Cranbrook & Sissinghurst, the hidden gems of Kent

Nestled within the picturesque countryside of the High Weald of Kent, England, two hidden gems await those who seek a blend of historical charm and natural beauty. Cranbrook and Sissinghurst, neighbouring destinations, offer visitors a delightful journey through time and space, with their rich heritage, quaint architecture, and enchanting gardens. In this itinerary, we will explore the unique allure of these two destinations and why they are a must-visit for anyone seeking an escape from the hustle and bustle of everyday life.

Top Things to do in Cranbrook, Kent

DAY 1 – Morning

Stepping into Cranbrook is like taking a journey back in time. This charming market town is known for its preserved medieval layout, complete with cobbled streets and historic buildings that whisper tales of centuries past. The centrepiece of Cranbrook is the Union Windmill, a beautifully restored smock mill that stands as a testament to the town’s agricultural heritage. Visitors can learn about the town’s history at the Cranbrook Museum, which offers insights into everything from the Iron Age to the Victorian era. Admire the paintings from the ‘Cranbrook Colony’ a group of artists who settled in the area from 1853 onwards and were inspired by seventeenth-century Dutch and Flemish painters. Their works were mainly romanticized views of the countryside and sentimental images of bucolic simplicity, which became a popular and had many imitators including William Henry Knight.

Cranbrook’s architecture is a true highlight, with timber-framed buildings lining the streets, some of which date back to the 15th century. St. Dunstan’s Church, often referred to as the Cathedrale of the Weald, is a magnificent example of Perpendicular Gothic architecture and dominates the skyline with its elegant tower.

To learn more about the history of the town you can also take a self-guided tour around Cranbrook.

Cranbrook museum from the front

DAY 1 – Lunch

There are many cafés to pick from in Cranbrook, for your first lunch we recommend Arthur’s (could be the most dog friendly café in Kent), where you can snack on fresh wraps, sandwiches or homemade pastries and cakes. The Wendy House specialises in cakes with some delicious lunch options like their popular salad bowls. Food for Thought, is a no fuss café where you can order a very British jacket potato or ploughman’s lunch for example (this one is for our international visitors, but we still love them!).

Shopping in Cranbrook

DAY  1 – Afternoon

Cranbrook is full of independent shops, browse the boutiques along the quaint High Street overlooked by the iconic Union Windmill. Support a good cause by shopping at the Glasshouse plant shop, a social enterprise offering second chance to women prisoners reaching the end of their prison sentence through horticulture. Oast & Rye is based in one of the oldest buildings in Cranbrook and offers sustainable candles and fragrances. Duck and Dog is a home & lifestyle store offering a new take on country chic. Maisie K.  is a elegantly curated (and colour coordinated) ladies fashion boutique.  Be sure to visit Blighty’s, named after a humorous weekly magazine which was issued to British troops during the First World War, for your souvenir shopping. The shop owners pride themselves in offering British made goods.

DAY 1 – Dinner

There is a diverse range of dinner option in Cranbrook, Kypseli is an authentic Greek Taverna while Cloudberry (open select days) serves British cuisine with a seasonal changing menu. In the United Kingdom, your will find some delicious Indian cuisine. After their success in surrounding locations, Jumeira have opened another restaurant in the heart of Cranbrook.

The George Hotel also have a pub offering of both food and drinks. If you’d like to try some local beer, Larkin’s Alehouse is the place to be in town.

For an after dinner treat check what’s on at the Queen’s Hall  from comedy to cinema and concert, there is something for everyone.

Find out what Sissinghurst Garden is Famous for.

DAY 2 – Morning

A short journey from Cranbrook takes you to Sissinghurst Castle & Gardens (National Trust Property), a world-renowned destination for garden enthusiasts. The Sissinghurst Castle & Gardens, designed by Vita Sackville-West and her husband Harold Nicolson, are a masterpiece of horticultural design. Divided into distinct “rooms,” each with its own theme and plantings, the gardens offer a captivating experience that changes with the seasons. From the vibrant colours of the Rose Garden to the tranquil serenity of the White Garden, Sissinghurst’s gardens are a true feast for the senses.

Beyond its gardens, Sissinghurst Castle itself is a historic treasure. The tower, a remnant of a medieval manor, offers panoramic views of the surrounding Kentish landscape. Visitors can explore the castle’s rooms, which are filled with art, books, and memorabilia that provide insight into the lives of its former occupants. The property is now owned by the National Trust and both employees and volunteers work hard to maintain this local gem.

