Winchester: Historic Walking Tour

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Join us on a captivating journey through the historic streets of Winchester as we embark on a fascinating walking tour. Immerse yourself in the rich history and architectural wonders of this enchanting city as our knowledgeable guide unveils its secrets and stories at every turn.

Arrive by Car: There are a number of council and private car parks available. Durngate Car Park and Chesil St Multi Storey Car Park are reasonably priced. This tour assumes you have parked in Chesil St Multi Storey Car Park

St Peter's Church

Chesil Theatre
CC BY-SA 2.0 / Des Blenkinsopp

As you leave the car park, onto Chesil Street, you almost immediately see St Peter’s Church.

This medieval church, also known as St. Peter’s Cheesehill, was constructed prior to 1142, a time when the Priory of St. Denis asserted ownership over the ‘chapel of St. Peter outside Eastgate’.

The church’s layout and orientation strongly indicate that it served as a boundary marker for the Chesil suburb and possibly fulfilled a defensive function. The tower stands out as the most remarkable feature, crowned by a pyramidal tile roof believed to have been added in the 18th century. After World War II, the church ceased to be used for worship and fell into a state of significant disrepair by the 1960s.

When Chesil Street underwent expansion, the building faced the threat of demolition. Fortunately, the Winchester Preservation Trust intervened and successfully saved it. Remarkably, this was the Trust’s inaugural project. The Winchester Dramatic Society took responsibility for maintaining the church’s upkeep in exchange for rent-free use of the premises. The interior of the church now serves as a theatre, with the nave transformed into a stage, the vestry adapted as a dressing room, and the tower utilized as a wardrobe.

Location: Chesil Theatre, Chesil Street, Winchester, UK
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Old Chesil Rectory

The Chesil Rectory
CC BY-SA 2.0 / Des Blenkinsopp

Head to the right of the church up Chesil Street towards the junction with Bridge Street. On the corner is one of the most photogenic timber-framed buildings in Winchester; the Old Chesil Rectory.

The Old Chesil Rectory is now a well-liked restaurant, the Rectory proudly displays a sign near its low entrance proclaiming its construction in 1450. However, a survey conducted by the City of Winchester raises some doubts about this date and suggests that the house likely dates back to the early 16th century. Nevertheless, as a passionate medieval enthusiast, a few years’ difference doesn’t diminish its exquisite charm in my eyes!

Originally a private residence, the Rectory later became the rectory house for St. Peter Cheesehill following the Reformation. Around 1760, the house was divided into two separate tenements, but this division was removed in 1890. Standing three stories tall, the building features stunning half-timbering filled with plaster on the upper two floors, while the ground floor predominantly showcases brickwork.

In traditional late-medieval style, the upper floors project outward over the ground floor, and the gable ends are adorned with beautifully carved barge boards. This building, sometimes affectionately referred to as Cheese House, holds historical significance as the location of Winchester’s inaugural Sunday school.

Location: The Chesil Rectory, Chesil Street, Winchester, UK | Hours: Monday to Thursday Lunch 12noon – 14:30 | Dinner 17:30 – 21:00 Friday & Saturday Lunch 12noon – 14:30 | Dinner 17:30 – 21:30 Sunday Lunch 12noon – 15:00 | Dinner 18:00 – 20:30 | Website
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Winchester City Mill (National Trust)

CC BY-SA 2.0 / Geoff Cooper

Cross over Chesil Street and headed west along Bridge Street, over the River Itchen.

Winchester City Mill has been a prominent landmark in the historic city of Winchester, the capital of King Alfred’s Wessex, for centuries, dating back to Saxon times. With a remarkable history spanning over 1000 years, it is believed to be the oldest functioning watermill in the United Kingdom. As a rare surviving example of an urban working corn mill, Winchester City Mill underwent a reconstruction in 1744. After being entrusted to the care of the National Trust in the 1920s, the mill was meticulously restored to its full operational state in 2004.

Upon entering, you can delve into the mill’s captivating and extensive history. You can witness the mill in action by National Trust volunteer millers who conduct flour milling demonstrations (subject to availability), showcasing the traditional process of stoneground wholemeal flour production powered by the mighty River Itchen.

