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

Telegraph

22-02-2025

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 a Natural Landscapes (formerly Areas 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
Oxfordshire
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.
2. Ivinghoe Beacon and Gallows Hill
Buckinghamshire
This is a walk amongst 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.
3. Tring Park & Grim's Ditch
Hertfordshire
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.
4. Pulpit Hill and Whiteleaf Hill
Buckinghamshire
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 from nearby Chequers), 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.
5. Three Villages Pub Crawl
Buckinghamshire & Oxfordshire
This is a starry route, with three of the loveliest villages in the Chilterns (Fingest, Turville and Skirmett), two of the best watering holes (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 the distance covered is not too taxing.
From The Chequers, follow 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 with fabulous views of the famous Cobstone Windmill on Turville Hill to the north. From Skirmett head north-east through Adams Wood, up over the hill and back into Fingest.
6. Warburg Nature Reserve and Stonor Park
Oxfordshire
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.
7. Ashridge Park and Frithsden Beeches
Hertfordshire
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.
8. Cholesbury Hill Fort
Buckinghamshire
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.
9. Rupert Brooke Walk, Parslow's Hillock
Buckinghamshire
Famous for his love of the English countryside, the poet Rupert Brooke walked regularly in the Chilterns. This route explores the woodland to the east of Prince's Risborough which he regularly crossed on the way to Wendover station. Turn right out of the pub and then first left along Kiln Lane. At the end follow the bridleway and then the Chiltern Way along Grim's Ditch north into Hillock's Wood and then east to Hampden House. The Hampden family owned the site from before the Norman Conquest and lived in the house until 1938. Follow the maze of pathways that loop back round across Hampden Common and through Monkton Wood to Lacey Green.
10. Hambleden Explorer
Buckinghamshire
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.
For more inspiration on where to stay, read Telegraph Travel guide to the best hotels in the Chilterns