How to Spend a Day in Winchcombe

Winchcombe is the place to come to avoid the Cotswolds crowds. Although there is plenty to do and see in and around Winchcombe, it rarely features on the popular Cotswold Itinerary blogs. Therefore, like Moreton in Marsh, it allows you to see a more local side of the Cotswolds.

Winchcombe is also slightly different from the other Coltswoldian villages (yes, I’m making up words again!). It has the honey-coloured stone manor houses and cottages that you expect to find in this Area of Outstanding Natural Beauty. However, it also has the old white and black half-timbered homes, reminiscent of Shakespeare’s Stratford upon Avon.

A photo of the town of Winchcombe taken from a nearby field.

Located in the county of Gloucestershire, the Winchcombe derives from the old English words wincel and cumb, which means “valley with a bend”. They were not wrong! Winchcombe is often thought of as a walker’s mecca. Sitting at the foothills of Cleeve Hill (the tallest point in the Cotswolds), there are no end of paths leading up Cleeve Hill. Whether you want a short 5km hike or a multiday trek, Winchcombe is the place to be! The Cotswold Way passes through, and you also have the figure of 8 Winchcombe Way 42-mile path. I’ve only walked sections of that one, but I’m hoping to complete it over a weekend this summer.

In this blog I will share with you the best things to do in Winchcombe, as well as my favourite restaurants and some suggestions of where to stay.

Best Things to Do in Winchcombe

Of course, I will start as I always do, with walking suggestions! I personally think the best possible way to experience the Cotswolds is on foot. The countryside is fantastic, and there are so many hidden gems that can only be accessed with a bit of self-powered effort! The added benefit of exploring on foot is that cake becomes guilt-free!

When in Winchcombe, you need to walk up the Cleeve Hill!

On the way up Cleeve hill, looking over an old dissused quarry

Located at 330 meters above sea level, Cleeve Hill is the highest point in the Cotswolds. OK, I know that’s not exceptionally high, but there are 101 different ways to reach the top of Cleeve Hill, and they are all worthwhile. I personally would recommend hiking up from Winchcombe via Bellas Knap. However, if you really don’t fancy walking, you can drive pretty much to the summit!

Winchcombe is a Site of Special Scientific Interest (SSSI). It supports a rich and diverse calcareous grassland community and contains two rare species of plants in the UK: Nit-grass and Rough Marsh-mallow. You’re unlikely to realise this when you are walking, but what you will spot are the fantastic views! Cleeve Hill is known for its outstanding views of the Malvern Hills, River Severn, and sometimes even as far as the Black Mountains of Wales! There is a range identifier on the summit that will help you identify what you are seeing.

One of the many paths leading up Cleeve Hill

Cleeve Hill is also the perfect spot to catch a sunrise or a sunset, thanks to its 360-degree views. But probably the most impressive thing you can do from Cleeve Hill is to admire that night sky. It is one of the best spots in the area to spot astrological events such as meteor showers and passing comets. But even if there isn’t anything quite that spectacular going on, just lying on the grass and looking up at the starry sky is good enough.

Being very close to Cheltenham, Cleeve Hill can get very busy in nice weather as it’s popular with dog walkers, kite runners, and picnickers alike. However, its relatively flat dome shape summit means there is plenty of space for everyone!

Don’t get caught short!

Just beware not to get caught short! There aren’t many toilet facilities that I am aware of, and not many bushes to hide behind! When a friend and I were walking the Cotswold Way, we saw a guy doing his best to hide behind the only shrub in sight while alleviating an upset tummy! I’m not sure who was more scared after the encounter, him or us?!

Learn About History at Belas Knap

Belas Knap is a neolithic period chambered long barrow situated just below the summit of Cleeve Hill. It is a type of Cotswold Severn Cairn monument, the kind mostly found around the River Severn and known to have similar trapezoid shapes. The long barrow dates back to 3000 BC and has four burial chambers. Skeletons, thought to be from the Bronze Age, were found during excavations of the burial ground. In addition, Romano-British pottery was also found. These remains are now exhibited at the Winchcombe Museum. The site has since been restored and is, in my opinion, one of the best things to do in Winchcombe – especially for history enthusiasts!

If you like history, there is plenty more of it in Winchcombe. Several roman sites surround Winchcombe, including the remnants of two villas. However, the most remarkable period for Winchcombe was during the Saxon era, when the Kinds of Murcia chose Winchcombe as their base. Unfortunately, there are few remnants from this era.

