The Charming Chilterns in Spring B&B

Guided Walking Holiday - 5 Nights

– 24-29 April 2022 –  

Ancient woodlands and rolling hills with fantastic views

bluebell woods 2

Next departures:

Key info:


  • Exploring the beautiful countryside, picture postcard villages and rich history of my part of the Chilterns.

  • Spending your evenings in relaxing and comfortable accommodation whilst enjoying the variety of enticing, locally sourced food and drink Berkhamsted has to offer.

  • Walking sections of the Ridgeway National Trail and the Hertfordshire Way.

  • Discovering the secrets of the area with a local, knowledgeable guide.

The Chilterns:

The charming Chilterns are an area of rolling hills just a few miles northwest of London. Despite their proximity to the capital they are beautiful and unspoilt. Mostly woodland and chalk grassland, they are dotted with attractive villages with their traditional brick and flint cottages and medieval churches.  One of the most dramatic features of the area is the chalk escarpment, a ridge running south west to north east, which rises up steeply from the Vale of Aylesbury and slopes gently south east towards London.  Underlying chalk gives rise to clear chalk streams which are important wildlife habitats, supporting some of the country’s most threatened plant and animal species including the water vole and the brown trout.

Join me for guided walks in the Charming Chilterns using the ancient trails through this beautiful countryside. This Area of Outstanding Natural Beauty has been my home since I was a nipper and I am looking forward to sharing my knowledge of its history and wildlife with you.

Map of The Chilterns area supplied by AONB

© Chiltern Conservation Board

Daily Itinerary:

Here is the day-by-day itinerary, click on the day to learn more.

Independent travel to ‘The Kings Arms’ in Berkhamsted. Check-in is from 3pm. We will gather in the Greene Lounge at 18:30 to meet the tour leader for a short briefing before dinner.

Distance: 20.2km/12.5 miles Ascent/ descent: 300m/ 984ft

We start with an introductory circular walk straight from the hotel, through the town and up into the wooded commons around the Ashridge Estate. We stop here for an optional Pub lunch before returning to the hotel via the path next to the Grand Union canal.

Trees at the Ashridge Estate

Our Highlights:

  • Berkhamsted Castle, where the crown of England was passed to Duke William of Normandy following the defeat of King Harold at the Battle of Hastings in 1066.
  • The Ashridge Estate and the impressive Ashridge House. Surrounded by ancient beech woodlands, the house was built as a monastery but later became home to King Henry VIII before being passed to the Earls of Bridgewater.
  • Lunch at the charming village of Little Gaddeston at the Bridgewater Arms.
  • Strolling back to the hotel along the Grand Union Canal. The canal was commissioned and financed by the Third Duke of Bridgewater, Francis Egerton.

Distance: 18.2km/ 11.3 miles  Ascent/ descent: 250m/ 820ft

We will drive to the village of Chipperfield, near Kings Langley. This walk starts high up before descending to the river Chess. We will pass  through some of the chocolate box villages that surround the river before we return to Chipperfield. We can stop for a cheeky drink in The Two Brewers before returning home.

The River Chess

Our Highlights:

  • Passing through the little villages of Chenies, Latimer and Flaunden.
  • The river Chess and its surrounding area which is scenic, rich in wildlife and has a long and fascinating history. Starting high in the Chilterns, the Chess is a classic chalk stream, fed by waters stored deep below in the Chiltern Hills. It is one of the largest chalk rivers that leave the Chiltern Hills destined for the river Thames.

The Rex Cinema: This evening you are free to enjoy the delights of Berkhamsted or, you could opt to go to the cinema (see further information below). Tickets sell out fast so please specify when you pay your balance if you are interested. (costs not included).

Distance: 19.3km/ 12 miles. Ascent/ descent: 250m/ 820ft

We take the train one stop from Berkhamsted to Tring, where we start our circular walk. We will enjoy stunning views all the way to Ivinghoe Beacon where we’ll stop for a picnic lunch. Then we continue through woodland, passing the Bridgewater monument before returning to the station via the charming village of Albury.

