Southern Highlands Concerts 2026: Your Complete Transport Guide to Bowral, Mittagong & Robertson…

Southern Highlands Concerts 2026: Your Complete Transport Guide to Bowral, Mittagong & Robertson Events

Published: February 21, 2026

The Southern Highlands is experiencing a cultural renaissance in 2026, with world-class concerts, intimate vineyard performances, and comedy showcases transforming this picturesque NSW region into a premier entertainment destination. From Jimmy Barnes’ 40th Anniversary Tour at Centennial Vineyards to Julia Zemiro at The Attic Bowral, Damien Leith’s Roy Orbison tribute, and the Sydney Comedy Festival showcase, the region’s diverse venues are hosting extraordinary talent just 90 minutes from Sydney.

But here’s what most concert-goers overlook: the Southern Highlands’ charm (rolling hills, winding country roads, limited public transport) creates unique transport challenges. When you’ve paid $80–200 for premium concert tickets and booked accommodation at heritage B&Bs or boutique hotels, the last thing you want is rideshare unavailability, designated driver stress, or navigating unfamiliar rural roads after dark with wildlife hazards.

This comprehensive guide covers every major concert and event in the Southern Highlands from February through May 2026, with detailed transport strategies for each venue so you can focus on the music, wine, and spectacular countryside instead of logistics.

![Map showing the 125km route from Sydney to Bowral via M5 and Hume Motorway highlighting winding country roads through Southern Highlands with wildlife warning signs]

📊 Quick Guide for Busy Concert-Goers

Major Concerts:

• 🎸 Jimmy Barnes — March 27 at Centennial Vineyards (up to 2,000+ capacity)
• 🎭 Ross Noble — April 20 at Bowral Memorial Hall
• 🎤 Julia Zemiro — March 13 at The Attic Bowral
• 🎵 Live on the Lawn — Feb 21 at Artemis Wines (wine + music)
• 🎸 Sydney Comedy Festival — May 20 at Bowral Memorial Hall

Transport Reality:

• ❌ Rideshare (Uber/DiDi): Non-existent post-concert
• ❌ Taxis: 15-car fleet for 2,000+ concert-goers = impossible
• ❌ Driving: 90min dark country roads + wildlife + designated driver ruins vineyard experience
• ✅ Professional chauffeur: Fixed pricing, everyone drinks, guaranteed service

Why Southern Highlands Driving Is Dangerous After Dark:

• Kangaroos and wombats active 7 PM — 1 AM (peak concert hours)
• Winding country roads with minimal lighting
• Unfamiliar routes through rural areas
• Fatigue after 90-minute initial drive + 2-hour concert

Book Concert Transport Now → | Save $50 First Booking →

Southern Highlands Concert Calendar 2026: February to May

February 2026 Concerts

Rachel Scott & Duo Agostino
Date: Thursday, February 20, 2026
Venue: Exeter Village Hall, Exeter
Genre: Classical chamber music
Capacity: Intimate (~150)

Damien Leith Presents Roy Orbison: A Tribute
Date: Thursday, February 20, 2026, 7:30 PM
Venue: The Estate Camden, 490 Cawdor Road, Grasmere
Genre: Tribute concert (Roy Orbison classics)
Tickets: Premium pricing ($120–180)
Capacity: ~300

Live on the Lawn
Date: Friday, February 21, 2026, 5:00 PM — 9:00 PM
Venue: Artemis Wines, 110 Mittagong Road, Wildes Meadow
Genre: Live music + wine tasting
Tickets: $65 (includes wine tasting + gourmet food trucks)
Capacity: ~500 (outdoor lawn setting)
Special Notes: BYO picnic rugs, no BYO alcohol

Amber Kenny Live
Date: Friday, February 21, 2026
Venue: Dormie House, Moss Vale Golf Club
Genre: Local country/folk artist
Capacity: Intimate venue (~100)

Tangled Up in Bob (Bob Dylan Tribute)
Date: Thursday, February 27, 2026
Venue: Highlands Golf Club, Mittagong
Genre: Bob Dylan tribute
Capacity: ~200

Music4Can Assist Fundraising Concert
Date: Thursday, February 27, 2026, 7:00 PM
Venue: Bowral Memorial Hall, 363 Bong Bong Street, Bowral
Genre: Charity fundraiser with local artists
Capacity: ~400

Tapestry: The Carole King Experience
Date: Friday, February 28, 2026
Venue: Robertson Public House & Kitchen, Hoddle Street, Robertson
Genre: Carole King tribute
Capacity: ~150

March 2026 Concerts

Orpheus Quintet (Emerging Artists Series)
Date: Monday, March 3, 2026, 7:30 PM
Venue: St Jude’s Anglican Church, Bowral
Genre: Classical chamber music
Capacity: Intimate church setting (~200)

Pakedano (Swing/Jazz)
Date: Thursday, March 12, 2026
Venue: CTC Robertson (Community Technology Centre)
Genre: Swing and jazz
Capacity: Small community venue (~80)

Julia Zemiro
Date: Thursday, March 13, 2026, 8:00 PM
Venue: The Attic, Bowral
Genre: Comedy/entertainment
Tickets: Premium ($85–120)
Capacity: Boutique venue (~120)

Jimmy Barnes 40th Anniversary Tour ⭐ MAJOR EVENT
Date: Friday, March 27, 2026, Gates 5:00 PM
Venue: Centennial Vineyards, 252 Centennial Road, Bowral
Genre: Australian rock legend
Tickets: $150–250+
Capacity: 2,000–5,000+ (venue capacity can increase for major touring productions)
Gates Open: 5:00 PM
Support Act: ~6:30 PM
Jimmy Barnes Expected: ~7:30–8:00 PM
Special Notes: Premium wine available for purchase, gourmet food vendors, BYO picnic allowed

IMPORTANT: For large-scale touring productions like Jimmy Barnes’ 40th Anniversary Tour, Centennial Vineyards capacity can significantly increase beyond standard 2,000, making pre-booked transport even more critical as local infrastructure becomes completely overwhelmed.