As with the rest of the Cotswolds, Winchcombe started to prosper during the Middle Ages. Not only because of the wool trade like the other major Cotswolds towns. It was actually the fact it became a pilgrimage site with travellers coming from far and wide to see the relic of Saint Kenelm. Because of all these travellers a collection of inns appeared in the early 1500s. One of these, the Corner Cupboard, still stands today!  

Have a Picnic at Hailes Abbey

Some of the remaining arches of Hailes Abbey, one of the best day trips to do from Winchcombe

Set in the charming Cotswold countryside, Hailes Abbey was founded in 1246 by the Earl of Cornwall. This Cistercian Abbey used to be a place of pilgrimage and the centre of monastic life. It was founded as the sister establishment of Beaulieu Abbey in Hampshire and was once an architectural masterpiece, although now it lies in ruins.

Usually, monasteries belonging to the Cistercian order did not feature such elaborate decorations as they were thought to distract monks from their religious duties. But by the time Hailes Abbey was built, these restrictions were lifted. It featured intricately carved and painted stonework tinted with gilt and enormous sculpted ceiling bosses – some of which can still be found today.

The Abbey is also the resting place of the Earl of Cornwall, his second wife, and two sons. While not much of the original building remains today, the Abbey’s ruins, set amidst the undulating hills of Cotswolds, serve as the perfect setting for a picnic on a bright sunny day!

The Abbey is within easy walking distance of Winchcombe and is on both the Winchcombe Way and Cotswold Way National footpaths. The walk is only 2km each way, although you can always include it as part of a longer circular route. If you don’t fancy the wall, you can always drive there! There is free parking opposite the Abbey.

Opening Times and Admissions Fees

Hailes Abbey is open Wednesday to Sunday between 10 am and 5 pm. However, opening times may vary depending on the time of year and although normally closed on Mondays they do tend to open on bank holiday Mondays. I recommend checking their website before visiting for the most up to date timings.

Hailes Abbey is an English Heritage site and is therefore free for English Heritage members. If you are not a member however you are looking at £7.00 for adults and £4.20 for kids between the ages of 5 and 17. They offer a special rate for families (2 adults and up to 3 kids) at £18.20, or for single parent families (1 adult and up to 3 kids) of £11.20.

Address: Hailes, Cheltenham GL54 5PB

Pick your own fruit at Hayles Fruit Farm

Just up the road from Hailes Abbey is Hayles Fruit Farm, a third-generation family-owned business. As well as being able to pick your own fruit, the farm also has a fully stocked farm shop, a tea room serving delicious cakes, cooked breakfasts and light lunches, a fishing lake, and a campsite.

Depending on what time you visit will depend on what fruit you can pick.

  • Strawberries: May to September
  • Plums: August to September
  • Apples: August to October
  • Pears: September to October
  • Pumpkins: October

Whether you just want some lunch after your Hayles Abbey visit or you want to spend a day out in nature, Hayles Fruit Farm is always a great option for the whole family. They also have a campsite, if you wish to reconnect with nature! You can find my Cotswolds Camping recommendation here.

Address: Hayles Fruit Farm, Winchcombe, Cheltenham GL54 5PB

Explore the Stunning Sudeley Castle and Gardens

Studeley Castle gardens

Nestled in the Cotswold Hills, Sudeley Castle is a Grade I listed monument featuring 10 gardens within a 1200-acres estate. The Sudeley Castle was first built in 1443 by the then Lord High Treasurer of England, Ralph Boteler. Since then, the castle has been passed down several times in history. King Richard III built its famous banquet halls, and the castle is also the final resting place of King Henry VIII’s sixth wife, Catherine Parr. This made Sudeley Castle the only privately owned castle in the world to be the burial ground of a Queen of England. As of today, Sudeley continues to be the home of Elizabeth, Lady Ashcombe, and her family.

Parts of the castle are open seasonally to the general public. Some sections are used as a hotel, and the rest is where Elizabeth, Lady Ashcombe, and her children and grandchildren live.

Sudeley Castle always has an extensive range of events going on, from Sculpture Safaris to Food Festivals and everything in between. The much-acclaimed Giffords Circus often makes an appearance there every year too.  

The grounds of Sudeley Castle, one of the best things to do in Winchcombe

Opening Times and Admission Fees

Sudeley Castle is open daily between 10 am and 5 pm between the months of March and October. If you are visiting at the start of March or end of October do check their website, as the dates vary slightly year on to year.

Adult entry fee is £19.50 whilst kids over the age of 3 cost £8.75. Family tickets (2 adults, 2 kids) are available for £48.00.

Address: Sudeley Castle & Gardens GL54 5LP

St Kenelm’s Well

The views from the walks that surround Winchcombe are always beautiful!

