With its magnificent castle, pretty riverside setting, long countryside walks, and a feast of fantastic restaurants, the Queen's home town is fit for a royal wedding – and a fabulous weekend break too
Windsor oozes pomp and pageantry, and the layers of history are almost tangible. Windsor Castle, a fort and royal residence, has dominated this spot since 1070. William the Conqueror chose the site for its advantageous position: a day’s march from the Tower of London; right by the Thames; with commanding views of the western approach to the capital. The fortress has been continuously inhabited ever since, and extended and refurbished by almost every subsequent sovereign. This makes it the largest and oldest occupied castle in the world.
It was originally built as a fort, and the first monarch to use it as a house was Henry I in 1110. His grandson, Henry II, converted it into a palace. In 1215, King John rode out from Windsor to sign the Magna Carta at nearby Runnymede. In 1642, Oliver Cromwell used it as a prison; during the Restoration, Charles II made it more magnificent than ever, adding a new set of State Apartments. When Queen Victoria made the castle her official residence, Windsor became the centre of the British Empire. Having survived the Second World War and a terrible fire in 1992, the castle remains the town’s crowning glory.
There is, however, more to Windsor than its imposing stronghold. While history lurks around ever cobbled corner, this is a living, breathing town too, just one that barely does a double take when the Queen drives or rides by, or when Prince Philip drives his carriage down the Long Walk.
Pedestrianised Peascod Street is the main shopping thoroughfare. Nearby, Windsor Royal Shopping arcade occupies the grand Victorian Railway Station, where a purse-destroying gamut of high-end outlets sit amid original 1850s features. The bulk of the tourist bustle centres on High Street and Thames Street, which sweeps down past the castle in a tumble of pubs and restaurants towards the River Thames. Most of the town's attractions are a short stroll from the castle.
Follow High Street all the way to the footbridge, cross the Thames and you’re in Windsor’s sister-settlement, Eton. Separated by the river, they’re essentially two towns in one, and have had close ties since Henry VI founded Eton College in 1440. Princes Harry and William both went to school here, and blended in easily with all the other teenage boys in billowing school gowns. Now an enclave of little independent ships, Eton’s quaint High Street feels like a natural extension of its larger neighbour.
To escape most of the seven million tourists that pour into Windsor and Eton annually, head into Windsor Great Park. Once a vast Norman hunting forest, this 20 sq km green space is now a mix of gardens, woods and open grassland grazed by herds of deer.
Start early, and head straight for Her Majesty’s home (the Royal Standard flag will be flying if she’s in residence). Windsor Castle’s walls guard the glorious State Apartments, the Drawings Gallery, Queen Mary’s Dolls House and St George’s Chapel; in winter, the five Semi-State Rooms are also open. Admission (£21.20) includes an audio tour, and a visit to the castle takes three hours. Keep an eye on the time if you want to catch the Changing the Guard (11am on selected days; visit changing-guard.com for a schedule).
Explore the cobbled streets next to the castle before heading to the elegant, Grade I-listed Guildhall. Designed by Sir Christopher Wren in 1690, it hosted the marriage of Prince Charles and Camilla Parker-Bowles, and the civil partnership of local residents Elton John and David Furnish. It’s also home to the Windsor & Royal Borough Museum (£2).
Head back past the castle gates and Queen Victoria’s statue to follow the road down to the Thames. Cross the footbridge into Eton to visit its college, where 19 prime ministers and many young royals (including William and Harry) have studied. Guided tours run on certain dates (May-October). Cross the bridge again to finish at Bel & The Dragon, which has been an inn since the 11th century.
Today, take time to explore some of the countryside that surrounds Windsor. There are plenty of possible walks but this 15km loop combines pretty villages and parkland. Start in Home Park (off Romney Lock Road), which runs alongside the Thames. Part of the Crown Estate, the park is Windsor’s main sports field.
