A Perfect Dorset Winter’s Day Out: Symondsbury Holloways, Hell’s Lane & a Roast in Seatown

This has been on my Dorset bucket list for years and it massively exceeded my expectations!

If you’re looking for the ultimate outdoorsy Dorset winter’s day out; a decent family-friendly hike and utterly beautiful views and adventures, this route through Symondsbury, the Holloways including Hell’s Lane and on to Seatown is one of the most magical ways to spend a crisp, sunny day.

We set off as a family for a winter walk starting in Symondsbury, with its charming village, countryside views and famous ancient sunken lanes. From climbing the iconic Colmer’s Hill to exploring the moss-covered Holloways, warming up with a hearty roast in Seatown, this is the perfect blend of nature, adventure and cosy coastal food.

Whether you’re walking with young kids, enjoying a couples’ escape, or planning a friends’ hike (with the option to add Golden Cap, the highest point on the South Coast), this itinerary blends Dorset’s best scenery into one unforgettable winter’s day.

Start Your Adventure: Park in Symondsbury Village

Symondsbury is easy to find, with free parking right in the village (we parked on a quiet lane), and plenty of signposts leading you onto the walking paths. It’s a lovely place to begin; quiet, picturesque and home to the iconic Colmer’s Hill, which you can already see rising above the village rooftops.

Climb Colmer’s Hill for 360° Views

If you choose to, you can begin your walk with the rewarding ascent of Colmer’s Hill. It’s a short, steep climb that children can manage (my 5 and 8 year olds were fine), and the views from the top are incredible - sweeping panoramas across the Dorset countryside, out towards Seatown Beach and the Jurassic Coast.

It’s the perfect warm-up and a brilliant photo spot.

Walk Across to Hell’s Lane - Enter the Magical Holloways

From Colmer’s Hill, follow the well-marked path that leads you across the countryside and down into the Holloways; ancient sunken lanes carved by centuries of footsteps, hooves and wagon wheels. The twisting tree roots, high moss-covered banks and peaceful dappled light make it feel like stepping into a fairytale. One of my favourite films as a child was David Bowie's Labyrinth and it felt like you were on parts of the Labyrinth adventure!

Soon you join Hell’s Lane, the most dramatic and atmospheric section of them all.

It’s narrow, mysterious, stunningly beautiful and a dream spot for winter photography or content. Make sure you bring your wellies as there's a lot of water coming down and some sections even flowing!

This part of the walk is ideal for children, with plenty to explore and a ‘secret woodland tunnel’ feel the whole way down.

Follow Hell’s Lane All the Way to North Chideock

Stay on Hell’s Lane as it winds down into North Chideock, giving you a wonderful sense of Dorset history and landscape. At the bottom, you’ll emerge from the enclosed banks into open countryside with far-reaching views.

Cross the Gorgeous Green Fields Back Towards Symondsbury

From North Chideock, loop back via the open fields and rolling green farmland. This is a complete contrast to the shaded Holloways - bright, wide and with huge Dorset skies overhead. It feels spacious, free and full of sheep and wildlife to spot.

Drop Back Down Through More Holloways to Your Car

As you near Symondsbury again, you re-enter another beautiful run of Holloways, giving your return journey the same magical woodland feel as earlier - a perfect ending to the walk.

Once back in the village, you can stop for a drink at the estate café or head straight to the coast for the next part of your day.

Extend Your Adventure: Seatown, The Anchor Inn & Optional Golden Cap

After our walk, we hopped in the car (approx. 10–12 minutes) and headed to Seatown, one of the most beautiful spots on the Jurassic Coast.

Sunday Lunch at The Anchor Inn, Seatown

Right on the beach, The Anchor Inn serves a brilliant roast with unbeatable sea views.

The cosy interior is perfect on winter days, or you can sit outside on sunny ones and listen to the waves. We had a drink outside to take in the views and then headed inside by the cosy fire for our roast. The staff are super friendly and it was a really great atmosphere as well as delicious food.

Optional: Hike Up Golden Cap

If you’re not walking with small children -  or you’re hungry for more adventure, you can add the climb up Golden Cap, the highest point on the South Coast.

The trail starts right from Seatown.

Bonus: The Sea Sauna at Seatown

And for anyone who loves cold-water therapy, there’s now a sea sauna on the beach - the perfect way to finish your winter’s day out with an unforgettable hot-cold plunge experience.

This route is one of Dorset’s most magical winter walks - combining panoramic views, ancient Holloways, atmospheric woodland, open countryside and a cosy coastal pub lunch. Whether you’re visiting as a family, planning a romantic day out, or looking for a new walking challenge, Symondsbury to Hell’s Lane and on to Seatown offers the perfect blend of beauty, adventure and relaxation. With the option to tackle Golden Cap and even enjoy a sea sauna, it’s a Dorset day out you’ll want to repeat again and again.