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The Burrows of Penrose · Guest Guide

Southern Highlands
Events Calendar

Penrose · Bundanoon · Bowral · Moss Vale · Berrima · Robertson · 2026

A curated guide to the festivals, shows, markets and gatherings of the Southern Highlands — all within easy reach of your stay at The Burrows. Whether you're after a lively Scottish gathering, a quiet ramble through open gardens, or cycling through rolling hills, the Highlands has something on every month.

Festival & Fair
Music & Arts
Market
Garden & Nature
Sport
Country Show
Arts Trail & Culture
Community
January Summer

Long golden summer days — the Highlands is lush and green. A quieter month for major events but perfect for exploring the bush, waterfalls, and Fitzroy Falls.

Mid January
Bowral Show
Two-day country agricultural show with livestock, horse events, local produce and family fun at the Bong Bong Picnic Racecourse.
📍 Bong Bong Picnic Racecourse, Bowral
Every 2nd Saturday · 11am
Music@11
Monthly recital series by Arts Bundanoon showcasing talented young musicians and visiting artists. Intimate and charming.
📍 Bundanoon
Monthly year-round
February Late Summer

Warm evenings, the first hints of autumnal cool approaching. A great time to walk the gorges around Bundanoon and explore Morton National Park.

13–14 February
Kangaroo Valley Show
Classic country show day celebrating local agriculture with livestock, horses, produce, rides and community spirit in the beautiful valley.
📍 Kangaroo Valley Showground
Ongoing
Bundanoon Portrait Prize
Artists from across Australia capture faces and stories of the Southern Highlands — a unique community art event with exhibition.
📍 Bundanoon
March Early Autumn

Arguably the most beautiful month in the Highlands — the deciduous trees begin to turn gold and red, and the air is crisp and clear.

6–7 March
Robertson Show
Classic country event in the rich farming town of Robertson, with livestock, horses, produce and traditional show-day fun.
📍 Robertson Showground
13–15 March
Moss Vale Show
Multi-day country show with livestock, horse events, pavilion displays, fresh produce and the always-popular mullet competition.
📍 Moss Vale Showground
26–29 March
Bowral Autumn Music Festival
A highlight of the cultural calendar — a long weekend of chamber music celebrating Australian artists in beautiful heritage venues.
📍 St Jude's Church & venues, Bowral
28 March
A Day On The Green
Much-loved outdoor concert set against the vines at Centennial Vineyards — live music, wine and golden autumn vibes.
📍 Centennial Vineyards, Bowral
April Autumn

Peak autumn colour — the Highlands is at its most spectacular. April is the biggest month on the calendar with multiple major events.

18 April ⭐ Major Event
Bundanoon is Brigadoon — 45th Annual Highland Gathering
Australia's largest Scottish gathering draws 12,000+ visitors to Bundanoon for pipe bands, Highland dancing, heavy athletics, a grand street parade, clans and all-day festivities. Street parade from 9am, Opening Ceremony 10am.
📍 Bundanoon Oval, Erith St — just down the road from Penrose!
15–19 April
Rowany Festival — Medieval Gathering
A unique medieval-style camping event at Camp Wombaroo bringing together history, music, costumes and hands-on experiences in the bush.
📍 Camp Wombaroo, High Range
18–19 April
Open Gardens & Plant Fair
Beautiful private gardens open to the public with rare plants, expert talks and stalls — a relaxed and inspiring celebration of gardening.
📍 Southern Highlands Botanic Gardens
Easter Weekend
Burrawang Easter Markets
Beloved Easter tradition in the charming village of Burrawang — artisan stalls, local produce and a community feel.
📍 Burrawang Village
May Late Autumn

Cool, still mornings with misty valleys — perfect walking weather. The last of the autumn colour lingers in the village gardens.

Every 2nd Saturday · 11am
Music@11 Recital Series
Monthly intimate music recitals featuring talented local and visiting artists across a variety of genres.
📍 Bundanoon
Monthly — 2nd Saturday
Monthly
Berrima Classic Car Meet
Vintage and classic car enthusiasts gather over coffee in beautiful Berrima on the last Sunday of every month, 8–10am. Free community event.
📍 Berrima Village
Last Sunday each month
June Winter

Winter arrives — frosty mornings, cosy fires and mist rolling through the valleys. Perfect for slow days with hot chocolate in Bundanoon or Berrima.

Late June (dates TBC)
Bundanoon Winterfest
After a break in 2025, Winterfest returns in 2026 with something new — a week-long celebration of Bundanoon winter with markets, live music, warming food and community gatherings around braziers.
📍 Bundanoon Village
Ongoing June
Christmas in July preparations
Local estates and venues begin their winter Christmas lunches — Milton Park, Peppers Craigieburn and others offer special mid-winter dining events.
📍 Various venues, Southern Highlands
July Winter

The coldest month — but full of warmth inside. School holidays bring families to the Highlands. Some mornings may see frost on the paddocks around Penrose.

July (dates TBC)
Bundanoon Winterfest
Continues through July — evening events, workshops, pop-up dining and community gatherings celebrating the joys of Highlands winter.
📍 Bundanoon Village
23–26 July ⭐ Major Event
Southern Highlands Writers' Festival
Now in its 15th year — Australia's finest authors, thinkers and performers gather for four days of talks, panels and literary dinners. The opening gala Literary Dinner at Berkelouw Bookbarn is unmissable.
📍 Berkelouw Bookbarn (Berrima) & Empire Cinemas (Bowral)
July School Holidays
Sturt Winter School — Kids Art Classes
Daily art classes for children during the school holidays — a wonderful family activity in the Highlands winter.
📍 Mittagong
August Late Winter

Winter's last hurrah — days are lengthening and the early wattle blooms begin to dot the roadsides with gold. Spring feels close.

