Chepstow
Located where Wales meets England, Chepstow is a historic riverside town that makes the perfect day out for your stay at Penterry Holidays. From castles and peaceful riverside walks to independent shops and excellent places to eat, there’s plenty to explore within a short drive of Orchard Cottage and Anne’s Retreat.
Chepstow at a Glance
- Distance from Penterry Holidays: Around 10 minutes’ drive
- Best for: History, riverside walks, dining out, independent shopping
- Vibe: Compact, friendly market town with a spectacular setting above the River Wye
Things to See & Do in Chepstow
Chepstow Castle
Chepstow Castle is one of the highlights of the area and a must-visit during your stay. Perched high above the River Wye, it’s reputed to be the oldest surviving stone fortification in Britain. Explore towering walls, atmospheric courtyards and sweeping views along the river – it’s especially beautiful in the late afternoon light.
For up-to-date opening times, ticket prices and events, see the official Cadw Chepstow Castle page.
Riverside Walks & the Wye
The River Wye shapes the whole feel of Chepstow. Stroll the riverside from the town bridge, pause to watch the tides, or follow waymarked paths that link into longer Wye Valley walks. It’s an easy way to soak up the scenery before heading back to the peace of Penterry.
Historic Streets & Independent Shops
Chepstow’s compact centre is full of character, with narrow lanes, Georgian and medieval buildings and a mix of local shops. Browse delis, galleries and boutiques, pick up picnic supplies or treat yourself to local produce to enjoy back at your cottage or hut.
Food & Drink
Chepstow is a handy spot for an evening out or a leisurely lunch during your stay. You’ll find:
- Traditional pubs for a relaxed pint and hearty meals
- Cafés and tearooms ideal for coffee stops and light lunches
- Restaurants ranging from casual bistros to more refined dining
The wider Wye Valley is also known for excellent food, from farm shops to Michelin-starred restaurants, all within easy driving distance of Penterry Holidays.
Practicalities & Getting There
- Parking: Several public car parks around the town centre and near the castle
- Supermarkets & essentials: A choice of supermarkets and convenience stores for stocking up
- Transport: Chepstow has a railway station and good road links via the M48 and A48
Why Stay at Penterry for Visiting Chepstow?
Chepstow gives you history, bustle and great places to eat – Penterry gives you space, stillness and starry skies. After a day exploring the castle, riverside and town, you can be back at Orchard Cottage or Anne’s Retreat in minutes, lighting the woodburner or sinking into a super king bed in complete peace.
Use Chepstow as your local hub, then retreat to your own private corner of the Wye Valley when you’re ready to unwind.