Straddling Kent and Sussex, this High Weald cycling trip is packed with wonderful gardens and grand castles spread across a charming landscape. Visit Sissinghurst and Great Dixter as well as other gardens known as the very best in Britain as you pedal ups and downs to the sea. Medieval history is ever-present in the timber framed architecture and on full show in the small town of Rye whilst epic castles abound with a final night’s stay in magnificent Hever Castle.
The High Weald has a history of horticulture be it farming, viticulture, gardens or now a vibrant locally produced food and drink scene. The ever beautiful rolling terrain with its short steepish hills, and a maze of back lanes and traffic free bridleways is one where E-bikes will be appreciated! Tranquil and sometimes remote, the High Weald is dotted with woods, beguiling hamlets and haphazard field patterns and embraces a laid back sometimes quirky culture of small holdings and independent businesses. We love its authenticity!
With several two night stays in characterful inns and hotels, and E-bikes which we recommend, you will have have time to enjoy vineyards, local beers and exceptional food over and above the magical gardens, castles and landscape.
Holiday details
Price
- Classic
-
from £2,455 per person
- Luxury
-
from £3,420 per person
Based on two people sharing a room
Duration
8 nights
Start & Finish
Starts Staplehurst station ends Hever Station. Both are 1 hour from central London. Staplehurst is also 15 minutes by train from Ashford International with direct trains to mainland Europe. Tour starts Friday.
Hotels
- Classic
-
5 inns and a small hotel
- Luxury
-
A castle, 3 inns and 2 boutique hotels
Holiday type
Self-guided so you are free to explore at your own pace. More info...
Activity level
Not so gentle cycling (gentle level 5 if you have an E bike) More info...
Electric bikes
Available and recommended
Mileage
5 days of cycling 11- 25 miles (18 - 40 km) per day with 2 further days of optional cycling
Terrain
Many short steep slopes
What’s included?
Ensuite accommodation every night with breakfast. The services of our friendly local Hosts. Luggage transfers between hotels. Touring bikes and accessories. 24/7 phone contact number. Adventure Handbook with our local tips. GPS Routes on an App with waterproof phone holder. Guidebook or OS maps. Protection of your funds. Advice, help and guidance planning your trip.
Entry to all the castles and gardens on this tour. A private guided walking tour of Rye. Train ticket from Rye to Three Oaks. Read About Our Trips for further details
Traffic-free
15% traffic free on cycle paths and bridleways, the rest on quiet back lanes
Options
- Play golf at the Nick Faldo designed Chart Hills Club near Sissinghurst or at Rye Golf Club
- Book an exceptional dinner at a Michelin green starred restaurant near Ticehurst
- On the classic tour upgrade to stay at Hever castle
Itinerary day-by-day
Classic
-
1. Day one
Arrive Staplehurst
We meet you at Staplehurst station and transfer you to your accommodation where you stay 2 nights - welcome to the High Weald! Settle into your inn and enjoy the rural vibe. Your Host will meet you later today or tomorrow morning to run through your itinerary, answer any questions and fit your bicycles ready for the off tomorrow!
-
2. Day two
Sissinghurst circular ride
What a day! Pedal the few miles to the famous gardens at Sissinghurst enjoying the many garden rooms and the romantic setting and planting. Take your time, you have a very flexible itinerary. Follow back lanes to explore further if you wish to see two key historic small towns of the Weald - Cranbrook as well as Tenterden if you cover the full distance. Both are highly attractive with some quirky shops. Along the way, drop in for a tour and tasting at Kent's oldest vineyard or enjoy craft beers at a family owned brewery. It's a day of ups and downs through small woods and a charming rural scene peppered with so much to see and discover. Return to Sissinghurst for a second night.
6,14,19 or 28 miles (10,22,30 or 45 km)
-
3. Day three
Sissinghurst to Rye
Heading south to the coast, it's not long before you reach grand Bodiam Castle - a 14th century moated affair with a ruined interior. A few miles along you find Great Dixter with its ground breaking garden and medieval house. This is an astonishing place and we leave you to draw your own conclusions. Tear yourself away for a dreamy meandering ride through vineyards, timber framed farms and cottages with pockets of woodland and a few refreshment stops and old inns. Reaching Rye, where you stay 2 nights, the medieval buildings are cheek by jowl on the narrow cobbled streets and alleys, once a smugglers haunt when the town was a Cinque Port. Its castle still stands but the sea is a short distance away now, due to silting.
28 miles (45 km)
-
4. Day four
Enjoy Rye and the coast
Unravel the history of Rye with your 1 hour Private guided walking tour after breakfast. The day is then yours to enjoy either the delights of the town itself or take a short circular ride along the sandy coast or a longer ride to find the interesting seaside town of Hastings with its castle and Old Town. A great day!
Optional 15 or 25 miles (24 or 40 km)
-
5. Day five
Rye to Ticehurst
Start the day with a short train hop to avoid a busy road as you leave Rye and ride inland. Electric bikes come into their own today with lots of short steep wooded hills, typical of the pretty Wealden landscape. You might detour to Battle, where England's future was sealed by William the Conqueror or visit a vineyard. Crossing a few brooks on idyllic tracks, you reach Bateman's - the beautiful and tranquil setting of Rudyard Kipling's family home and garden with a working water mill. Just a few miles now from your overnight stay, you can enjoy the wonderful 12 acres of gardens at Pashley Manor either today or tomorrow. Stay 2 nights in Ticehurst's quirky inn.
