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Countryside Guided Walks

Guided walks with the MonLife Countryside Access Team

The Monmouthshire Countryside Access Team arrange a series of guided walks in the beautiful Monmouthshire Countryside. The walks, led by trained volunteers, will take you on journeys of discovery in the Monmouthshire Countryside. They vary in length from 3 to 10 miles, but are usually around 6 or 7 miles. They will take you through fields and woodlands and along lanes and rivers, encountering points of interest on the way. Some level of fitness will be needed for the walks, but you will not be on a route march and leaders will adjust the pace to suit the group. This is a great opportunity to keep fit, improve your wellbeing, make new friends and find out more about our fantastic county in the safe hands of our knowledgeable leaders.

Skenfrith to Box Farm

Saturday 18^th October 2025

10:30am (Approx 4 hours)

This 6.25 mile (10km) walk follows part of the Three Castles Walk through lanes and open fields towards Grosmont. Field paths then rise to Brook House Farm, from where the walk descends the Black Brook Valley back to Skenfrith.

It should take about 4 hours to complete.

Click here to book your free tickets and for more information.

Ancient Hill Fort and fantastic views near Llandenny

Sunday 2nd November 2025

10:00am (Approx 3 hours)

A 5 mile (8 km) circular walk through undulating countryside and country lanes passing an ancient hill fort starting near the village of Llandenny. One steep slope and 10 stiles. Paths good but can be muddy in places.

It should take about 3 hours to complete.

Click here to book your free tickets and for more information.

Wentwood to Penhow Circular Walk

Saturday 15th November 2025

10:00am (Approx 4 hours)

On this 7 mile (12 km) walk we will be climbing up onto Gray Hill to view the Standing Stones and enjoy fantastic views towards the Severn Estuary. We will continue through Llanvair Discoed with its ancient dove cote to reach Penhow with its church and castle. We will return via Mynydd Alltir-fach. Two steep slopes and lots of stiles.

It should take about 4 hours to complete.

Click here to book your free tickets and for more information.

Non guided circular walks to enjoy

Number of results: 50

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Chepstow Town Trails

Address

Chepstow TIC, Bridge Street, Chepstow, Monmouthshire, NP16 5EY

Telephone
01291 623772

chepstow.tic@monmouthshire.gov.uk

Chepstow

Chepstow has three town trails. All start / finish at Chepstow TIC in the Castle car park, but you can pick them up at any point in the town centre. The full trail takes approximately 90 minutes. Look out for plaques of information in pavements and…
Walking or Cycling across the Severn Bridge

Address

The Severn Bridge, Chepstow, Monmouthshire, NP16 5AA

Chepstow

Walk or cycle across the (old) Severn Bridge along the M48 on this just under 5 mile route. It's a great way to experience the Severn Estuary, and to visit two countries in one walk.
Health Walk - Caldicot Castle

Address

Caldicot Castle Car Park, Church Road, Caldicot, Monmouthshire, NP26 4HT

Telephone
01633 644850

countryside@monmouthshire.gov.uk

Caldicot

A 1.3 mile walk through Caldicot Castle Country Park.
8 Wentwood to Gray Hill Circular Walk

Address

Cadira Beeches car park, Usk Road, Wentwood, Usk, Monmouthshire, NP15 1NA

Telephone
01633 644850

countryside@monmouthshire.gov.uk

Wentwood, Usk

Path temporarily closed due to major problems with the route.
A strenuous 7.6 mile walk in woodland and common near Shirenewton.
22 Mitchel Troy to Cwmcarvan

Address

Mitchel Troy Church car park, Mitchel Troy, Monmouthshire, NP25 4HT

Telephone
01633 644850

countryside@monmouthshire.gov.uk

Mitchel Troy

A 5 mile walk with lots of ups, downs and spectacular views from Mitchel Troy, west of Monmouth.
Health Walk - Mathern & St Pierre

Address

Mathern Road near Millers Arms, Mathern, Chepstow, Monmouthshire, NP16 6JD

Telephone
01633 644850

countryside@monmouthshire.gov.uk

Chepstow

2.7 miles from the village of Mathern, through farmland and the St Pierre golf course.
Great British Walks

Address

Singleton Court Business Park, Monmouth, Monmouthshire, NP25 5JA

Telephone
+441600713008

info@great-british-walks.com

Monmouth

Based in Monmouth close to the Wye Valley Walk and the Offas Dyke Path, this Monmouthshire based walking holiday company have been organising self-guided tours throughout Wales and the UK for 15 years.
17 Buckholt Wood