Walk around the perimeter of the park to enter Datchet; in Tudor and Stuart times this village was home to royal courtiers and rich merchants. Follow the Thames, which snakes south, crossing it at Southlea Road. Continue into Old Windsor, the oldest Saxon Town in Berkshire; this even held the seat of government until Henry I moved in upriver at Windsor Castle.
Bear right after the Toby Carvery and take Crimp Hill up to Bishopsgate Road, which leads to the Bishopsgate entrance to Windsor Great Park. From here, head west to the Copper Horse, a statue of George III on horseback, commissioned by his son, George IV.
The statue marks the southern end of the Long Walk; stroll down this 4.26km avenue, which unrolls downhill like a (thigh-achingly long) red carpet all the way to the George IV entrance of Windsor Castle, passing grazing herds of oblivious deer en route.
Finish by resting your feet at the Two Brewers (Park Street; booking strongly advisable if eating), a cosy 17th-century pub that lies just by the castle gates, and where the Wanderlust team are often found. Children aren't allowed in, but well-behaved dogs are!
You could easily spend day three outside of Royal Berkshire: Windsor is well placed for exploring some of England’s most exciting cities – London is only 30 minutes away by train, and Oxford just under an hour. However, there’s still plenty more regal countryside and important British history to be discovered.
To see where King John sealed the Magna Carta – one of the most important documents in English history – head to the rolling hills and graceful meadows of nearby Runnymede. A Magna Carta Memorial stands at the foot of Cooper’s Hill. Other monuments dot the area: visit the Kennedy and Air Forces Memorials too.
A stone’s throw across the river sits the 2,000-year-old Ankerwycke yew tree and the ruins of a 12th century Benedictine priory. Legends abound about this spot, including that it was where King Henry VIII wooed soon-to-be wife Anne Boleyn.
For a Thames trip, French Brothers offers a variety of cruises, including a 40-minute Windsor round-trip (£9; year round) and a four-hour one-way sail from Runnymede to Hampton Court (£16.40; March-September). Or take a leisurely restaurant cruise on the Bateaux Windsor.
If you’d rather keep your feet on firm ground, take to the 294km Thames Path, which runs through Windsor; for example, you could walk from Windsor to Maidenhead (13km), then catch the train back.
When to go: Year round. Visit between September and March for access to Windsor Castle’s Semi-State Rooms; the castle closes entirely on 17-18 June 2018.
Getting there: Windsor is 1.6km from Junction 6 of the M4. There are two railway stations, Windsor & Eton Central (connects with Slough, where fast trains run to London Paddington and Reading) and Windsor and Eton Riverside (connects with London Waterloo). Heathrow is 20km east; bus routes 71 and 77 link Windsor and Terminal 5.
Getting around: The compact centre is best explored on foot. Buses serve the wider area; an Explorer FirstDay ticket offers unlimited travel for 24 hours for £8.
Where to stay: The Macdonald Windsor Hotel (23 High St; 01753 483100) offers opulence right opposite the castle; doubles from £129pn.
Where to eat: There’s an overwhelming choice of chain restaurants and independent eateries around Windsor and Eton. For elegant candle-lit dining, Gilbey’s in Eton High Street is a cut above, while family-run Al Fassia remains one of the UK’s best Moroccan establishments. Set down a little cobblestone alley, Sebastians has delicious pizzas and authentic Italian food. See also the mentions of the Two Brewers pub and Bel & The Dragon in the Days 1 and 2 sections.
Foodies with fat wallets may want to head 8km west to the small village of Bray, home to a superfluity of Michelin-starred marvels, including Heston Blumenthal’s The Fat Duck and Alain Roux’s The Waterside Inn. Heston also owns two pubs in the village, The Crown and The Hind's Head. Upmarket Italian Caldesi in Campagna has a strong local following. Alternatively, in Old Windsor, the Oxford Blue is a renowned gastropub; you may see Elton John there as he lives literally just up the road.
Top tip: The splendid Cliveden House is a short journey from Windsor. The walkable grounds are now owned by the National Trust (£12.70 entry), the mansion itself now a posh hotel.
Further info: windsor.gov.uk