If you’re ready for a short break somewhere quintessentially English and naturally beautiful, the Cotswolds has to be high on your list.  An area of outstanding natural beauty, the hills and valleys of this part of England’s heartland reward exploration.  With just two days, you won’t see everything that the Cotswolds has to offer.  But you’ll have an understanding of what makes this part of the country so very special.  I’m taking you on a Cotswold weekend break to remember.

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Cotswolds Weekend Break_ Two Day Itinerary

Where To Go For Your Cotswolds Weekend Break

As the Cotswolds covers a wide area, nestling in between Bath, Oxford and Stratford-on-Avon.  I’ve chosen to focus this itinerary on the northern part of the Cotswold Hills.  It includes a number of the legendary Cotswolds villages and towns, plus walking trails and attractions in the area.  We started our journey in Stratford-on-Avon, itself a wonderful place to explore.  From Shakespeare’s birthplace to boating on the river and taking in the wild devices of the MAD (Mechanical Art and Design) museum, there’s an incredible time to be had there.

Read more: 24 hours in Shakespeare Country: Stratford-on-Avon

Two Day Cotswolds Weekend Break: South from Stratford on Avon

Cotswolds Weekend Break_ Two Day Itinerary - Shipston on Stour

Taking the road south from Stratford to Shipston on Stour, you begin to see the typical honey stone cottages of the Cotswolds.  Once you reach the thatched cottages of Tredington, sweetly laced with blossom in spring, I like to feel that the Cotswolds journey has begun.


This village is renowned for its antiques, but it has plenty else to offer the visitor.  There’s the clockmakers’ shop, with its overdoor clock offering sage advice to us all on time management.  There;s a sweet shop nearby, and the fine deli, the Taste of the Country.  If it’s picnic weather, you really should pick up your provisions there.  Or stop off for lunch at The George, a great pub and restaurant with rooms.

Long Compton and The Rollright Stones

Cotswolds Weekend Break_ Two Day Itinerary - Rollright Stones

We drove on to Long Compton with its beautifully thatched lychgate and fascinating church.  A short diversion off the main road takes you to the Rollright Stones.  These neolithic stones are laid either side of the road.  Head to the King Stone, and you’ll be rewarded with a spectacular view.  Cross the road to the King’s Men, and there’s an equally good view to the other side of the hill.  This is a place to stretch your legs from the journey, maybe enjoy a picnic if you’ve not eaten in Shipston, and marvel at just how those stones got lifted into their positions.

Chipping Norton

Cotswolds Weekend Break_ Two Day Itinerary - Chipping Norton

This small market town – Chipping being a version of the old word for market Ceapen – has always been a hub for Cotswolds trade.  The market here has been a feature of the town’s life since the 13th century.  On the day we last visited, a market was in full bustle.  Looking around at the selection of baskets on offer, I couldn’t help but wonder how little our needs have changed over the centuries.  I can well imagine similar stocks at the medieval version of today’s market.

The town was a major wool-trading venue in the 15th century.  St Mary’s church is a “wool church”, showing just how wealthy the town became on the basis of fleece.  St Mary’s is full of light, with clerestory windows above the nave giving a sense of great height.

One of the things that I love about Chipping Norton is that it remains real.  You can still meet your everyday shopping needs, grab a takeout for a rushed dinner, and get on with the day to day business of your life here.

Cotswolds Weekend Break_ Two Day Itinerary - Chipping Norton

Chipping Norton Almshouses

Don’t forget to check out the beautiful almshouses.  They have a history born in sadness, having been founded by Henry Cornish after he lost ten of his twelve children in childhood.  Originally set aside in the seventeenth century for eight honest and godly older widows, the almshouses were supplemented by 12 further cottages offered at affordable rents.  The town benefited much from Henry Cornish’s sense of philanthropy.

Bliss Mill

If you see an unusual building up on the hill, with a dome and tower above, that will be Bliss Mill.  Once manufacturing high quality tweed, the Mill is now converted into luxury apartments.  There’s a convenient parking spot on the way out of town to pull over and capture some pictures of this magnificent building, and its follyesque tower.

Cotswolds Weekend Break_ Two Day Itinerary

Cotswold Weekend Break – Dinner And Overnight Accommodation

For our visit, we were delighted to be the guests of The Crown at Church Enstone, some 4 miles from Chipping Norton.  You can read our review of our overnight stay at The Crown on the Birmingham Press.

There’s also the opportunity to stay in Chipping Norton itself, where you’ll find all kinds of options from hotels to inns, bed and breakfasts and even accommodation on a farm.  Nearby Moreton-in-Marsh has many more options for dinner and your overnight stay.

For more information about dining and accommodation in the area, check out the Cotswolds Information and Tourist Guide.

Cotswolds Weekend Break – Day Two

Wherever you are waking up in the Chipping Norton area, our first stop for the day is the pretty town of Moreton-in-Marsh.

Moreton-in-Marsh: Whimsy And Charm

Cotswolds Weekend Break_ Two Day Itinerary - Moreton in Marsh

Pretty Moreton is one of the main market towns in the Cotswolds.  It has a long leafy main street, lined with shops, restaurants and other businesses.  The tree lined grass – complete with benches – in the middle of the street makes the town feel as though it surrounds its own lengthy and linear park.  Full of the typical honeyed Cotswold stone, the buildings have charm and character.  That same charm extends to the businesses in the town.  Where else could you find a toy shop marked by a dappled toy rocking horse rampant as if on a coat of arms above its door?  And the wonderfully named Toy Cottage as its next door neighbour?

