Chiltern Hills AONB · Hertfordshire
The Greyhound, Aldbury — Ashridge & Bridgewater Monument loop.
6.4 km · 175 m · ~2h · Loop · Easy · 55 min from N6 · AllTrails 4.6★ on 82 reviews · Pub: 4.4★ on 963 · Sun 12:00–21:00
The destination pick. Aldbury is the gold-standard pretty Hertfordshire village — duck pond, medieval stocks, Norman church, half-timbered cottages, two pubs on the green and a 5,000-acre National Trust estate (Ashridge) immediately above it. Park in the village, lunch at The Greyhound, then climb up Toms Hill Road into Ashridge Forest, past the 108-foot Bridgewater Monument (built 1832 by the canal-building Duke), out across Pitstone Common with sweeping Chiltern views, and back down to the village. Beech woodland in fresh May leaf, deer about, broad rides — good for two dogs together; on lead through the few grazing sections.
Lunch: The Greyhound on Stocks Road — 4.4★ on 963 reviews, dog-friendly bar, tables out front overlooking the pond, Sun open till 21:00. The Trooper round the corner is the up-tier alternative — 4.4★/621, listed in the Good Food Guide Top 100 Local Restaurants 2024, slightly more refined kitchen. Booking essential at both for a Sunday. Poppies Café and Church Farm Café are mid-walk options if anyone wants a coffee stop, and the National Trust Monument Café sits at the loop's halfway point.
AllTrails ·
The Greyhound ·
The Trooper ·
Map
Chiltern Hills AONB · Hertfordshire
The Cricketers, Sarratt — Chess Valley loop.
7.4 km · 175 m · 2h–2h 30m · Loop · Moderate · 37 min from N6 · AllTrails 4.7★ on 1,131 reviews · Pub: 4.4★ on 1,074 · Sun 11:00–22:30
If you want the shortest drive and the best-rated walk in the Chilterns. Park on the village green, lunch at The Cricketers, then drop straight off the green down to the River Chess — one of only ~200 chalk streams in the world — through water meadows and watercress beds, climbing gently back up via Sarratt Church End onto the green. Working farmland with intermittent livestock so leads through the field stretches; a few stiles and kissing gates, otherwise wide path-and-track underfoot. Le Carré used Sarratt as the fictional MI6 training school, a small literary footnote if anyone's read Tinker Tailor.
Lunch: The Cricketers on the green, dog-friendly bar, garden out onto the green. If they're full, The Boot two doors down is 4.5★/1,036 and opens 9:30 for breakfast; The Cock Inn is also on the green. All three pubs sit at the same point on the loop.
AllTrails ·
The Cricketers ·
The Boot ·
Map
Chiltern Hills AONB · Buckinghamshire
The Royal Standard of England, Forty Green — Penn Circular.
9.5 km · 258 m · 2h 35m · Loop · Moderate · 55 min from N6 · AllTrails 4.5★ on 133 reviews · Pub: 4.5★ on 2,969 · Sun 12:00–22:00
If the pub is the point. Claims an 800-year history as the oldest free house in England — beams you have to duck under, stained glass, log fires, a priest hole where Charles I supposedly hid, and a film and TV CV that includes Hot Fuzz (the shoot-out scene), Midsomer Murders, Endeavour and The Theory of Everything. Critically: large free car park with information signs for the local walks. The 5.9-mile loop runs out through Coppice Hoop woods, across grazing pasture and rolling Chiltern beechwood, through Penn village (with The Crown Inn as a midway pit-stop if needed), and back. Reviewers consistently start the loop here. Several stiles but with dog gaps; on lead through the grazing fields.
Lunch: The Royal Standard. Dog-friendly bar, log fires, hearty English food, kitchen on through the afternoon. Booking essential for Sunday.
AllTrails ·
The Royal Standard ·
Map
