Churchill Country Retreat Things to Do Near Chailey, East Sussex

The best part of a stay at Churchill Country Retreat is what’s right outside. The house sits on the edge of Chailey Common Local Nature Reserve, in the heart of the Sussex Weald. Within half an hour’s drive you can take a steam train, walk through the forest that inspired Winnie the Pooh, taste award winning English sparkling wine and watch opera on a summer lawn.

This is our guide to the area, put together from years of welcoming guests to North Chailey. Use it to plan days out, or just as proof that one week isn’t enough.

Step Outside the Front Door

Slow down on the private drive. Deer, badgers and foxes are regular visitors, and early mornings and dusk are the best times to see them.

From the house you can walk straight onto miles of public footpaths. Chailey Common Local Nature Reserve is one of the largest areas of heathland left in the Weald. It’s open, quiet and good for walking the dog before breakfast.

When you want lunch, The Sloop Inn is a walk across the fields. You earn your pint on the way there and walk it off on the way back.

Within Three Miles: Steam, Gardens and Live Music

The Bluebell Railway (1.3 miles). England’s best loved heritage steam railway runs from Sheffield Park, just up the road. There’s something on all year: SteamLights trains at Christmas, Father Christmas specials for the little ones, murder mystery evenings and dining trains for a proper night out.

Sheffield Park and Garden (2.2 miles). A National Trust landscape garden built around a chain of lakes. It’s beautiful in spring and spectacular in autumn, when the trees turn.

Trading Boundaries (2.2 miles). Part café, part restaurant, part treasure trove of vintage world furniture, and an award winning live music venue at night. Check the gig listings before you arrive.

Heaven Farm (2.8 miles). A working family farm at Furners Green, known for its nature trail and spring bluebell walk.

Butterbox Farm (1 mile). A local farm raising Dexter beef, lamb and Saddleback pork. Worth a visit for fresh produce to cook back at the house.

Ashdown Forest and the Hundred Acre Wood

Ashdown Forest covers around 6,500 acres of open heathland and woodland. It’s also the countryside that inspired A.A. Milne’s Winnie the Pooh stories. Bring sticks for Poohsticks Bridge, pack a picnic and let the children run.

To see the forest on horseback, there are two riding centres about 7.4 miles away, including Ashdown Riding. Pony trekking works for beginners and confident riders alike.

Gardens Worth the Trip

The Weald has some of the finest gardens in England, and three of the best are close by.

Borde Hill Garden (4.9 miles). Garden rooms, rare trees and parkland.

Wakehurst (6.6 miles). Kew’s wild botanic garden, home to the Millennium Seed Bank.

Sheffield Park and Garden. Close enough to visit twice in different seasons.

Sussex Wine Country

Sussex has well over 100 vineyards and makes some of the finest sparkling wine in the world. Many offer tours and tastings, and several have their own cafés and restaurants.

Closest to the house is Bluebell Vineyard Estates at Furners Green. Also within easy reach are Ridgeview near Ditchling and Bolney Wine Estate.

For a full day out, it’s worth the drive to Rathfinny, Artelium and Nyetimber. Book a driver and make a day of it.

Culture, History and a Night at the Opera

Glyndebourne (8 miles). World class opera in the Sussex countryside, with black tie, a picnic on the lawns and champagne at the interval. If you’re staying during the festival season, book early.

Historic Lewes (7 miles). A castle, independent shops, old pubs and the Harvey’s Brewery. It’s one of the most characterful towns in the South East.

Charleston (11 miles). The country home of the Bloomsbury Group, painted from floor to ceiling.

Firle Place (11 miles). A historic house at the foot of the Downs.

Chartwell (19 miles). Sir Winston Churchill’s family home for over 40 years, now cared for by the National Trust. It’s a fitting day out from a house called Churchill.

Hever Castle (15 miles). The childhood home of Anne Boleyn, with a moat, a maze and a lake.

Days Out with the Children

• Drusillas Park (14 miles). A zoo designed with young children in mind.
• Knockhatch Adventure Park (14 miles). Indoor and outdoor play, animals and activities.
• The Bluebell Railway. A steam train ride is still the easiest win with small children.

Coast and Downs

When the sun is out, Brighton is 12 miles away, with the beach, the pier and The Lanes. Eastbourne is 20 miles away and quieter, with a classic seafront.

The South Downs Way can be reached from several car parks a short drive from the house. It’s 100 miles of chalk ridge with views over the Weald on one side and the sea on the other.

Events and Golf

The South of England Showground at Ardingly (5.9 miles) hosts antiques fairs, country shows and concerts throughout the year. Check what’s on during your dates.

Golfers will find East Sussex National 6 miles away, with two championship courses.

Getting Here

• By train: Haywards Heath station has trains to London in around 50 minutes.
• By air: Gatwick Airport is 14 miles away and Heathrow is 38 miles away.
• By car: Parking for four to five vehicles at the house.

Make Churchill Country Retreat Your Base

Six bedrooms, sleeps 11, and the whole of the Sussex Weald within reach. View the house and check availability.

Frequently Asked Questions

What is there to do near Chailey, East Sussex?

The Bluebell Railway, Sheffield Park and Garden, Ashdown Forest, Glyndebourne and several vineyards are all within a short drive of Churchill Country Retreat.

Is Churchill Country Retreat near the Bluebell Railway?

Yes. Sheffield Park station is about 1.3 miles from the house.

How far is Churchill Country Retreat from London?

Haywards Heath station has trains to London in around 50 minutes, and Gatwick is 14 miles away.

Is Churchill Country Retreat good for large groups?

Yes. The house sleeps 11 across six bedrooms, with parking for four to five cars.