Saint Kenelm was an Anglo-Saxon saint revered throughout medieval England. A little above the town of Winchcombe sits a conduit house with the St Kenelm’s Well. It is a sacred pilgrimage site, especially on 17 July, celebrated as Kenelm’s feast day. According to various local legends, the spring, which feeds the water in the well, is said to be associated with St Kenelm. But even if the history behind it is not what interests you, it is worth the walk! From Sudeley Castle it makes for a beautiful circular walk to go up to St Kenelm’s Well. It is a 6 km long route and is accompanied by stunning countryside views.

The walk starts from Back Lane Car Park, which only costs £1 for the full day. The postcode for the car park is GL54 5PZ. There are toilets in the car park, but these cost 20p so make sure you have change!

Visit the Nearby Guiting Power Village

Guiting Power is a small village and civil parish with a population of just about 300. The village sits between Winchcombe and Stow on the Wold, on the valley of River Windrush. Several walking trails pass through Guiting Power, including Warden’s Way, starting at Bourton on the Water and the Diamond Way, passing through Chipping Campden. The village is best known for the Guiting Music Festival, which takes place every July and lasts for 10 days. You can expect folk, jazz, and classical music artists.

However, what I love most about this quaint little town is that it appears to have stopped in time. There isn’t much to it other than the Hollow Bottom pub, but despite it, it is worth a visit!

Take a Ride on Gloucestershire Warwickshire Steam Railway

Photo of a steam train

Winchcombe is one of the stations on the Gloucestershire Warwickshire Steam Railway. It is a volunteer-run heritage railway system that once used to be known as the Honeybourne Line – a part of the Cheltenham – Stratford-upon-Avon – Birmingham line on the Great Western Railway. However, due to damages, it was closed in 1976 and opened again in 1984 after preservation works became successful. Today, it is a 28-mile long round trip starting at Cheltenham Racecourse and ending at Broadway. This steam engine train crosses some spectacular countryside and is a great thing to do when in Winchcombe!

Admire the Stone Cottages on Vineyard Street

The beautifully row of cottages in Winchcombe

If you’ve had enough of going out and about and would like some time within the town to just walk around and take in Winchcombe’s charm, then head to Vineyard Street. This quintessential Cotswold street is lined with stone cottages, and each cottage features flowering vines framing the front doors. I hate to say it, but it might just be the most Instagram-worthy spot in Winchcombe!

Stroll by the River Isbourne

The River Isbourne is a tributary of the River Avon. You can walk from its source on Cleeve Hill to Evesham, where it joins the River Avon, relatively easily. However, if you’re not one for long walks, just find a quiet spot by the river within Winchcombe. It is exceptional during the Spring when the trees bloom or when the leaves have all turned auburn in autumn. Several fluffy, grassy patches along the river make the perfect spot for an afternoon picnic. It is by far one of the most relaxing things to do in Winchcombe.

Go Paragliding!

If you are looking for a little more adrenaline in your life, why not try your hand at paragliding! I talk about it more in my post about unique things to do in the Cotswolds. Cotswold Paragliding offers flights from Cleeve Hill which is conveniently located close to Winchcombe. Seeing the Cotswolds from the air is truly spectacular and if you are worried about it being scary, don’t be! Unlike skydiving or bungee jumping it is actually a very calm experience.

Operating Hours: March to September, 7 days a week, sunrise to sunset. September to March weekends only.

How to book? Please visit their website and buy a flight voucher. Once you have booked the voucher, you need to contact them via WhatsApp to get it booked.

Hop Onto Some Winchcombe Walks:

You know how much I love walking, and Winchcombe is a great place to base yourself if you want to spend the weekend hiking. Aside from the hikes mentioned already up Cleeve Hill, there are also a number of specific footpaths that start off in Winchcombe.

Winchcombe Way

A gorgeous photo of a lamb munching on the horizon

The Winchcombe Way is a 42-mile long figure of eight footpath, with Winchcombe town at its centre. This is a great trail if you want to discover spots that few locals even know about! I have yet to walk Winchcombe Way in its entirety, so make sure to check back after the summer, as I hope to do it over the course of a weekend! The sections I have walked though, are as beautiful as they get in the Cotswolds.

Isbourne Way

The Isbourne Way is a waymarked 14-mile long trail (one way). The footpath only opened in 2014 and follows the River Isabourne’s source from Cleeve Hill to Evesham, concluding at the River’s confluence with Warwickshire Avon. It passes through a wide variety of landscapes such as forests, vast open countryside, villages, towns, pubs and markets, and even points of interest such as mills and churches. You will definitely enjoy plenty of variety on this day hike.

