Forest of Dean & Wye Valley – Autumn Walking Break
Discover the Forest of Dean & Wye Valley in Autumn
Autumn is a wonderful time to explore the Forest of Dean and Wye Valley. Woodland turns shades of gold, copper and red, the rivers wind through colourful hillsides, and the quieter paths make for some lovely days of walking.
Join Large Outdoors for a three-night midweek walking break, giving us three full days to explore this beautiful corner of the country. From the sweeping views at Symonds Yat to the historic surroundings of Tintern Abbey, we'll discover a mixture of woodland trails, riverside paths, hilltop viewpoints and fascinating local history.
We'll stay in a comfortable hotel in Monmouth, with breakfast included each morning and the chance to enjoy relaxed group meals in the evenings. All transport to our walks is organised, and with complimentary station collection from Chepstow, you can enjoy the whole break without needing a car.
With a maximum of eight guests and a leisurely walking grade, there's plenty of time to enjoy the scenery, stop for photographs and get to know your fellow walkers. Whether you're joining on your own or travelling with a friend, it's a friendly way to make the most of the autumn countryside.
Holiday at a Glance
Duration
3 nights · 3 walking days
Walking grade
Leisurely
Distance
Approx. 7-10 miles per day
Price
From £425pp
Group size
Maximum 8
Accommodation
Hotel
Transport
Car-free · Transport included
Meals
Breakfasts included
Check Dates & Book Your Place
Select a date to check availability, room options and prices.
Upcoming departure dates
Monday 2 - Thursday 5 November 2027
Deposits – Pay a 20% deposit when booking more than 12 weeks before departure. The remaining balance is due 12 weeks before departure.
Three Nights of Autumn Walking in the Forest of Dean & Wye Valley
Autumn is a wonderful time to explore the Forest of Dean and Wye Valley, when the woodlands turn shades of gold, copper and red, and the countryside takes on a completely different character.
Join Large Outdoors for a three-night midweek walking break, giving us three full days to discover this beautiful corner of the country. From peaceful woodland trails and riverside paths to sweeping viewpoints and historic landmarks, we'll enjoy a varied selection of walks at a relaxed, sociable pace.
Our base is the historic market town of Monmouth, where the Rivers Wye and Monnow meet. With its independent shops, cafés and welcoming pubs, it's a lovely place to return to after a day outdoors, with opportunities to enjoy dinner together in the evenings.
With a maximum of eight guests, comfortable hotel accommodation and all transport to our walks organised, you can simply enjoy the walking, autumn scenery and company. And with an extra night compared with our regular weekend, there's even more time to explore.
Trip Highlights
Three nights and three days of walking – An extended break with more time to explore the Forest of Dean and Wye Valley.
Autumn woodland colours – Discover forest trails and colourful countryside at one of the loveliest times of year.
Riverside walks and viewpoints – Enjoy the River Wye, Symonds Yat and beautiful views across the surrounding countryside.
Historic towns and landmarks – Explore Monmouth, Ross-on-Wye and the surroundings of Tintern Abbey.
Small-group, sociable walking – A maximum of eight guests, a friendly walking guide and plenty of opportunities to get to know your fellow walkers.
Suggested Itinerary
As always, we may need to adjust routes based on weather conditions or other circumstances - but rest assured, we'll always have a wonderful alternative ready!
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You can check into our hotel in Monmouth from 15:00.
For guests travelling by train, we offer a complimentary collection from Chepstow railway station at 17:00. This can be arranged when booking or by contacting Large Outdoors at least seven days before the trip.
Your Large Outdoors guide will meet everyone in the hotel bar from 18:00 for introductions and a chat about the walking days ahead.
We'll then head into Monmouth for a relaxed group dinner at a local pub or restaurant. It's a lovely opportunity to get to know your fellow walkers before our first day exploring the countryside.
Evening meals and drinks are not included.
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Walking distance: Approximately 8–10 miles
After breakfast, we'll travel to the start of our first walk, following the beautiful River Wye through a landscape of woodland, meadows and peaceful riverside paths.
Autumn brings wonderful colour to this part of the valley, with the surrounding trees turning shades of gold, orange and copper.
Our route takes us towards Symonds Yat Rock, one of the Wye Valley's best-known viewpoints. A climb through the woodland rewards us with sweeping views over the river's distinctive horseshoe bend and the surrounding countryside.
We'll have time to enjoy the scenery and stop for refreshments at the café before continuing along woodland trails and riverside paths.