April 2026 Concerts

Ross Noble
Date: Sunday, April 20, 2026, 7:30 PM
Venue: Bowral Memorial Hall, 363 Bong Bong Street, Bowral
Genre: Comedy
Tickets: $75–110
Capacity: ~400

Creedence Clearwater Experience (CCR Tribute)
Date: Wednesday, April 23, 2026
Venue: Robertson Public House & Kitchen, Hoddle Street, Robertson
Genre: Creedence Clearwater Revival tribute
Capacity: ~150

May 2026 Concerts

Sydney Comedy Festival Showcase
Date: Tuesday, May 20, 2026, 8:00 PM
Venue: Bowral Memorial Hall, 363 Bong Bong Street, Bowral
Genre: Comedy lineup (multiple comedians)
Tickets: $65–95
Capacity: ~400

![Southern Highlands vineyard concert setting showing outdoor amphitheatre at Centennial Vineyards with rolling hills and grapevines]

Why Southern Highlands Concert Transport Is Different

The Unique Challenge: Rural Charm Meets Limited Infrastructure

The Southern Highlands isn’t Sydney’s CBD or Melbourne’s Southbank. What makes it magical (heritage towns, vineyard estates, country roads) also creates transport complexity:

The Reality:

• Limited rideshare availability: Uber/DiDi drivers scarce in Bowral/Mittagong, virtually nonexistent in Robertson/Exeter
• No train service: Nearest station is Moss Vale (limited evening services)
• Designated driver requirement: Vineyard concerts + wine tasting = someone stays sober
• Rural roads after dark: Unfamiliar winding country roads, wildlife hazards, limited lighting
• Minimal taxi coverage: Few local taxis, pre-booking essential but unreliable

The Wildlife Danger: Why Night Driving Is Genuinely Hazardous

![Warning sign showing kangaroo crossing symbol on dark Southern Highlands country road with limited street lighting]

Peak Wildlife Activity Hours: 7 PM — 1 AM (exactly when concerts run)

Southern Highlands roads pass through native bushland where kangaroos, wombats, and wallabies are most active during evening hours. Collisions with large kangaroos at 80–100 km/h can cause:

• Severe vehicle damage
• Serious injuries to passengers
• Total loss of vehicle in worst cases
• Hours stranded on dark country roads waiting for assistance

High-Risk Roads Between Venues:

• Mittagong Road (to Artemis Wines)
• Centennial Road (to Centennial Vineyards)
• Illawarra Highway (Sydney to Robertson)
• Moss Vale Road (between towns)

Professional chauffeur drivers:

• Navigate these roads nightly
• Know high-risk wildlife zones
• Use defensive driving techniques
• Maintain safe speeds on unfamiliar winding sections

For Major Events Like Jimmy Barnes:

When 2,000–5,000 people descend on Centennial Vineyards, the local transport infrastructure simply cannot accommodate simultaneous demand. Rideshare becomes non-existent, taxi ranks have 90-minute waits, and country roads gridlock.

Real Customer Testimonial:
“We almost got stranded after the last vineyard concert when Uber showed a 2-hour wait and no drivers available. We’d prepaid Cars on Demand and our driver was already waiting for us at the designated spot while 200+ people were frantically trying to get rideshare. Best decision we made all weekend.”
 — Sarah M., Sydney (attended previous Centennial Vineyards concert)

Distance & Travel Times to Southern Highlands Venues

From Sydney

DestinationDistanceNormal Travel TimeConcert Night TrafficBowral125 km90–110 min110–140 minMittagong120 km85–105 min105–130 minRobertson140 km105–125 min125–155 minMoss Vale130 km95–115 min115–140 min

Route: M5 South-Western Motorway → Hume Motorway (M31) → Exit at Mittagong/Bowral

From Canberra

DestinationDistanceNormal Travel TimeConcert Night TrafficBowral180 km120–140 min140–170 minMittagong175 km115–135 min135–160 minRobertson195 km135–155 min155–185 min

For Canberra residents attending Southern Highlands concerts, professional chauffeur service eliminates navigation stress on unfamiliar routes.

Key Venue Locations

Centennial Vineyards (Jimmy Barnes, major concerts)
252 Centennial Road, Bowral NSW 2576
From Bowral town center: 8 minutes (5 km)

Bowral Memorial Hall (Ross Noble, Comedy Festival, Music4Can)
363 Bong Bong Street, Bowral NSW 2576
Central Bowral location (walking distance to hotels/restaurants)

Robertson Public House & Kitchen (Tapestry, CCR Experience)
62–64 Hoddle Street, Robertson NSW 2577
From Bowral: 25 minutes (22 km)

Artemis Wines (Live on the Lawn)
110 Mittagong Road, Wildes Meadow NSW 2577
From Mittagong: 15 minutes (12 km)

The Estate Camden (Damien Leith)
490 Cawdor Road, Grasmere NSW 2570
From Sydney CBD: 70 minutes (75 km)

Highlands Golf Club, Mittagong (Tangled Up in Bob)
21 Range Road, Mittagong NSW 2575
From Mittagong center: 5 minutes (3 km)

Southern Highlands Transport Options: What Works (and What Doesn’t)

Option 1: Driving Yourself (The Designated Driver Dilemma)

How It Works:

Drive from Sydney (90–110 minutes), park at venue, one person stays sober all night.

