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For a start there’s its rather delightful location as the River Wye snakes its way to join the River Severn just a couple of miles downstream. The western end of the Severn Bridge links the town with neighbouring Gloucestershire and makes an iconic sight as it reaches across the river to join Wales and England.
And, of course, there’s that dramatic castle overlooking the town like a domineering but protective patriarch. The magnificent Norman castle at Chepstow perches on top of a limestone cliff that hangs over the river, and guards the main river crossing. Miraculously intact this is actually one of the oldest castles in Britain, dating all the way back to the Norman Conquest, and the impressive Great Tower still features its original architecture.
You can learn all about the castle’s history in the museum that is housed in the Lower Bailey and to bring your understanding of Chepstow’s history up to date you can nip across the road from the castle into the 18th century town house in which a kid-friendly museum brings the town’s industrial and social history to life.
If its myth and legend that you are after then Chepstow can provide you with plenty of romantic legends too. It is said that a cave in the cliff underneath the castle is where King Arthur and his trusty knights are resting and conserving their powers until the next time that Britain needs saving from dark forces.
The name Chepstow derives from the old English ‘chepe stowe’ which means market place or trading centre. The town centre today has over 130 shops within easy walking distance and the pedestrianised St Mary's Street contains antique shops, craft and gift shops, cafes and restaurants.
Markets and festivals still define the rhythms of the weeks and changing of the seasons here. The Chepstow Farmer’s market is held on the second and fourth Saturday of every month and the Chepstow Show draws farmers from miles around to display their wares and compete for prizes every August. Meanwhile in July the Two Rivers Folk Festival offers three days of music and dance and there is the Chepstow Festival packed with medieval re-enactments, pageantry and drama.
For those partial to a flutter you are in the right town: Chepstow Racecourse is the leading horse racing course in Wales. You will find it on the edge of the town, in the grounds of the ruined Piercefield House. The racecourse itself was first opened in 1926, and has held the Welsh National since 1949.
With its stunning but central location, historical sights and contemporary shopping, hotels and restaurants, river views and racecourse excitement, Chepstow offers an ideal place to explore Wales and Southwest England.
Situated in Chepstow, this spa hotel is 2.5 mi (4.1 km) from Chepstow Castle and 2.9 mi (4.6 km) from Chepstow Racecourse. Thornbury Castle and Tintern Abbey are also within 12 mi (20 km).
Situated in the historical district, this inn is within 1 mi (2 km) of Chepstow Castle and Chepstow Racecourse. Thornbury Castle and Tintern Abbey are also within 12 mi (20 km).
Situated in Chepstow, this bed & breakfast is within 1 mi (2 km) of Chepstow Castle and Chepstow Racecourse. Tintern Abbey and Lydney Harbour are also within 12 mi (20 km).
Located in Tintern, this hotel is 0.2 mi (0.3 km) from Tintern Abbey and within 6 mi (10 km) of Chepstow Racecourse and Chepstow Castle. Clearwell Caves and Puzzlewood are also within 9 mi (15 km).
Located in the heart of Chepstow, this hotel is within 1 mi (2 km) of Chepstow Castle and Chepstow Racecourse. Thornbury Castle and Tintern Abbey are also within 12 mi (20 km).
Situated in Beachley, this inn is 2.9 mi (4.7 km) from Chepstow Castle and within 9 mi (15 km) of Chepstow Racecourse and Tintern Abbey. Lydney Harbour is 11.5 mi (18.4 km) away.
Situated in Chepstow, this hotel is 0.1 mi (0.1 km) from Chepstow Castle and 1.3 mi (2.2 km) from Chepstow Racecourse. Thornbury Castle and Tintern Abbey are also within 12 mi (20 km).
Situated in Chepstow, this bed & breakfast is 0.2 mi (0.4 km) from Chepstow Castle and 1.4 mi (2.3 km) from Chepstow Racecourse. Thornbury Castle and Tintern Abbey are also within 12 mi (20 km).