A Walking Holiday in Swanage and Dorset 2027
Saturday, October 10th, 2026
Date: 16th – 20th June 2027
Base Location: Swanage, Dorset
Price: £80
Overview: A four day holiday of walking and community in June 2027, based in the Victorian seaside town of Swanage, the county of Dorset and the Jurassic Coast. Picture above; approaching Lulworth Cove.
This trip features a steam train ride to Corfe Castle to start one of the walks, across stunning panoramic view scenery to reach Lulworth Cove for our ‘middle day’ walk.
The first day’s linear walk is from Worth Matravers, along the coastal path back to Swanage, via Anvil Point Lighthouse, Durlston Head and Peveril Point.
And Monday’s circular walk is from our base in Swanage to Old Harry Rocks, where seals and dolphins are often spotted, then refreshments in Studland before returning to Swanage via an inland cross country path which retains the views over the coast.
There’s also no reason why more modest walkers shouldn’t skip the middle days’ walk and do tourism instead. With three walks in three days, some participants may be wise to have a rest day in the middle of the three days. …or take the shorter, 5 mile option (see below).
Please Note: As Dorset’s most spectacular walks are its coastal paths, two of the three days’ walks are linear routes, rather than circular routes, for which we will need to get taxis either there or back. We will arrange taxi sharing in groups of four, if not seven, to share the cost. Taxi prices in the area are pretty reasonable.

You’ll need to arrange your own accommodation for the Friday, Saturday and Sunday nights.

It doesn’t really matter what time you arrive in Swanage on the Friday night, but if you’re arriving early enough you can rendezvous to dine and socialize with those from the group who have already arrived, should you wish to.
I’ll be around from 6:00 pm until at least 9:00 pm.
Start Time: 10:30 am
Meet Point: Swanage Railway, Swanage BH19 1HB. (Meeting one lady at Worth Matravers, Swanage BH19 3LE)
Distance: 6.5 miles
Parking: We’ll be getting shared taxis from the centre of Swanage to Worth Matravers.
Our first walk is a linear coastal path from the village of Worth Matravers back into Swanage.

Worth Matravers.

Priest’s Way.





Anvil Point Lighthouse.

Durlston Head.



Peveril Point.
Start Time: 9:45 am
Meet Point: Swanage Railway, Swanage BH19 1HB
Distance: 5 miles or 10 miles
Parking: As we’ll be meeting in Swanage you’ll already be parked. 🙂
Please note that this is a linear walk. We will need to get taxis back from Lulworth Cove to Swanage, so we will arrange taxi sharing in groups of four, if not seven, to share the cost.
For this walk we’ll meet at Swanage Railway Station, a heritage railway with diesel and steam locomotives, and travel together to the start point for the walk at Corfe Castle. The train journey is £14. If you would rather drive to Corfe Castle you can, and park at Castle View Visitor Centre, meeting the group at 10:25 am. (If you do this, after the walk instead of getting a taxi back to Swanage from Lulworth Cove, you’ll get a taxi back from Lulworth Cove to Corfe Castle to collect your car).
You Choose: I’m giving you the option of doing this walk as a five mile walk, and getting transportation to the end point at Lulworth Cove, because the full walk to Lulworth Cove is ten miles and has a steep 41% incline hill at the end. Some stronger walkers won’t be bothered by this, but for those who would rather stop after five miles you can stop at Whiteway Car Park, also known as Lulworth Range Car Park, where we’ll have a taxi arranged to take you to Lulworth Cove (you might have to wait a short while).
For those who do choose the 5 mile option, while you’re in Lulworth Cove waiting for the remainder of the group to finish the walk, you could walk to Durdle Door and back. It’s just over a mile each way, and the coastal path is clearly marked and very obvious, with tourists walking in both directions marking it out.




As we start our walk we can turn and look back on Corfe Castle.


















Lulworth Cove.




West Lulworth Village.
Start Time: 10:30am
Meet Point: Swanage Railway, Swanage BH19 1HB
Distance: 6 miles
Parking: As this walk starts in Swanage you’ll already be parked! 🙂
For this walk we’ll also start by meeting outside the Swanage Railway Station, as we did on day two, and this walk then takes us along the beach front, up the coast and on to Old Harry Rocks.
Then we’ll continue to Studland and refreshments at The Bankes Arms, which has great views from it’s beer garden across Studland Bay.
Finally, we’ll take our last leg of the last walk back across country to Swanage, on a route which, whilst inland, still allows us to see the coast view.