Winchcombe Gateway Walks

Winchcombe is one of the ten Cotswold Gateway Towns, which is where the name Winchcombe Gateway Walks comes from. The Winchcombe Gateway Walks are six different walks you can do while in town – each one leading you to a truly mesmerising location. These six trails include Winchcombe to Sudeley Castle (2 miles), Winchcombe to Langley Hill (4.5 miles), Sudeley, Kenelm, and Monks Hole (4.75 miles), Winchcombe to the source of the River Isbourne (6 miles), Winchcombe to Belas Knap Long Barrow (5.5 miles), and finally Farmcote to Hailes Abbey (7.6 miles).

The Winchcombe Cotswolds Walking Festival

Apart from its many walking trails, Winchcombe is also known worldwide for its three days long Walking Festival, which takes place every year during the month of May. The first Winchcombe Walking Festival took place in 2009, and every year since it has been getting bigger and better! Throughout the three days, there are guided walks that you can join with varying levels of difficulty and different points of interest. From market hopping to pub crawls, to nature hiking – there is something for everyone here!

Would you prefer to explore the Cotswolds with a guide?

Then check out these tours:

Places to Eat in Winchcombe

Winchcombe is a little different to other Cotswold villages as it has white and black wooden houses as well as the honey coloured stones

North’s Bakery

North’s Bakery was first established in 1955 in Wales. Ever since, several branches have propped open around the country by the North family members – all of whom are bakers. There is a North’s Bakery in Winchcombe, in the Cotswold, and I can tell you, it was my saviour during the Cotswold Way. OK, maybe that is an exaggeration, but the shortbread millionaire we bought there 33km into our first day certainly gave me the fuel I needed to make it up Cleeve Hill that afternoon!

The most delicious shortbread millionaire

They are known for their traditional breads like Cobber, Stoneground, and Wholemeal, as well as some specialty breads like Walnut and Raisin. They also make their own chocolate, pastries, and seasonal cakes. But the one thing that truly steals the show is their shortbread millionaire – truly one of the best I’ve had in a really long time!

Address: 10 North St, Winchcombe, Cheltenham GL54 5LH

The Corner Cupboard Inn

You can’t come to a historic town and not enjoy a historic inn! The Corner Cupboard was established in 1550 and has been serving weary travellers ever since. As well as offering accommodation, they also serve locally sourced traditional British food alongside a great selection of ales. I’ve only been there for dinner, however I have heard they do a great Sunday roast!

Address: 83 Gloucester St, Winchcombe, Cheltenham GL54 5LX

Wesley House

The Wesley House Bar and Grill is definitely one of the best places to eat in Winchcombe. Located within a historical building, patrons can dine inside, surrounded by traditional decors, or they can choose to have their meals in the open atrium, overlooking the Cotswold countryside. They have a wide range of dishes on their menu, however my personal recommendations would be their slow-cooked porchetta, tomato, and fennel fondue, or the pan-roasted pollack.

Address: High St, Winchcombe, Cheltenham GL54 5LJ

Where to Stay in Winchcombe

Winchcombe high stret

It is worth noting that I live in Moreton in Marsh, and therefore I have no need to stay away in the Cotswolds. With this in mind, the following are not recommendations based on my experience. Instead, I have made suggestions based on the research I have done.

The Lion Inn

The Lion Inn caught my eye because it is pet friendly! When we travel through the UK, we always take our dog, Suki, with us, and finding good pet-friendly places can be challenging! What used to be a coaching inn in the 15th century is now a luxurious stay with an in-house pub and restaurant, tastefully done up in the Cotswold charm. They have eight en-suite bedrooms, each fitted with the comfort that only The Lion Inn is known for!

Address: 37 North St, Winchcombe, Cheltenham GL54 5PS

No 5 Vineyard Street

No 5 Vineyard Street is a beautiful self-catering honey-coloured cottage built with Cotswold stone. Definitely one of the best places to stay in Winchcombe, No 5 Vineyard Street is another pet-friendly property. The cottage comes with two bedrooms, one bathroom, a fully equipped kitchen, a fireplace, and even a cosy garden to sunbathe in during the summer months!

Sudeley Castle Cottages

If you come to Winchcombe and don’t experience at least one night at the luxurious royal cottages at the Sudeley Castle, did you even visit Winchcombe!? Imagine waking up inside a centuries-old castle, feeling like you’re playing a part in a movie. Most of these cottages have private gardens and patios, which will make you feel like royalty – if only for a day or so!

