Best gravel rides in the Chilterns

The Chilterns sit awkwardly close to London. Close enough to feel commutable; just hilly enough to feel like a real ride. Gravel-wise they’re an undersold AONB — the Ridgeway gets the touring traffic, but the chalk-and-flint bridleways in the south-east corner are quieter, drier, and thread together better than people give them credit for.

Three loops we keep coming back to, in rough order of effort. All start within a 60-minute train of London, all serve a proper coffee stop within two-thirds of the day.

1. Henley → Stonor → Pishill

The friendliest of the three. Out from Henley along the Thames Path for a flat warm-up, up Stonor on lanes, then you’re into the network of bridleways through Pishill and Maidensgrove. The chalk gets sticky in winter — go between April and October or be ready for full mudguards.

Coffee stop: The Five Horseshoesin Maidensgrove, roughly two-thirds in. Pub rather than café, but does flat whites and lets you chain the bike to the garden fence.

2. Tring → Ashridge → Aldbury

The pretty one. Ashridge Forest’s wide forestry tracks link into the National Trust estate’s gravel network, and the back side of Ivinghoe Beacon has a rideable chalk descent that’s the closest the south-east gets to a Lake District run-out. Three steep ramps in the second half — pace yourself.

Coffee stop: The Greyhound Inn in Aldbury, right in the village square. Outside seating in summer; warm cake and decent pies in winter.

3. Wendover → Coombe Hill → Princes Risborough

The serious one. Coombe Hill is the highest point in the Chilterns and the gravel descent off its western shoulder is narrow, fast, and properly committing — drop the saddle, ease off, treat it as a cyclocross course. The loop drops down to Princes Risborough for lunch and climbs back up the Whiteleaf Cross hill on the way home, which is a more sensible choice than it sounds because the gradient is even and the road is quiet.

Coffee stop: Bekonscot Café in Princes Risborough — about 50 km in, with secure bike parking out the back. Best almond croissant in the southern half of the AONB.

Stringing them together

If you’re visiting from outside the south-east and want a weekend, do Tring → Wendover on the Saturday (linked by 8 km of canal towpath; both stations on the same line) and Henley as the lighter Sunday. Good gravel pubs are spaced about 18 km apart across the whole AONB, so you can stitch an unsupported version together if a sag wagon isn’t your style.

For weekly group rides in the area, browse the gravel-focused clubs on CycleConnect — High Wycombe CC and Watford Velo both run regular Sunday spins in the AONB during summer.

See an event we should know about, or a route we should add to the next post? Drop us a note— we’ll ride it before we write about it.