last tasting at 4pm; terrace kitchen 11:30am to 4pm. Allow 45 minutes and book ahead
Cost $15 each, with $5 back when you buy a bottle
Checked on the official website, 7 Oct 2026
BERRIMA
Dinner at Leo's by Night, Bendooley Estate
After dark, Bendooley's cellar door near Berrima becomes an intimate, softly lit restaurant. The menu is separate from the daytime Book Barn, and the wine list covers the estate's full range. Arrive early to browse the Berkelouw bookshop, a bookselling name since 1812.
When Thursday, Friday and Saturday from 6pm; bookings essential. The Book Barn bookshop is open daily 9am to 5pm
Cost Winter 2026 menu: starters $18 to $25, mains $37 to $66; 10% weekend surcharge
Checked on the official website, 7 Oct 2026
BERRIMA
Fire-cooked 'feed me' dinner at Eschalot
Eschalot cooks over fire in a heritage-listed stone cottage in Berrima village. The 'feed me' menu is a shared, continuous run of dishes, built for two or more. Much of the produce comes from its own kitchen garden and nearby growers.
When Thursday 6pm to 11pm; Friday and Saturday 12pm to 11pm; Sunday 12pm to 10pm
Cost Feed me menu $95, $130 or $195 a person
Checked on the official website, 7 Oct 2026
The old chimneys of Joadja, beside the distillery. Photo: Gonzo Gooner · CC BY 3.0 · Wikimedia Commons ↗
JOADJA
Whisky in a ghost town at Joadja Distillery
Joadja was built in the late 1870s by Scottish shale-oil miners, who brought their skill at making sly grog. Today a distillery beside the abandoned town grows its own barley and ages single malt in Spanish sherry casks. Tours and tastings are free; just turn up.
When Saturday and Sunday 10am to 4pm; no booking needed
Cost Free tour and tasting; bottles from $44
Checked on the official website, 7 Oct 2026
The old Goulburn Brewery buildings. Photo: Mike Young · CC BY-SA 3.0 · Wikimedia Commons ↗
GOULBURN
Wayback beers in Goulburn Brewery's old malt house
Goulburn Brewery dates from 1836 and calls itself Australia's oldest mainland brewery. The Maltings Bar fills the restored original malt house. Order a Sparkling Ale, the brew that started it all, with a plate of local produce.
When Wednesday and Thursday 12pm to 10pm; Friday 12pm to midnight; Saturday 11am to midnight; Sunday 11am to 5pm
Cost Pay per drink and dish; prices are not listed online
Checked on the official website, 7 Oct 2026
For couples: 3 date ideas in the Southern Highlands
The Bradman Oval pavilion in Bowral. Photo: Bjenks · CC BY-SA 3.0 · Wikimedia Commons ↗
BOWRAL
The Bradman Museum, then the 1.7 km Bradman Walk
Bowral's cricket museum sits beside an oval with views to Mount Gibraltar, and houses the International Cricket Hall of Fame. Afterwards, follow the flat Bradman Walk past the childhood home, school and church of the 'Boy from Bowral'.
When Museum daily 9am to 4pm; the walk is a 1.7 km loop of about 45 minutes
Cost Museum $30 each; the walk is free (guide at reception or online)
Checked on the official website, 7 Oct 2026
BOWRAL
Peonies and a house tour at Retford Park
Retford Park is a pink Italianate homestead from 1887, set in heritage gardens in the middle of Bowral. Spring brings the peonies, and a guided tour shows the art and furniture inside. The free regional gallery, Ngununggula, is next door.
When Wednesday to Sunday 10am to 4pm. House tours Wed to Fri at 10:30am and 12:30pm, weekends also 2:30pm; book ahead
Cost House tour and garden $35 each; garden only $17; the gallery is free
Checked on the official website, 7 Oct 2026
Harper's Mansion, Berrima. Photo: Graeme Bartlett · CC BY-SA 3.0 · Wikimedia Commons ↗
BERRIMA
Lose each other in the maze at Harper's Mansion
Built in 1834 from local red brick and sandstone, Harper's Mansion looks down over Berrima. Tour the Georgian house, then wander two acres of cool-climate garden with heritage roses. Save time for one of the largest hedge mazes in Australia.