DAY 2 – Lunch

After your visit to the castle and gardens you can enjoy a spot of lunch at the café or head over to the heart of the Sissinghurst village to the Milk House, a gastropub with outdoor seating looking over fields of orchards. Just up the road towards Biddenden, The Three Chimneys is a delightful a delightful 15th century public house. Enjoy a hearty meal by the fireplace in winter or in the beer garden during the warmer months.

A walk through the High Weald of Kent

DAY 2 – Afternoon

Cranbrook is at the heart of the High Weald, a designated Area of Outstanding Natural Beauty (AONB), making it a beautiful place to stroll or take a longer walk. There are five circular walks that depart from the centre of Cranbrook. The first trail ‘Cranbrook Walk’ is 3 miles (4.8km) taking approximately 2 hours taking you to the village of Sissinghurst where you can stop for a bite at The Milk House before returning. It is also the path to access Sissinghurst Castle and Gardens on foot. The walks ‘Cranbrook – A walk through time’ North and South each take 1.5h-2h. These walks will take you past some of Cranbrook’s most historic buildings.

For those that enjoy hiking, there are two longer walks also departing from the centre of Cranbrook. The first is the ‘Sissinghurst- A walk through time’ which is 10 miles (16 kms) and takes approximately 5 hours. The route takes you northwards from Cranbrook through woods, past ancient houses and mills and over the rolling Wealden landscape to Sissinghurst Castle. Walk along the moat as you admire the tower from afar. The route then proceeds through orchards towards Sissinghurst village, past the parkland estate of Great Swifts on its return to Cranbrook town, finishing at St Dunstan’s churchyard, the starting point of the walk. Your second walking challenge is the ‘Goudhurst- walk through time’. This walk through ancient woodland and iconic Wealden landscape leads to the picturesque village of Goudhurst, once infamous for its smugglers named ‘The Hawkhurst Gang’, and today a quaint village with plenty of character. The Star and Eagle is the perfect place to rest for food and drink, before continuing your walk. The return journey towards Cranbrook passes through the splendour of 500-year-old Old Park Wood, with its carpets of bluebells in the spring.

DAY 2 – Dinner

For your final evening in Cranbrook & Sissinghurst we recommend exploring the eateries in the surrounding villages. Did you know that Kent is becoming known as a world class wine producer? The soil has the same qualities as the Champagne region, rivalling our French neighbours. The area is surrounded by vineyards so we recommend taking a Wine Tour or visiting the nearby Balfour winery for a wine tasting and delicious sharing boards.

Alternatively, you can sample what Kent, known as the Garden of England, has to offer at Green Micheline Starred, The Small Holding near Lamberhurst or Water Lane the hidden gem surrounded by a walled garden near Hawkhurst village both offering farm to table seasonal menus.

Where to Stay in Cranbrook and Sissinghurst

Why not extend your stay… More things to do around Cranbrook and Sissinghurst.

Cranbrook & Sissinghurst offer a harmonious blend of heritage architecture and natural beauty. Cranbrook’s medieval charm and well-preserved architecture transports visitors to a bygone era, while Sissinghurst Castle’s exquisite gardens provide a glimpse into a world of creativity and romance. If you’re seeking a tranquil escape that’s rich in heritage and allure, Cranbrook & Sissinghurst are the perfect place to base yourself to explore the surrounding area.

Nearby must-visit outdoor attractions include Bedgebury National Pinetum and Forest, Go Ape tree top adventures and Bewl Water , the largest water reservoir in the Southeast, where you can enjoy water sports, cycling and walking. Continue your heritage discovery at Bayham Abbey and Scotney Castle (National Trust) near Lamberhurst or Hole Park near Tenterden. Approximately 35-minute drive from Cranbrook and Sissinghurst, you can explore Royal Tunbridge Wells, the Royal spa town of Kent. Promenade through the historic Pantiles, the colonnaded walkway filled with cafes, boutiques and sample the waters from the Chalybeate Spring. Royal Tunbridge Wells has an abundance of independent shops, boutiques and antique shops making it a unique shopping destination. Be sure to visit The Amelia Scott Cultural centre to learn how Tunbridge Wells became ‘Royal’ or take a free self-guided audio tour around the town.

Cranbrook and Sissinghurst map

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