Parking at Major Venues:

Centennial Vineyards (Jimmy Barnes):

• On-site parking: Limited capacity (~300 cars for standard events, up to 1,000 for major tours)
• Overflow parking: Adjoining fields (20-minute walk in dark)
• Exit chaos: Single-lane exit, 60–90 minute queues post-concert (longer for 5,000+ capacity events)

![Aerial view of Centennial Vineyards showing main amphitheatre area, on-site parking zones, and overflow field parking with walking distances marked]

Bowral Memorial Hall:

• Street parking: Bong Bong Street and surrounding streets
• Council car parks: Nearby but fill quickly
• Generally manageable for 400-capacity events

Robertson Public House:

• Limited on-site parking (~30 cars)
• Street parking in Robertson village
• Generally sufficient for 150-capacity venue

Artemis Wines (Live on the Lawn):

• Vineyard parking: Grass parking areas
• 500+ capacity means parking spreads across vineyard grounds
• Muddy conditions if recent rain

The Reality:

Pros:

• ✓ Flexibility to explore Southern Highlands during the day
• ✓ Cost-effective for groups willing to forfeit drinking

Cons:

• ✗ Someone must stay completely sober (at vineyard concerts, this defeats the purpose)
• ✗ 90+ minute drive after 10 PM on winding rural roads
• ✗ Fatigue risk (180+ km round trip same day)
• ✗ Wildlife hazards on country roads after dark (kangaroos, wombats) — SERIOUS SAFETY CONCERN
• ✗ Exit queues at major events (Jimmy Barnes = 60–90+ min waits)
• ✗ Unfamiliar winding roads with minimal lighting

When It Makes Sense:

• Group of 6+ where one person genuinely doesn’t drink
• Staying overnight in Southern Highlands (driving next morning sober)
• Attending afternoon events with no alcohol consumption

Better Option: Book professional chauffeur service from Sydney so everyone enjoys the wine and music without designated driver stress or wildlife collision risks.

Option 2: Rideshare/Uber in Southern Highlands (Almost Non-Existent)

The Harsh Reality:

Rideshare in the Southern Highlands barely exists, especially for evening events.

Typical Experience:

Bowral/Mittagong (Best Case):

• Daytime availability: Limited (5–10 minute wait)
• Evening availability after 7 PM: Very limited (15–30 minute wait, frequent “no drivers available”)
• Post-concert (10 PM+): Essentially zero

Robertson/Exeter/Bundanoon (Worst Case):

• Any time availability: Rare to non-existent
• Concert nights: Zero drivers

Why Rideshare Fails Here:

• Driver base too small: Few Uber/DiDi drivers operate in Southern Highlands
• Low population density: Not profitable for drivers to wait between rides
• Concert surge doesn’t attract drivers: Unlike Sydney where surge brings more drivers, Southern Highlands is too remote
• Post-concert chaos: When 2,000–5,000 people at Centennial Vineyards all request Uber simultaneously, there might be 3–5 drivers total in the entire region

Real Example from Previous Centennial Vineyards Concert:

600+ concurrent Uber requests, 4 drivers available. Average wait time: “No cars available.” Many attendees stranded until calling taxis or friends.

When Rideshare Might Work:

• Never for evening concert departures
• Possibly for afternoon events in Bowral only (not guaranteed)

Smart Alternative: Pre-book Sydney concert transport with FIXED PRICING. No surge, no waiting, no stress.

Option 3: Local Taxis (Limited and Unreliable)

Southern Highlands Taxi Services:

Bowral/Mittagong Taxis:

• Small fleet (approximately 10–15 taxis total)
• Pre-booking: Recommended but not guaranteed
• Concert nights: Overwhelmed by demand

The Reality:

Normal Evening (Non-Concert):

• Pre-booked taxi for 8 PM pickup: 70% chance it arrives on time
• On-demand taxi: 20–45 minute wait

Major Concert Night (Jimmy Barnes):

• Pre-booked taxi: 40% chance of no-show (better fares elsewhere)
• Taxi rank at venue: 90–120 minute queues, insufficient supply
• Phone bookings: “All cars allocated” messages

Cost Examples:

• Sydney CBD → Bowral: $280–350 (if you can find a taxi willing)
• Bowral → Centennial Vineyards → Bowral: $60–80
• Mittagong → Robertson → Mittagong: $80–100

When Taxis Work:

• Small local transfers within Bowral during daytime
• Pre-booked for departure (not arrival) at smaller venue events

Why Taxis Fail for Concerts:

• Insufficient fleet for major events
• Reliability issues with pre-bookings
• No guarantees on pricing or availability

Option 4: Bus Services (Non-Existent for Evening Events)

The Southern Highlands does not have public bus services operating during evening concert hours. Bus services are limited to daytime weekday routes between towns and are not viable for concert transport.

Option 5: Train to Moss Vale + Taxi (Complicated and Risky)

How It Would Work:

1. Train from Sydney Central to Moss Vale (2–2.5 hours)
2. Taxi from Moss Vale to venue (15–30 minutes depending on location)
3. Concert
4. Taxi back to Moss Vale
5. Train to Sydney (last train typically ~10:30 PM)

Why This Fails:

• Last train timing: Most concerts end 10–11 PM, missing last train to Sydney
• Taxi unavailability: Getting taxi from venue back to Moss Vale station after concert = nearly impossible
• Limited train frequency: Miss the connection, you’re stranded
• Total travel time: 5+ hours round trip for 2-hour concert

When It Might Work:

• Staying overnight in Southern Highlands (train day before, train return next day)
• Afternoon events ending by 4 PM

Better Option: Professional chauffeur service door-to-door eliminates the train/taxi coordination nightmare.

