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The 10 best walks in the Chiltern Hills – all starting and ending at a characterful pub

Chilterns best walks uk england start end hike pub character food drink summer 2022 - Getty
Chilterns best walks uk england start end hike pub character food drink summer 2022 - Getty

For keen walkers, the Chilterns offer the promise of an adventure playground on the doorstep of the nation’s capital, just an hour from central London. They are also a haven for flourishing wildlife populations including muntjac and fallow deer, badgers, exotic birds and butterflies (including a healthy population of the endangered Duke of Burgundy) and rare species of wildflowers.

Around 320 square miles have been designated as an Area of Outstanding Natural Beauty (AONB) with a network of more than 2,000 miles of footpaths stretching from beyond Dunstable in Bedfordshire (north east) to Goring in Oxfordshire (south west) as well as parts of Hertfordshire and a healthy chunk of Buckinghamshire in its central section.

Layers of history are revealed in the area’s long barrows (Neolithic), round barrows (Bronze Age) and sections of both the Ridgeway and the Icknield Way, two of the most ancient tracks in the British Isles. The Ashridge Estate, run by the National Trust since 1926, is a 5,000-acre haven of woodlands stretching from Berkhamstead to Ivinghoe Beacon in the north. Climb the Bridgewater Monument (open at weekends from April to October) for a stupendous view over the entire area.

The Chilterns are home to some quintessentially English pubs, and all those selected here have been picked for their great service, excellent food and hearty walker-friendly welcome.

1. Stoke Row & Berins Hill

6½ miles

A walk with the promise of a meal and a drink at one of the most atmospheric gourmet country pubs in the area, where Kate Winslet celebrated her first marriage. The trail takes in woodland paths, rolling countryside and some sweeping views from Berins Hill over Oxfordshire. Don’t miss the Maharaja’s Well in Stoke Row, gifted to the village by the Maharaja of Benares in the mid-19th century.

Follow the trail north behind the pub skirting Bush Wood and Oakingham Bottom before joining English Lane. At English Farm, head west across Ipsden Heath (Woodland Trust) and on to Well Place. Then follow the Chilterns Way to Berins Hill before crossing the valley at Yewtree Brow and heading back east to the pub.

Start/finish

The Crooked Billet, Stoke Row (thecrookedbillet.co.uk)

Explorer map 171

OS Grid Reference SP683841


2. Ivinghoe Beacon and Gallows Hill

8 miles

This is a walk among some of the best views in the Chilterns – as you traverse a chalk escarpment with the wind in your hair. The Ivinghoe Hills form the northernmost finger of the Chiltern uplands, crossed by both the Icknield Way and the Ridgeway (in use for more than 5,000 years). Don’t miss the climb up the 172 steps to the top of the Bridgewater Monument at the Ashridge Estate.

Follow the road north from the Greyhound before taking the bridleway on your left up through the woods and along the steep escarpment to the Bridgewater monument. Follow the scarp line due north to Ivinghoe Beacon (the start/finish of The Ridgeway) and Gallows Hill to the east. On the return leg, take the south-western branch of the Icknield Way Trail and a short section of road back into Aldbury.

Chilterns best walks uk england start end hike pub food drink Ivinghoe summer 2022 - Getty
Chilterns best walks uk england start end hike pub food drink Ivinghoe summer 2022 - Getty

Start/finish

Greyhound Inn, Aldbury (greyhoundaldbury.co.uk)

Explorer map 181

OS Grid Reference SP964125


3. Maharaja’s and Grim’s Ditch

3½ miles

A walk to delight history buffs, this trail follows the chalk escarpment through Bull’s Wood and along the Icknield Way, through countryside that was once part of the grounds of Tring House. The latter is famous for the obelisk built to commemorate the secret meetings between Charles II and his lover Nell Gwyn in the nearby summerhouse. The return leg follows Grim’s Ditch, an Iron Age earthwork.

