From medieval marvels to marvellous coffees and craft beers, Winchester is an ancient kingdom that’s rolling with the times. Located by the River Itchen and on the fringes of South
Downs National Park, this cathedral city makes for an ideal weekend getaway – and is less than an hour away from London by train.
This guide covers the essential things to see and do across a weekend in Winchester, so you can spend less time searching for the best and focus on enjoying it instead. Whether
you’re planning a trip away for two, or taking the kids along, you’ll find plenty of good food, intriguing history and great outdoors.
Where to stay
Winchester Royal Hotel (St Peter Street)
Grand city centre hotel, five minutes from Winchester High Street. Award-winning restaurant on site and family rooms available.
The Westgate (2 Romsey Road)
Elegant pub offering stylish, airy rooms with views of the city. The well-stocked bar offers local tipples and an impressive whisky collection.
16a (Parchment Street)
Luxury self-catered home with three individual rooms available to book. Guests can enjoy a library, large kitchen and movie room.
Day one
Breakfast at Josie's
Fresh off of the train and in need of some fresh coffee or orange juice? Head to Josie’s (28 Jewry Street) for breakfast. This family-run spot is all about homely Hampshire food and can be found just a five-minute walk from Winchester train station, via City Road.
Feast on wholesome breakfast plates filled with all the usual suspects – avocado and poached eggs, toast and oats – or their speciality stacks of plump, freshly made pancakes. There are both sweet and savoury options available, depending on how much of a sugar rush you’re after.
Enjoy breakfast at Josie's
Visit Winchester Cathedral
Standing at the heart of the city, Winchester Cathedral (9 The Close) is one of the largest and most striking gothic cathedrals in all of Europe. Its rich and varied history spans 15 centuries; passed from Anglo-Saxon to Norman rule, host of a Tudor wedding, then saved from collapse in the 1900s by deep-sea diver William Walker, who worked underwater in total darkness for six years to fix centuries of subsidence.
The Great Screen
Entrance to Winchester Cathedral costs £8.50 (children under 16 go free), but you can get 2-for-1 tickets when you travel by train. On arrival, join the guided cathedral tour (included in your ticket price) that takes place every hour (10am-3pm on Saturdays).
The West Window
Afterwards, you can join another free tour of one of the oldest parts of the cathedral: the crypt. This fascinating underground world still floods during rainy months and houses Antony Gormley’s Sound II. This serene sculpture is made of lead statue and was fashioned from a plaster cast of the artist’s own body.
Browse Winchester’s independent shops
A few doors down from Josie’s, you’ll find The Consortium (39 Jewry Street), a retro shop selling a range of vintage furniture and unique furnishings, from homeware to handbags. It’s a great introduction to Winchester’s thriving independent shopping scene – and a chance to buy something special to take back home.
Onwards from here, walk to the edge of Jewry Street and down the High Street, admiring its network of winding side streets. Take a left towards Parchment Street to browse its jewellery shops and boutiques.
In the opposite direction, The Hambledon (10 The Square) is well worth a browse. This independent department store overlooks Winchester Cathedral and is split across three cool, airy floors, selling everything from clothing and beauty to books.
Refuel with coffee and cake
After touring the cathedral you deserve to rest your feet, and there are a couple of lovely coffee shops close by. The Dispensary Kitchen (5-6 The Square) has a charming, modern interior of marble tables and sash windows that offer views over the cathedral and its grounds. They serve all manner of cakes and pastries plus some brilliant banana bread.
If you’re serious about your coffee, then seek out Coffee Lab (6 St Thomas Street), which is tucked away on a side street behind the front of the cathedral. Not only is their coffee ground from the finest-grade beans from around the world, their staff specialise in creating incredible, intricate coffee art. Definitely one for Instagram.
Explore the Great Hall
Next up is a trip to the Great Hall (Castle Avenue) to view the country’s most infamous piece of medieval mythology: King Arthur’s Round Table.
The Table hangs at the head of the Hall and is believed to have been constructed in the 13th or 14th century. See for yourself the names of the 24 knights written around the table’s edge, with King Arthur on his throne adorning the top.
