Chipping Norton & The Cotswolds Walking Break
A Sociable Two-Night, Hotel-Based Walking Break in the Heart of the Cotswolds National Landscape
Experience Type: Multi-Day Experience
Duration: 2 nights
Accommodation: Hotel
Transport: Car-Free Experience
Group Size: Maximum 12
Level: Active
Age: 18+
Dogs: No dogs, except trained assistance dogs
What to Expect on This Walking Weekend:
Sociable Walking Weekend – A friendly and relaxed trip, perfect for solo travellers and those looking to make new friends.
Stay in a Historic Cotswold Market Town – Based in Chipping Norton, with walks from the hotel door.
Explore the Cotswolds National Landscape – Rolling hills, ancient routes, and breathtaking views.
Visit the Rollright Stones – A Neolithic stone circle, burial chamber, and legendary standing stone.
Flexible Evenings – Group dinners, pub visits, and free time to explore Chipping Norton’s cosy streets.
Book today…
A Scenic Walking Holiday in the Cotswolds
Join Large Outdoors for a sociable walking weekend based in the historic market town of Chipping Norton, where we’ll explore the rolling countryside, historic trails, and ancient landmarks of the Cotswolds National Landscape.
This trip is perfect for solo travellers, friends, and anyone looking to join a welcoming group. We’ll be staying in a comfortable hotel in Chipping Norton, with single and twin-sharing rooms available, offering a great base for two days of walking. All walks start and finish at the hotel, meaning no need for transport.
Over the weekend, we’ll cover a 15-mile scenic route through the Salt Way and the Cotswold countryside, followed by a shorter 8-mile route exploring Shakespeare’s Way and visiting the Rollright Stones, a mystical stone circle steeped in legend. Evenings are relaxed and sociable, with group meals and the chance to enjoy Chipping Norton’s welcoming pubs.
If you love exploring new places, walking in beautiful countryside, and meeting like-minded people, this is the perfect trip for you!
Exploring the Cotswolds National Landscape
Suggested Itinerary
Here’s what we’ve got planned - of course, we may have to offer alternatives or make amendments if the weather misbehaves or other unexpected situations arise!
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Chipping Norton, Cotswolds National Landscape
Check-in at our hotel is available from 15:00, giving you time to settle in or explore Chipping Norton before meeting the group.
At 18:00, our guide will be in the hotel bar to welcome everyone before we enjoy dinner together. This is a great chance to meet new friends, go over the itinerary, and get ready for a fantastic few days of walking.
Arriving Early? Things to Do in Chipping Norton
Explore the Historic Market Town – Chipping Norton is full of independent shops, cosy cafés, and characterful buildings.
Visit Chipping Norton’s Almshouses – Built in the 17th century, these historic homes add to the town’s charm.
Check Out the Theatre – The Theatre Chipping Norton is one of the UK’s most renowned small theatres.
Take a Stroll to Bliss Mill – This iconic former tweed mill is a beautiful landmark on the edge of town.
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Approx. 15 miles | Active rating
After a cooked buffet breakfast, we set off straight from the hotel for a stunning walk through the Cotswolds National Landscape. Our route follows sections of the Salt Way, an ancient trading route, before leading us through rolling fields, historic villages, and woodland paths.
Highlights Along the Route:
Salt Way – A centuries-old trackway once used for transporting salt across England.
Cotswold Hills – Open countryside with expansive views across the Cotswolds and beyond.
Charlbury – A charming Cotswold village with stone cottages and a rich history.
After completing the loop, we return to the hotel to freshen up before heading to a local pub for a relaxed drink. Tonight’s dinner is not included, giving you the flexibility to choose a meal at one of Chipping Norton’s excellent pubs or restaurants.
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Approx. 8 miles | Leisurely rating
After another hearty breakfast, we set off on a walk exploring Shakespeare’s Way, a historic route linking Stratford-upon-Avon with London, said to have been used by the playwright himself.
One of the most fascinating stops along the way is the Rollright Stones, a Neolithic and Bronze Age stone circle with a mystical past.
The Rollright Stones – Ancient Mystery
King’s Men Stone Circle – A 4,000-year-old ring of stones, steeped in folklore.
Whispering Knights – A burial chamber thought to date back over 5,000 years.
The King’s Stone – A solitary standing stone, tied to local legends of a king turned to stone.
After completing our loop, we return to Chipping Norton, where we’ll find a café or pub for a final lunch before saying our goodbyes.
Exploring the Cotswolds National Landscape
Essential Information
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Meeting Time: Check-in from 15:00.
The Large Outdoors host will meet you in the bar from 18:00.
Meeting Location:
Premier Inn
Spring Street,
Chipping Norton,
OX7 5NNParking: Chargeable on-site parking is available at this hotel, charged at a discounted price of £3 per 24 hours for Premier Inn Guests. Simply find a space and pay less to park using the kiosk outside our hotel. This car park is managed by Horizon.
Finish Time: We aim to finish on the final day between 15:00 and 17:00 - the exact finish time may depend on the planned/chosen activity, group dynamic, weather conditions, whether the group chooses to grab a coffee or lunch together during/after, etc. If you’ve travelled via public transport, please ensure you book onward travel accordingly (i.e. an open return ticket), to allow for flexibility.
