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 would barely do a double take when the late Queen drove by in her Land Rover. The late Prince Philip also loved Windsor and would regularly drive 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 down hill 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 shops, 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.
Day 1: Absorb the history
Start early, and head straight for what was Her Majesty’s favourite home (the Royal Standard flag used to fly if she was in residence, the Union Jack if she wasn't). 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). If you're there in the evening on a Thursday, Friday or Saturday, have a glass of vino at Number 19 Wine Bar. Co-owned by a former Wanderlust staffer, it offers a fine range of wines as well as cheese and charcuterie boards.
Day 2: Take a stroll
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.
There is disappointingly little to see today of this rich history, although if you are into old churches, you could divert down to Church Road to see the 13th Century church of St Peter & Paul. Otherwise, bear right after the Toby Carvery and after half a mile, turn right up Crimp Hill. About halfway up you will pass the gates to Elton John's principle home on the left. You will come out on Bishopsgate Road; turn right to head 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 enroute. The gates in front of you are the Cambridge Gates, and where the public laid flowers following the passing of Her Majesty
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 Wanderlust's founder is often found as it is her favourite pub. Children aren't allowed in, but well-behaved dogs are! Alternatively, if you needed refreshment on the walk we recommend the Fox and Castle in Old Windsor or the Fox & Hounds at Bishopsgate.
Day 3: Mess about on the river
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 little-visited 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. You can see the ruins from Runnymede but if you want to visit you'll have to drive round to Wraysbury.
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.