Option 6: Premium Chauffeur Service ⭐ RECOMMENDED

Why Professional Transport Is the Southern Highlands Solution:

For vineyard concerts, premium events, and groups traveling from Sydney or Canberra, professional chauffeur service solves every regional transport challenge.

How It Works:

1. Pre-Book Your Full-Day Experience:

• Book 1–2 weeks before concert
• Specify pickup location (Sydney CBD, Eastern Suburbs, North Shore, Canberra, etc.)
• Choose departure time (typically 3–4 PM for evening concerts)
• Select vehicle: Sedan (1–3 passengers), SUV (4 passengers), Mercedes V-Class people mover (5–7 passengers)

2. Afternoon Departure & Southern Highlands Exploration:

• 3:00–4:00 PM: Pickup from your Sydney/Canberra location
• 4:30–5:30 PM: Arrive Southern Highlands
• Stop at cafes, galleries, antique shops in Bowral/Mittagong
• Pre-concert dinner at local restaurant
• Cellar door wine tasting (for non-concert vineyard venues)

3. Concert Drop-Off:

• 6:30–7:00 PM: Drop-off at venue entrance
• No parking stress
• No walking from distant overflow lots
• Step out fresh and ready

4. Flexible Concert Pickup:

Option A: Pre-Arranged Time:

• “Pick us up at 10:30 PM”
• Driver waiting at designated spot

Option B: On-Call Flexibility:

• “We’ll text when concert ends”
• Driver monitors event timing
• Adjusts for encores/delays

5. Evening Return — Safe Navigation:

• Relax in executive comfort for 90-minute return
• Everyone can drink at concert
• Professional driver handles wildlife hazards safely
• No fatigue driving
• No unfamiliar winding road stress

What You Get:

✓ Fixed Pricing: Quote includes full day, no surprise surge charges
✓ Everyone Drinks: No designated driver required
✓ Wildlife Safety: Professional drivers trained in regional road hazards
✓ Exploration Time: Arrive early, explore Southern Highlands attractions
✓ Luxury Fleet: Mercedes, BMW, Audi executive vehicles
✓ Regional Expertise: Drivers know Southern Highlands routes and shortcuts
✓ Guaranteed Service: Not dependent on rideshare/taxi availability
✓ Group Value: Split cost among 4–7 people = comparable to driving
✓ Advanced Technology: Real-time tracking and communication
✓ 24/7 Support: 1300 638 258 for any questions

Pricing Examples:

Sydney CBD ↔ Centennial Vineyards (Jimmy Barnes):

• Full-day package (6–7 hours including exploration time)
• Sedan (1–3 people): Get quote
• SUV (4 people): Get quote
• V-Class People Mover (5–7 people): Get quote

Sydney Eastern Suburbs ↔ Bowral Memorial Hall (Ross Noble/Comedy):

• Full-day package
• Get instant quote

Canberra ↔ Robertson Public House (Tapestry/CCR):

• Shorter distance, competitive pricing
• Get Canberra quote

The Math: Why Professional Service Makes Sense

Scenario: Group of 6 attending Jimmy Barnes at Centennial Vineyards

DIY Driving Option:

• Fuel (250 km round trip): $40–50
• Parking: $20–30
• Designated driver: Can’t drink at vineyard concert (huge downside)
• Driver fatigue: 3+ hours driving same day
• Wildlife collision risk: Unquantifiable but genuine danger
• Total cost: $60–80 + one person’s ruined experience + safety risks

Professional Chauffeur:

• Full-day package: Get quote
• Split 6 ways: Typically $60–100 per person
• Everyone drinks and enjoys
• No fatigue, no stress, no wildlife risks
• Total value: Comparable cost, vastly superior experience and safety

For Couples: Even for 2 people, professional service often costs less than:

• Accommodation for overnight stay ($200–350 Southern Highlands hotels)
• Plus designated driver sacrifice
• Plus fatigue and wildlife risks

For Interstate Visitors:

Combining Sydney Airport pickup + Southern Highlands concert + return to Sydney hotel creates seamless door-to-door experience.

Get Instant Quote for Southern Highlands Concert Transport →

Venue-Specific Transport Strategies

Centennial Vineyards (Jimmy Barnes — March 27) ⭐ MAJOR EVENT

Venue: 252 Centennial Road, Bowral
Expected Attendance: 2,000–5,000+ (capacity increases for major touring productions)
Event Type: Outdoor vineyard amphitheatre
Unique Challenges: Largest Southern Highlands concert, limited local transport

Why This Concert Requires Planning:

Jimmy Barnes is Australian rock royalty. His 40th Anniversary Tour at Centennial Vineyards will be the biggest Southern Highlands concert of 2026. This means:

• Transport overwhelmed: Local taxi fleet (~15 cars) cannot serve 2,000–5,000 people
• Rideshare non-existent: Uber doesn’t operate at scale in Bowral
• Parking exit chaos: Single-lane vineyard exit creates 60–90+ minute queues (potentially longer for 5,000+ attendance)
• Wine tasting component: Designated driver ruins the vineyard concert experience

Professional Transport Strategy:

Afternoon Package (Recommended):