25 miles (40 km)
-
6. Day six
Ticehurst to Scotney Castle and Pashley Manor
Enjoy a laid back start today. with the option of a day off or a special visit to gorgeous Scotney Castle with its gardens and Victorian mansion taking in Bewl Water, a flooded valley. You can also walk or cycle to Pashley Manor gardens as they are very close to your village and not to be missed. Spoilt for choice!
Optional 17 or 19 miles (27 or 30 km)
-
7. Day seven
Ticehurst to Tunbridge Wells
There's variety aplenty today as you weave through pine forests and countless orchards of hops, vines and fruit. Woodland pockets and valleys shelter village greens and pretty hamlets and their inns from scenic Goudhurst to Royal Tunbridge Wells. Once a notable spa town and now an elegant and historic location, you will have the opportunity to relax and explore here. Your hotel tonight is in the heart of the town.
24 miles (38 km)
-
8. Day eight
Tunbridge Wells to Hever Castle
The shorter, less hilly pedal this morning is designed to give you much of the day at 14th Century moated Hever Castle. This epic dwelling has 600 years of history and a fascinating interior. The grounds include beautiful gardens and a huge lake surrounded by acres of woodland. It's a grand ending to your tour of the High Weald. Your overnight stay is less than a mile away or consider upgrading and stay in the Hever Castle's very special guest wing.
11 miles (18 km)
-
9. Day nine
Depart Hever
After a King's breakfast we transfer you to nearby Hever station for your onward journey.
Luxury
-
1. Day one
Arrive Staplehurst
We meet you at Staplehurst station and transfer you to your accommodation where you stay 2 nights - welcome to the High Weald! Settle into your inn and enjoy the rural vibe. Your Host will meet you later today or tomorrow morning to run through your itinerary, answer any questions and fit your bicycles ready for the off tomorrow!
-
2. Day two
Sissinghurst circular ride
What a day! Pedal the few miles to the famous gardens at Sissinghurst enjoying the many garden rooms and the romantic setting and planting. Take your time, you have a very flexible itinerary. Follow back lanes to explore further if you wish to see two key historic small towns of the Weald - Cranbrook as well as Tenterden if you cover the full distance. Both are highly attractive with some quirky shops. Along the way, drop in for a tour and tasting at Kent's oldest vineyard or enjoy craft beers at a family owned brewery. It's a day of ups and downs through small woods and a charming rural scene peppered with so much to see and discover. Return to Sissinghurst for a second night.
6,14,19 or 28 miles (10,22,30 or 45 km)
-
3. Day three
Sissinghurst to Rye
Heading south to the coast, it's not long before you reach grand Bodiam Castle - a 14th century moated affair with a ruined interior. A few miles along you find Great Dixter hall with its ground breaking garden and medieval house. This is an astonishing place and we leave you to draw your own conclusions. Tear yourself away for a dreamy meandering ride through vineyards, timber framed farms and cottages with pockets of woodland and a few refreshment stops and old inns. Reaching Rye, where you stay 2 nights, the medieval buildings are cheek by jowl on the narrow cobbled streets and alleys, once a smugglers haunt when the town was a Cinque Port. Its castle still stands but the sea is a short distance away now, due to silting.
29 miles (46 km)
-
4. Day four
Enjoy Rye and the coast
Unravel the history of Rye with your 1 hour Private guided walking tour after breakfast. The day is then yours to enjoy either the delights of the town itself or take a short circular ride along the sandy coast or a longer ride to find the interesting seaside town of Hastings with its castle and Old Town. A great day!
Optional 15 or 25 miles (24 or 40 km)
-
5. Day five
Rye to Ticehurst
Start the day with a short train hop to avoid a busy road as you leave Rye and ride inland. Electric bikes come into their own today with lots of short steep wooded hills, typical of the pretty Wealden landscape. You might detour to Battle, where England's future was sealed by William the Conqueror or visit a vineyard. Crossing a few brooks on idyllic tracks, you reach Bateman's - the beautiful and tranquil setting of Rudyard Kipling's family home and garden with a working water mill. Just a few miles now from your overnight stay, you can enjoy the wonderful 12 acres of gardens at Pashley Manor either today or tomorrow. Stay 2 nights in Ticehurst's quirky inn.
25 miles (40 km)
-
6. Day six
Ticehurst to Scotney Castle and Pashley Manor
Enjoy a laid back start today. with the option of a day off or a special visit to gorgeous Scotney Castle with its gardens and Victorian mansion taking in Bewl Water, a flooded valley. You can also walk or cycle to Pashley Manor gardens as they are very close to your village and not to be missed. Spoilt for choice!
Optional 17 or 19 miles (27 or 30 km)
-
7. Day seven
Ticehurst to Tunbridge Wells
There's variety aplenty today as you weave through pine forests and countless orchards of hops, vines and fruit. Woodland pockets and valleys shelter village greens and pretty hamlets and their inns from scenic Goudhurst to Royal Tunbridge Wells. Once a notable spa town and now an elegant and historic location, you will have the opportunity to relax and explore here. Your hotel tonight has a wonderful and dramatic setting.
24 miles (38 km)
-
8. Day eight
Tunbridge Wells to Hever Castle
The shorter, less hilly pedal this morning is designed to give you much of the day at 14th Century moated Hever Castle. This epic dwelling has 600 years of history and a fascinating interior. The grounds include beautiful gardens and a huge lake surrounded by acres of woodland. You stay the night in the splendid guest wing of the castle - there's no grander a finale to your tour of the High Weald than this!
11 miles (18 km)
-
9. Day nine
Deaprt Hever
After breakfast we transfer you to nearby Hever station for your onward journey.