Chepstow

Chepstow is well served by rail and road.

• 🌍 The Priory Church of St Mary, Upper Church St, NP16 5HA, ☏ +44 1291 620980. Founded in 1071. Benedictine monks from Cormeilles in Normandy (Chepstow's twin town) were there until the Dissolution of the Monasteries between 1536 and 1540. Today it serves as Chepstow's parish church. 
• 🌍 Chepstow Castle, NP16 5EY, ☏ +44 1291 624065. Open daily 9:30-5PM except Jul Aug 9:30AM-6PM, Nov-Feb 10AM-4PM; closed 24/25/26 Dec and 1 Jan. Members free; adult £8.30; family £28.10; disabled person and companion free; juniors (aged 5-17) and seniors (aged 65+) £6.10; all children under 5 receive free entry. (updated Apr 2023)
• 🌍 Chepstow Museum, Gwy House, Gwent, Bridge St, NP16 5EZ (is opposite the Castle car park.), ☏ +44 1291 625981. 11AM-4PM. free. 
• 🌍 The Severn Princess. Restoration project of one of the Beachley/Aust ferry boats, which ran before the Severn Bridge was opened in 1966, has been rescued from Ireland and is being restored. 

• 🌍 Chepstow Racecourse, St Lawrence Rd NP16 6BE (A mile north of town on A466). This has flat-racing April-Sept and jumps races Oct-March. (updated Jan 2019)
• 🌍 National Diving & Activity Centre, Tidenham NP16 7LQ (A48 two miles east of town), ☏ +44 1291 630046, info@ndac.co.uk. Closed. Large flooded quarry with shallow-to-moderate training areas but the deepest part goes down to 70 m. The business folded in Feb 2022 and it remains to be seen if another will take it on. There's nowhere else inland in Britain for diver training at such depths, and the water-filled hole in the ground isn't going anywhere else. (updated Feb 2022)

Long distance walks from Chepstow are:

• Wye Valley Walk follows the east river bank, plunging through Tidenham Tunnel to reach Tintern, and continuing to Monmouth.
• Offa's Dyke Path is the same as Wye Valley Walk to Monmouth. It continues north along the border, eventually to Prestatyn on the north coast.
• Wales Coast Path follows the entire convoluted coastline of Wales. Its south terminus is at the border, and the local section passes through Chepstow and Caldicot to Newport.

The centre of the town is dotted with ceramic markers on walls and in the floor for places of interest and a couple of suggested walk routes. If you find yourself at a loose end having viewed the Museum and the Castle at the lower end of Chepstow, there are a few suggestions for a pleasant stroll up to the Town Gate:

• standing in the car park facing the castle, notice a path to the left going up the hill. This leads to The Dell, a green oasis that gets overlooked by some. There are different views of the surprisingly long castle wall. You can even scramble up close to the wall and walk along until you get to the Barbican end of the castle. Approaching the top of The Dell you have an option of climbing some grassy steps and entering the main car park via the "hole in the wall", an ancient stone doorway in the Town Wall, and then finding your way into the upper town via various alternative exits at the far side. The other option is to exit the iron gate at the top of The Dell and turn left to reach the outside of the Town Gate at the traffic lights.
• the middle option involves starting from the Museum, and strolling up Bridge Street past a row of bow-windows on the right, past the Powis Almshouses (1716 - see if you can read the tablet high up on the wall), past The Five Alls public house (check the inn sign), up cobbled Hocker Hill Street (some say Hawker Hill), past St Maur where Horatio Nelson stayed in 1802, according to the plaque on the wall. You can now walk straight ahead to the Town Gate or veer left up the High Street.
• the third option, starting from the Museum, is to head towards the river, passing Afon Gwy, a place to eat and sleep, on the left. Take a stroll over the 1816 iron bridge (not that much newer than the world's oldest (1781) at Ironbridge, a 100 miles or so to the north). The castle is particularly photogenic from the bridge, and especially so when the tide is in. The rise and fall of the tide, at 12 m, is the second highest in the world. Come back off the bridge to the Bridge Inn and walk along the river bank, which is less pleasant since the flood defences were built in 2001, obscuring the view and re-arranging the seats (they used to line the river bank facing the river). Spot the wall plaque recording the fact that the leaders of the Chartist Insurrection were transported from the Port of Chepstow to Van Diemen's Land (Tasmania) on the 3 February 1840. Just before you reach the Boat Inn, turn right and make your way up Lower Church Street, through the iron-railinged path across the graveyard of St Mary's Church, across to Upper Church Street from where, opposite the Montague Almshouses (1615), you can amble up the pedestrianized St Mary Street and the High Street to the Town Gate.