3:00 PM: Pickup from Sydney (Sydney premium transport)
4:30 PM: Arrive Bowral, lunch at Biota Dining or Hogget Kitchen
5:30 PM: Explore Centennial Vineyards cellar door (wine tasting)
6:30 PM: Drop-off at amphitheatre entrance
10:30 PM: Pickup after concert, safe return to Sydney with professional wildlife-aware driver

Cost per person (group of 6): Typically $60–100 including full day experience

Why It Works:

• Everyone tastes wine
• Explore Southern Highlands properly
• No parking stress
• Professional return navigation with wildlife safety expertise

Customer Experience:
“The 90-minute exit queue at Centennial Vineyards after the last major concert was insane. We watched from our comfortable Mercedes as hundreds of cars inched forward. Our driver knew a back route and we were on the Hume Motorway within 15 minutes. Worth every dollar.”
 — Michael T., North Shore Sydney

Book Jimmy Barnes Concert Transport →

Bowral Memorial Hall (Ross Noble, Comedy Festival, Music4Can)

Venue: 363 Bong Bong Street, Bowral
Capacity: ~400
Event Type: Indoor theatre/hall
Unique Advantage: Central Bowral location

Transport Strategy:

For Sydney Visitors:

Option A: Stay Overnight in Bowral (Luxury Accommodation Transfers)

• Afternoon chauffeur from Sydney
• Check into Bowral hotel (Peppers Manor House, Gibraltar Hotel, or Berida Hotel)
• Walk to Memorial Hall (5–10 minutes from most hotels)
• Enjoy Bowral restaurants/bars after show
• Return to Sydney next morning

Option B: Same-Day Return

• 5:00 PM pickup Sydney
• 6:30 PM arrive Bowral (dinner at Birch Restaurant)
• 8:00 PM concert at Memorial Hall
• 10:30 PM pickup, return Sydney

Parking Note:

If driving yourself, Bowral Memorial Hall has reasonable street parking for 400-capacity events. However, designated driver still required, and 90-minute drive home after 10 PM on country roads with wildlife hazards remains a concern.

Robertson Public House (Tapestry, CCR Experience)

Venue: 62–64 Hoddle Street, Robertson
Capacity: ~150
Event Type: Intimate pub venue with restaurant
Unique Challenge: Furthest venue from Sydney, minimal local transport

Why Robertson Is Special:

Robertson is a charming village 140 km from Sydney, known for its connection to the film “Babe” (filmed nearby). The Public House hosts quality tribute acts in an intimate setting with excellent food.

Transport Strategy:

Full-Day Robertson Experience:

2:00 PM: Pickup Sydney
3:45 PM: Arrive Robertson
4:00–6:00 PM: Explore Robertson village, Robertson Pie Shop (famous), local galleries
6:00 PM: Early dinner at Robertson Public House
8:00 PM: Concert (Tapestry or CCR tribute)
10:30 PM: Depart Robertson, return Sydney with professional night-driving expertise

Why Professional Transport Is Essential Here:

• Robertson is remote: 25 km from Bowral, zero rideshare coverage
• Country roads: Particularly winding and dark (Illawarra Highway high wildlife zone)
• Intimate venue: Pub atmosphere encourages drinking, defeating designated driver option

Cost per person (group of 4): Typically $70–110 including exploration time

Artemis Wines — Live on the Lawn (February 21)

Venue: 110 Mittagong Road, Wildes Meadow
Event: Live music + wine tasting, 5:00–9:00 PM
Tickets: $65 (includes tasting + food trucks)
Capacity: ~500 (outdoor lawn)
Unique Appeal: Picnic-style vineyard event

Transport Strategy:

Afternoon Vineyard Package:

3:00 PM: Pickup Sydney
4:30 PM: Arrive Artemis Wines
5:00–9:00 PM: Live on the Lawn (wine, food, music on picnic rugs)
9:30 PM: Depart for Sydney return

What Makes This Perfect for Chauffeur Service:

• Wine tasting focus: Defeats designated driver option
• Afternoon timing: Earlier finish (9 PM) means reasonable return time
• Picnic atmosphere: Relaxed vineyard setting enhanced by no driving stress
• BYO picnic rugs: Driver can assist with setup logistics

Why DIY Driving Fails:

Artemis Wines is a winery. The entire point is wine tasting. Having a designated driver at a wine-focused event defeats the purpose.

The Estate Camden — Damien Leith (February 20)

Venue: 490 Cawdor Road, Grasmere (Camden area)
Distance from Sydney: 75 km (closer than Southern Highlands proper)
Event Type: Intimate tribute concert (Roy Orbison)

Transport Strategy:

Evening Concert Package:

5:30 PM: Pickup Sydney
6:45 PM: Arrive The Estate Camden
7:30 PM: Damien Leith concert
10:00 PM: Return Sydney

Alternative for Camden Residents:

While The Estate is technically closer to Sydney than Bowral, it’s still rural with limited transport. Professional service recommended for premium concert experience.

Interstate Visitors: Combining Southern Highlands with Sydney

Many concertgoers, especially for major events like Jimmy Barnes, fly to Sydney specifically for Southern Highlands weekends.