If river levels are particularly high, our guide will choose a suitable alternative route through the Forest of Dean.
Back in Monmouth, there's time to explore the town's historic streets, visit the medieval Monnow Bridge or simply relax before another sociable evening meal together.
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Walking distance: Approximately 8–10 miles
Today we'll explore the beautiful countryside surrounding Ross-on-Wye, another of the Wye Valley's attractive market towns.
Our walk combines riverside paths, peaceful woodland trails and rolling countryside, with plenty of opportunities to appreciate the autumn scenery.
Along the way, we'll discover one of the area's ancient Iron Age hillforts, adding a little local history to our day. The route includes a mixture of gentle climbs and flatter sections, with time to enjoy the views and stop for breaks.
After our walk, we'll have some free time in Ross-on-Wye. You might fancy browsing the independent shops, exploring the riverside or finding somewhere for a well-earned cup of tea.
We'll then return to Monmouth for our final evening together.
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Walking distance: Approximately 6–8 miles
After breakfast and checking out of our hotel, we'll head to Tintern Abbey, one of the Wye Valley's most recognisable historic landmarks.
Set beside the River Wye and surrounded by wooded hillsides, the abbey makes a wonderful starting point for our final walk.
We'll follow the riverside before gradually climbing through woodland towards Devil's Pulpit, a limestone viewpoint overlooking the valley. From here, we'll enjoy one of the area's classic views, looking directly across towards the ruins of Tintern Abbey.
Our route then follows part of the historic Offa's Dyke Path, taking us through more beautiful autumn woodland before descending towards Tintern.
There should be time for a final cup of tea or slice of cake before we return to Monmouth and say our goodbyes.
For guests travelling by train, we'll provide a drop-off at Chepstow railway station between 16:00 and 17:00. We recommend booking an open or flexible return ticket to allow for changes to our finishing time.
Essential Information
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Meeting Locations & Times
Our autumn walking break begins at the Premier Inn Monmouth, where you can check in from 15:00 on Monday.
Your Large Outdoors guide will meet everyone in the hotel bar from 18:00 for introductions and a chat about the walking days ahead.
Hotel address:
Premier Inn Monmouth
Portal Road
Monmouth
NP25 5FPTravelling by Train
Chepstow railway station is the most convenient station for guests using our complimentary collection service.
We offer a free group collection from Chepstow on Monday afternoon, so there's no need to arrange your own transport from the station to the hotel.
Station Pickups
Our complimentary collection from Chepstow railway station is at 17:00 on Monday.
You can request this during booking or contact Large Outdoors afterwards to arrange it.
Station collections must be booked in advance, at least seven days before departure.
Travelling by Car & Parking
Parking is available at the Premier Inn Monmouth.
If you're driving, you can make your own way to the hotel and meet the group in the bar from 18:00.
Transport During the Trip
All transport between our hotel and the walking routes is included throughout the break.
Your guide will take care of the driving and arrangements, so you can relax and enjoy exploring the Forest of Dean and Wye Valley.
Ferries & Boat Transfers
There are no scheduled ferry or boat transfers on this walking break.
Departure & Return Travel
On Thursday, we aim to finish between 15:00 and 17:00, depending on the day's walking route and conditions.
We'll return to Monmouth following our final walk, with a complimentary drop-off at Chepstow railway station between 16:00 and 17:00 for guests travelling by train.
If you're travelling home by public transport, we recommend booking a flexible or open return ticket to allow for any changes to our finishing time.
Important Travel Information
Please arrange your Chepstow station collection at least seven days before departure.
There are no additional travel requirements or arrangements for this walking break.
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Accommodation Location
We'll be staying for three nights at the Premier Inn Monmouth, conveniently located in the historic market town of Monmouth, with shops, cafés, pubs and restaurants nearby.
Hotel address:
Premier Inn Monmouth
Portal Road
Monmouth
NP25 5FPAccommodation Type
Our accommodation is a comfortable hotel, providing a convenient base for exploring the Forest of Dean and Wye Valley.
You'll have your own room or a shared room, depending on the option selected when booking.
Bedrooms & Sleeping Arrangements
All accommodation is in standard hotel bedrooms, with comfortable beds and en-suite facilities.
There are no bunk beds.
Room Options
The following room options may be available, subject to availability when booking:
Shared Female Room – Share a room with another female guest.
Shared Male Room – Share a room with another male guest.
Twin Room – For two guests booking together who prefer separate beds.
Double Room – For two guests booking together who are happy to share a bed.
