The Best Times to Visit Berkshire

Want to know when the best times to visit Berkshire are? Our guide of reasons to go is full of inspiration to help you plan your cottage holiday with the top picks of things to see and do month-by-month. From country rambles and cycling to a whole host of summer festivals, the best time to visit depends on what you want to do.

Whether you’re planning a cottage holiday with family or a romantic retreat for two, find out what’s on offer throughout the year to get the most out of your stay in Berkshire. Find out when to go to attend the main events at Royal Ascot or get into the festive spirit with Christmas markets and pantomimes.

Bringing a furry friend? No problem. With the glorious Berkshire Downs on your doorstep and many attractions and dining places allowing dogs, there’s plenty happening throughout the year for your dog to enjoy too.

The Berkshire Downs

Visiting Berkshire in January

The Berkshire Downs are great for blowing out the cobwebs following the inevitable overindulgence of Christmas. Wrap up and find miles of walking trails in Windsor Great Park, Bracknell Forest, or along the Thames Path which connects Reading, Henley-on-Thames, Marlow, Maidenhead and Windsor. To really get the blood pumping, hike to Lowberry Hill, the highest point in the Berkshire Downs, there’s a six-mile circular route from Compton.

Alternatively, you could get your steps in while shopping in the January sales. Windsor, Reading and Bracknell all have fabulous shopping centres where all of the high street names can be found as well as independent stores.

And Ascot isn’t just for the summer months. The racecourse hosts a number of meets throughout the year, when you can enjoy a flutter and warming winter dishes. Children under 18 go for free.

In the evenings, warm your feet by a crackling fire inside your cosy cottage.

Candlelit dinner

Visiting Berkshire in February

A cottage holiday in February is something to look forward to after the excitement of Christmas and New Year has passed. Whether you’re looking to entertain the kids over February half term or treat your loved one to a mini break for Valentine’s Day, February is a great month to visit Berkshire.

Keep an eye on the Lunar New Year calendar for a chance to see colourful parades around the county. Maidenhead High Street and Windsor Royal Station burst into life with red dragons and other mythical creatures as Chinese communities there celebrate.

And with Valentine’s on 14th February, get plenty of one on one time with your significant other during romantic walks through historic estates or while exploring historic cities such as Windsor and Reading. Round it off with a candlelit dinner at one of the county’s fine gastropubs before retreating to your luxury hideaway.

Windsor Castle

Visiting Berkshire in March

Berkshire has no shortage of gardens and estates to witness spring springing. Wander the crocus strewn lawns of Basildon Park and watch fluffy ducklings and goslings taking to the water at the Nature Discovery Centre in Thatcham. Many trust properties and museums put on bun-tastic events in the lead up to Easter too – from spring-themed walking trails to Easter bonnet parades.

In Reading, the 12th century Caversham Court Gardens and manor, located on the banks of the River Thames, make for a lovely morning stroll. And with better weather coming, your chances of witnessing a Changing the Guard March in Windsor are better. This regal parade with a marching band sets off from the Victoria Barracks on Sheet Street and makes its way up the High Street and into Windsor Castle. The march is weather dependent and dates are decided by the British Army.

Ascot Races

Visiting Berkshire in April

The flowers continue to wake from their winter slumber in April with bluebells, tulips and daffodils breaking ground. Bracknell Forest is a great place to walk among a sea of bluebells and listen out for baby birds chirping in the canopy. Home to several SSSI’s, Bracknell Forest is teeming with wildlife.

In Windsor, the official season opener of the Royal Windsor Racecourse takes place. See some of horse racing’s rising stars during this relaxing and atmospheric day, a great introduction to the sport. April is also when the launch of Flat Season at Newbury Racecourse takes place, often with a beer festival. Royal Ascot’s official season opener follows in June.

With the weather drying up, why not rent a boat and cruise the canals? The Thames flows through many of Berkshire’s top towns and villages including Reading, Windsor and Streatley and Goring.

Eton College

Visiting Berkshire in May

May is when Reading shines as a festival destination with a jam packed calendar of events. From food and beer to music, film and comedy, there’s a festival to cater to nearly every interest. If visiting with the family, the Reading Children’s Festival runs through May and into the start of June. This event has been going for more than 30 years. And new in 2023 was the Reading Walks Festival where volunteers take groups on guided walking tours to discover the city’s history and culture.

In May, heritage tours of Eton College start running (May to September). Take this opportunity to roam the hallways that many of the country’s top figureheads once did, including Princes William and Harry, Boris Johnson and Goegre Orwell.

And in the horse racing world, the Royal Windsor Horse Show returns to Windsor Castle for a week this month.

Visiting Berkshire in June

In June, take advantage of the warm weather with country strolls, bike rides and picnics along the banks of the Thames. With so much unspoiled natural beauty in Berkshire, you could stay a week and not do the same walk twice.