Complete Package: Fly In For Concert Weekend

Example Itinerary: Jimmy Barnes March 27

Friday, March 26:

• Fly into Sydney (from Melbourne, Brisbane, Perth, Adelaide)
• Sydney Airport transfer to Sydney hotel
• Explore Sydney Friday night

Saturday, March 27 (Concert Day):

• 2:00 PM: Chauffeur pickup from Sydney hotel
• 3:30 PM: Arrive Bowral, explore galleries/shops
• 5:00 PM: Cellar door at Centennial Vineyards
• 7:00 PM: Jimmy Barnes concert
• 10:30 PM: Return to Sydney hotel

Sunday, March 28:

• Explore Sydney
• Evening: Sydney Airport transfer for return flight

Transport Package Pricing:

• Sydney Airport → Hotel (Friday): Quote
• Hotel → Southern Highlands → Hotel (Saturday full day): Quote
• Hotel → Sydney Airport (Sunday): Quote

Benefits:

• ✓ Seamless door-to-door across entire weekend
• ✓ Single provider, consistent service
• ✓ No rental car required
• ✓ Everyone drinks at concert
• ✓ Professional drivers handle unfamiliar Sydney to Southern Highlands routes

Book Interstate Concert Weekend Package →

What to Expect: Southern Highlands Concert Experience

The Vineyard Concert Atmosphere

Centennial Vineyards (Jimmy Barnes):

Expect a relaxed, premium atmosphere:

• Gates open 5:00 PM (arrive early for cellar door)
• Food trucks and gourmet vendors on-site
• Wine available for purchase (Centennial’s own labels)
• BYO picnic allowed (chairs, rugs, etc.)
• Natural amphitheatre with tiered lawn seating
• Support act typically 6:30 PM
• Jimmy Barnes expected ~7:30–8:00 PM
• Show runs 90–120 minutes
• Encore expected (Jimmy always delivers)

Weather Considerations (Late March):

• Autumn weather, cool evenings (15–20°C)
• Bring layers/jackets
• Occasional rain possibility (check forecast)

Artemis Wines (Live on the Lawn):

More casual, family-friendly:

• Picnic rugs essential (provided if needed)
• Wine tasting included in ticket
• Food trucks for dinner
• Sunset views over Wildes Meadow
• Multiple acoustic acts throughout evening

The Heritage Hall Experience

Bowral Memorial Hall:

Classic country hall atmosphere:

• Seated theatre-style
• Excellent acoustics
• Licensed bar
• 400-capacity feels intimate
• Perfect for comedy (Ross Noble) and music fundraisers

St Jude’s Bowral (Orpheus Quintet):

Church concert setting:

• Beautiful heritage church architecture
• Classical music acoustics
• Intimate 200-capacity
• Often includes post-concert supper

The Pub Venue Experience

Robertson Public House:

Authentic country pub with quality entertainment:

• Restaurant seating for dinner + show packages
• Bar area for drinks
• Intimate stage (150 capacity)
• Excellent food (modern Australian)
• Tribute acts in cozy setting

Common Southern Highlands Concert Mistakes (And How to Avoid Them)

Mistake #1: “I’ll Just Get an Uber After the Show”

Reality: There are no Ubers in Robertson. There are barely Ubers in Bowral. For major events like Jimmy Barnes, rideshare is non-existent.

Solution: Pre-book professional transport 1–2 weeks before concert.

Mistake #2: “I’ll Drive and One Person Won’t Drink”

Reality: You’re going to a vineyard concert. The designated driver watches everyone else taste wine, then drives 90+ minutes on dark country roads with wildlife hazards while tired.

Solution: Professional chauffeur means everyone enjoys the full experience safely.

Mistake #3: “I’ll Book Accommodation and Walk to the Venue”

Reality: This works ONLY for Bowral Memorial Hall if staying in central Bowral. It does NOT work for:

• Centennial Vineyards (5 km from town)
• Robertson venues (25 km from Bowral)
• Artemis Wines (remote vineyard location)

Solution: Book luxury Southern Highlands accommodation + professional transport for venue flexibility.

Mistake #4: “I’ll Take the Train to Moss Vale and Figure It Out”

Reality: Moss Vale station is 10–25 km from concert venues with zero public transport and minimal taxis. You’ll be stranded.

Solution: Door-to-door chauffeur service from Sydney eliminates train coordination.

Mistake #5: “I’ll Book Transport the Day Before”

Reality: For major events (Jimmy Barnes with 2,000–5,000 capacity), professional services allocate vehicles weeks in advance. Last-minute availability isn’t guaranteed.

Solution: Book transport when you buy concert tickets.

Mistake #6: “The Drive Will Be Fine, I’m a Confident Driver”

Reality: Confidence doesn’t prevent kangaroo collisions at 90 km/h on unfamiliar winding roads after dark. Wildlife activity peaks 7 PM — 1 AM (exactly concert hours).

Solution: Professional drivers navigate these hazards nightly with defensive driving training and regional road knowledge.

Insider Tips: Maximizing Your Southern Highlands Experience

Tip #1: Arrive Early, Explore the Region

Southern Highlands offers far more than just concerts:

Bowral:

• Bradman Museum & International Cricket Hall of Fame
• Corbett Gardens (tulip displays in spring)
• Dirty Janes Antiques
• Art galleries on Bong Bong Street

Mittagong:

• Mittagong Antiques Centre
• Local cafes and bakeries

Robertson:

• Robertson Pie Shop (featured in “Babe” movie)
• Robertson Heritage Railway Station
• Local galleries

Moss Vale:

• Leighton Gardens
• Historic town center

Pro Tip: Book afternoon pickup (2–3 PM) for evening concerts, allowing 3–4 hours exploration time before the show.

