Your Garden Route Event Guide - 30 July

A warm welcome to all our subscribers and a special hello to new members joining the ONTHEROUTE community this week! We have an exciting fortnight lined up across the region, headlined by the prestigious Klein Karoo Klassique in Oudtshoorn, Jo Black performing live in George, and James Stewart and John Ellis bringing their Sting and The Police tribute to the coast.

If you enjoy staying in the loop with regional happenings, please forward this newsletter to a friend or neighbour who would love to discover what is taking place locally.

Oudtshoorn

Klein Karoo Klassique

The annual festival celebrating classical music, fine wine, and regional cuisine returns to Oudtshoorn. The multi-day program includes performances by the Stellenbosch University Choir, chamber music recitals by the Take Four Piano Quartet, the Anna Davel & Melisizwe Plaatjie Collective, and the popular Die Wynmeester gourmet food and wine tasting.

• Date: 7 August - 9 August
• Time: Various times
• View full event schedule here: https://www.klassique.co.za/eng/

George

Boschendal Fine Wine Dinner

An exclusive culinary evening featuring premier Boschendal vintages paired with a specially curated multi-course menu. Guests will experience gourmet dining alongside insights into South African viticulture.

• Date: Thursday, 30 July
• Time: 6:30 pm
• Venue: Henry White's Restaurant at Fancourt, George

Fashion Theatre Showcase

A multi-disciplinary stage production combining contemporary runway fashion with dramatic performance art. Local designers and performers collaborate to highlight regional creative talent in a structured theatre setting.

• Date: Friday, 31 July
• Time: 6:00 pm
• Venue: George Arts Theatre, George

Tuiniqua Sop & Sjerrie Evening

A cozy winter community evening featuring warm artisan soups, fortified wines, and live vocal entertainment by popular performer Tobi Jooste.

• Date: Thursday, 6 August
• Time: 6:00 pm
• Venue: Tuiniqua Centre, 13 Kerk Street, George

The Wiggle Room Pop-Up Experience

Cape Town's acclaimed pop-up dining and social experience visits Fancourt for an exclusive weekend. Guests will enjoy innovative gastronomy, curated mixology, and sophisticated soundscapes.

• Date: 7 August - 8 August
• Venue: Henry White's Restaurant at Fancourt, George

TEDxGeorge Women Conference

An inspiring half-day conference featuring local thought leaders, innovative speakers, and interactive panel discussions focusing on leadership, innovation, and community growth.

• Date: Saturday, 8 August
• Time: 9:00 am
• Venue: Fancourt Estate, George

Jo Black Live in Concert

Renowned South African musician Jo Black delivers a powerful live performance featuring his signature rock anthems and uplifting stage presence.

• Date: Saturday, 8 August
• Time: 3:00 pm
• Venue: Outeniqua Park Rugby Stadium, George

Mossel Bay

Songs of Sting & The Police Live

Multi-platinum award winner James Stewart and former Sugardrive frontman John Ellis bring their acclaimed acoustic performance to the coast. Attendees can expect raw, stripped-down interpretations of classic hits originally crafted by Sting and The Police, set against sweeping coastal views.

• Date: Thursday, 30 July
• Time: 7:30 pm
• Venue: Pinnacle Point Golf Estate, Mossel Bay

TIME TO THRIVE Sip & Shop

An evening lifestyle market and social gathering featuring local artisanal vendors, handcrafted decor, regional wines, and community networking.

• Date: Saturday, 1 August
• Time: 6:30 pm
• Venue: ReedValley Wine Estate, Mossel Bay

A Trip Down Memory Lane

Musicians James Marais and Monique Cassells present an energetic tribute show taking audiences on a retro musical journey through classic rock 'n' roll, pop favorites, and nostalgic duets.

• Date: Saturday, 1 August
• Time: 7:00 pm
• Venue: ReedValley Wine Estate, Mossel Bay

Wilderness

Songs of Sting & The Police Live in Wilderness

Following performances across the Western Cape, musicians James Stewart and John Ellis deliver an intimate evening of classic rock and pop reimagined for acoustic guitar and vocal harmony.

• Date: Friday, 31 July
• Time: 8:00 pm
• Venue: ANEW Resort Wilderness, Wilderness

SOX 3-Day Trail Run

Known as one of South Africa's most diverse three-day trail running challenges, this event takes runners through mountain single track in the Outeniqua Mountains, lush indigenous forests, and spectacular Wilderness coastal trails.

• Date: 7 August - 9 August
• Venue: Fairy Knowe Hotel, Wilderness

Knysna

Galpalooza Women's Day Celebration

An empowering festival celebrating Women's Day with live acoustic bands, pop-up market stalls, wellness workshops, and gourmet food options.

• Date: Sunday, 9 August
• Time: 1:00 pm
• Venue: Blend Country Restaurant & Pub, Knysna

Songs of Sting & The Police Live at Simola

An acoustic performance held on the hills overlooking the Knysna Lagoon. Performers James Stewart and John Ellis revisit iconic tracks with storytelling and acoustic arrangements.