The Great Hall
The Hall is also all that remains of Winchester Castle, built by William the Conqueror, and is a great place to learn about the battles faced by the city through the ages. There’s an interactive element to things here too, which kids will love. Try on authentic medieval costumes and explore the secret passages dotted throughout the building.
Dine out in the city
You’ll have your plate full when it comes to choosing somewhere for dinner, thanks to Winchester’s first-rate food and drink scene. There’s something for all tastes and pocket depths, starting with Three Joes (9 Great Minster St), where the welcome is warm and the wood-fired pizza is simple and unpretentious. There’s a great value menu for Little Joes too.
If you’re after something a bit smarter and a name you can trust, book a table at Rick Stein’s first seafood restaurant outside of Cornwall (7 High Street), the River Cottage Kitchen, beautifully located in Abby Mill Gardens, or the Ivy Brasserie (103-104 High Street).
Dine out on your day of history at the Chesil Rectory (1 Chesil Street), a 600-year-old Grade II listed building formerly owned by Henry VIII. Don’t let appearances fool you though – the food here is thoroughly modern, with a five-course local tasting menu (£45) and wine pairing (£40) served every Saturday evening.
Day two
Winchester Farmers’ Market
If you can, schedule your weekend away over the second or last Sunday of the month to experience one of the biggest and best farmers’ markets in the UK.
Winchester Farmers’ Market (High Street, 9am-2pm) hosts more than 80 local producers selling everything from regional meats and cheeses to honey, bread and cakes. Grab yourself a piping hot egg and bacon roll and enjoy breakfast-on-the-go as you browse.
Visit literary Winchester
Follow the path back down St Catherine’s Hill, turning left onto Garnier Road. After 700m or so there will be a small river path on your right – join this to experience Keats’ Walk.
19th century English poet John Keats lived in Winchester and was supposedly inspired to pen ‘Ode to Autumn’ after walks along the River Itchen’s water meadows. This riverside path opens out onto College Way, which leads to College Walk, where you can delve into more literary history.
There’s also Winchester College, where some of the Harry Potter series was filmed, the house where Jane Austen spent the final months of her life (not open to the public, but marked by a plaque) and P&G Wells (11 College Street), an independent book store that’s been trading for more than 250 years.
The South Downs Way to St Catherine’s Hill
Winchester enjoys a prime position on the westernmost point of the South Downs National Park, so even in the heart of the city you’re only a short walk from scenic countryside.
From the Farmers’ Market, walk south on High Street, past the statute of King Alfred the Great, to Winchester City Mill (174 High Street). This is the official starting point of the South Downs Way – a 100-mile route that unfurls through wooded hills, meadows and hamlets all the way to Eastbourne.
The City Mill
You can walk two miles of the Way up to St Catherine’s Hill, following the route signs marked with white acorns and blue arrows. You can also pick up maps and additional information from the Mill before you set off.
The route will take you along the Itchen Navigation and past some of the city’s famous sights, including the ruins of Wolvesey Castle (34 College Way). Once you reach the top of St Catherine’s Hill (Garnier Road), you’ll be 70m above the river and able to enjoy dramatic views of the city and Itchen Valley below. The summit also has an Iron Age fort, dating back to Norman times, which adds a historic edge to your experience of Hampshire’s great outdoors.
Sunday lunch at The Wykeham Arms
Just round the corner from College Street is your final stop of the day: The Wykeham Arms (75 Kingsgate Street). This pub has been quenching the thirsts of travellers for more than 200 years and is teeming with local history. Observe the bric-a-brac items hanging on the walls and the dining tables that are ex-school desks from Winchester College.
Dining Room, the Wykeham Arms
But this place can compete with the best new breweries on the block, and was voted Town Pub of the Year by the Good Pub Guide 2018. Order one of their superb Sunday roast dinners, with options including two types of beef, pork belly and roast Norfolk chicken, all topped off with some extra special trimmings, like honey roast carrots and butternut squash puree.
Bags packed and bellies full, it’s time for home. Luckily, Winchester train station (Station Road) is less than a mile away, so you can walk (about 20 minutes) or book a taxi through local firm Wessex Cars. Trains from Winchester to London Waterloo run twice an hour on a Sunday (excluding any planned improvements), so you can be home by supper.