Getting to Winchcombe using public transport

Sudeley Castle Gate house

The easiest way to get around the Cotswolds is definitely by car. However, it is also possible to do it by using public transport. The closest train station to Winchcombe is Cheltenham, which is well served from London and other major UK cities.

From Cheltenham you have a couple of options. Although slow, you could take the steam train, which is very scenic and features as one of the top things to do in Winchcombe! Or you could take the W Bus from Cheltenham to Broadway, which stops off in Winchcombe.

However you decide to arrive in Winchcombe, and whether you come for a weekend, a week or just a day, I hope you have a wonderful time exploring all the great things this great town has to offer.

If you have any suggestions I have missed, do let me know in the comments!

Pin with a photo of some of the pretty Winchcombe houses


  1. Winchcombe looks so bucolic and peaceful. I’d definitely stay at the castle cottages. It looks like there is a fair deal of history to explore. here.

  2. The Cotswolds are simply one of the most beautiful parts of England. I’d love to walk the Winchcombe Way and visit Sudeley Castle & Gardens, I dont think i’ve been before. I can’t wait to go back and do some of these things!

  3. Winchcombe looks like a cool destination! thanks for putting under my radar, I love the architecture and I would love to take the ride on Gloucestershire Warwickshire Steam Railway! And obviously take a nice picture of the train!

  4. I love visiting places like this that are packed with history. Haven’t made it down to Winchcombe yet but I’ll add it to my list for sure!

  5. You have so many great places on here. I would most definitely want to stay at the Sudeley Castle Cottages. They sound just perfect for a romantic getaway. Excellent list of best things to do!

  6. Great post! Sudeley Castle and Gardens looks unbelievably gorgeous. Saving this for future trip planning!

  7. Thank you for such a helpful post about visiting Winchcombe! It looks like a fantastic place to visit for history and nature lovers. I would love to visit the castle and abbey and also stroll those charming streets and try the Corner Cupboard Inn!

  8. This looks awesome, and as we’re looking to travel in the area next year, I have saved it for my research later. I especially would be interested in the Gloucestershire Warwickshire Steam Railway. That looks like so much fun. 🙂 Thank you so much!

  9. The castles always have such beautiful gardens alongside them. I love Sudeley Castle and would love to see it in person!

  10. There’s so much to do in Winchcombe – I had no idea! It looks like some great hiking and hill walking. Would love to explore this area!

  11. Squeeee this is the closest I have come to visiting one of the spots you blog about right before I read about it! We were in the Cotswolds (visiting Coltswoldian villages) last week! It is such a gorgeous area with rolling hills, fab pubs and pretty villages. Winchcombe looks like a brilliant base to stay in the area – i really like the sound of the ling distance walks like the winchcombe way.

    Btw, we ended up hiking near Painswich Beacon if you ever go near there – the countryside was sooo flipping pretty!

    1. Painswick Beacon and that area is lovely. We walked around there as part of the Cotswolds Way. Next time you are in the Cotswolds let me know, would be great to meet up!

      1. Thanks Bea, will do!
        It’s a bit tough whenever we get back to the UK we spend all the time with family, so it is always hard to fit in time for mates. At some point we’ll come back for longer though!

  12. This sounds like such a lovely place to visit! I would love to pick fresh fruit and tour the lovely grounds of the castle. Thank you for sharing!

  13. I am sure we need to plan a visit to the Cotswolds one day. So good to know that Winchcombe is a bit different than others. I can see why it brings back thoughts of Stratford on Avon. It looks like there are lots of great outdoor spots. And good ones to take a picnic to. Especially if the picnic basket is filled with fresh produce. We love train travel so it would be fun to plan to ride on the Gloucestershire Warwickshire Steam Railway. Looks like a lovely spot to stay for a few days.

  14. The Cotswolds are such a lovely part of England and you’ve shared some great things to do in Winchcombe. Thankyou!

  15. The Cotswolds look picture-perfect. I love all the history you incorporated into your post. The architecture is spectacular and the hikes are so inviting. I would love to hike across those picturesque rolling hill vistas.

  16. Winchcombe looks awesome! Would love to stroll the streets or tour the castles. Such a lovely looking area!

  17. Totally with you on the “smaller” Cotswold towns. I lived in Oxford and preferred the less well-known places. Burford could be a circus except in winter. Lovely post, brings back the good memories, thank you!

    1. You are so right. Living in the Cotswolds means I avoid any of the touristy spots on bank holidays and throughout the summer. But there are so many other hidden gems that people often don’t know about.

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