Best Festivals & Events on the Isle of Wight: Year-Round

Nestled off England’s south coast, the Isle of Wight is a vibrant gem known not only for its stunning natural beauty but also for its calendar of festivals and events that bring the island to life year-round. From world-famous music festivals that draw global crowds to charming local fairs steeped in tradition, the island offers something for every interest and age. Whether you're a music lover, foodie, history buff, or sailing enthusiast, there’s always something exciting happening just around the corner.

This guide explores the Isle of Wight’s most beloved and iconic annual events, offering insights into what makes each one special. Whether you’re planning your first visit or returning for more, this overview will help you discover the perfect time to experience the island’s vibrant cultural heartbeat.

Get ready to mark your calendar with the best the Isle of Wight has to offer—season by season.

Spring Festivals (March - May)

Isle of Wight Walking Festival

The Isle of Wight Walking Festival is one of the UK’s largest and most loved walking events, inviting locals and visitors to explore the island’s breathtaking scenery on foot. Held each spring and autumn, this festival offers an extensive programme of guided walks that wind through dramatic coastlines, rolling countryside, ancient woodlands, and charming villages—providing an immersive experience into the island’s natural beauty and heritage.

Themed walks cater to a wide range of interests and fitness levels. Wildlife enthusiasts can enjoy birdwatching or nature trails through conservation areas, while history buffs might opt for guided tours of ancient ruins, smugglers' routes, or Victorian landmarks. Coastal treks offer panoramic views of the English Channel and dramatic cliffs that are sure to inspire.

A key feature of the festival is its inclusivity—walks are designed for all ages and abilities, from gentle strolls to challenging hikes. Many events are free, though some may require a small registration fee or donation, especially for charity-led walks. Pre-booking is advised, as spaces can fill quickly. Whether you’re a seasoned hiker or just enjoy a casual amble, the Isle of Wight Walking Festival is a welcoming and enriching way to discover the island’s unique charm on foot.

Summer Festivals (June - August)

Isle of Wight Festival

The Isle of Wight Festival is the island’s flagship music event and one of the most iconic festivals in the UK, drawing tens of thousands of music lovers to its fields each summer. Set in Seaclose Park, Newport, the festival boasts a legendary history and a reputation for attracting world-class performers across multiple genres, including rock, pop, indie, and electronic music.

The lineup consistently features global superstars alongside emerging talent, creating a dynamic and diverse musical experience. Past headliners have included The Rolling Stones, David Bowie, Fleetwood Mac, and more recently, artists like Lewis Capaldi and Muse. But the experience doesn’t end with the music—festivalgoers can also enjoy comedy tents, wellness zones, eclectic food and drink stalls, and boutique camping complete with luxury glamping options.

First held in 1968, the festival quickly gained international fame, particularly after the monumental 1970 edition, which saw over 600,000 attendees and performances by Jimi Hendrix and The Who. Though it paused for several decades, the festival was revived in 2002 and has since evolved into a modern musical extravaganza while maintaining its countercultural roots.

Whether you're there for the headliners, the laid-back atmosphere, or the sheer joy of live music in a scenic setting, the Isle of Wight Festival offers an unforgettable summer escape.

Cowes Week

Cowes Week is one of the world’s premier sailing regattas, held each August in the historic port town of Cowes. With roots dating back to 1826, this iconic event combines top-tier competitive sailing with a lively festival atmosphere, attracting crews and spectators from across the globe.

Each day features a series of thrilling races on the Solent, where hundreds of boats—from sleek racing yachts to classic vessels—compete in over 40 classes. Ashore, Cowes buzzes with excitement, offering live music, pop-up bars, gourmet food stalls, and family-friendly entertainment. The event culminates in a dazzling fireworks display, a much-loved tradition.

Why not enjoy the spectacle from the shoreline, join a spectator boat, or even take part in sailing taster sessions. Whether you're a seasoned sailor or a curious first-timer, Cowes Week is a unique chance to immerse yourself in the energy of one of sailing’s greatest traditions.

Garlic Festival

The Isle of Wight Garlic Festival is a quirky and beloved celebration of the island’s renowned garlic-growing heritage. Held annually in August near Newchurch, the festival brings together foodies, farmers, and families for a flavour-packed weekend.

Expect sizzling cooking demos, garlic-infused dishes from street food vendors, and artisan stalls offering everything from garlic fudge to chutneys. Live music, kids' zones, and local crafts add to the fun, making it a true family affair.

More than just a food fest, the Garlic Festival champions local agriculture and showcases the island’s commitment to homegrown, sustainable produce in a fun and festive setting.

Autumn Festivals (September - November)

Isle of Wight Literary Festival

Celebrating the written and spoken word, the Isle of Wight Literary Festival is a cultural highlight that brings together a vibrant mix of authors, poets, playwrights, and avid readers each autumn. Hosted annually in the historic seaside town of Cowes, the festival offers an engaging line-up of talks, workshops, and book signings that appeal to literary lovers of all ages and tastes.

The programme spans a wide range of genres—from historical fiction and contemporary thrillers to memoirs, politics, poetry, and children’s literature. Notable past speakers have included bestselling authors and thought leaders, providing valuable insight into the creative process and current literary trends. For families, there are dedicated children’s storytelling sessions and interactive events, while aspiring writers can take part in writing workshops and Q&A sessions with publishing professionals.