Annual (August)
F.O.C.K. — Festival of Canoe & Kayak
Family-friendly festival of recreational paddling in Kangaroo Valley — races, social events and the legendary Canoebertoss on the Kangaroo River.
📍 Kangaroo Valley
Every 2nd Saturday · 11am
Music@11 Recital Series
Monthly recitals showcasing local and visiting musicians — a warm community arts staple year-round.
📍 Bundanoon
Monthly — 2nd Saturday
September Spring

Spring arrives and with it the Highlands' most beloved spectacle — the Tulip Time Festival. The gardens and roadsides burst into colour. Book ahead — accommodation fills fast.

September → October ⭐ Major Event
Tulip Time Festival
One of Australia's oldest flower festivals — over 80,000 hand-planted tulip bulbs transform Corbett Gardens into a sea of colour. Markets, live music, long lunches and roving performers throughout. Open daily 9:30am–4:30pm, extended Saturdays to 6pm.
📍 Corbett Gardens, Bowral (and Tulip Trail across the region)
19–20 September
Kangaroo Valley Craft Beer & BBQ Festival
The festival's 10th year at The Friendly Inn — a day of craft beers, smoky BBQ, live music and relaxed country vibes.
📍 The Friendly Inn, Kangaroo Valley
September
Babe's Country Fair — Robertson
In the town where the iconic film Babe was made — a joyful, family-friendly country fair celebrating Robertson's rural heritage. Back for a second year.
📍 Robertson
October Spring

Spring in full swing — warm days return. A packed month including the Bowral Classic cycling event and the Bundanoon Garden Ramble. The October long weekend draws huge visitor numbers.

Continues to early October
Tulip Time Festival
The festival wraps up in early October — last chance to wander the gardens in full bloom.
📍 Corbett Gardens, Bowral
October Long Weekend
Food, Wine & Music Festival in the Vineyards
Set among the vines, a weekend celebration of local produce, Southern Highlands wines and live music — a highlight of the spring season.
📍 Southern Highlands Vineyards
17–18 October ⭐ Major Event
Bowral Classic — 10th Anniversary Gran Fondo
A decade of Australia's most-loved cycling event. Three courses: 85km, 120km and 150km — all passing through the Highlands' most scenic roads including Bundanoon. Event Village at Loseby Park with live music, food and wine. Guests may see cyclists passing through the region on race day.
📍 Start: Bong Bong St, Bowral · Passes through Bundanoon & Moss Vale
24–25 October
Bundanoon Garden Ramble
Eight gorgeous private gardens in and around Bundanoon open for one weekend only — from intimate cottage gardens to large country estates. A lovely, relaxed wander.
📍 Bundanoon & surrounds — very close to Penrose
16–18 October
Kangaroo Valley Heritage & Harvest Festival
Celebrating the valley's rich heritage with exhibitions, live entertainment and local produce showcases.
📍 Kangaroo Valley
November Late Spring

Warm and green — the roses are out and the Highlands is at its lush best. The ARTSTrail makes November an arts-lovers' paradise.

Early–Mid November ⭐ Major Event
Southern Highlands ARTSTrail
Two weekends of studio visits across the Shire — over 55 local artists open their studios, galleries and workshops for free self-guided exploration. A wonderful way to discover local talent and take home something unique.
📍 Various studios throughout the Southern Highlands — free entry
Late November
BASH — Buenos Aires in the Southern Highlands
A beloved annual tango festival drawing dancers from across Australia and New Zealand to Bundanoon for a weekend of dancing, music and community. Now in its 20th year — one of the longest-running festivals in Oceania.
📍 Bundanoon
December Early Summer

The holiday season arrives in the Highlands — Christmas markets, carols in heritage venues and the special magic of summer evenings at altitude.

2nd Sunday December
Berrima Schoolyard Christmas Market
Special December edition of the beloved Berrima markets — festive stalls, local produce and Christmas gifts in the historic schoolyard setting.
📍 Berrima Public School
Throughout December
Christmas at Heritage Estates
Hopewood House, Milton Park and Peppers Craigieburn host festive Christmas lunches, carols evenings and special seasonal dining events throughout the month.
📍 Various heritage venues, Southern Highlands
Yerrinbool
Yerrinbool Community Christmas
A charming village-style Christmas celebration in the community hall at Yerrinbool — very close to Penrose and a lovely local tradition.
📍 Yerrinbool Community Hall

Recurring Markets & Regular Events

Happening every week or month — check local websites for exact dates
Bundanoon Makers Market
1st & 3rd Sunday of each month (except Jan)
8:30am–2pm · Bundanoon Soldiers' Memorial Hall
Arts, crafts, local produce, baked goods
Moss Vale Showground Market
3rd Sunday of each month · 9am
Artisans, craft, jams, fresh flowers, food trucks
Shady undercover area
Berrima Schoolyard Markets
4th Sunday of each month (Feb–Nov) · 9am–1pm
Christmas market 2nd Sunday December
Fundraiser for Berrima Public School
Peppers Manor House Country Markets
4th Saturday of each month · 9am–1pm
Local artisan and handmade goods
High tea bookings available
Berrima Classic Car Meet
Last Sunday of each month · 8–10am
Free community event in Berrima village
All welcome — no car required!
Music@11 Recital Series
2nd Saturday of each month · 11am
Year-round · Arts Bundanoon
Intimate music performances