Sole Occupancy Room – A private room for one guest.
Bathrooms
All bedrooms have private en-suite bathrooms, so you won't need to share bathroom facilities with other rooms.
Bedding & Towels
All bedding and towels are provided by the hotel, so there's no need to bring your own.
Tea and coffee-making facilities are also available in the bedrooms.
Breakfast
Breakfast is included on Tuesday, Wednesday and Thursday mornings.
Breakfast is provided at the hotel before we head out for our walks.
Please let us know about any dietary requirements when booking.
Packed Lunches
Packed lunches are not included in the trip price.
You'll need a packed lunch for each of our three walking days. There are shops in Monmouth where you can purchase supplies before setting off.
We also recommend bringing snacks and a reusable water bottle.
Evening Meals
Evening meals are not included in the trip price.
On Monday evening, we'll aim to arrange a sociable group meal at a local pub or restaurant, giving everyone a chance to get to know one another.
We'll also have opportunities to enjoy dinner together on Tuesday and Wednesday evenings after our days exploring the Forest of Dean and Wye Valley.
Everyone simply pays for their own food and drinks.
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Accommodation & Meals
Included:
3 nights' hotel accommodation at Premier Inn Monmouth
Breakfast on Tuesday, Wednesday and Thursday mornings
Not included:
Packed lunches on Tuesday, Wednesday and Thursday
Evening meals and drinks
Guiding & Support
Included:
Experienced Large Outdoors walking guide throughout the break
3 days of guided walking exploring the Forest of Dean and Wye Valley
Walking routes planned and organised by your guide
Transport & Transfers
Included:
Complimentary collection from Chepstow railway station at 17:00 on Monday, when booked in advance
Transport between the hotel and our walking locations throughout the break
Return transfer to Chepstow railway station on Thursday, if required
Not included:
Travel to your chosen meeting point at the start of the break
Onward travel from Monmouth or Chepstow at the end of the break
Additional Costs & Exclusions
Not included:
Personal travel or activity insurance
Optional activities or excursions not included in the itinerary
Personal purchases and other expenses during the break
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This Forest of Dean & Wye Valley Autumn Walking Break is graded Leisurely.
We'll enjoy three days of guided walking at a relaxed, sociable pace, with plenty of opportunities to stop for photographs, admire the autumn colours and enjoy the scenery.
Our walks are approximately 8–10 miles on Tuesday and Wednesday, and 6–8 miles on Thursday.
Terrain & Conditions
The Forest of Dean and Wye Valley offers a varied landscape of ancient woodland, riverside paths, rolling hills and countryside trails.
We'll follow a mixture of woodland tracks, grassy footpaths, riverside trails and sections of established walking routes, including the Offa's Dyke Path.
Although much of the walking is relatively gentle, there are some climbs and descents, particularly around Symonds Yat Rock and Devil's Pulpit. Paths can be uneven, muddy or slippery, especially after autumn rainfall.
Fitness & Experience
You don't need to be an experienced walker, but you should be comfortable walking up to 10 miles over the course of a day, including some hills and uneven woodland paths.
We'll walk together at a steady pace, allowing time for breaks, photographs and enjoying the surroundings rather than rushing to finish.
A reasonable level of walking fitness and some experience of longer countryside walks will help you get the most from this break.
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Walking Clothing & Footwear
The Forest of Dean and Wye Valley offers a mixture of woodland trails, riverside paths and rolling countryside. As we're visiting in November, paths may be muddy, wet or slippery with fallen leaves.
We recommend bringing:
Comfortable, waterproof walking boots or walking shoes with good grip.
A waterproof jacket and waterproof trousers.
Comfortable walking trousers or leggings.
Warm layers, such as a fleece or insulated jacket.
Walking socks.
A warm hat and gloves for chilly autumn mornings.
An extra warm layer for stops and exposed viewpoints.
What to Carry on Walks
You'll need a comfortable day rucksack for carrying your essentials during our walks.
We suggest packing:
A packed lunch and snacks for each walking day.
A reusable water bottle.
Any personal medication you may need.
A fully charged mobile phone.
A small personal first aid kit.
Sunglasses and sun cream, depending on the weather.
A waterproof cover or dry bag to keep belongings dry.
Clothing for Accommodation
The Premier Inn provides bedding and towels, so there's no need to bring these.
Pack comfortable clothes and footwear for relaxing at the hotel and joining the group for evening meals in Monmouth. There's no dress code.
