Windsor High Street

Upcoming events at Windsor High Street

Markets & Fairs

Maidenhead Farmers' Market

About Maidenhead is the longest continuously-running farmers' market in Berkshire. Whether it's seasonal local produce you're after, connection to the grower, farmer or baker, or just a pleasant, relaxed shopping experience that all the family can enjoy, then look no further - we are the place to come! Quality, traceability and local provenance are the key principles behind our ethos. You can be sure that what you're getting is genuine own produce and each stallholder will be delighted to tell you exactly how it's produced, grown or processed and the ingredients used. Join our customer loyalty scheme which rewards regular visits with vouchers to spend at the market! Maidenhead Farmers' Market takes place on the second Sunday of the month.

Sun 14 JunWindsor High Street

via Windsor High StreetLocal gem

Markets & Fairs

Ascot Farmers' Market

About Ascot Farmers' Market takes place on the third Sunday of the month. The Market is located in Ascot Racecourse's Car Park 3 with the fantastic Grandstand as a backdrop. You will find around twenty stalls offering a great choice of fresh produce, pies and pastries, dairy products and plants. Free on-site parking means a stress-free shopping experience. We look forward to seeing you at Ascot Farmers' Market.

Sun 28 JunWindsor High Street

via Windsor High StreetLocal gem

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Community

Parallel Windsor

About Parallel Windsor is the UK's national celebration of disability inclusion and wellbeing. Our award winning event is held in the grounds of the majestic Windsor Great Park and staged on the iconic Long Walk. The format of Parallel Windsor features a range of challenge events for everybody of all ages, health conditions and abilities. Walk, push or run - there are no cut off times, highlighted by our slogan of 'Start Together, Finish Whenever'. Parallel Festival Programme 2026 Nearer the time you'll be able to take a look at the Parallel Festival Programme and dive into all the exciting, inclusive activities and amazing entertainment planned for this year’s Parallel Windsor! Our selection of distances range from 100m, 1k, 5k, 10k and our very own SuperSensory1K. The shorter distances start and finish on the historic Long Walk, with 2 stunning routes in The Great Park for the 5k and 10k; all finishing against the backdrop of Windsor Castle. Everybody who starts gets a medal, t-shirt, water and goody bag. Festival of Inclusivity festival zones Parallel Windsor's wonderfully vibrant Festival of Inclusivity will have a variety of themed areas including: Sensory Space, Quiet Space, Arts & Crafts, Cookery, Family Entertainment, Inclusive Sport and Animal Kingdom. As a fully accessible event, Parallel Windsor has on-site parking, accessible toilets (including RevoLOOs), free accessible shuttles between Windsor train stations & Windsor Great Park, medical support and quiet space.

Sun 5 JulWindsor High Street

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Community

Racing to Zero Summer Mile Weekend at Ascot

About Celebrate the season in style at Ascot’s midsummer marvel. Prepare to unpack your picnic on the pristine lawns and tuck into an action-packed afternoon of fun and thrills. With the Flat season in full bloom, the Racing to Zero Summer Mile Weekend is a celebration of speed, skill, sun-kissed days and sustainability. Throughout the racecourse, you’ll find vibrant community and environmental showcases as part of our Racing to Zero strategy to reduce the environmental impact of our events. Back at the track, one of the most important mile races of the season takes place on the Saturday. The Group 2 Summer Mile Stakes often attracts some of the protagonists from Royal Ascot as well as those with loftier ambitions ahead. Mohaather won this in 2020 before going on to Group 1 glory while Master Of The Seas was a classy winner in 2023 who went on to win at the Breeders’ Cup.

Fri 10 JulWindsor High Street

via Windsor High StreetLocal gem

Free! (worth double-checking)

Community

Fi.Fest

Experience Fi.Fest: a feel good family-friendly summer music festival in Fifield, perfectly placed between Windsor and Maidenhead in Berkshire. Join…

Fri 10 JulWindsor High Street

via Windsor High StreetLocal gem

Community

King George Weekend at Ascot

About One of Ascot’s greatest occasions, King George Weekend presents a sparkling midsummer cocktail of style, socialising and world-class racing. The racecourse is in full bloom and the atmosphere is electric with top-quality action on the track. Off the track, the racecourse is a whirlwind of colour and laughter as racegoers don summer occasionwear, catch up with friends and sample the many bars and eateries on offer under the summer sun. Welcome to a world where sport and style collide. Where spectators don their finest summer attire, soak up the sensational atmosphere, and socialise against a backdrop of sumptuous scenery. All while marvelling at the majestic action on the racetrack. Here, Europe’s finest middle-distance horses gather to showcase their extraordinary talents and compete for one prestigious prize. And no race sets hearts pounding with anticipation quite like the King George VI and Queen Elizabeth Stakes. Beyond the racing, guests revel in camaraderie while indulging in the finest food and basking in the midsummer sunshine. Book tickets for the King George Weekend here.

