The Offa’s Dyke Path runs for 177 miles from Chepstow to Prestatyn, crossing beautiful landscapes along the England–Wales border. For first-time walkers, tackling the full route might feel daunting. The good news is you don’t have to do it all at once.

Here are the best sections of Offa’s Dyke Path to try if you’re new to long-distance walking.

Chepstow to Monmouth – The Wye Valley Starter

If you’re beginning your walking journey, the Chepstow to Monmouth stretch is ideal. It’s about 17 miles and follows the River Wye through woodland and past the historic ruins of Tintern Abbey.

• Scenic river views

• Gentle climbs compared to tougher northern sections

• Historic interest with abbeys and castles

👉 Make it a relaxed trip with our Guided Walks designed to introduce you to this section.

📖 Learn more about the Wye Valley on the National Trails site.

Hay-on-Wye to Kington – Book Town to Border

This 14-mile stage is a favourite for walkers who enjoy a mix of rolling countryside and charming market towns. Starting in Hay-on-Wye, famous for its bookshops, it finishes in Kington, a quiet border town.

• Gentle terrain for first-timers

• Plenty of accommodation and dining options

• A great balance of countryside and culture

👉 Stay in comfort with our handpicked Places to Stay.

Knighton to Brompton Crossroads – A Taste of the Challenge

While known as one of the toughest sections of the trail, this shorter 7-mile stretch gives newcomers a real sense of achievement. It includes steep ascents and panoramic views across the Welsh hills.

• A rewarding challenge without committing to long distances

• Fantastic viewpoints perfect for photos

• Ideal for training or testing your fitness

👉 Travel light with our Luggage Transfers so you can focus on the walk.

📖 Read a detailed stage breakdown on the Long Distance Walkers Association.

Tips for First-Time Walkers

• Start small: Choose a section of 1–2 days before planning a longer holiday.

• Bring good footwear: The trail has mixed terrain, from river paths to hill climbs.

• Plan your stays: Booking accommodation close to the path saves tired legs at the end of the day.

• Consider a guided option: Having a leader can reduce navigation worries and let you focus on the experience.

👉 See our full Walking Holiday Packages to find the right trip for you.

Ready to Try Offa’s Dyke Path?

Walking parts of Offa’s Dyke Path is a brilliant way to experience the beauty and history of the England–Wales border without committing to the entire route. Start with these sections, and you might just find yourself planning the full 177 miles next time.

👉 Begin your adventure today with our Guided Walks and Accommodation.