When Saturday and Sunday 11am to 3pm
Cost $15 each, or $12 concession
Checked on the official website, 7 Oct 2026
Views and climbs: 2 date ideas in the Southern Highlands
Fitzroy Falls in Morton National Park. Photo: Timothy M Roberts · CC BY-SA 2.0 · Wikimedia Commons ↗
FITZROY FALLS
Fitzroy Falls from the side, on the East Rim track
Fitzroy Falls drops more than 80 metres into the valley. Walk 1.25 km from the visitor centre to Warragong lookout for a side view of the falls. Carry on to Yarrunga lookout over the creek gorge, through forest, heath and rainforest.
When Track open daily; the visitor centre is open 9am to 4pm. The East Rim and Wildflower tracks are 6.7 km return, 2 to 3 hours
Cost Parking $4 per vehicle per day
Checked on the official website, 7 Oct 2026
Belmore Falls from the lookout. Photo: Maksym Kozlenko · CC BY-SA 4.0 · Wikimedia Commons ↗
ROBERTSON
Kangaroo Valley views on the Belmore Falls track
From Hindmarsh lookout near Robertson, the whole of Kangaroo Valley spreads out below. A short track follows the escarpment past several more lookouts. The last one looks straight across to Belmore Falls.
When Morton National Park is always open; 1.8 km return, 30 minutes to an hour. The last stretch of road from Robertson is narrow, winding dirt
Cost Free
Checked on the official website, 7 Oct 2026
Shows and music: 1 date ideas in the Southern Highlands
Inside the Empire cinema on Bong Bong Street. Photo: Chris.sherlock3 · CC BY-SA 4.0 · Wikimedia Commons ↗
BOWRAL
London theatre on screen at Bowral's Empire Cinema
The Empire on Bong Bong Street screens National Theatre Live broadcasts, filmed in London theatres. Next up is Golden Boy, a 1930s New York drama about a young violinist lured into boxing. The production is staged with a live string quartet.
When Saturday 21 and Sunday 22 November 2026 at 1pm
Cost $25 each, or $23 concession
Checked on the official website, 7 Oct 2026
Can't decide? Let the deck pick your the Southern Highlands date
Stuck for date night ideas, or for things to do together at the weekend? Instead of scrolling lists, let the deck deal you one date idea at a time. Swipe right on the ones you like, left on the ones you don't, and within a few minutes you have a shortlist to choose from, or just take the first one you both said yes to.
How it works
Swipe to decide. Each card is one date: what to do, where it is, when it's on and what it costs. Swipe right (or tap Save) to keep it, left (or Skip) to see the next.
Share it with your date. Share sends a link that opens the deck on the same card, so the other person can say yes too.
Keep the ones you like. Saved ideas stay under the deck and on the map. Sign in and they're kept in My Places on every device.
Filter by the kind of date. Food and drink, shows and music, on the water, views and climbs, making something together, or ideas for couples.
Where the date ideas come from
Every idea of ours names a real place and was checked on its official website: what it is, when it's on and what it costs, with a link to that website and the date it was checked. Ideas with an end date leave the deck once they finish. Photos come from Wikimedia Commons and are credited on each card. Mixed in are bookable tours and experiences, clearly marked, with today's prices.
Questions
Can it pick a date for us?
Yes. Swipe until one appeals, or save a few and choose between them. For a single answer, the date wheel picks one at random.
Is it free?
Yes. Many of the ideas are free too: walks, lookouts, galleries, markets and swims.
Do we need an account?
No. Saves stay in your browser; sign in only if you want them on other devices.
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Every idea links to the place’s own website and was checked there on the date shown; times and prices change, so check before you go. Photos from Wikimedia Commons, credited on each.