Trip-Specific Extras
We'll be exploring the Forest of Dean and Wye Valley during autumn, so a few extras may be particularly useful:
A camera or phone for capturing the autumn woodland colours, riverside scenery and views from Symonds Yat and Devil's Pulpit.
A small torch or headtorch, useful during the shorter November days and darker evenings.
Binoculars if you enjoy watching birds and wildlife.
A spare pair of walking socks, particularly useful if conditions are wet.
A waterproof bag for protecting spare clothing and valuables from rain.
Full Kit List
We've put together a useful walking kit list to help you prepare for your holiday.
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Booking Confirmation
Once you've booked, you'll receive a confirmation email with your booking details and our full booking terms.
Deposits & Balance Payments
If you've paid a deposit, we'll automatically email you a reminder when your remaining balance is due. Balances are normally due 12 weeks before departure.
Your Trip WhatsApp Group
Ahead of your trip, we'll invite you to join a dedicated WhatsApp group for your holiday.
It's a great way to say hello to your fellow walkers, ask questions and get to know everyone before you arrive. Most of our guests join us on their own, so it's a nice way to break the ice.
Joining is entirely optional.
Final Details
A couple of days before departure, we'll send you a final reminder with your guide or host's name and contact number, along with any important last-minute information.
Keeping Up to Date
Everything you need to plan your trip, including meeting locations, times, accommodation and travel arrangements, is provided on this page.
We recommend checking back here from time to time before departure, as we'll update the page if any arrangements change. You don't need to wait for your final email to organise your travel.
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Can I join this walking break on my own?
Absolutely! Most people who join Large Outdoors book on their own, so you'll be in good company. Our breaks are designed to be friendly and sociable, with plenty of opportunities to get to know your fellow walkers.
How is this different from your regular Forest of Dean & Wye Valley weekend?
This is an extended three-night midweek break, giving us three full days of walking rather than the two days offered on our regular weekend.
It's also timed for autumn, when the Forest of Dean and Wye Valley are particularly colourful. We'll have more time to explore the woodland, riverside paths and historic landmarks at a relaxed pace.
I've never been on a guided walking break before. Is this suitable?
Yes! Our guide takes care of the routes, transport and arrangements, leaving you free to enjoy the walking and company.
You don't need previous experience of guided walking holidays, but you should be comfortable walking up to 10 miles in a day, including some hills and uneven paths.
Will we see the autumn colours?
Early November is often a lovely time to enjoy the changing colours of the Forest of Dean and Wye Valley, with woodland turning shades of yellow, orange and copper.
However, the timing and intensity of autumn colours vary each year depending on the weather, so we can't guarantee exactly how the trees will look during our visit.
Will we visit Tintern Abbey?
Yes, our planned final-day walk begins around Tintern Abbey and includes views of the historic ruins from the surrounding countryside.
Our itinerary focuses on walking and exploring the landscape, rather than a formal guided tour of the abbey. Entry to the abbey itself is not included.
Can I skip a walk if I don't feel up to it?
Yes, you're welcome to take a day off from walking and enjoy some free time in Monmouth. Just let your guide know in advance.
Please bear in mind that our transport follows the planned walking itinerary, so alternative arrangements may be at your own expense.
Can I come with a friend or partner?
Of course! You're very welcome to book together. We offer double and twin rooms for guests travelling together, as well as shared and sole occupancy options, subject to availability.
Will there be time to explore Monmouth?
Yes. We'll be staying in Monmouth for all three nights, so there'll be opportunities to explore its historic streets, independent shops and cafés.
We'll also aim to enjoy relaxed group meals in local pubs or restaurants during the evenings, although you're welcome to make your own arrangements.
What happens if the weather is poor or the River Wye is flooded?
We normally walk in a range of weather conditions, so come prepared with waterproofs and warm layers.
River levels can rise after heavy rainfall, particularly during autumn. If flooding, strong winds or slippery paths make a planned route unsuitable, your guide will choose an appropriate alternative.
Our priority is to enjoy three good days of walking while keeping everyone safe and comfortable.
Check Dates & Book Your Place
Select a date to check availability, room options and prices.
Upcoming departure dates
Monday 2 - Thursday 5 November 2027
Deposits – Pay a 20% deposit when booking more than 12 weeks before departure. The remaining balance is due 12 weeks before departure.
Questions Before You Book?
Not sure whether this walking holiday is right for you? We're always happy to help with questions about the walks, accommodation or joining us on your own.
Email hello@largeoutdoors.com or get in touch through WhatsApp.