• Green Man and the Gatekeeper, Now at Taurus Crafts, The Old Park, Lydney, GL15 6BU (On the A48, Gloucester road from Chepstow, about 8 miles to Taurus Crafts - Look for the Bull sculpture on your left.), ☏ +44 1594 843860. 11:00 to 17:00 daily. Gifts in leather, ceramics and pewter. 

If you support charity shops, Chepstow has about five (it does sometimes vary), watch out for them. St Mary Street has some shops which deal in antiques and objects which one day might be antiques. Every three weeks or so, on a Saturday morning, there is a Farmers' Market in the Place de Cormeilles, adjacent to the Town Gate. Every oother Sunday morning there is a market in the High Street with arts and crafts, food vendors, local market stalls, jewellery, and traditional market fayre. Other shops and cafés also open and the town bustles with activity!

There is a fish and chip shop just outside the Town Gate (The Arch), in Albion Square, and a Chinese takeaway a little further up Moor Street, on the right; there is another sandwiched between the main car park and Bank Street, where you can also sit down. There is an Indian Restaurant at the top of Hocker Hill Street. There are quite a few pubs serving food as well as tea-rooms. Chepstow even has a local department store, Herbert Lewis, in the High Street, which has a coffee shop. Late in 2004, a Greek Meze Bar opened in Welsh Street.

• The Coach and Horses Inn, Welsh Street. serves proper good-quality home cooking with a specials menu that changes daily. 

there is a lot of pubs here

• George Hotel, ☏ +44 1291 625363. Is just outside the Town Gate, in Moor Street. 
• Chepstow Hotel, ☏ +44 1291 626261. Is about half a mile up the hill from the Town Gate, on the Newport Road. 
• 🌍 Beaufort Hotel, Beaufort Square, NP16 5EP, ☏ +44 1291 622497. Is in the town centre at the top end of St Mary Street. 
• Castle View Hotel, ☏ +44 1291 620349. Is opposite the Castle (as you would expect). 
• The First Hurdle Guest House. Comfortable B&B in central Chepstow location. 
• Coach and Horses Inn, Welsh Street, ☏ +44 1291 622626. 
• Monmouthshire Holiday Cottage & Barn (Monmouthshire holiday cottage), Itton Chepstow, ☏ +44 1291 641856. Check-in: 1400, check-out: 1000. Pet friendly Clare's Cottage sleeps 4 and Dolly's Barn sleeps 2 both properties have beautiful views. 3 miles from Chepstow From £240 per week. 
• B&B accommodation can be booked through the Chepstow Tourist Information Centre, Bridge Street (opp. Castle), ☏ +44 1291 623772. 

• A few miles upstream from Chepstow, on the river Wye, are the ruins of the Cistercian Tintern Abbey, founded in 1131.
• The first part of the Wye Valley Walk, which starts at the bottom of The Dell, by the Castle will take you to Tintern. The Offa's Dyke Path will also get you there. Cross the 1816 Bridge over the Wye and follow the steep path up the hill on the other side. You really need walking boots because there are usually some muddy sections. Allow about 3–4 hours for either way. Go one way and come back the other is a good day out, lunching in Tintern.
• Go climbing at Woodcroft, a couple of miles out of Chepstow, on the Gloucestershire side of the Wye. Wintour's Leap is a limestone cliff popular with climbers and considered "the gem of the Wye Valley".
• Visit the Dean Forest Railway which is based at the Norchard Steam Centre, on the B4234 Forest Road between Lydney and Whitecroft, about 9 miles from Chepstow. Entrance is free on non-passenger train days. An example of steam train fares is Adult: £6.50, Senior: £5.50, Child aged 5 to 16: £4.50, child under 5 is free, for all day, travel as many times as you like. But see the web site for alternatives.
• A map of the area (available from most good bookshops and tourist information centres in Chepstow) will allow you to plan your own walks - although beware that several footpaths marked do not exist or will not be in a suitable state. Nonetheless, this can allow some excellent views of the landscape without going far from Chepstow. Check that the map does mark footpaths clearly before buying however, as many don't.