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The Premier Inn Chipping Norton offers a comfortable and convenient stay in the heart of the Cotswolds National Landscape, with modern rooms, an on-site restaurant, and an ideal location for exploring the surrounding countryside.
Accommodation Address:
Premier Inn
Spring Street,
Chipping Norton,
OX7 5NNRoom Types:
Single Rooms (en-suite bathroom) are for one participant.
Double Rooms (en-suite bathroom) sleep up to two participants booking together, in a Double bed.
Twin Rooms (en-suite bathroom) for for two people sharing and will have two single beds.
Shared Male / Female Rooms (en-suite bathroom) ideal for those happy to share with another participant. -
Included:
2 nights’ bed & breakfast accommodation.
A hearty cooked breakfast each morning, prepared by the accommodation.
A Large Outdoors host/guide to welcome you, deal with the logistics for your experience.
Guided walks on two days (Days 2 & 3).
The chance to make new friends and meet like-minded people - Large Outdoors is all about making outdoor adventures sociable.
Pre-event support from the Large Outdoors team - give us a shout if there’s any advice or information you need and check out our Blog for useful articles too.
Not included:
Travel to and from the meeting location or train station collection.
Dinner on each evening - we’ll book a table at a local pub to enjoy dinner as a group and you can purchase whatever you fancy from the menu available.
Packed Lunches - for these we will stop at a local bakery and you can purchase what you wish for lunch.
Any extra (i.e. not mentioned above in ‘Included’) excursions or activities that you may partake in which incur a cost.
Alcoholic drinks - please feel free to bring something with you to enjoy at the accommodation. There are also a couple of pubs in the village for a post-walk pint or two!
Any food, drinks or goods you choose to purchase at any shops, restaurant, pubs or cafés visited.
Travel/activity insurance - we recommend having insurance to cover, at a minimum: cancellation and curtailment; medical and emergency expenses (including repatriation); personal accident; injury and death.
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Please see our Residential (Walking) Kit List.
The compulsory items are selected for your safety, which is of paramount importance to us at Large Outdoors. Each participant should have the items listed.
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What level of fitness is needed?
This trip is rated ‘Active. The longest walk will be around 15 miles.Can I attend on my own?
Absolutely! In fact, the majority of our attendees are solo travellers.When should I arrive?
You are welcome to arrive from 15:00 onwards on Friday evening. Dinner will be served at the accommodation at around 19:30. If you intend to arrive after 22:00, please let us know.I’d prefer vegetarian or vegan meals - can this be arranged?
Yes, absolutely! We will always supply a vegetarian or vegan meal, but please note this must be requested well ahead of the trip - the remote location of our accommodation means we can’t pop out to buy additional ingredients. Complete the dietary section during the booking process and if your dietary needs change ahead of the trip please email the office and we’ll update your booking.I’d prefer gluten-free meals - can this be arranged?
We will provide meals using gluten-free ingredients, but due to the shared nature of the kitchen we cannot provide strictly gluten-free meals. Please let us know you’d like gluten-free ingredients ahead of time by completing the dietary section during the booking process.I am allergic to a specific ingredient - can you provide meals for me?
Due to the shared nature of the kitchen we are unable to provide meals suitable for those suffering from many allergies. Please contact the office before booking to discuss your requirements.What transport is provided during this trip?
We do not provide transportation during this trip.Can I bring my dog?
Dogs are not allowed on this trip, except for registered assistance dogs.
This map is provided for guidance regarding the general location. For detailed meeting information, please refer to the 'Meeting Time & Location' section.
Discovering Chipping Norton
Nestled in the Cotswolds National Landscape, Chipping Norton is a historic market town known for its lively atmosphere, independent shops, and classic honey-coloured stone buildings. Once a major centre for the wool trade, its 17th-century almshouses and iconic Bliss Mill reflect its rich heritage.
The town’s Market Square is home to traditional markets, and its theatre is one of the UK’s best-loved small venues. With its charming streets and friendly pubs, Chipping Norton is the perfect base for a walking weekend.
Exploring the Cotswolds National Landscape
The Cotswolds National Landscape is one of England’s most picturesque rural areas, known for its rolling hills, honey-coloured stone villages, and historic walking trails. Covering nearly 800 square miles, the region stretches across multiple counties, offering an unspoiled mix of open countryside, winding lanes, and timeless market towns.
Walking through the Cotswolds means following in the footsteps of history. Trails such as the Salt Way, Cotswold Way, and Shakespeare’s Way reveal centuries-old routes once used by traders, poets, and travellers. These paths wind through peaceful woodlands, across open fields, and past charming villages, each with its own story to tell.
The area is also home to remarkable ancient landmarks. The Rollright Stones, a mysterious Neolithic stone circle, stand as a reminder of Britain’s prehistoric past. Nearby, the Whispering Knights burial chamber and the King’s Stone add to the myths and folklore surrounding these ancient sites.
Beyond the walking trails, the Cotswolds National Landscape is a haven for wildlife, with wildflower meadows, hidden valleys, and rich woodlands providing a home for deer, badgers, and an array of birdlife. The region’s charming villages and historic market towns, built from distinctive Cotswold stone, complete the picture, making this a truly special place to explore on foot.