The primary venue is the elegant Northwood House, a Grade II-listed mansion that adds a stately backdrop to the festivities. Events also take place in surrounding venues across Cowes, offering an intimate setting for meaningful discussions and connections. With its rich programme and welcoming atmosphere, the Isle of Wight Literary Festival not only entertains but inspires, making it a must-visit for anyone with a passion for literature and storytelling.

Isle of Wight International Classic Car Show

The Isle of Wight International Classic Car Show is a must-see for automobile enthusiasts, showcasing an impressive selection of vintage and classic cars from across the UK and beyond. Held each September, this free event draws collectors, restorers, and admirers to marvel at vehicles spanning decades of automotive history.

The show features everything from elegant pre-war models to retro sports cars and beloved British classics, all meticulously maintained by passionate owners. Attendees have the chance to chat with the car owners, gain insights into restoration stories, and snap photos of these timeless machines.

Split across two locations—Newport Quay and Ryde Esplanade—the event offers distinct experiences at each site. Newport provides a picturesque riverside backdrop, while Ryde offers a more relaxed, coastal vibe. Both venues include live music, local food and drink vendors, and family-friendly entertainment, making it a fantastic day out whether you're a car buff or just along for the fun.

Isle of Wight Day

Isle of Wight Day is a vibrant celebration of the island’s unique culture, community pride, and local traditions. Held annually in September, the day unites residents and visitors through a wide range of activities that shine a spotlight on all things Isle of Wight.

From colourful parades and lively street parties to concerts, craft markets, and heritage displays, the event is bursting with island spirit. Schools, businesses, and community groups all get involved, creating a festive atmosphere that radiates across towns and villages. Traditional costumes, local produce, and artistic performances are proudly showcased, adding a deeply personal and authentic touch.

Visitors are warmly welcomed to join in the fun—whether by waving a flag at the parade, dancing to live music, or chatting with locals at a community project. Isle of Wight Day is a heartfelt invitation to experience the island’s charm, creativity, and camaraderie in one joyful, unforgettable celebration.

Winter Festivals (December - February

Christmas Events on the Isle of Wight

The Isle of Wight transforms into a magical winter wonderland during the festive season, offering an array of Christmas events that capture the spirit of the holidays. From markets to twinkling light displays, the island is brimming with seasonal cheer for all ages.

A standout event is the Victorian Christmas at Osborne House, where costumed characters, traditional stalls, and festive entertainment recreate the magic of a bygone era. Robin Hill’s illuminated winter woodland trail enchants with dazzling lights, music, and interactive displays. Local craft fairs across the island offer unique handmade gifts, perfect for holiday shopping.

Families will find plenty to enjoy, with Santa’s grottos popping up in towns and attractions, festive workshops for kids, and even pop-up ice skating rinks adding to the fun. Whether you're exploring historic venues or sipping mulled wine beneath fairy-lit trees, Christmas on the Isle of Wight is a heartwarming, memory-making experience.

Planning Your Visit

Accommodation

Booking accommodation during major Isle of Wight festivals—such as the Isle of Wight Festival or Cowes Week—requires early planning. Cottages are a popular choice for their charm, comfort, and flexibility, but they fill up quickly around big events. Aim to reserve several months in advance, especially if you’re looking for sea views or proximity to festival venues.

Transportation

Reaching the Isle of Wight is easy, with frequent ferry services from Portsmouth, Southampton, and Lymington via Wightlink, Red Funnel, or Hovertravel. Once on the island, Southern Vectis buses offer reliable service to most major towns and festival locations. For added freedom, consider renting a car or bringing your own vehicle on the ferry. During major festivals, park-and-ride services or shuttle buses may also be available to ease congestion near event sites.

Insider Tips

To make the most of your festival experience, arrive early to secure good spots and avoid queues. Embrace the local scene by sampling food from independent stalls or nearby pubs—many of which showcase Isle of Wight produce. Don’t forget comfy shoes, layered clothing, and a reusable water bottle to stay festival-ready all day long.

Looking for more Isle of Wight inspiration?

The Isle of Wight offers an unforgettable calendar of festivals and events that celebrate music, culture, food, heritage, and community spirit throughout the year. Whether you're drawn to the energy of a world-class music festival, the charm of a vintage car show, or the warmth of a local craft fair, there's something to suit every interest and age.

With so much to see and do, why not plan your visit around one of these incredible events? It’s the perfect way to experience the island’s vibrant personality, meet locals, and create lasting memories in a unique setting. Check out our comprehensive selection of Isle of Wight guides, where we give you insightful tips such as the Best Walking Trails on the Isle of Wight or if this is your first vist then read our Top 10 things to do on your IOW holiday.

About Us

cottages.com is your go-to destination for an extensive selection of memorable cottage holidays. With a wealth of experience spanning over 45 years, we boast a portfolio of over 20,000 holiday homes spread across the UK, catering to every budget. We're committed to maintaining a high standard of service to our customers by abiding by ABTA's Code of Conduct Our excellent Trustpilot rating reflects the high level of customer satisfaction we strive for. We believe in keeping things simple, so you can focus on making lasting memories with your loved ones from the moment you book with us.