Address

Monmouth Town Centre, Glendower Street,, Monmouth, Monmouthshire, NP25 3DF

Telephone
01633 644850

countryside@monmouthshire.gov.uk

Monmouth

A 6 mile walk to the north of Monmouth
3 Raglan Healthy Footsteps

Address

St Cadoc's Church, Monmouth Road, Raglan, Monmouthshire, NP15 2DS

Telephone
01633 644850

countryside@monmouthshire.gov.uk

Raglan

A 1.4 mile walk on level paths in Raglan.
Celtic Trails Walking Holidays

Address

5 Ashweir Court, Tintern, Monmouthshire, NP16 6SE

Telephone
01291 689774

walk@celtic-trails.com

Tintern

Celtic Trails are a premier provider of self-guided walking holidays, dedicated to creating memorable experiences for walkers of all levels.
18 Monmouth King's Wood Circular Walk

Address

Drybridge Community Nature Park, Rockfield Road, Monmouth, Monmouthshire, NP25 5AS

Telephone
01633 644850

countryside@monmouthshire.gov.uk

Monmouth

A 6.1 mile walk from Monmouth including a section of the Offa’s Dyke Path in King’s Wood.
16 Goytre Hall Wood Walk

Address

Goytre Hall Wood, Old Abergavenny Road, Goytre, Abergavenny, Monmouthshire, NP7 9DL

Telephone
01633 644850

countryside@monmouthshire.gov.uk

Goytre, Abergavenny

A gentle 1.8 mile walk taking in woodland and the Monmouthshire and Brecon Canal at Goytre Wharf, south of Abergavenny.
12 Clytha and Bettws Newydd

Address

Clytha National Trust car park, Old Abergavenny road, Raglan, Monmouthshire, NP7 9BW

Telephone
01633 644850

countryside@monmouthshire.gov.uk

Raglan

A 6 mile walk along the Usk Valley Walk and back via Bettws Newydd and the National Trust’s Clytha estate, in countryside between Abergavenny and Raglan.
5 St Arvans Roundabout

Address

St Arvans Memorial Hall, A466, St Arvans, Chepstow, Monmouthshire, NP16 6DN

Telephone
01633 644850

countryside@monmouthshire.gov.uk

Chepstow

A 5.4 mile hilly walk around the community of St Arvans north of Chepstow.
19 Redbrook to Penallt

Address

Redbrook car park, Redbrook Road, Redbrook, Monmouthshire, NP25 4LP

Telephone
01633 644850

countryside@monmouthshire.gov.uk

Redbrook

A walk of 4.4 miles in the Wye Valley south of Monmouth. Sustained ascent and descent.
Wye Valley Greenway

Address

Tintern, Monmouthshire, NP16 6SZ

Tintern

The Wye Valley Greenway is a five mile shared use route between Tintern and Chepstow, mostly following the old Wye Valley railway line down the eastern side of the River Wye.
Health Walk - Bulwark Walk

Address

Severn Bridge Social Club, Bulwark Rd, Bulwark, Chepstow, Monmouthshire, NP16 5JN

Telephone
01633 644850

countryside@monmouthshire.gov.uk

Bulwark, Chepstow

2.6 miles around the Bulwark area of Chepstow, taking in the Wales Coast Path through Warren Slade.
Health Walk - Dixton Church Walk

Address

Monmouth Leisure Centre, Old Dixton Road, Monmouth, Monmouthshire, NP25 3DP

Telephone
01633 644850

countryside@monmouthshire.gov.uk

Monmouth

A 1 mile Monmouth walk along the River Wye to Dixton Church and back.
Geoffrey of Monmouth Trail

Address

Monnow Street, Monmouth, Monmouthshire, NP25 3EG

countryside@monmouthshire.gov.uk

Monmouth

A 1.75 mile walk on which you'll learn a little about Geoffrey & his links to Monmouth, as well as other interesting facts.
Health Walk - Drybridge & Watery Lane Walk

Address

Bridges Centre Car Park, Drybridge Park, Monmouth, Monmouthshire, NP25 5AS

Telephone
01633 644850

countryside@monmouthshire.gov.uk

Monmouth

A 2.75 mile walk through Drybridge Nature Park and Vauxhall Fields, returning along Watery Lane.