Following much of the 170 mile Chiltern Cycleway, this tour covers the entire Chiltern Hills area: from the Thames at Henley in the south west, to Hitchin in Hertfordshire in the north east. The chalk hills are a designated area of outstanding natural beauty, known for their red kites, beech woods, soaring views, idyllic brick and flint villages and innumerable hidden dry valleys. The cycling is challenging but rewarding, and we have found a characterful selection of village inns for your overnight stays.

Our Chiltern Challenge offers 4 days of cycling. You have several choices as to how you tackle the route. Starting from Tring, you can cycle the lot over 2 days, or spread it out over 4 days. In the latter case, there's the option of doing it over two weekends, rather than on 4 consecutive days. The prices quoted below apply regardless of how you choose to tackle it.

For further details of your route, see classic hotel itinerary.

Holiday details

Price from
Classic £285 per person based on two people sharing a room. for 2 nights. £525 per person for 4 nights based on two people sharing a room. Bike hire is not included but is available. As with all our tours, luggage transfers are included
Extras included
There are no extras, however you’ll love what’s included as standard
2 or 4 nights
Start & Finish
Starts daily from Tring or Amersham and is circular. By train, Amersham is 35 minutes from London Marylebone and Tring is 45 minutes from London Euston
Classic Hand picked accommodation in village inns
Activity level
Not so gentle cycling. More info...
Electric bikes
2 or 4 days of 36 to 52 miles (58 -83km) per day
Several tough hills, generally short but steep, each day
Almost totally on roads but most with low traffic

Stay 2 nights at any of the stops and enjoy our circular rides

View Chiltern Challenge in a larger map
Cycling holiday in the Chilterns - The Dunstable Downs