Walking in Pickering

Walking in Pickering

5 trails you will love
Forest Holidays


Looking for a place to plan your next UK walking family  holiday? Look no further than The North Yorkshire Moors offering 550 square miles of scenic views to be explored. If you’re seeking respite from your usual 9-5 routine, North Yorkshire is an ideal choice.

Spend the day meandering through the heather moorland, join cliff-top trails for spectacular views and walk along sandy beaches at sunset before returning to a cosy forest cabin.


1. Cleveland Way

Cleveland Way is number one and on our list for very good reason! Just a 35-minute drive from Pickering expect captivating views surrounded by 109 miles of beautiful countryside and wild heather moorland. This trail offers a varied landscape with coastal views at points, offering distant views of fishing villages and hidden coves. What will you discover along the way?  

2. Cawthorn Roman Camps, Cropton

If you're looking for short walks near Pickering, Cawthorn Roman Camp is just a 15-minute drive away. This charming open meadow features Roman built forts and a camp overlooking the breath taking North Yorkshire Moors National Park. This circular trail is marked along the way, making it a safe and easy walk to follow, a great option for a leisurely afternoon walk with the whole family. The compact terrain makes it ideal for those with mobility issues and families with young children. Wrap up warm for this slow paced 1-mile loop, as the area is exposed so can get chilly in colder weather!

Blooming heather moorland in North Yorkshire

Discover the true beauty of North Yorkshire

3. Pickering Castle and Newbridge

Located centrally in the market town of Pickering, you will find Pickering Castle and Newbridge trail. Receive a history lesson as well as a pleasant stroll on this trail. Wander through the 12th century castle ruins to view the remains, which were once a hunting lodge and holiday home. This moderate, circular walk is surrounded by a grassy moat including a few climbs and descents at points. Allow approximately 1 hour to complete this 3.4km, the perfect choice for a weekend walk for the whole family.

4. Bridestones, Crosscliff & Blakey Topping

This trail offers a bit of everything and is only a short drive away from Pickering, making it an ideal choice for families with young children or pets that just can’t wait to arrive! A feast for your eyes, enjoy magical woodland views, open grassy moorland, and unique rock formations. Head to Blakey topping for incredible stretching views of North Yorkshire but don’t forget to take your camera with you, to snap the moment!

Sunset view of Blakey Topping, North Yorkshire Moors

End your walk catching the sunset

5. Hole of Horcum

 Hole of Horcum is our fifth and final trail, featuring idyllic views of the countryside across a 5 mile radius. If you’re looking for a challenging walk, this moderate trail is a circular route taking up to 3 hours to complete without stops. If you fancy a refresh and maybe a bite to eat in between, The Horseshoe Inn makes a great stop before finishing the journey, taking in the breath-taking views that surround you, complete with a full belly.   

These remarkable walking trails offer some of the best views that North Yorkshire has to offer, taking you through some of the most beautiful towns and villages. Experience woodland walks, rocky coastal paths, sandy beaches, and of course iconic heather moorlands. Local to the market town of Pickering, you will find lots of local amenities including cafés, bars, and restaurants. Book a solo trip to re set your mind or plan a break with loved ones.

Just 15 minutes away from Pickering, our cosy log cabins close by: Cropton and Keldy are situated 3.9 miles apart, offering the perfect base to rest and re coup after a day’s walking. Book a Golden Oak cabin complete with a warm log burning stove to provide a feeling of true comfort and relaxation, the perfect setting to plan your next walking adventure.   

Couple next to a log burner in the cabin at Forest Holidays

Rest your feet after a day's walking in North Yorkshire