Location: National Trust - Winchester City Mill, Bridge Street, Winchester, UK | Hours: Wed-Sun10:00 - 17:00 | Website
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King Alfred on Broadway

King Alfred Statue, Winchester
CC BY-SA 3.0 / BobW66

King Alfred, a scholar, soldier, and statesman, revitalized Winchester following the Dark Ages and established it as his capital. Today, a magnificent bronze statue of him commands attention on The Broadway.

Location: King Alfred the Great - Statue, The Broadway, Winchester, UK | Hours: 24Hours | Price: Free
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Guildhall Winchester

Winchester New Guidhall
CC BY-SA 2.0 / David Pearson

Nestled in the center of the city, the Guildhall is a splendid Victorian structure that offers a captivating array of live entertainment and events. From tribute bands to craft shows and festivals, there is always something exciting happening within its walls.

Moreover, the Guildhall serves as the residence of the Winchester Visitor Information Centre. Here, you can conveniently purchase tickets for the majority of events hosted at the Guildhall.

Location: Guildhall Winchester, The Broadway, Winchester, UK
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River Itchen Walk

River Itchen Walk
CC BY-SA 2.0 / Trevor Harris

As you cross over the bridge immediately turn left to walk alongside the River Itchen.

Winchester’s River Itchen is celebrated for being a remarkable chalk stream characterized by its exceptionally clear waters and thriving ecosystem visible along its shores. This unique waterway is home to a diverse range of wildlife, including otters, water voles, white-clawed crayfish, butterflies, and kingfishers. It is worth noting that chalk streams are a rare natural phenomenon, with only approximately 210 of them worldwide, and an impressive 160 of these can be found in England. The presence of such a precious and vibrant chalk stream adds to the natural beauty and ecological significance of Winchester and its surroundings.

The path follows the route of the old city walls. You soon come to the remains of the Roman City Walls of Winchester and also pass the Alms-houses of St Mary Magdalen Hospital. The other side of the wall

The Weirs Walk continues to the water meadows and St Cross.

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Wolvesey Castle (Ruins of old Bishop’s Palace)

Wolvesey Castle, Winchester
CC BY-SA 4.0 / Mike Peel

Follow the wall as it curves to the right onto College Street. To your right are the ruins of old Bishop’s Palace, accessed via the The Pilgrims’ School playing fields.

The medieval Bishops of Winchester held significant wealth and influence, serving as trusted advisors and close relatives to kings. Wolvesey, located just a short distance from Winchester Cathedral, served as their primary residence during the Middle Ages. The extensive ruins that remain today largely date back to the magnificent 12th century palace constructed by Bishop Henry of Blois, who was King Stephen’s brother.

Although now in a state of decay, the buildings still evoke a sense of their former splendour. One notable event took place on July 25th, 1554, when the East Hall was adorned with luxurious silk and gold hangings for the grand wedding banquet of Queen Mary and Philip of Spain. This occasion marked the last significant celebration held within these walls, leaving a lasting impression of the opulence and grandeur that once graced Wolvesey.

Location: Wolvesey Castle (Old Bishop's Palace), College Street, Winchester, UK | Hours: Open 10am-4pm daily October to 1st March | Price: Free Entrance | Website
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Winchester College

Winchester College War Cloister
CC BY-SA 2.5 / Andrew Powers

Walk up College Street and Winchester College is on your left.

Winchester College, established by William of Wykeham in 1382, is renowned worldwide as a prestigious and illustrious educational institution. Led by knowledgeable Tour Guides, one-hour tours offer a captivating exploration of the school’s medieval core, encompassing Chamber Court, Chapel, College Hall, Cloisters, and the 17th Century School building. Daily tours commence at the Porters’ Lodge on College Street, SO23 9NA. Tickets can be obtained on the day from the Tour Guide at the Porters’ Lodge or pre-booked through the website (see link below).

