When September arrives in the Chilterns, the rolling hills shimmer with late-summer warmth, woodland trails are generously dappled with new light, and small villages and market towns begin to quiet down—yet also start to hum with seasonal events and cultural vibrancy. Whether you're drawn by immersive living history, rooted community events, or a breath-taking countryside challenge, the Chilterns offer both cultural charm and wild beauty. Here’s your guide to September’s standout happenings across this enchanting Area of Outstanding Natural Beauty.

Highlight Events & Local Culture in the Chilterns This September

1. Chilterns 3 Peaks Challenge (Sunday 14 September 2025)

• Where: Starting at Princes Risborough School, the routes stretch across the serene Chiltern Hills.
• What Happens: Participants choose from three hiking distances—7, 10.5, or 18.5 miles—through varied terrain, rolling landscapes, and panoramic vistas—all in aid of Rennie Grove Peace Hospice Care. It’s family-friendly, dog-welcoming, and deeply meaningful. Registration fees (£16 for adults, £10 for under 15s, £50 for family tickets) support hospice care, with a suggested sponsorship goal of £250 per walker (£534 earns a free Rennie Grove hoodie).

2. Chiltern 50 Ultra Challenge (Saturday 27 September 2025)

• Where: Henley-on-Thames and the surrounding Chiltern countryside.
• What Happens: A demanding yet rewarding endurance event offering 10 km, 25 km, and a full 50 km loops across historic trails, nature reserves, and undulating hills. Perfectly accessible from London, it includes full support—marked routes, rest stops with food, medics, massage, and concludes with a lively basecamp BBQ, bar, camping, and celebratory atmosphere. Finishers receive a medal, T-shirt, and glass of fizz.

3. Crafts and Skills of the Iron Age at Chiltern Open Air Museum (6–7 September 2025)

• Where: Chiltern Open Air Museum, Chalfont St Giles.
• What Happens: Step into a recreated Iron Age village—experience roundhouse living, hand-spun wool dyeing, amber jewellery crafting, flint knapping, traditional tanning, and authentic cooking methods including bread baked on hot stones and hearth-cooked meals. This immersive weekend is ideal for families and history lovers alike.

4. Chilterns Weekend Walkers Festival (Sunday 7 September 2025)

• Where: Lane End, near High Wycombe.
• What Happens: A day tailored for walking enthusiasts—choose from six guided walks ranging from a leisurely 4.5-mile stroll to more strenuous hikes. The walk culminates in a community picnic with optional pub drinks and great camaraderie. Free to attend, it's hosted by the Ramblers walking charity and designed for both newcomers and regular hikers.

5. Royal Chilterns Way Bikepacking (Launched Late Summer)

• Where: Across Reading, Henley-on-Thames, Chesham, Berkhamsted, Wendover, Marlow, and beyond.
• What Happens: A new 280 km multi-day bikepacking route through the Chilterns’ natural heart. Designed for bikes like gravel, cyclocross, or mountain, it features off-road segments, quiet lanes, and considerable elevation (~3,383 m in total). Ideal for independent cyclists looking for scenic multi-day adventures, with route details and GPX files freely available via Cycling UK.

More to Explore in the Chilterns This Month

• Chiltern Open Air Museum: Beyond the Iron Age weekend, this living museum features over 35 rescued vernacular buildings—cottages, farmhouses, a Victorian toll house, a former chair factory, and more—set within 45 acres of woodland and parkland. Hands-on crafts and folk events run year-round.
• Nature Walks & Wildlife: Wander through ancient sites like Widdenton Park Wood, home to oak–beech woodland and spring-fed mires, or the Aston Rowant National Nature Reserve, where red kites glide above orchid-rich chalk grasslands. Both spots are gorgeous for autumnal walks and wildlife spotting.
• Cycling on the Chiltern Way: Tackle the 170-mile Chilterns Cycleway loop, connecting rural Bedfordshire, Buckinghamshire, Hertfordshire, and Oxfordshire. Perfect for scenic day trips or longer jaunts on quiet roads.

Conclusion & Where to Stay

September in the Chilterns is an enchanting blend of heritage, physical challenge, and untouched beauty. From Iron Age storytelling and family hikes to ultra-distance challenges and cycle adventures, the region invites you to engage deeply—with countryside, culture, and community.

For a thoughtful and smooth stay, pair your trip with Pass the Keys – Adam. Whether you're seeking a cosy cottage with woodland views or a quaint village home near walking trails, Adam’s well-managed short lets offer comfort, character, and local insights to fully immerse you in the Chilterns’ charm.