Tip #2: Combine Concert with Winery Tours

If attending a non-vineyard concert, add wine tasting earlier:

Top Southern Highlands Wineries:

• Centennial Vineyards (cellar door separate from concert venue)
• Artemis Wines
• Joadja Distillery (craft spirits)
• Dormie House (at Moss Vale Golf Club)

Strategy:

• 2:00 PM pickup Sydney
• 3:30–5:30 PM wine tasting tour (2–3 wineries)
• 6:00 PM dinner
• 8:00 PM concert
• Return Sydney

Tip #3: Book Heritage Accommodation for Full Weekend

Premium Southern Highlands Hotels:

• Peppers Manor House (Bowral): 5-star country estate
• Gibraltar Hotel (Bowral): Boutique luxury
• Bendooley Estate (Berrima): Vineyard accommodation
• Briars Country Lodge (Burradoo): Heritage B&B

Weekend Strategy:

• Friday: Arrive via chauffeur, check in, explore Bowral
• Saturday: Concert day with professional transport
• Sunday: Explore region, return Sydney afternoon

Tip #4: Seasonal Considerations

Autumn (March-May):

• Best time for Southern Highlands
• Crisp evenings (bring layers)
• Harvest season at vineyards
• Stunning foliage colors

Winter (June-August):

• Cold evenings (5–12°C)
• Fireplace season (cozy pub venues)
• Fewer outdoor concerts

Spring (September-November):

• Tulip Time Bowral (September)
• Mild weather
• Garden blooms

Tip #5: Food Strategy for Concert Days

For Vineyard Concerts (Centennial, Artemis):

• Food vendors on-site (gourmet food trucks)
• BYO picnic allowed
• Arrive early for cellar door cheese plates

For Town Venues (Bowral Memorial Hall):

• Book dinner reservation pre-concert:
• Biota Dining (modern Australian)
• Hogget Kitchen (farm-to-table)
• Birch Restaurant (contemporary)
• Bowral Brasserie (French)

For Robertson Public House:

• Dinner + show packages available
• Book restaurant seating when buying concert tickets

Accessibility: Southern Highlands Concert Transport for Everyone

Mobility Considerations:

Most Southern Highlands venues offer accessibility:

Centennial Vineyards:

• Wheelchair accessible paths to amphitheatre
• Accessible viewing areas
• Accessible facilities

Bowral Memorial Hall:

• Wheelchair accessible entrance
• Accessible seating
• Accessible facilities

Robertson Public House:

• Ground floor venue
• Accessible entrance
• Accessible facilities

Professional Accessible Transport:

✓ Wheelchair-accessible vehicles available (request when booking)
✓ Driver assistance with mobility aids
✓ Direct drop-off at accessible entrances
✓ Coordination with venue accessibility staff

Contact: admin@carsondemand.com.au | 1300 638 258

Booking Your Southern Highlands Concert Transport

How to Book

Option 1: Online Booking

Visit: carsondemand.link/register

Booking Process:

1. Select “Point-to-Point Transfer” or “Hourly Charter”
2. Enter pickup location (Sydney address, hotel, or airport)
3. Enter destination (Centennial Vineyards, Bowral Memorial Hall, etc.)
4. Select date and pickup time
5. Choose vehicle type:

• Sedan (1–3 passengers)
• SUV (4 passengers)
• Mercedes V-Class (5–7 passengers)
• Toyota Granvia (8–10 passengers for large groups)

1. Add return journey or select “hourly charter” for full-day package
2. Get instant quote
3. Book with secure payment

Option 2: Phone Booking (Recommended for Complex Itineraries)

For multi-stop Southern Highlands experiences (winery tour + concert + dinner):

📞 Call: 1300 638 258 (24/7)

Our team can customize:

• Winery tour routes
• Restaurant reservations coordination
• Multiple-venue concert weekends
• Interstate visitor packages

Option 3: Email Inquiry

For group bookings (8+ passengers) or corporate accounts:

📧 Email: admin@carsondemand.com.au

What to Include When Booking

For best service, provide:

✓ Concert Details: Which event? (Jimmy Barnes, Ross Noble, etc.)
✓ Pickup Location: Sydney suburb, Canberra, or airport
✓ Passenger Count: 2? 6? 10?
✓ Timing Preference: Afternoon exploration or direct to venue
✓ Return Timing: Fixed time or flexible after concert
✓ Vehicle Preference: Sedan, SUV, or people mover
✓ Special Requests: Winery stops, dinner reservations, accessibility needs

Pricing Structure

Full-Day Southern Highlands Packages (6–8 hours):

Includes:

• Pickup from Sydney/Canberra
• Afternoon exploration time
• Concert drop-off and pickup
• Return journey
• All tolls and parking

Pricing varies by:

• Distance (Sydney closer than Canberra)
• Vehicle size (sedan vs. people mover)
• Hours required (6 hours vs. 8 hours)

Get instant quote: carsondemand.link/register

Typical Cost Per Person (When Split):

• Group of 2: $150–250 per person
• Group of 4: $80–140 per person
• Group of 6: $60–100 per person
• Group of 8+: $50–80 per person

Comparable to driving costs when you factor in fuel, parking, and designated driver sacrifice, but vastly superior experience and safety.

New Customer Offer

First-time Cars on Demand customers save $50 with our welcome offer.

Frequently Asked Questions

Q: How far in advance should I book for Southern Highlands concerts?

A: For major events like Jimmy Barnes at Centennial Vineyards (2,000–5,000 capacity), book 2–4 weeks in advance to guarantee vehicle availability and preferred timing. For smaller venues (Robertson Public House, The Attic), 1–2 weeks is typically sufficient. Our large fleet can often accommodate last-minute bookings, but don’t risk it for premium events.

Q: What if the concert runs late or has extended encores?

A: We monitor event timing and our drivers stay informed. For flexible return bookings, simply text your driver when the concert ends. For pre-arranged pickup times, reasonable wait time is included. Southern Highlands concerts typically end 10:00–11:00 PM as advertised.

Q: Can you accommodate multiple stops (winery tour + concert)?