From the pub, locate the path heading north west along the eastern boundary of Bull’s Wood to the obelisk and the summerhouse. Retrace your footsteps briefly before following the Icknield Way south west along the escarpment with great views over Tring Park and continue to Hastoe. Return along Grim’s Ditch and back around to the pub.

Tring Park Chilterns best walks uk england start end hike pub food drink summer 2022 - Getty
Tring Park Chilterns best walks uk england start end hike pub food drink summer 2022 - Getty

Start/finish

The Greyhound, Wigginton (greyhoundtring.co.uk)

Explorer map 181

OS Grid Reference SP938101


4. Pulpit Hill and Whiteleaf Hill

4 miles

Although relatively short, this route takes in stunning scenery, prehistoric burial mounds and picturesque villages. Whiteleaf Hill has a Neolithic long barrow and two Bronze Age round barrows, while above the beech forest on Pulpit Hill is a hill fort with some great views looking north west. Grangelands Nature Reserve, meanwhile, is a haven for wildflowers.

From The Plough (expect celebrities and maybe the former Prime Minister David Cameron, who famously forgot to scoop up his daughter Nancy after a visit here), follow the bridleway north through Grangelands Nature Reserve and up on to Pulpit Hill. Then take the Ridgeway and the North Bucks Way to Great Kimble before heading south west through the villages of Askett, Monks Risborough and Whiteleaf before the final yomp over Whiteleaf Hill back to the pub.

Chilterns best walks uk england start end hike pub food drink summer 2022 Pulpit Hill - Getty
Chilterns best walks uk england start end hike pub food drink summer 2022 Pulpit Hill - Getty

Start/finish

The Plough at Cadsden (ploughatcadsden.co.uk)

Explorer map 181

OS Grid Reference SP824047


5. Three Villages Pub Crawl

3½ miles

This is a starry route, with three of the loveliest villages in the Chilterns (Skirmett, Fingest and Turville), three of the best watering holes (The Frog, The Chequers and The Bull and Butcher), the Cobstone Windmill (which featured in the film Chitty Chitty Bang Bang), the set of the Vicar of Dibley (Turville) and some fine old medieval churches. It’s steep in places, but on the assumption you’ll be taking advantage of the hostelries along the way, the distance covered is not too taxing.

Follow the Chiltern Way east opposite the Frog and loop around through Adams Wood, up over the hill and down across the valley into Fingest. Continue along the Chiltern Way through Turville before leaving it and heading south, crossing Dolesden Lane into Great Wood. Follow in a loop around back to Skirmett. The final leg has the best views of the Turville Windmill to the north.

Chilterns best walks uk england start end hike pub food drink summer 2022 Charming Turville - Getty
Chilterns best walks uk england start end hike pub food drink summer 2022 Charming Turville - Getty

Start/finish

The Frog at Skirmett (thefrogatskirmett.co.uk)

Explorer map 171

OS Grid Reference SU775902


6. Warburg Nature Reserve and Stonor Park

9 miles

A challenging walk through both Warburg Nature Reserve, a Site of Special Scientific Interest (SSSI), and Stonor Park. High up in the Chiltern Hills, the Warburg Reserve (a site of ancient woodlands and grasslands) has its own microclimate and is renowned for birds, butterflies and wildflowers, particularly orchids. Meanwhile Stonor House, home to the Stonor family for over 800 years, has a fascinating history to match (see stonor.com for opening times). This route passes through the Deer Park in front of the house.

Turn left out of the pub and follow the road for 100 yards to a footpath through trees on your left. After 400 yards take the left-hand trail and loop through Warburg NR and south along the valley to Bix Bottom and Middle Assendon. Head directly north to Coxlease Farm before looping around Stonor Deer Park. The route back takes you through Stonor itself and along the Chiltern Way back to the pub.