Dust off your fascinator and get ready for a flutter as the official start of Royal Ascot week commences. Ladies Day also takes place this month. This quintessentially British pastime is a great event to plan your cottage holiday around, whether it’s with a group of friends or family. Keep your eyes peeled for a celebrity sighting inside the Royal Enclosure, where the royal family watch the races.

Spend those balmy summers’ evenings outside with an al fresco dinner at your cottage and raise a glass to your holiday by a log burning fire when the sun goes down.

Picture Of Party People At Music Festival

Visiting Berkshire in July

There’s lots happening for music lovers in Berkshire in July, whether you’re a pop princess or jazz connoisseur. Pack a picnic and while away the hours in Windsor’s Alexander Gardens where musicians take to the bandstand at weekends throughout the summer.

Henley-on-Thames comes to life too when the Henley Festival arrives in town. Here, music, comedy, art and food have been bringing the community together since 1983. From pop to jazz, and household names to up and coming talent, this five-day boutique event has something for all generations.

On a glorious sunny day, you’ll want to maximise your time outdoors. Enjoy walking and cycling in the Berkshire Downs, cruising on the Thames, out of bounds activities in Bracknell Forest and lots of events aimed at families throughout the school holidays.

A family in bright colours cycling on a summer's day

Visiting Berkshire in August

There’s nothing quite like the great British summertime: a steady diet of barbecues, picnics and ice-cream, hours spent exploring the great outdoors, and quality time with loved ones as schools close their doors.

Whether it’s a week or long weekend you’ve got, there’s so much to fill your days with. Go on one of the many hiking or cycling paths in the Berkshire Downs or rent a boat and see the county from the Thames.

Windsor Castle, Basildon Park, and Highclere Castle beam against blue skies and lush lawns in summertime. And it’s top hats at the ready for Gentlemen’s Day at Royal Windsor Racecourse.

On particularly hot days, cool off in style at Thames Lido, a restored Edwardian swimming pool with a Mediterranean restaurant, pool bar and spa.

Windsor Royal Shopping Centre

Visiting Berkshire in September

If you’re not tied to the school holidays, September is a lovely time for a cottage holiday in Berkshire when you can soak up the last of those summer rays without the crowds of high season.

While away the days exploring the countryside by foot or bicycle, enjoy long lunches at quaint country pubs, get your best frock out and watch a horse race, or shop until you drop on the high streets of Windsor, Reading and Bracknell.

If you happen to be in Windsor on a Wednesday, look out for the Morris dancers performing and teaching routines to the public at various locations around town.

Crunchy leaves in Autumn

Visiting Berkshire in October

Autumn is a beautiful time to explore the Berkshire countryside. Feel the leaves crunching beneath your feet, clutch cold, smooth conkers in your hands, and crisp air filling your nostrils.

The October half term brings lots of events for families to get stuck into at heritage properties, castles and museums, from pumpkin picking to spooky trails.  In Windsor, the castle’s sumptuous state rooms open up to the public for the season (October to March) where you can take a peek inside George IV’s private quarters. And the town’s very own Oktoberfest takes place at Windsor and Eton Brewery.

Alternatively, why not stock up on some cosy winter knits in Reading, home to three shopping centres, Windsor or Bracknell.

Fireworks Display Celebration

Visiting Berkshire in November

From pretty country villages adorned in Christmas decorations to organised light switch-ons and festive markets, a cottage holiday in Berkshire in November is sure to rouse your yuletide spirit.

Before that, there’s bonfire night and if you happen to be staying around 5th November, there’s a choice of organised firework displays to attend at Windsor and Ascot Racecourses and elsewhere.

Shortly after, Christmas fairs and light switch ons take over. Windsor Great Park is transformed into a magical winter wonderland with light installations taking the form of  mythical creatures, fairies and fireflies. This light extravaganza starts in mid-November and ends in January. And in Reading, wander the stalls for traditional trinkets and tasty festive treats with a hot chocolate or mulled wine in hand. There’s also an annual Christmas fair at Ascot Racecourse.

When it’s time to shut the world out, enjoy a hot shower or bubbly bath and toast your feet in front of the fire ready to hunker down inside your luxury bolthole for the night.

Christmas Market

Visiting Berkshire in December

If you’re looking for a getaway with family and friends over the festive season, Berkshire has lots to offer. In addition to the Christmas markets and light displays, pantomime season is well and truly underway.

Head to the Theatre Royal in Windsor or the Reading Rep for classics like Aladdin and the Wizard of Oz or a ballet performance of The Nutcracker. Nothing quite gets you into the Christmas spirit like a panto and with a sleepy English cottage to return to, you can look forward to a truly nostalgic Christmas getaway.

Prepare the Turkey dinner and all the trimmings with ease inside your cottage’s well equipped kitchen, or let somebody else worry about the cooking with a wide selection of country pubs and restaurants to choose from.

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