Fri 24 JulWindsor High Street

via Windsor High StreetLocal gem

Free! (worth double-checking)

Community

Fi.Fest

Experience Fi.Fest: a feel good family-friendly summer music festival in Fifield, perfectly placed between Windsor and Maidenhead in Berkshire. Join…

Sun 26 JulWindsor High Street

via Windsor High StreetLocal gem

Community

Dubai Duty Free Shergar Cup at Ascot Racecourse

About Dubai Duty Free Shergar Cup – A Racing Experience Like No Other Step into the extraordinary at the Dubai Duty Free Shergar Cup, a one-of-a-kind raceday that combines world-class horse racing with unforgettable entertainment. This global celebration brings together elite jockeys from across the globe for an exhilarating team competition, followed by a spectacular live music concert. A Unique Team Racing Challenge Unlike any other event on the international racing calendar, the Shergar Cup sets aside traditional rivalries as top jockeys join forces to compete for the ultimate team prize. Across six thrilling races, expect high-energy action that captivates both seasoned racing fans and first-time visitors. More Than Just Racing The excitement begins before the first race with team presentations in the Parade Ring - your chance to meet the stars of the day. After the final winner is crowned, the atmosphere shifts to celebration as the post-racing concert kicks off. Each year, chart-topping artists take the stage, ensuring the day ends on a high note with incredible live performances.

Sat 8 AugWindsor High Street

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Food & Drink

The Big Ascot Food & Wine Racing Weekend

About The Big Ascot Food & Wine Racing Weekend – A Feast for the Senses Savour the perfect blend of gourmet delights and thrilling Flat racing at the Big Ascot Food & Wine Racing Weekend. Across two unforgettable days, indulge in a vibrant selection of food stalls, sip fine wines and watch Michelin-starred chefs showcase their skills in live cooking demonstrations. With an array of delicious options, this is a social occasion not to be missed. Friday – Racing Meets Culinary Excellence The weekend kicks off with an exciting programme of races that often reveal future stars of the sport. Highlights include the much-loved LK Bennett Lady Amateur Jockeys Handicap, alongside competitive two-year-old contests, one of which famously featured future multiple Group 1 winner Paddington in 2022. It’s a day full of promise and discovery. Saturday – High Stakes and Heritage Saturday brings seven spectacular races, headlined by the prestigious £100,000 Heritage Handicap over a mile and a half. This contest sees talented three-year-olds battle for glory and has produced unforgettable moments, including Chalk Stream’s victory in 2021 for Her Majesty Queen Elizabeth II; her final Ascot winner. Expect drama, speed and racing excellence from start to finish.

Fri 4 SeptWindsor High Street

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Community

BetMGM Autumn Racing Weekend at Ascot

About Autumn Racing Weekend & Beer Festival at Ascot Experience the perfect pairing of world-class racing and craft beer at Ascot’s Autumn Racing Weekend & Beer Festival, held in association with CAMRA (Campaign for Real Ale). This two-day celebration combines thrilling Flat racing with an incredible selection of over 160 beers, ciders and perries, plus plenty of delicious food options to satisfy every craving. Friday – Racing Talent and Real Ale The penultimate meeting of Ascot’s Flat season promises excitement on and off the track. Friday’s highlight is the £100,000 Listed Noel Murless Stakes, a prestigious contest for promising young staying horses. Between races, explore the beer festival and sample an astonishing variety of real ales, ciders and perries, all curated by CAMRA. Saturday – High-Class Racing and Social Vibes Saturday delivers top-tier racing action with the Cumberland Lodge Stakes and Bengough Stakes, two competitive Group 3 contests. Plus, don’t miss the £180,000 BetMGM Challenge Cup, the richest seven-furlong handicap in the UK. With wine bars, curated cocktails and gourmet food stalls complementing the beer festival, this is the ultimate autumn raceday for racing fans and foodies alike.

Fri 2 OctWindsor High Street

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Community

Neverland: The Peter Pan Drone Light Show

About Get ready for an unforgettable experience as the magic of Neverland lights up the skies above Windsor! Step into the world of Peter Pan as Peter, Wendy and Tinker Bell take flight in a spectacular drone light show inspired by J.M. Barrie’s classic tale. Hundreds of illuminated drones will paint dazzling scenes in the night sky, accompanied by an atmospheric soundtrack that brings this beloved story to life. Watch as Windsor is transformed into a glowing panorama of colour, light and imagination. From the rooftops of London to the mysterious realm of Neverland, this extraordinary aerial performance invites you to soar with the Lost Boys on an adventure you’ll never forget. An Afternoon and Evening of Family Fun at Royal Windsor Racecourse The drone display is just one part of an afternoon and evening packed with entertainment for visitors of all ages. Highlights include: 600 drones forming breathtaking displays Cinematic storytelling soundtrack Immersive sound and light effects Meet‑and‑greet roaming characters from Neverland Easter egg trail Funfair rides* Face painting & glitter tattoos* Dog‑friendly activity zone Bouncy castles Food and drink stalls Fancy dress competition Cheerleading performances Singing mermaids and dancing characters Cloud Nine candyfloss art* Windsor ukulele band Pirate stilt walkers *Additional small fees apply for funfair rides and face painting.

