Isle of Wight Ultra Challenge
Great challenges need great settings – and few are better than the Island’s stunning coastal path. Up to 2,000 adventurers will take on the Isle of Wight in May 2025 – all out to push themselves further. It’s along the spectacular southern cliffs, past the iconic Needles, and up to historic Cowes. For Full Island challengers it’s on to historic Ventnor, and back to our welcome basecamp in Chale after an epic 106km journey. You’ll get full support and hospitality all the way, and with 3/4, 1/2, & 1/4 Island Challenges plus the NEW and scenic ‘Southern 50 loop’ and 10 mile ‘Cowes Medina Estuary’ options also available – there’s an Isle of Wight Challenge for everyone
Isle of Wight Walking Festival
Walk this way! The Isle of Wight Walking Festival returns in Spring and Autumn 2024. The Spring Walking Festival will be from Saturday 11th May to Sunday 19th May and the Autumn Walking Festival will be from Saturday 5th October to Sunday 13th October. An event for keen hikers, relaxed wanderers, and curious explorers alike, the Isle of Wight Walking Festival is a friendly coming together in the great outdoors for all ages, offering a chance to meet new people, learn and discover the many wonders of the Wight. With a plethora of routes on offer to suit all abilities, the Isle of Wight Walking Festival is an inclusive event providing a guided tour through the Island’s varied landscape, thriving wildlife and rich heritage. This friendly festival hosts a variety of walks led by knowledgeable volunteer walk leaders. You’ll easily find a walk that suits you – whether you’re looking for a shorter stroll or a day long hike across the Island. There will be themed walks too. Over half the Isle of Wight is an Isle of Wight National Landscape (formerly known as Area of Outstanding Natural Beauty) and the Island is a UNESCO Bisosphere Reserve. Add 500 miles of well-maintained and signposted footpaths and you’ll see why the Isle of Wight is the perfect place for a walking festival. The Isle of Wight Walking Festival is easy to get to. The majority of walks are free, why not grab your gear and explore the Island.
Wolverton Folk and Blues
A day-long Festival of Folk & Blues set in the stunning grounds of Wolverton Manor, Shorwell (15 minutes walk from Northcourt) on Saturday 11th May 2024. 11.30 am to 8.00 pm. Since its successful launch in 2011, the family-friendly festival has been gaining momentum with fantastic bands/artists each year, along with locally produced food, children’s activities, a tea tent, and not forgetting the Real Ale tent!
Walk the Wight
The Walk the Wight annual charity event raises funds for the Mountbatten hospice. The full walk is 26.5 miles starting at Bembridge and finishing at Alum Bay, taking between 8-12 hours approximately. Walkers set off from Bembridge between 6am and 8am.
Cowes Classics Week
Celebrating its 18th year, Cowes Classics Week is all about racing traditional yachts on the water and enjoying fabulous social events ashore. Over 150 boats will be sailing varied courses set in the Solent including Metre boats, Classic Racing Dayboats, Classic Yachts, Old Gaffers and Spirit of Tradition Yachts. Racing will run from the 30th May to the 2nd June 2025 and there will be two races a day or three if weather conditions permit. The event attracts a wide variety of classic yachts ranging from fleets of one-design dayboats, to unique classics from a bygone era. The week will hold many social parties held at different club venues including afternoon tea, as well as a gala awards ceremony to celebrate the sailing. Cowes Classics Week provides a week of varied, challenging and fun racing in Cowes. Cowes Classics Day – free event On Sunday 1st June, Cowes Classics Day, preceding the start of Cowes Classics Week, promises to enthral all those with an interest in classic cars and boats. A display of 50+ classic and interesting cars will be on The Parade. There will also be a unique collection of classic motor boats on Trinity Landing, a visit by a WWII Motor Gun Boat and flying displays including a Spitfire. There will also be a food and drink stall on the Parade, live music to recall the era of classic cars, the Isle of Wight’s own Chitty-Chitty-Bang-Bang replica in the morning, and other attractions for all ages.
Round the Island Race
The annual Round the Island Race, run by the Island Sailing Club, is something of a unique event in the sporting calendar and is the fourth largest mass participation event in the UK (after the London Marathon, Great North and South Runs). It’s rare to find a sporting occasion that encourages enthusiastic amateurs to compete against the elite pros and Olympians of a sport, all on an equal footing and around the same racecourse. This race does just that and celebrates the varied collection of sailors that compete, all of whom love to have a cracking day out on the water. Few things can compare to the sight of hundreds of boats racing, whether you’re within the fleet yourself or spectating onshore from one of the many excellent vantage points on the stunning Isle of Wight coastline.
Isle of Wight Festival
The award-winning Isle of Wight Festival is steeped in history and famed for mixing iconic legendary artists with the hottest up and coming acts. Year on year, 55,000 stylish, free-spirited Festivalgoers come together in a beautiful location, for one of the most distinctive events of the season. With the best atmosphere around and a friendly vibe, as soon as you set sail across the Solent it feels like the holiday has already begun. Whether you’re a seasoned festival pro or a first-timer, you’ll leave with memories that’ll last a lifetime.
The Royal Isle of Wight County Show
The Royal Isle of Wight County Show – one of the Island’s flagship events – returns in 2025 on Saturday 12th and Sunday 13th July. Since 1833 it’s been an opportunity for the agricultural community to come together and showcase their talents, produce and passion for what they do. Over the years the event has expanded to feature a full slice of Island life, packed full of fun and entertainment.
Ventnor Fringe
Ventnor Fringe, the Island’s multi award winning arts festival, which features gigs, comedy and performances in unusual spaces around Ventnor, is set to return from the 18th – 27th July 2025. Discover the best new music, comedy and theatre at the Isle of Wight’s largest arts festival, Ventnor Fringe. Taking place over 10 days the festival transforms the Island’s southernmost town with a whole world of pop-up venues and bars in every conceivable space, hosting over 150 different shows offering something for everyone. From cutting-edge cabaret to spectacular circus, events take place in a ‘Festival Village’ in the beautiful Ventnor Park where there are a number of Big Tops and tented venues, but venture beyond this main site and you may discover events in ancient churches, underground bunkers, locals front rooms and even a 1930s Parisian bus!
Cowes Week
The regatta has evolved enormously since 1826, and now between 800 and 1,000 boats in up to 40 different handicap, one-design and multihull classes race every day for eight days. It is this complete mixture of classic and ultra-modern designs that gives the regatta its uniqueness. Several classes that raced more than 50 years ago are still racing today; Dragons, Flying Fifteens, Redwings, Sea View Mermaids, Solent Sunbeams, Swallows, Victories and X-one-designs. New classes are also introduced as they increase in popularity. Around 8,000 competitors now participate, ranging from Olympic and world-class yachtsmen to weekend sailors. The spectacle that the racing provides, together with the vibrant festival atmosphere, attracts over 100,000 visitors to Cowes during the event.