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Visit Winchester: An Insider’s Guide to Days Out in Winchester

Nestled in the heart of Hampshire, Winchester is a city steeped in rich history, cultural significance, and timeless charm. It stands as a testament to centuries of human endeavour, adorned with architectural wonders and ancient streets. From its legendary cathedral that dominates the skyline to the quaint lanes lined with timber-framed houses, here is our insider’s guide on everything you need for your visit to Winchester.

History of Winchester

The Priory Gate is a late 15th-century gate once gave access to courtyard of Medieval Priory. Winchester. Hampshire. England. UK.
Image Credit: Andrew Michael via iStock

Winchester’s history spans over 2,000 years. It started as an Iron Age settlement and later evolved into the Roman town of Venta Belgarum. This Roman settlement evolved over centuries and became the regional capital. Its grid-patterned streets accommodate splendid houses, shops, temples, and public baths. By the 3rd century, wooden town defences were transformed into sturdy stone walls, expanding Winchester to nearly 150 acres. 

The Dark Ages saw the rise of the Anglo-Saxons and over the next century, the invading kings established their respective kingdoms. Among them, Alfred the Great played a vital role in shaping Winchester’s destiny. He fortified the city creating a network of fortified towns to defend against Viking invasions.

By the 9th Century, Winchester became the capital of the Kingdom of Wessex and its prominent location on the banks of the river Itchen facilitated trade and communication allowing it to prosper. In 1066, the Norman conquest reshaped England with William the Conqueror claiming Winchester as his own. 

Winchester continued to thrive as a centre of commerce, education, and governance and its medieval streets, timber-framed buildings, and historic landmarks tell tales of centuries past. Today, Winchester seamlessly blends its ancient heritage with modern life allowing visitors to explore its roots and history.

Best Time to Visit Winchester

Winchester, UK - November 26th 2021: A view of the Christmas Market in the grounds of the historic Winchester Cathedral in the city of Winchester, Hampshire, UK.
Image Credit: Chris Dorney via iStock

There is no perfect season or time to visit Winchester.

Spring (March to May) offers mild temperatures and colourful blooms, perfect for exploring local culture. Summer (June to August) is the peak tourist season and offers longer days and warm temperatures, ideal for indoor and outdoor activities. Autumn (September to November) brings cooler weather and stunning autumnal colours, making it perfect for scenic walks. Winter (December to February) despite the colder temperatures and shorter days, offers a cosy atmosphere and festive decorations.

Deciding when to visit Winchester comes down to the season that best suits your preferences.

Getting Around

bus on broad street in Winchester, Hampshire, UK
Image Credit: Mangopear Creative via Unsplash

Winchester is a fairly easy town to navigate on foot, by car, or via public transport. 

The no. 5 Stagecoach bus runs every 10 minutes from 8 am until 5 pm. Plan your journey via the Stagecoach website.

There is also the park-and-ride bus service that runs every 10 minutes during peak hours, however, this service does not run on Sundays. Check out the park-and-ride bus timetable on the Winchester Gov website.

Top 5 Things to do in Winchester

The medieval Cathedral Church of the Holy Trinity, Saint Peter, Saint Paul and Saint Swithun, commonly known as Winchester Cathedral, in the city of Winchester, England.
Image Credit: Kirk Fisher via iStock

Winchester is steeped in history, so on your next visit to Winchester, check out these 5 things to do:

1. Winchester Cathedral

Begin your visit to Winchester with a trip to the iconic Winchester Cathedral. Renowned for its gothic architecture and Norman transepts and tower. Marvel at the intricate carvings and impressive stained glass windows before climbing the tower for breathtaking views of the city and surrounding countryside.

2. The Great Hall

Home to the legendary Arthurian Round Table, The Great Hall is one of the finest examples of a 13th-century aisled hall. It offers a unique historical experience allowing visitors to discover its history, battles, secrets and trials. 

3. Winchester Science Centre and Planetarium

With live science shows, interactive exhibits, and a 360-degree dome experience, Winchester Science Centre and Planetarium is perfect for the whole family. Zoom through the solar system, strum a chord on a 10m long guitar, and enjoy learning about the world of STEM (Science, Technology, Engineering, and Maths).

4. The Watercress Line

Also known as the Mid-Hants Railway, the Watercress Line runs from New Alresford to Alton. It was used for transporting locally grown watercress to London Markets, and now allows visitors the chance to explore the history and charm of Winchester. Every station is unique and there are picturesque views along the way.

5. ClueCapers Escape Rooms

If you’re looking for unusual, quirky things to do in Winchester, ClueCapers is one of the top-rated escape rooms in Winchester. Offering indoor and outdoor games packed with puzzles. Teams of 2 to 6 players are given 75 minutes to solve riddles and various challenges in the hopes they can escape the surreal world. Be quick as time is running out. It’s the ideal place for groups of friends, family, or colleagues.