The Ridgeway National Trail

Our Highlights:

  • Walking to ‘Ivinghoe Beacon’ along part of the final section of ‘The Ridgeway National Trail’.
  • Albury Nowers nature reserve, home to the Chalk Hill Blue butterfly.
  • Pitstone Hill with its expanding panoramic views over the Vale of Aylesbury all the way to Ivinghoe Beacon where the long-distance Ridgeway path finishes.
  • Walking through ancient beech and oak woodlands.
  • Ashridge monument, dedicated to Frances Eggerton, commonly known as The Canal Duke.

The charming little village of Albury with its village pond and stocks.

Distance: 20.1km/ 12.5 miles. Ascent/ descent: 350m/ 1148ft.

Taking the local bus up the valley we start our walk from the town of Tring. Using the canal towpath, we walk out of Tring and up towards Wendover Woods where we will lunch in the woodland centre. From here we join the Ridgeway National Trail to make our way back to Tring.

Field in front of a hill in the distance

Our Highlights:

  • The Wendover canal, which is an arm of the Grand Union canal, originally used as a feeder to supply water to the main canal – but now this is a beautiful natural walkway.
  • Walking up to Wendover Woods and the highest point in the Chilterns on Haddington Hill.
  • Boddington Hill Iron Age hill fort.
  • Tring Park with views down to Tring Park Mansion which was designed by Sir Christopher Wren in 1685 and is now used as a school for performing arts.

Distance: 8.9km/ 5.5 miles. Ascent/ descent: 230m/ 755ft

Today is departure day. Check-out is at 11.00. After breakfast we drive to the little town of Wendover. From here we will walk up onto Coombe Hill and return through woods and farmland. 

Wendover High Street

Our Highlights:

  • Walking out from the village of Wendover and through a nature reserve with many endemic flowers, through coppiced woodland to arrive at a war memorial / viewpoint from the top of Coombe Hill.
  • Passing the rolling hills, farms and woodlands of the Chilterns.
  • The small town of Wendover with its many pubs, interesting shops (including a chocolatier that also sells ice cream) and restaurants.

Lunch can be taken in Wendover and from here we say goodbye.

Departing frog with suitcase

Please note that if weather conditions are bad, or conditions change locally then it may be necessary to diverge from a part of the programme at short notice.  Every effort however will be made to keep to the advertised programme.


The holiday is offered on a bed and breakfast basis, for the 5-nights. 

Standard double room –  £450 per person for single occupancy


Our Accommodation:

The Kings Arms:  147 High Street, Berkhamsted, Hertfordshire HP4 3HL. 

We will be staying at the historic market town of Berkhamsted, famous for its ruined castle. Our hotel is an 18th-century coaching inn and is situated on the High Street. It is locally owned and run. 

The rooms have been recently refurbished and redecorated and are quiet, comfortable, with en-suite bathroom, tea/ coffee making facilities. There is WIFI throughout, with breakfast in the restaurant from 07:00 each day. Every evening at 18:30 we will meet at the hotel, in the Greene Lounge, named after the locally born author Graham Greene, for drinks and an overview of the following day’s walk before going for dinner.  

Our package includes ‘Standard Double’ rooms and a hearty full ‘a la carte’ breakfast. Click here for the menu. 

For dinners you can either make your own arrangements or asked to be included on a group booking at the hotel or one of the many restaurants in town. 

Parking is at the sister hotel, The Penny Farthing which is 500m further along the high street. Access via St. Johns Well Lane. Please ask in advance if you would like help with your bags. Click here for exact location.


Our Centre:

Sitting in a valley, our centre for the tour is the market town of Berkhamsted.

The town is steeped in history which you will learn more about on the tour. The High Street forms the natural route through and dates back as a pre-roman route through the Chiltern Hills which was known by its old Saxon name Akeman Street. 