Location: Winchester College, College Street, Winchester, UK | Hours: Monday - Sunday 14:15 and 15:30 | Price: Adults £10, Concessions £8.50 (No charge for children under 11) | Website
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Jane Austen's House, Winchester

Jane Austen
CC BY-SA 2.0 / Peter Broster

Located just west of the College on 8 College Street, you will find a modest cream-colored house adorned with a discreet plaque above its entrance.

This unassuming dwelling is known as ‘Jane Austen House,’ where the renowned novelist spent her final days. Prior to her time here, Austen resided in nearby Chawton, only coming to Winchester in the company of her beloved sister Cassandra to seek medical treatment.

Although Austen did not pen any of her celebrated novels within these walls, this secluded abode holds great significance for many devoted Jane Austen enthusiasts. It stands as a cherished destination on their personal ‘Austen pilgrimage.’ It is important to note that the house is not accessible to the general public. Nevertheless, for admirers of Jane Austen, this unpretentious residence serves as a poignant reminder of the beloved author’s final chapter before her passing on July 18, 1817, and her subsequent interment in Winchester Cathedral.

Location: 8 College Street, Winchester, UK
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Winchester's Pilgrim's Hall & Priors Gate

Priory Gate, St Swithun Street, Winchester
CC BY-SA 1.0 / Hassocks5489

As we continued along College Street, we followed its gentle curve to the right and arrived at Kingsgate, one of the remaining medieval city gates.

Kingsgate holds a special appeal due to two notable features. To the right, as you pass beneath the arched entrance, you will come across a charming little bookshop cleverly integrated into the gateway structure.

For a different perspective, venture through the arch and direct your gaze to the left. Here, you will discover a staircase leading up to St Swithuns upon Kingsgate, a petite medieval church positioned atop the gateway arch. It is believed that this church originally served as a chapel for the cathedral’s labouring craftsmen.

Take a moment to appreciate the remnants of medieval stained glass adorning the east window and explore the intriguing memorials that adorn the walls. Keep an eye out for a particularly unique feature—a piscina ingeniously built into a window ledge on the north wall.

Adjacent to Cheyney Court, there stands an even more ancient timber-framed edifice, positioned at a right angle. This remarkable structure is known as Pilgrim’s Hall, erected around 1290 to accommodate pilgrims visiting the revered shrine of St Swithun in the cathedral. The highlight of Pilgrim’s Hall is its venerable hammer-beam roof, believed to be the oldest surviving example of such a roof in England. To the northern side of the hall lies Pilgrim’s School, an institution established during the medieval era but housed in buildings from the 17th and 18th centuries.

Continuing straight ahead, we found ourselves venturing deeper into the heart of the cathedral close. Although numerous historic buildings grace this area, they are not regularly open to visitors. Directly ahead stands The Deanery, an exquisite medieval structure dating back to the 14th century. Encompassed within the Deanery is a late 17th-century library that was fashioned from the original medieval long gallery.

Adjacent to the Deanery, accessed through a gateway from the 13th century, lies Dean Garnier’s Garden. This tranquil walled garden offers a serene setting, affording a captivating view of the cathedral’s northern façade.

Location: Priors Gate St Swithun St Winchester SO23 9LS
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Winchester Cathedral

Winchester Cathedral, The Close, Winchester
CC BY-SA 1.0 / Hassocks5489

A Cathedral has graced the city of Winchester since approximately 648 AD. The foundations of the present-day Cathedral were laid out in 1079 under the supervision of Walkelin, the first Norman Bishop. Upon the completion of this new edifice, consecrated in 1093, a momentous occasion took place on 15 July: the solemn transfer of the relics of St. Swithin, accompanied by the dismantling of the “Old Minster.”

The Norman Cathedral, boasting a length of 535 ft (164m), held the distinction of being the longest structure of its kind at the time. Interestingly, it surpassed the current structure by 13m. The Norman towers at the West front were later removed around 1350.

However, the Cathedral faced its share of challenges. Plans to construct towers on the transept ends were abandoned due to unfavourable ground conditions, and in 1107, the central tower collapsed. To rectify these issues, a remarkable endeavour took place between 1905 and 1912. William Walker, a diver, collaborated with a team of 150 individuals to underpin a significant portion of the Cathedral walls.