A: Absolutely. Hourly charter packages allow complete flexibility for winery tours, restaurant stops, and concert attendance. Most clients book 6–8 hour packages for afternoon arrival, exploration, dinner, concert, and return.

Q: Do you provide transport for groups larger than 7 people?

A: Yes. Our Toyota Granvia people movers accommodate 8–10 passengers. For groups of 12–20, we coordinate multiple vehicles departing and arriving together. Hens parties, birthday groups, and corporate outings regularly book group packages.

Q: What happens if I’ve had too much wine at the vineyard concert?

A: That’s exactly why we exist. Professional chauffeur service means everyone can fully enjoy vineyard wine tastings and concert beverages without designated driver concerns or safety risks. Our drivers are trained professionals who ensure safe, comfortable return regardless of passenger condition.

Q: Can you pick up from multiple Sydney locations?

A: Yes. For groups gathering from different Sydney suburbs, we can coordinate multiple pickups (Eastern Suburbs + North Shore, for example) en route to Southern Highlands. Specify addresses when booking for efficient routing.

Q: Do you operate from Canberra to Southern Highlands?

A: Yes. Canberra to Southern Highlands is actually closer than Sydney for some venues (Robertson particularly). Canberra residents attending Southern Highlands concerts regularly use our services.

Q: What if weather is bad (rain, storms)?

A: Professional chauffeur service is especially valuable during adverse weather. Our drivers are experienced in country road conditions, and you avoid driving stress in rain/fog. For outdoor concerts, we monitor weather and adjust timing if events are delayed or relocated indoors.

Q: How do your drivers handle wildlife hazards?

A: Our drivers navigate Southern Highlands roads nightly and are trained in defensive driving for wildlife zones. They know high-risk areas (particularly Mittagong Road, Centennial Road, Illawarra Highway), maintain safe speeds through winding sections, and use high beams appropriately on rural roads. Wildlife collision risk is significantly reduced with professional drivers versus unfamiliar city drivers on dark country roads.

Q: Can we bring picnic supplies, wine, etc. in the vehicle?

A: Yes, within reason. For vineyard concerts, guests often bring picnic rugs, portable chairs, and food. Our executive vehicles have ample luggage space. However, excessive BYO alcohol is discouraged as vineyard events sell their own wines.

Q: Do you provide transport from Sydney Airport directly to concerts?

A: Yes. Interstate visitors flying in specifically for concerts can book Sydney Airport pickup → Southern Highlands concert → Sydney hotel (or return to airport) as a complete package.

The Verdict: Why Southern Highlands Concerts Demand Professional Transport

The Southern Highlands is NSW’s hidden gem for live music, offering intimate venues, world-class vineyards, and heritage town charm that Sydney and Melbourne mega-venues can’t replicate.

But here’s the reality: this region’s rural character (the very thing that makes it special) creates transport challenges that DIY solutions cannot solve:

• Rideshare doesn’t exist in meaningful quantities
• Taxis are limited and unreliable for events
• Designated driver ruins the vineyard concert experience
• Country roads after dark create genuine safety concerns with wildlife
• Major events overwhelm local infrastructure (2,000–5,000 people at Centennial Vineyards)

For anyone traveling from Sydney, Canberra, or interstate to attend concerts at Centennial Vineyards, Bowral Memorial Hall, Robertson Public House, or Artemis Wines, professional chauffeur service isn’t a luxury. It’s the solution that makes Southern Highlands concerts actually enjoyable and safe.

The Choice Is Yours

❌ Drive yourself: Designated driver can’t drink, 90+ minute return on dark country roads with wildlife hazards, parking exit queues
❌ Hope for Uber: Non-existent post-concert, stranded
❌ Book local taxi: Unreliable, insufficient fleet for major events

✅ Pre-book professional chauffeur: Fixed price, everyone drinks, full-day Southern Highlands experience, guaranteed service, wildlife safety expertise, zero stress

For couples, groups, or interstate visitors, professional transport delivers the complete Southern Highlands concert weekend you actually want.

Ready to Book Your Southern Highlands Concert Experience?

Major Upcoming Concerts:

🎵 Jimmy Barnes — March 27 at Centennial Vineyards (BOOK NOW — 2,000–5,000 capacity)
🎭 Ross Noble — April 20 at Bowral Memorial Hall
🎤 Julia Zemiro — March 13 at The Attic Bowral
🎵 Live on the Lawn — February 21 at Artemis Wines
🎸 Creedence Clearwater Experience — April 23 at Robertson Public House
🎭 Sydney Comedy Festival Showcase — May 20 at Bowral Memorial Hall

Don’t wait until the week before. Book your transport when you buy concert tickets.

📱 Book Online: carsondemand.link/register
📞 Call 24/7: 1300 638 258
📧 Email: admin@carsondemand.com.au

New customers save $50 with our welcome offer

The Southern Highlands concert season is extraordinary. Your transport experience should match.

About Cars on Demand

Established in 1990, Cars on Demand is Australia’s premium chauffeur service with a 99.99% on-time reliability record. Operating nationwide across Sydney, Melbourne, Brisbane, Perth, Adelaide, Canberra, Darwin, and regional NSW (including Southern Highlands), we serve corporate clients, interstate visitors, and concert-goers who demand professional service.

Unlike rideshare platforms that fail in regional areas, we provide guaranteed transport to venues across NSW’s Southern Highlands with advanced dispatch technology, executive fleet standards, and drivers who know regional routes and wildlife hazard zones.

Learn why discerning travelers choose Cars on Demand for Southern Highlands concert weekends and regional event transport.