There are gifts and treats aplenty to be had here.  You can also pick up some deli supplies for lunch.  There’s a supermarket just outside the town centre for more provisioning if needed.  If you are in the mood for a picnic, gather your vittles now.

Batsford Arboretum

Cotswolds Weekend Break_ Two Day Itinerary - Batsford Arboretum

The exquisite Batsford Arboretum is our next stop, just a mile and a half from Moreton-in-Marsh.  Please note that there is no access from Batsford Village, and you will need to consult the Arboretum’s website for directions.

Batsford is a magical place.  There are nearly 3,000 specimens from all over the world, with a focus on the Far East.  Visit in the spring and you can enjoy the National Collection of Japanese Flowering Cherries.  I didn’t realise that these trees have a relatively short life at around 50 years.  So trees are grafted at around the middle of their lifespan to replace any losses.  Autumn is a great time to see the collection of Acers – Japanese Maples – in full blaze.

With more collections including bamboo and magnolias, plus pines and oaks, mountain ash and whitebeams, there’s an absolute wealth of beauty here.  It’s not just visually stunning.  Batsford smells wonderful too: all fresh earth and leaves and foliage.  If you haven’t managed to shed your stress thus far, Batsford will chase it far, far away.

Chipping Campden

Cotswolds Weekend Break_ Two Day Itinerary - Chipping Campden Gate Houses

Cotswold Way

The second Chipping of our trip, Chipping Campden is home to the start- and end – of the Cotswold Way, one of the UK’s national walking trails.  You can see the sign in the middle of the town, together with a beautiful roundel with a quote from T.S. Eliot.  There are 102 splendid miles to explore between here and Bath (despite the stone saying 100 miles, cartography clearly having become a little more detailed over the years).

Cotswold Way Marker - Chipping Campden

Another linear town grown around its road, Chipping Campden has a unity of design seldom found.  It’s as though someone built it as a single entity – like Portmeirion in Wales – rather than it growing organically over time.  Every building seems to fit perfectly to the next.  That’s not so say it all looks the same.  But instead it’s totally harmonious.

Chipping Campden - Ceiling of the Market Hall

Chipping Campden Market Hall

The iconic Market Hall, built in 1627, stands in the middle of the High Street.  Sir Baptist Hicks built the Market Hall to provide shelter to traders, a function it still performs today.  Beautiful as it is from the outside, you need to wander inside to appreciate its fantastic cruck timbers and the intricacy of the stones underfoot.  They are worn down by many years of traders and buyers alike.  Imagine all the trades that have taken place under this roof over the centuries.    The Market Hall was almost sold to an American in the 1940s, but was bought by the town and passed on to the National Trust, in whose ownership it remains today.

The Arts and Crafts Movement In Chipping Campden

Over at the Court Barn Museum, you’ll find the history of craft and design in the North Cotswolds.  The Arts and Crafts Movement reacted to the changes brought by industrialisation in the nineteenth century.  Older, simpler manufacturing methods were protected.  There’s more design history at the Gordon Russell Museum, celebrating the work of this furniture designer and cabinet maker.

Snowshill And Lavender

Visiting The 21 Prettiest Towns And Villages In The Cotswolds - Snowshill Lavender

Our final stop for this trip is the lovely village of Snowshill.  Set on top of the hill above Broadway, this secluded place has an array of pretty cottages.  You’ll also find Snowshill Manor, a National Trust property complete with a dovecote and terraced gardens designed by Charles Wade.

Read more: Broadway – Village full of Cotswolds charm

Love the smell of lavender?  Then you should pay a visit to Cotswold Lavender, where you can visit the farm when its fields are a sea of fragrant purple flowers.  Its products are available during all seasons, and also feature chamomile items.

Things To Bring Back From Your Cotswold Weekend Break

If you want to bring back gifts or momentos from your Cotswold weekend break, there are plenty of choices here.  If you are UK-based, Batsford Arboretum has a garden centre where you can select from all kinds of beautiful plants.  The towns of Chipping Norton, Chipping Campden and Moreton-in-Marsh have a selection of gifts from antiques to preserves and chutneys and clothes and accessories to home decor and toys.  Snowshill Lavender will see you provided for toiletries for months.

Your Cotswold Weekend Break: Making a Longer Weekend Of it

Cotswolds Weekend Break

If you have time to explore further, then there are plenty of other choices you can make.  We’ve traveled what we think are the 21 prettiest villages in the Cotswolds, so you can explore each and every one of these spots if you have the time.

More Quintessentially English Spots To Explore

If you are staying in Oxfordshire, I’d highly recommend the area of the Vale of White Horse.  With everything from hilltop chalk horses to Thames Path meanderings, a town famous for bun-throwing, a folly and Salvador Dali’s diving helmet, you can’t get a more ecclectically English selection of things to see and do.

Love village life?  Then take yourself over to the Welsh border to visit Herefordshire’s Black and White Village Trail.  This stunning area is bamed after its black and white timbered and half-timbered houses.

And if you want to get your full quota of what it means to be English, then step no further than here: a guide by my fellow travel writers on 25 Essentially English Experiences.  There are plenty cool and unusual choices to enjoy here.

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Cotswolds Weekend Break_ Two Day Itinerary







Author: Bernie

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One thought on “Cotswolds Weekend Break: Your Two Day Itinerary

  1. This looks so dreamy! I haven’t been to the UK but this is definitely moving it to the top of my list!

    Posted on September 26, 2019 at 4:04 pm