Throughout its 900+ year history, the Cathedral has undergone extensive remodelling and expansion. In 1202, the construction of the Retrochoir commenced. Between 1350 and 1410, the West front was rebuilt, and the Nave underwent remodelling in the Perpendicular style. This involved meticulously cutting the Norman stonework in its original location and recasting the piers.

The elevations underwent modifications, transitioning from the initial three-story design to a two-story structure. This was achieved by removing the heads of the Norman arched arcade and resetting them at a higher level. Additionally, the entire Nave was re-vaulted during this period. In 1500, the East bay of the Lady chapel was reconstructed, adding another chapter to the Cathedral’s ever-evolving narrative.

Location: Winchester Cathedral, The Cl, Winchester, UK | Hours: Monday–Saturday: 9.00am–5.00pm, Sunday: 12.30pm–3.00pm. Last entry 30 mins before close. Morning Prayer 8am Holy Eucharist 8.30am Evensong 5.30pm | Price: Adult - £12.50 | Website
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Butter Cross, High Street, Winchester
CC BY-SA 1.0 / Hassocks5489

Upon leaving St Lawrence, we proceeded up the passage that led us to the bustling High Street. Positioned to the right of the passage stands the remarkable Buttercross, an exquisite example of an early 15th-century pinnacled market Cross, showcasing the distinctive Perpendicular style of architecture. Known by various names, including the City Cross and High Cross, this structure served as a central gathering point for farmers’ markets.

Although it now holds the status of a Scheduled Ancient Monument, there was a time when its preservation was not a top priority. In 1770, the Paving Commissioners sold the Buttercross into private ownership. However, when the new owner attempted to remove the cross from its location, the citizens of Winchester fiercely rallied together and thwarted the attempted relocation.

Adorned with a dozen figures, the lower level of the cross features four notable individuals associated with Winchester’s history. Among them are Alfred the Great, the revered King of Wessex, William of Wykeham, a prominent figure in the founding of Winchester College, Lawrence de Anne, a medieval mayor of the city, and St Amphibalus, a Christian martyr from the early 4th century who was believed to have a church dedicated to him in Winchester during the post-Roman era.

Location: Buttercross Monument, High Street, Winchester, UK | Hours: 24 Hours | Price: Free
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Winchester City Museum

Winchester City Musueum
CC BY-SA 3.0 / BabelStone

Winchester City Museum holds the distinction of being one of the earliest Museums constructed specifically for that purpose outside of London. Within its walls, visitors can explore a fascinating array of items that showcase the local heritage. A notable recent inclusion is the Roman “Venta” Gallery, where numerous significant archaeological discoveries are proudly exhibited.

Additionally, the museum features meticulously recreated period shop interiors, offering a glimpse into the past. Among these authentic recreations are a family-run Tobacconists shop and a Chemists, both taken from actual shops once situated on the bustling High Street. These meticulously curated displays add depth and charm to the museum’s collection, providing visitors with a captivating journey through time.

Location: Winchester City Museum, The Square, Winchester, UK | Hours: Daily 10:00 - 17:00 | Price: Adult: £8.00
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Winchester’s Military Museums

Peninsula Square, Winchester
CC BY-SA 1.0 / Hassocks5489

Winchester’s Military Museums is a collection of six military museums located in close proximity to each other on a historic site near the city center of Winchester, adjacent to the Great Hall.

The six museums are:

  • HorsePower, the Regimental Museum of The King’s Royal Hussars
  • The Royal Hampshire Regiment Museum
  • The Royal Green Jackets Museum
  • The Rifles Museum
  • The Gurkha Museum
  • The Guardroom Museum, the Museum of the Adjutant-General’s Corps

Each museum operates independently and offers a unique and valuable experience. While each museum is worth a visit on its own, exploring Winchester’s Military Museums provides an opportunity to visit all of them and enjoy a fascinating day out.