Old Harry Rocks.



The Bankes Arms pub at Studland has tremendous views across the bay.

This video shows Lulworth Cove, the ‘finishing line’ of our middle day walk.
This video shows the resort charm of Swanage, where we’ll be based.
Refunds cannot be given except on a first come basis if the full capacity of the event is reached AND someone from the Waitlist pays for the event.
This is an inclusive, boundaries respecting group. Participants must act in accordance with this at all times. Failure to do so will result in instant removal from the event and group without refund.
Don’t book any accommodation before you’ve confirmed your place with me.
You can call me on 07758 351 527.
I look forward to seeing you there,
James

A Walking Holiday in the North York Moors
Saturday, October 10th, 2026
Date: 19th – 23rd May 2027
Base Location: Skipton, North Yorkshire
Price: £80
Overview: A four day walking and community holiday in May 2027 that will outright spoil us with a smorgasbord of special visits, including the famous Bolton Abbey, the famous Malham Cove, the even more famous ‘Brontë Country’ village of Haworth, which inspired Wuthering Heights alongside the South Pennine hills which it sits high in – and a day in Knaresborough, dubbed Yorkshire’s own Little Venice.
Malham Cove is a spectacular, 70m high curved limestone formation that was formed by a waterfall carrying meltwater from glaciers at the end of the last Ice Age more than 12,000 years ago. It’s also where they filmed a Harry Potter scene from the Deathly Hallows Part I.
We will have some flxibility as to which day which do which trip, according to the forecast. For example, for activities such as punting on the river we’ll prioritise the sun.
You’ll need to arrange your own accommodation for the Wednesday, Thursday, Friday and Saturday nights.
It doesn’t really matter what time you arrive in Skipton on the Wednesday night, but if you’re arriving early enough you can rendezvous to dine and socialize with those from the group who have already arrived, should you wish to.
I’ll be around from 7:00 pm until at least 9:00 pm.
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A Long Weekend in Broadway and the Cotswolds
Saturday, October 10th, 2026
Date: 15th – 18th April 2027
Base Location: Broadway, Worcestershire
Price: £60
Overview: A long weekend of walking and community in the Cotswolds, based in the famous Worcestershire town of Broadway, and including the historic towns of Chipping Camden and Stow-on-the-Wold, and ending with a morning walk to a remote small quintessential Cotswolds village.
Start Time: 10:30am
Meet Point: By the War Memorial, The Green, High Street, Broadway WR12 7AA
Distance: 7.5 miles
Parking: We’ll already be based in the village, of course, but for those with accommodation outside of Broadway there are two public car parks, both about 700 metres, 7 minutes walk, from our meeting point at the War Memorial:
For both of these, 10 hours = £4, and both are open Mon-Sun 8:00 am to 6:00 pm. I recommend parking at the Shear House Car Park on Leamington Road, as the walk from there takes you down the beautiful High Street, so that can be considered the start of your walk to take in the sights.
The Saturday walk will be from the village of Broadway.
Broadway is famous for its attractive main street, the High Street, with its many beautiful buildings constructed in the mellow local stone. The village sits beneath the main ridge of the Cotswold Hills, providing this stunning backdrop.



This walk takes us along the Cotswold Way National Trail as a basis for visiting three villages of Stanton, Laverton and Buckland to the South.
There are a lot of great views on this route and some woodland to enjoy, too.
Stanton:

Laverton:

Buckland:

After the walk, our official tourist activity will be to visit Broadway Tower, a seven minute (4 mile) drive, but this is optional – spend the rest of the day however you wish to.
A Weekend in Cirencester and The Cotswolds for New Year
Saturday, October 10th, 2026
Date: 1st – 3rd January 2027
Base Location: Cirencester, Gloucestershire
Price: £45
Overview: A weekend of walking and community in New Year January 2027, based in the historic Gloucestershire town of Cirencester, and the Cotswolds, including the beautiful town of Painswick and the nearby Cirencester Park.
The area you’ll get very familiar with in Cirencester is Market Place (below), which is boarded on one side by the Church of St John Baptist, which is closer in stature and majesty to a cathedral than a regular church.
This is the centre of our ‘Base Camp’ Cirencester, and where we’ll meet for Sunday’s walk.

As it’s the first weekend of January the municipal Christmas decorations will still be up, too, and the town of Cirencester takes pride in its seasonal festivities.