Some amenities are as follows:

  • Street Market: Berkhamsted street market starts its stalls just outside our hotel on Saturdays and Wednesdays.  Here you can buy local products including artisan cakes, meats, cheese, bread and so much more.
  • Chemist: Boots the Chemist is 1 minute away but….if you fancy an old-style pharmacy, then turn left out of the hotel and continue to Dickman’s, just past the traffic lights on the right – you won’t miss it!
  • Coffee anyone? We have a Costa and a Nero close by but there are some interesting independent coffee shops, including the very popular ‘Fred and Ginger’ to the right side of the hotel.
  • Post Office: Turn left out of the hotel and walk for 4 minutes – there you have it!
  • Mini-Market / Supermarket: There is a small Tesco 30 seconds walk away from the hotel, or 5 minutes away there is a fully functioning Waitrose or 6 minutes away is a Marks and Spencer food hall.
  • Banks/ATMs: HSBC and Lloyds can be found close by, just turn left from the hotel.  The nearest ATM is outside the small Tesco

Additional Information:

This is not an exhaustive list but highlights the main requirements. Please note, some of the tracks can be muddy after prolonged rain.

Essential Items
  • Waterproof walking-boots. Properly worn in and which provide good grip
  • Waterproof jacket and over trousers
  • Rucksack
  • Gloves and a warm hat
  • Water bottle – 1 ltr
  • Sunscreen and sun hat
  • Several layers of clothing – which can be added or removed as required

Recommended items
  • Personal first aid kit
  • Sit Mat
  • Specialist walking socks

Optional items
  • Gaiters – these can be useful after rain
  • Blister kit
  • Flask for hot drinks
  • Walking poles (can be useful)

The hotel address is: The Kings Arms. 147 High Street, Berkhamsted, Hertfordshire HP4 3HL.

The Kings Arms, Berkhamsted

By train: the nearest mainline railway station is in Berkhamsted and is about a six-minute walk from our hotel. The station is 28 miles north west of London Euston on the West Coast Main Line. If you require transport from here there is a taxi firm based outside the station.

By car: (1) from the M25 take the A41 (junction 20), West towards Aylesbury. Continue for approximately 8 miles and exit at the Chesham interchange (A416). Turn left at the roundabout (pass over the dual carriageway), then turn left again towards Berkhamsted town centre. After 2 minutes, the road veers sharp right at some traffic lights, downhill onto Kings Road. Continue down and stay on the left side at the crossroads traffic lights and turn left onto the High Street. Follow the High Street and take the next road on the right (St John’s Well Lane) at a small roundabout. Follow the road around to the right, the Penny Farthing car park is on the right.

By car: (2) from the M1 take junction 8 on the A414 towards Hemel Hempstead. Continue all the way down to the Plough roundabout. Take the A4146 towards Hemel Hempstead train station, at the small roundabout, turn right on the A4251 (the old London Road) and continue to Berkhamsted.


The Kings Arms does not have a car park but their sister hotel’s parking can be used free of charge at the Penny Farthing which is only 500m further along the high street.

Directions to the car park:

The Penny Farthing Hotel - Google Maps

The Rex has been described as “Britain’s most beautiful cinema”. The building is Grade II listed, and in the art deco style. It is quite an experience. The seats upstairs are traditional cinema style but more comfortable. Downstairs they are cabaret style where snacks and drinks are served to you at the table.


It may be possible to have a group visit and watch a film during your holiday. If you would like to have this unique Berkhamsted experience then please advise upon booking that you are interested and we will keep you informed of prices and film titles. 

Watch The Rex Cinema History You Tube video

Four walks are covered by the following maps. I have copies of these maps to show you each evening in our briefings.

1:25:000. OS Explorer Map 181 for Berkhamsted – Ashridge – Wendover.

1:25:000. OS Explorer Maps: 171 &172 for Chipperfield & Chess Valley