Location: Winchester's Military Museums, Romsey Road, Winchester, UK | Hours: Monday – Saturday 10am – 4pm (last admission 3.30pm) | Price: Adults £5.00 | Website
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Winchester Castle

Winchester Round Table
CC BY-SA 4.0 / Mike Peel

Winchester Castle, one of the earliest castles constructed by the Normans after their victory at the Battle of Hastings, holds significant historical importance as a formidable Norman stronghold. It served as a seat of governance before the transfer of power to London.

Today, only fragmentary foundations remain of the once-mighty castle. However, a notable exception is the meticulously restored 14th-century Great Hall, commissioned by King Henry III. This hall played a central role in the social activities of the castle, serving as a place for dining, accommodation, and conducting official affairs. As we step inside, the interior reveals a minimalistic ambiance, adorned primarily by two prominent features. The first is an imposing statue of Queen Victoria, majestically seated, exuding regal grandeur. The second is an iconic symbol closely associated with Winchester—a massive round table, prominently displayed on the end wall.

Location: The Great Hall The Castle Castle Ave Winchester SO23 8UJ United Kingdom | Hours: 10am to 5pm daily (last entry is 4.30pm). There is no advance booking, simply buy your tickets on arrival. | Price: Adult: £4 Child (5-16 yrs): £3 | Website
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Winchester Corn Exchange

Winchester Corn Exchange
CC BY-SA 2.0 / Wayland Smith

In the mid-1830s, a consortium of local entrepreneurs joined forces to establish a private enterprise known as the “Winchester Corn Exchange Company.” Their aim was to fund and oversee the construction of a dedicated corn exchange for the town. They identified a plot of open land that had previously housed a 15th-century garden called “Forstersplace” as the ideal location.

Architect Owen Browne Carter was enlisted to design the new building in the Italianate style. Completed in 1838, it was constructed using yellow brick with ornamental stone details, at a cost of £4,000. The design featured a symmetrical facade consisting of eleven bays facing Jewry Street, with the end bays projecting forward as pavilions. The central section of three bays showcased a portico supported by four Tuscan order columns, adorned with an entablature, cornice, wide eaves, and a pediment embellished with modillions. The wings of the building boasted round-headed windows with voussoirs, while a central bell turret crowned the roof. The portico drew inspiration from the work of Inigo Jones, specifically his design for St Paul’s Covent Garden. The Gentleman’s Magazine described Carter’s design as an attempt to eschew the flimsy aesthetics of modern Grecian architecture and instead embrace the more authentic design principles advocated by Palladio in Italy, as well as English architects Jones and Wren.

Over time, the corn exchange’s primary function diminished considerably due to the widespread agricultural depression that plagued Britain in the late 19th century. Subsequently, the building underwent various transformations: it became a roller-skating rink in 1906, a theatre in 1915, and a cinema in 1917. In 1922, it was repurposed as a dance hall, then reverted back to being a cinema in 1933, and finally transformed into a public library in 1936. Hampshire County Council assumed management of the building in 1974.

Location: The Arc Winchester, Jewry Street, Winchester SO23 8SB, UK | Hours: Monday - Saturday: 9:30am - 5:00pm Sunday: 11:00am - 5:00pm | Website
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Hyde Abbey

Hyde Abbey Gatehouse
CC BY-SA 3.0 / JohnArmagh

The foundation of the abbey dates back to 1110, and it boasted an impressive Romanesque church that ranked among the finest in the country. On the gravel, three substantial concrete rectangles mark the spot where Alfred the Great, his wife Ealhswith, and their son Edward the Elder were laid to rest.

Hyde Abbey Gatehouse, is one of the few remaining remnants of the abbey. This gatehouse served as the primary public entrance to the abbey complex and later became the entryway to Hyde House, a grand Tudor residence that no longer exists. Stepping through the gate and following the path to the left, you will encounter a turf-covered bridge, one of the last surviving traces of the original abbey structures.

Location: Hyde Abbey Gatehouse, King Alfred Place, Winchester, UK | Hours: 24Hours | Price: Free
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