Sat 3 OctWindsor High Street

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Community

QIPCO British Champions Day

About QIPCO British Champions Day – The Ultimate Raceday at Ascot Celebrate the grand finale of the British Flat racing season at QIPCO British Champions Day, where Europe’s finest horses and jockeys compete for glory in seven spectacular races, including five prestigious Group 1 contests. From the iconic QIPCO Champion Stakes to the electrifying QIPCO British Champions Sprint Stakes, this is racing at its absolute peak. Witness History in the Making This is more than a raceday; it’s the moment champions are crowned. Watch as titles for Champion Jockey, Champion Apprentice and Champion Owner are decided in dramatic fashion, marking the culmination of months of fierce competition and dedication. Be part of the action as legends cement their legacy and history unfolds before your eyes.

Sat 17 OctWindsor High Street

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Children & Family

Around £1

Fireworks Spectacular Family Raceday at Ascot Racecourse

About Ascot Fireworks Spectacular Family Raceday – Jumps Racing Meets Autumn Fun Celebrate the start of the 2026/27 Jumps season in unforgettable style at Ascot’s Fireworks Spectacular Family Raceday. This action-packed day combines thrilling National Hunt racing with one of the region’s most dazzling fireworks displays, featuring over 20,000 fireworks lighting up the night sky. Racing Highlights On the track, enjoy an exciting programme of jumps races, headlined by the prestigious Sodexo Live Gold Cup Premier Handicap. It’s the perfect way to welcome the new season with top-class equestrian action. Family Entertainment & Fireworks Away from the racing, families can dive into a world of fun with spooky-themed activities and fairground rides (free until 4pm, with an optional £1 charity donation thereafter). After the final race, the skies come alive with a breathtaking fireworks display, included with your raceday ticket. Children under 18 go free when accompanied by a full-paying adult (no ticket required), making this an ideal day out for all ages. Please note: older teens may be asked for ID as proof of age. Important Ticket Information Fireworks-only tickets will be released closer to the event. Book early; prices increase on the day.

Sat 31 OctWindsor High Street

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Free! (worth double-checking)

Community

Ladbroke's November Racing Weekend

About November Racing Weekend at Ascot – Top-Class Jumps Racing Enjoy two days of high-quality National Hunt racing at Ascot’s November Racing Weekend, one of the standout fixtures in the late-year jumps calendar. This meeting is renowned for showcasing future stars, with promising novice hurdlers and chasers traditionally lining up on the opening day. Past contenders include Chantry House, Angels Breath, Many Clouds and Simonsig, names that went on to make racing history. Competitive handicaps across both disciplines ensure an action-packed start to the weekend. Special Offer: Queen Anne Enclosure tickets are free on Friday 20 November (a £1 booking fee applies, donated to Ascot Racecourse Supports). Saturday – Feature Races and Big Moments Saturday’s card is headlined by two prestigious Grade 2 contests: the Ladbrokes 1965 Chase and the Ladbrokes Ascot Hurdle, both run over mid-range trips. These races have a rich tradition of attracting elite talent, none more memorable than the epic 2019 duel between Altior and Cyrname in the 1965 Chase. With a history of producing thrilling finishes and future champions, this is a weekend no racing fan should miss.

Fri 20 NovWindsor High Street

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Community

Howden Christmas Racing Weekend at Ascot

About Christmas Racing Weekend at Ascot – Festive Fun and World-Class Jumps Racing Celebrate the holiday season in style at Ascot’s final race meeting of the year, combining top-class National Hunt racing with festive food, drink and entertainment. It’s the perfect way to kick off Christmas with family, friends or colleagues. Friday – Quality Racing to Start the Weekend Friday’s card features a strong line-up of Jumps races, including the Grade 2 Howden Noel Novices’ Chase, a contest that has produced future Cheltenham Festival winners such as Simonsig and Politologue. The day concludes with a competitive Listed Bumper, ensuring plenty of excitement on the track. Please note: family entertainment is available on Saturday only. Saturday – The Howden Long Walk Hurdle & Festive Fun Saturday brings Ascot’s most valuable Jumps meeting, headlined by the Grade 1 Howden Long Walk Hurdle, one of the season’s most prestigious long-distance hurdles. Off the track, enjoy a magical festive atmosphere with fairground rides, carol singing and seasonal entertainment designed to delight racegoers of all ages. Family Offer: Children under 18 go free when accompanied by an adult and do not require an admission ticket. Older teens may be asked for ID as proof of age.

Fri 18 DecWindsor High Street

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Event details on Near Here are aggregated from third-party sources and may change. Always verify times, location, availability, and any price directly with the organiser before travelling. See Terms.