The Saturday is a 7 mile walk from Painswick, known as ‘The Queen of the Cotswolds’, to Painswick Beacon. Painswick is one of the finest and best-preserved Cotswold settlements.

The Sunday starts (after breakfast) with a 6.5 mile walk round the glorious Cirencester Park, just five minutes’ walk from the Parish Church of St John Baptist, conveniently allowing us to start our second day walk from the town centre.

You’ll need to arrange your own accommodation for the Friday and Saturday nights.
Arrival in Cirencester on the 1st January is pretty flexible; it doesn’t really matter what time you get here.
But if you’re arriving early enough you can rendezvous to dine and socialize with those from the group who have already arrived, should you wish to, and celebrate New Year’s Day together.
I’ll be around from 7:00 pm until at least 9:00 pm. We’ll probably gather at The Kings Head Hotel on Market Place, Cirencester, GL7 2NR.


Christmas decorations on Black Jack Street.

Start Time: 10:30am
Meet Point: The Lych Gate entrance (pictured below) to St Marys Church, 3 New Street, Painswick, GL6 6XH
Distance: 7 miles
Parking: Stamages Lane Car Park (address: Stamage’s Lane, Painswick, GL6 6UZ) is 100 metres South down the hill from the Lych Gate of St Mary’s Church. There are a few on street parking spaces (with time restrictions); outside the Town Hall in Victoria Street and St Mary’s Street.

Painswick Beacon offers perhaps the best 360 degree panoramic views of the Cotswolds.
We’ll be walking to the Beacon from the town of Painswick and the famous Yew Tree lined path of St Mary’s Church.
First we go through the town’s Cotswold stone buildings and out into the countryside to meet up with The Cotswold Way.
Our return route is via Damsel’s Mill and the path alongside Painswick Stream, the Wysis Way.


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And return back to the Lych Gate and St Mary’s Church.

For those who are of a mind to, if there’s time you might like to detour after lunch to visit nearby Gloucester, with it’s cathedral next door to the The House of The Tailor of Gloucester, based on Beatrix Potter’s book.
Gloucester Cathedral was also used for filing the corridors of Hogwarts in the Harry Potter movies.

Start Time: 10:30am
Meet Point: Outside the Church of St John Baptist, Market Place, Cirencester
Distance: 6.5 miles
Parking: As we’ll already be in Cirencester we’ll already be parked!
Cirencester Park, and The Bathurst Estate, is right on our doorstep, so we can meet outside the big church in Market Place and stroll to the Cecily Hill Gates entrance to the park.
The park itself includes The Broad Avenue, a tree-lined boulevard of several miles, plus many side turns, so more than enough for us to enjoy a leisurely walk of around 6.5 miles including the ‘there and back’ from Market Place to Park Street.
Cecily Hill (road) also includes some beautiful historic buildings.
Although there is now an entrance fee for the park to the general public, you won’t need to pay this, it will be paid for you.



This photograph shows an aerial view of The Broad Avenue in Cirencester Park.

The walk back takes us right into the view of Cirencester church.

Video
This short video will give you a great insight into Cirencester Park and The Bathurst Estate.
After lunch, to start the journey home is the opportunity for you to take a route that drives through – or even stops at – nearby Bibury, possibly the most photographed village in the world.
Arlington Row, Bibury (below), is certainly the world’s most photographed cottages.
We walked from Bibury on our January 2026 trip to the Cotswolds, so we know the area quite well.


In addition to Cirencester Park, if you have a few minutes and wish to take a stroll, the Abbey Grounds Park is perfect.
It is right in the centre of town, the far side of St John Baptist Church in Market Place, and will give either a few minutes walk, or a full mile walk if you wish to walk the full triangle of its perimeter.
This area includes an offshoot of the River Churn.


For snacks, self-catering and packed lunch filling there’s an M&S Simply Food less than 300 metres along the street from St John Baptist Church and Market Place.
There’s also a Tesco Express within 250 metres from the church, down Cricklade Street.
Refunds cannot be given except on a first come basis if the full capacity of the event is reached AND someone from the Waitlist pays for the event.
This is an inclusive, boundaries respecting group. Participants must act in accordance with this at all times. Failure to do so will result in instant removal from the event and group without refund.
Don’t book any accommodation before you’ve confirmed your place with me.
You can call me on 07758 351 527.
I look forward to seeing you there,
James