Stonor House Chilterns best walks uk england start end hike pub food drink summer 2022 - Getty
Stonor House Chilterns best walks uk england start end hike pub food drink summer 2022 - Getty

Start/finish

Five Horseshoes (thefivehorseshoes.co.uk)

Explorer map 171

OS Grid Reference SU712890


7. Ashridge Park and Frithsden Beeches

6 miles

This walker-friendly pub is the perfect base for exploring the forested finger of land that takes in both the ancient pollarded trees of Frithsden Beeches as well as Ashridge Park – famous for its long drive from Ashridge House (now a business school) to the Bridgewater Monument which was laid out by Capability Brown and Humphry Repton.

From the pub follow the footpath south west before turning right (north west) when you meet the Hertfordshire Way. Take the detour through Frithsden Beeches and continue to Berkhamsted Common. Follow the Chiltern Way north across Ashridge Park looping back past the main house and along a delightful stretch of quiet country road back to the pub.

Bluebells Ashridge Park Chilterns best walks uk england start end hike pub food drink summer 2022 - Getty
Bluebells Ashridge Park Chilterns best walks uk england start end hike pub food drink summer 2022 - Getty

Start/finish

Alford Arms (alfordarmsfrithsden.co.uk)

Explorer map 181

OS Grid Reference: TL016099


8. Cholesbury Hill Fort

5 miles

Recommended by Chilterns AONB (see chilternsaonb.org for other walk suggestions), this walk starts in the ancient hilltop village of Cholesbury and follows rights of way across the open common into beech woodland. The route passes Cholesbury Camp, an Iron Age hill fort containing a rebuilt Norman church, one of only two in the country to be built inside a hill fort.

Head north east from the pub to Tring Farm before turning north west for a long, straight leg through Scrubs Wood. When you meet Grim’s Ditch, head back south along the Chiltern Way and across Buckland Common to explore the hill fort and then back to the pub.

Start/finish

Full Moon Pub (fullmoonpub.info)

Explorer map 181

OS Grid Reference: SU936068


9. Rupert Brooke Walk, Parslow’s Hillock

5 miles

Famous for his love of the English countryside, the poet Rupert Brooke walked regularly in the Chilterns and enjoyed a pint or two of ale at the Pink and Lily pub above Princes Risborough. This route explores the mixed woodland to the north east, which he regularly crossed on his way to the pub from Wendover station.

Follow the bridleway north through Hillock Wood with the escarpment of Windsor Hill to your left. At the road, turn left for 200 yards and take the next pathway on the right zigzagging along the edges of Kingfield Wood and Sergeant’s Wood. On the return, follow the mix of paths and short stretches of country road to Hampden House and back along the Chiltern Way to the pub.

Church Street Princes Risborough Chilterns best walks uk england start end hike pub food drink summer 2022 - Getty
Church Street Princes Risborough Chilterns best walks uk england start end hike pub food drink summer 2022 - Getty

Start/finish

The Pink & Lily (pink-lily.com)

Explorer map 181

OS Grid Reference: SP826019


10. Hambleden Explorer

4½ miles

Hambleden, nestling in a wooded fold of the Chiltern Hills, is one of those impossibly peaceful villages right out of central casting. The problem is dragging yourself away. If you manage it, the surrounding countryside is equally sublime and this walk through the woods to the west will make a meal in the Stag & Huntsman all the more delicious.

Head south into Ridge Wood and up on to Reservoir Hill before walking north into Great Wood. When the trail meets Shakespeare’s Way (shakespearesway.org), follow it down through the valley and back to the pub.

Chocolate box Hambleden Chilterns best walks uk england start end hike pub food drink summer 2022 - Getty
Chocolate box Hambleden Chilterns best walks uk england start end hike pub food drink summer 2022 - Getty

Start/finish

Stag & Huntsman (thestagandhuntsman.co.uk)

Explorer map 171

OS Grid Reference: SU784865

For more inspiration on where to stay, read Telegraph Travel guide to the best hotels in the Chilterns

This article is kept updated with the latest information.