June in Windsor and Henley is filled with vibrant, high-profile events that you won’t want to miss. From the world-renowned Royal Ascot at Ascot Racecourse to the thrilling rowing races at the Windsor & Henley Regatta, June is the perfect time to visit for an unforgettable experience. Whether you're attending Ladies Day at Ascot or cheering on competitors at the Henley Regatta, there's something for everyone to enjoy. And, of course, you’ll need the perfect place to stay, shop for your stylish attire, and find the most eye-catching hats for Ascot’s fashion-forward Ladies Day.
Here’s everything you need to know about the top events happening in Windsor and Henley this June, including accommodation options, the best spots to shop for Ladies Day dresses, and where to find the perfect millinery for Ascot.
1. Royal Ascot – Royal Ascot Week (June 16-20, 2025)
Held at the historic Ascot Racecourse, just a short distance from Windsor, the Royal Ascot is one of the most prestigious horse racing events in the UK. This five-day event is synonymous with elegance, luxury, and high society, attracting fashion lovers, celebrities, and royalty.
The highlight of the week is Ladies Day on June 19, 2025, when fashion and style truly take center stage. The event is renowned for its extravagant hats and glamorous dresses, with fashionistas competing for the coveted Best Dressed title. A key part of the experience is donning a show-stopping hat that adds a touch of drama and sophistication to your outfit.
2. Windsor & Henley Regatta (June 28, 2025)
For a more laid-back yet equally thrilling event, the Windsor & Henley Regatta on the River Thames is a must-see. This regatta brings together rowers from around the world to compete on one of the most scenic stretches of water in the UK. You’ll have the chance to watch the intense rowing races and enjoy the vibrant riverside atmosphere, with plenty of food stalls and scenic spots to enjoy along the way.
It’s an event that offers something for everyone, whether you’re a rowing enthusiast or simply looking for a day out by the water. The regatta is a popular event, attracting thousands of visitors to Windsor and Henley each year.
Where to Stay in Henley for the Regatta
For those attending the Windsor & Henley Regatta, Henley is the perfect place to stay. The town offers a range of luxurious hotels, charming guesthouses, and countryside retreats to ensure your visit is as relaxing as it is exciting.
1. Danesfield House Hotel & Spa
Just a short drive from Henley, Danesfield House Hotel & Spa offers a luxurious retreat set in stunning countryside. With its elegant rooms, beautiful gardens, and a fantastic spa, it’s the perfect place to unwind after a day at the regatta. The hotel’s grand surroundings and top-tier service make it a popular choice for those seeking a luxurious base for their Henley visit.
2. The Relais Henley Hotel
Nestled in the heart of Henley, The Relais Henley Hotel is a boutique property that blends modern comfort with historical charm. Located just minutes from the river and the regatta’s racecourse, this hotel offers a stylish and convenient location. Its chic interiors and sophisticated ambiance make it a perfect spot for those attending the regatta in style.
3. The Row Barge Hotel
For a more relaxed, riverside experience, The Row Barge Hotel is a great choice. Located on the Thames in Henley, this traditional inn offers a welcoming atmosphere with lovely views of the river. It's a more budget-friendly option, providing a cozy place to rest after a day at the regatta, with easy access to the town center.
4. The George & Dragon Hotel
Another excellent option in Henley is The George & Dragon Hotel, which offers a great blend of historic charm and modern amenities. The hotel is located close to the river, perfect for those looking to enjoy both the regatta and the picturesque views of Henley. It’s a charming and comfortable place to stay, offering a relaxing base for your visit.
Where to Shop for Your Dress for Ladies Day
Ladies Day at Royal Ascot is all about high fashion, so you’ll want to make sure you’re dressed to impress. Windsor and Henley offer a fantastic selection of shops for your Ladies Day outfit, with options ranging from high-end boutiques to high street stores.
1. Windsor Royal Shopping
Located in the heart of Windsor, Windsor Royal Shopping offers a variety of boutiques and designer shops perfect for picking up your Ladies Day dress. Whether you're looking for a classic, elegant gown or something a little more modern, you'll find a range of styles here. Shops like Hobbs and Reiss offer beautiful dresses and accessories, ideal for Ascot’s glamorous dress code.
2. The Royal Exchange
If you're looking for something a bit more unique, head to The Royal Exchange in Windsor, where you'll find an assortment of luxury brands and boutiques that cater to those seeking the perfect Ladies Day attire. From designer dresses to stylish accessories, you’ll be spoilt for choice.
3. Henley High Street
In Henley, Henley High Street is lined with a great selection of fashion boutiques that will help you find your perfect Ladies Day outfit. With everything from elegant dresses to chic accessories, this street is a haven for fashion lovers. For a more personalised experience, many of the boutique owners offer styling advice to help you pick the ideal dress for Ascot.
4. John Lewis in Windsor
For more high street and contemporary options, John Lewis in Windsor offers a wide range of stylish, affordable dresses for Ladies Day. The store offers a variety of fashion brands, catering to different styles and budgets. Their extensive collection ensures you’ll find something suitable for the event.
The Perfect Hats for Ladies Day: Millinery in Windsor and Henley
A trip to Royal Ascot wouldn’t be complete without an extravagant hat to complement your outfit, especially on Ladies Day. Ascot is renowned for its fashion, and the hats are just as iconic as the horse racing itself.
If you're looking for the perfect headpiece, Windsor and Henley are home to some of the finest milliners in the UK, offering everything from bold, dramatic designs to elegant, understated pieces.
1. Frocks & Frills in Windsor
For a chic and stylish hat for Ladies Day, Frocks & Frills in Windsor is the place to go. Specialising in vintage-inspired fashion, this boutique also offers a fantastic selection of hats and fascinators. Whether you're looking for something large and dramatic or more subtle, their collection is sure to impress.
2. The Hat Shop in Henley
Henley is home to The Hat Shop, a family-run business with a reputation for creating stunning bespoke millinery. They offer custom-made hats and fascinators, perfect for those attending Ladies Day. Their expert team will work with you to design a hat that complements your outfit and gives you a truly unique, head-turning look.
3. John Lewis in Windsor
In addition to dresses, John Lewis in Windsor also carries a lovely selection of hats and fascinators. From modern designs to classic styles, there’s something to suit every taste and budget. Their in-house stylists can help you choose the perfect accessory to complete your Ascot look.
Why June in Windsor and Henley is Unmissable
From the world-class Royal Ascot to the exciting Windsor & Henley Regatta, Windsor and Henley are the ultimate summer destinations in June. With top-tier events, excellent accommodation, and stunning shopping options, your visit will be full of glamour, excitement, and unforgettable memories.
Whether you're attending Ladies Day at Ascot, enjoying the thrilling regatta action, or shopping for the perfect dress and hat, there's no better place to be this June