Looking for more ideas? Read our blog on things to do in Winchester.

5 Best Places to eat in Winchester

Winchester, United Kingdom - November 13, 2016: The Chesil Rectory. The oldest restaurant in the City of Winchester. A person is walking in the adjacent street towards the road.
Image Credit: Peter Sterling

Whether you’re looking for traditional English pub grub, Chinese, or Japanese food, or simply a cafe with good coffee, Winchester has something for everyone. Here’s our top picks of places to eat in Winchester:

1. Chesil Rectory

Housed in a 600-year-old house, Chesil Rectory offers visitors a modern British menu featuring simple, classic, seasonal dishes. All dishes are created using locally sourced, fresh produce. Whether you’re looking for a cosy dinner or a special celebration, Chesil Rectory provides a memorable dining experience.

2. NAAFI Cafe

NAAFI Cafe, located on St. George’s Street, is a cosy cafe that serves a range of breakfast baps, sandwiches, cakes and more. Known for its freshly brewed coffee, tasty bacon baps, and much-loved tea, it offers a real taste of home to UK Forces and the wider public. Dog-friendly and family-friendly, it’s the perfect place to start your day.

3. Kyoto Kitchen

Known for its intimate setting and attentive service, Kyoto Kitchen is a highly-rated Japanese restaurant in Winchester. It specialises in sushi and sashimi and offers a menu that’s a symphony of flavours and textures. It will take your tastebuds on a journey to the heart of Japan. Whether you’re a sushi lover or new to Japanese cuisine, Kyoto Kitchen is an experience not to be missed.

4. The Wykeham Arms

The Wykeham Arms is a historic pub located in Winchester. The menu features a variety of dishes, from traditional pub grub to more sophisticated fare. With a charming atmosphere and excellent service, this pub is a firm favourite with locals and visitors alike.

5. The Royal Oak

Dating back to 1002, The Royal Oak is a quintessential English pub. Filled with character including ceilings of different heights and numerous nooks and crannies, this pub offers a unique dining experience. Choose from a range of real ales, gins, and cocktails as well as the usual pub classics.

Outdoor Activities in Winchester

Man walking through a meadow in Winchester with his dog
Image Credit: Nick Seagrave via Unsplash

When there’s a break in the rain, why not check out these favourite outdoor activities in Winchester:

1. Walking

If you visit Winchester when the weather is semi-decent, then a walk is a must. There are plenty of walking routes in and around Winchester.  Whether you’re looking for a straightforward out-and-back, a circular, or a pilgrims hike, there’s plenty to choose from for all fitness levels. 

Here are our favourites:

  1. St Catherine’s Hill
  2. Cheesefoot Head from Winchester
  3. Avington and Itchen Abbas Circular
  4. Hampshire Millenium Pilgrim’s Trail

Remember to wear good footwear as some trails can be across rough and muddy terrain.

2. Marwell Zoo

If you’re looking for things to do in Winchester for families, Marwell Zoo is a firm favourite for the whole family (although not directly in Winchester). It’s home to hundreds of animals
including giraffes, rhinos, tigers, meerkats, penguins, and lemurs. With a café onsite you can make it a great day out. Pre-booking is advised as it can get very busy during the peak
summer season.

3. Golf Courses in Winchester

Fancy a round of golf whilst visiting Winchester? There are plenty of options for all skill levels. Whether you’re looking to practice your swing or play a full round, these golf courses are worth checking out:

  1. Royal Winchester Golf Club
  2. Hockley Golf Club
  3. South Winchester Golf Club
  4. Winchester Golf Academy

Be sure to bring your clubs along just in case.

4. Cycling in Winchester

Winchester is known as being the gateway to the South Downs and is popular not just for walking routes. There are plenty of cycle routes in Winchester too. Whether you’re looking for a leisurely family ride, a challenging cycle, or a tour, there are plenty of options out there. 

Bespoke Biking is a bike hire company in Winchester that offers bike hire, tours, and rides around the city’s streets and hidden gems. Or want to try an electric bike? Head to The Cycle Company next to Shawford Train Station and let battery power help you explore Winchester. 

Check out some cycle routes on the Visit Hampshire website.

5. Wolvesey Castle Ruins

History lovers will love the historical ruins of Wolvesey Castle. The castle was built by Bishop Henry of Blois in the 12th century and now stands as a remarkable ruin and a significant part of Winchester’s history. Discover its weather-worn walls and picture its grandeur as you wall in the footsteps of late Bishops. 

Accommodation in Winchester

Image: No.5 Winchester

At Short Let Space, we have a wide range of holiday cottages in Winchester and the surrounding area. Whether you’re looking for a romantic bolthole for two, a family friendly
holiday cottage, or a cottage for a large group, we’ve got you covered. No matter your preferences our team are on hand to help. Give us a call on 01993 222200 or email us at

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