Spend a weekend in the Chilterns

Lauren Hill

Senior Contributor

An Area of Outstanding Natural Beauty and within easy reach of the capital, the Chilterns makes for an enticing escape where market towns, villages, vineyards and stately homes lie amidst verdant landscape. From setting out on walking trails to discovering this part of the country’s artisanal produce, here’s how to make the most of a weekend here.

Towns and villages

Many people start their exploration of the area by getting to know the region’s market towns and villages. Henley-on-Thames draws people from far and wide each summer for its famous Royal Regatta and the Festival of Music and Arts. Clustered on the edge of the River Thames, the small town is made up of historic streets and greenery-backed riverside walks with independent artisanal shops and inviting drinking and dining spots, as well as points of interest such as the Old Fire Station Gallery and River & Rowing Museum. You can follow the Henley Ale Trail and get out onto the water by hiring a boat or joining a scheduled riverboat trip. Hambleden Valley is three miles from Henley and the setting for several of the idyllic villages featured in films and TV series such as Midsomer Murders. Watlington in Oxfordshire is another site made famous by the detective drama — the Ridgeway National Trail and Oxfordshire Way are just half a mile from here and there are a number of speciality shops selling produce such as cheese and wine to drop into.

Chilterns trails

As an Area of Outstanding Natural Beauty, the Chilterns is crisscrossed with a network of trails for walking and cycling through valleys and woodland and between small villages. The circular Chiltern Way runs across around 134 miles of this area spanning Buckinghamshire, Oxfordshire, Hertfordshire and Bedfordshire, with three extra extensions offering alternative routes. Since it passes through a number of towns and villages including Hemel Hempstead and Chalfont St. Giles, you can pick the epic trail up from any number of different points. Walkers can also take on the Thames Path National Trail following the river as it passes the Chiltern Hills, a nationally protected area of countryside encompassing woodland, grassland and cultivated fields. The Chiltern Walking Festival takes place each year to introduce people to some of these bucolic walkways. Cyclists can instead follow the 170-mile signposted Chilterns Cycleway, which passes between towns and villages, taking in a number of country pubs. 

Food and drink

The Chilterns is largely characterised by its landscape and agriculture it’s shaped by. Since the Romans first planted vines on the region’s slopes, vineyards have thrived here, along with breweries and more recent artisanal arrivals like Puddingstone Distilllery, the creators of Campfire Gin. Several of these producers along with some of the farms welcome visitors in, with more products to be found in the historic market towns and small villages home to restaurants, pubs and artisanal shops. Visit Chiltern Valley Winery & Brewery, which lies within the Hambleden Valley, for tours and tastings, the cookery school and shop, and seek out the Puddingstone Distillery outside Tring for a gin tasting experience. Take a gastronomic cruise down the river from Henley-on-Thames, visit celebrated riverside pub The Little Angel, stop by the farmers’ market and book a table at the recently opened restaurant with rooms, Crockers Henley. Many more culinary hotpots are dotted throughout Amersham and Marlow, including the Hand and Flowers, which was the first pub in Britain to earn two Michelin stars.

Places to visit

Across its towns, villages and countryside, the Chilterns has an abundance of sites to visit. By seeking out the historic market town of Thame, you can take a self-guided Midsomer Murders Trail leading you between filming locations around the area. And by finding your way to the Chilterns ridges, you can then visit a number of windmills, such as Pitstone Windmill, which is one of the oldest in Britain; Frogmore Paper Mill, which is the oldest mechanised paper mill in the world; and Redbournbury Water Mill & Bakery, which is the last working mill on the River Ver. For more insight into the area, head to the Roald Dahl Museum in Great Missenden—the author lived in the Chilterns for over 40 years—Henley’s River & Rowing Museum giving insight into rowing and the River Thames, and Amersham Museum, which houses a collection of objects relating to local crafts. Several stately homes are also open to the public. You can see inside Hughenden Manor, which was home to Queen Victoria’s favourite Prime Minister, Benjamin Disraeli, and the base for a secret map-making organisation during the Second World War, and visit the historic home turned luxury hotel Cliveden House — either visit this National Trust estate and gardens by day or book a stay at the five-star hotel for the full experience.

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