• Date: Saturday, 1 August
• Time: 8:00 pm
• Venue: Simola Golf & Country Estate, Knysna

Grey High Jazz Band Live

A dynamic big band performance showcasing youthful musical excellence, featuring classic jazz arrangements, Latin rhythms, and contemporary swing.

• Date: Saturday, 8 August
• Time: 7:00 pm
• Venue: Freedom Church, Knysna

Plettenberg Bay

The Fool's Guide with Andrew Buckland

An acclaimed physical comedy and solo theatrical performance by veteran actor Andrew Buckland, navigating human interaction and technology with physical virtuosity.

• Date: Friday, 31 July
• Time: 6:00 pm
• Venue: White House Theatre, Plettenberg Bay

That’s a wrap!

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Best,

The ONTHEROUTE Team

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Save The Date

• Algoa FM Charity Golf Day - A fun-filled, retro-themed charitable tournament on the greens raising essential funds for local family care in partnership with George Child and Family Welfare. Location: George Golf Club, George. Date: 13 August.
• Chester's Got Talent Live - A lively community talent showcase spotlighting local artists and performers at a cozy pop-up theater. Location: Sedgefield. Date: 16 August.
• Watershed Unplugged in Wilderness - Craig Hinds of Watershed performs live for an intimate evening of South African music and acoustic storytelling. Location: Wilderness. Date: 19 August.
• Craig Hinds Live in Mossel Bay - Watershed frontman Craig Hinds performs an intimate acoustic set of iconic SA rock classics. Location: Mossel Bay. Date: 20 August.
• Watershed Unplugged in Knysna - An intimate acoustic concert featuring Watershed frontman Craig Hinds performing signature hits overlooking the lagoon. Location: Simola Hotel, Knysna. Date: 21 August.
• Koos van der Merwe – A Tribute - An evocative musical tribute and evening of classic song and storytelling celebrating famous poetic melodies. Location: George. Date: 22 August.
• Land Of The Low Automotive Festival - A car lifestyle showcase featuring custom vehicle builds, fitment displays, and live entertainment. Location: Plettenberg Bay. Date: 29 August.
• Tsitsikamma Ultra - A challenging and incredibly scenic 50-kilometer forest ultra-trail run designed for serious endurance athletes. Location: Storms River. Date: 29 August.
• Crous & Carstens Unplugged - Springbok Nude Girls members Arno Carstens and Theo Crous perform an intimate acoustic rock set. Location: Knysna. Date: 29 August.
• The Phantom of the Opera - A spectacular local staging of Andrew Lloyd Webber's legendary music of Phantom of the Opera and other cinematic master pieces. The Music of the Night will capture the haunting gothic romance and iconic operatic scores of this timeless Broadway classic. Location: Moedergemeente Kerk, George. Date: 4th September 2026
• Rock in die Tuin - An annual outdoor rock festival featuring top South African rock bands and live stage performances. Location: George. Date: 4 – 11 September.
• The Ultimate RNB & Jazz Festival - A major regional music festival celebrating smooth jazz and R&B with top national talent. Location: George. Date: 6 September.
• Cape Pioneer Trek - An elite, international multi-stage mountain bike race taking competitors through the rugged Karoo landscapes and lush forests. Location: Oudtshoorn. Date: 22 – 26 September.
• Plett ARTS Festival - A 10-day regional arts celebration featuring land art routes, twilight street meanders, jazz sessions, and gallery exhibits. Location: Plettenberg Bay. Date: 25 September – 4 October.
• Tsitsikamma Adventure Festival - An energetic weekend celebration featuring trail runs, mountain bike races, community street markets, art exhibitions, and live music. Location: Storms River and Tsitsikamma. Date: 2 – 4 October.
• George Musical Festival: Eden Soul & Jazz Reimagined - An outdoor showcase celebrating regional soul and jazz music with multiple performances, local food stalls, and art displays. Location: George. Date: 3 October.
• Meiringspoort Half Marathon - One of the country's most iconic and scenic road races, guiding runners through the majestic towering rock cliffs of Meiringspoort. Location: De Rust / Oudtshoorn. Date: 10 October.
• Garden Route Kite Festival - A vibrant family outdoor festival celebrating wind sports and raising funds for regional child welfare. Location: Sedgefield. Date: 18 October.
• Klein Karoo Dust 4 Glory Challenge - A high-energy obstacle course racing event navigating raw Klein Karoo terrain and natural obstacles. Location: Oudtshoorn. Date: 17 October.
• Leisure Isle Festival - A popular annual craft fair, fine art showcase, and gourmet food market set on Leisure Isle. Location: Knysna. Date: 7 – 8 November.
• Die Grootvoël Rally - A legendary gathering of motorcycle enthusiasts featuring custom bike displays, social rides, and outdoor entertainment. Location: Oudtshoorn. Date: 2 – 5 December.