The Curated Guide to Dog Walks We Keep Coming Back To
One of the joys of staying in one of our dog-friendly holiday cottages is discovering how many wonderful places there are to explore together. Living in Dorset, we’re incredibly lucky to have some of Britain’s finest walking country on our doorstep. From the Jurassic Coast and rolling countryside to ancient hillforts and hidden coves, there’s always somewhere new to discover.
Yet whenever we have a few hours free with Smarty, we almost always find ourselves returning to the same special places. They aren’t necessarily Dorset’s most famous walks, but they’ve become our favourites over the years because each one offers something different, whether that’s breathtaking coastal views, fascinating history, peaceful countryside, or simply the perfect place to finish with a pub lunch.
Whether you’re planning a weekend getaway or a longer stay in Dorset, we hope these walks inspire you to discover the county we love and to experience it beyond the guidebooks.
Osmington, Bran Point, Ringstead & White Nothe
A Walk Through Smugglers’ Country
A Walk Through Smugglers’ Country
Whether you’re staying in Weymouth, nearby in Dorchester, or elsewhere in Dorset, and we only had one coastal walk to recommend, this would be somewhere very close to the top of our list.
Starting near Osmington Mills, the path climbs gently towards Bran Point, then follows one of the most breathtaking stretches of the Jurassic Coast. The views seem to improve with every step, stretching west across Weymouth Bay towards Portland and east towards the dramatic chalk cliffs of White Nothe.
What makes this walk so memorable isn’t just the scenery. Ringstead Bay was once a favourite landing place for smugglers, while hidden among the surrounding fields lie the remains of a medieval village abandoned after the Black Death. Continue a little further, and you’ll discover the tiny St Catherine’s by the Sea Chapel, which has stood watch over the coastline for centuries, while nearby Burning Cliff tells the remarkable story of an underground fire that smouldered for years after oil shale ignited in the nineteenth century.
Every season brings something different. Spring carpets the clifftops with wildflowers, autumn offers crystal-clear views across the coast, and winter transforms the sea into a dramatic spectacle below the cliffs.
If we’re making a day of it, we nearly always finish at The Smugglers Inn. Sitting outside with lunch after a few hours on the coast path is one of our favourite ways to spend a Dorset Sunday.
Distance: approximately 10 miles
Park at the Smugglers Inn car park. Postcode: DT3 6HF
Maiden Castle
Walking Through 5,500 Years of History
Some places in Dorset make you stop and think. Maiden Castle is one of them. And this is a perfect walk if you are staying in Dorchester.
Rising above the county, it’s Britain’s largest Iron Age hillfort and one of the county’s most remarkable historic landscapes. Yet despite its significance, it often feels surprisingly peaceful.
We usually start near Martinstown, following quiet footpaths across open farmland before climbing onto the enormous earthworks. Walking around the vast concentric ramparts brings the history to life in a way that simply driving to the visitor car park never can.
The views are extraordinary, stretching for miles across the Dorset countryside, while skylarks provide the soundtrack for much of the walk. It’s somewhere that feels just as magical on a crisp winter morning as on a warm summer evening.
It’s one of the walks we often recommend to guests seeking something beyond the coast, combining fascinating history with peaceful countryside and plenty of space for dogs to enjoy the fresh air. The best way is to start and finish at the Brewers Arms in Martinstown. It’s a great pub serving traditional dishes with local ales, and it’s in a fantastic village location.
Corfe Castle & the Purbeck Hills
One of Dorset’s Most Rewarding Circular Walks
Corfe Castle may be one of Dorset’s best-known landmarks, but it doesn’t take long to escape the crowds.
Within minutes, you’re climbing into the Purbeck Hills, where spectacular views open up across the castle ruins and the surrounding countryside, and, on a clear day, all the way towards Poole Harbour.
This is one of those walks where we always seem to stop, turn around and admire the view. No matter how many times we’ve done it, seeing Corfe Castle towering above the Purbeck landscape never loses its appeal.
The route continues through peaceful farmland and open hills before looping back into one of Dorset’s prettiest villages, where independent cafés, galleries and traditional pubs make it easy to spend the rest of the afternoon exploring.
If we’re walking on a Sunday, we nearly always finish at The Greyhound Inn. Their Sunday lunches are among our favourite meals in Dorset, and in summer we’ll always try to grab a table in the beer garden. It’s a wonderful place to relax after a walk, and on some weekends there’s even live music or entertainment in the garden. But it’s the view of Corfe Castle that steals the show. And if you love Corfe Castle that much and want to discover more, our Explore guide will provide you with lots more inspiration.
Distance: Approximately 5 miles.
Park and start at the National Trust Corfe Castle car park. Postcode: BH20 5DR
Tout Quarry, Portland
Where Art Meets the Jurassic Coast
There really isn’t another walk in Dorset quite like this one.
Instead of simply following a coastal path, Tout Quarry leads you through a remarkable open-air sculpture park where nature has slowly reclaimed the old Portland stone workings. Today, more than 60 sculptures are carved directly into the Portland stone, making it one of the most unusual walks on the Jurassic Coast. Many blend so naturally into the landscape that they’re easy to miss if you’re not paying attention.
We love that every visit reveals another sculpture we’d somehow overlooked. But it’s the views that make us return. The views of the castle beach and Lyme Bay are spectacular and change with the seasons. It’s on sunny days, when the sea looks turquoise, that it looks its most stunning. Although our children always loved doing this walk during the Halloween half term, in these months the walk and the sculptures can take on a completely different atmosphere.
Whatever the season, it always feels like discovering one of Dorset’s best-kept secrets.
We usually round off the walk with a coffee or a spot of lunch at The Portland Heights Hotel Café. If the weather’s kind, it’s well worth sitting outside on the terrace, where the elevated views across Chesil Beach, The Fleet Lagoon and Lyme Bay are simply breathtaking. And if you’ve never been served by Bella, the hotel’s friendly robot server, that’s part of the experience too.
Distance: Approximately 2 miles.
Lulworth Cove to Fossil Forest
A Jurassic Coast Adventure Like No Other
Starting from Lulworth Cove Visitor Centre, this is one of our favourite coastal walks. It combines some of Dorset’s most spectacular scenery with one of its most fascinating hidden landscapes.
Following the South West Coast Path, the route climbs above Lulworth Cove towards Durdle Door, then continues to Dungy Head. Along the way, you’ll enjoy breathtaking views across St Oswald’s Bay, Man O’ War Beach and the iconic limestone arch of Durdle Door. It’s a walk we always seem to stop, turn around and admire the view.
From Dungy Head, the route loops inland towards Stair Hole before returning to Lulworth Cove. The final highlight is at the eastern end of the beach, where a path climbs above the cove to Fossil Forest. Here, you can see the fossilised remains of a 145-million-year-old forest, one of the Jurassic Coast’s most extraordinary geological treasures. Access can occasionally be restricted when the nearby Lulworth Ranges are in use for military training, so it’s always worth checking before you set off.
Back at the visitor centre, you’ve certainly earned a well-deserved coffee or lunch. We often choose Finley’s Café, The Lulworth Cove Inn, or The Boat Shed Café, all overlooking the cove or just moments away from it – the perfect way to round off one of Dorset’s most memorable walks.
Distance: Approximately 3 miles.
Park at The Lulworth Cove Visitor Centre. Postcode: BH20 5RQ.
Why We Keep Walking These Routes
Perhaps that’s the common thread running through all of these walks.
None of them was chosen because they appear in every guidebook. They became favourites simply because, over the years, we kept returning.
Some offer spectacular Jurassic Coast views, while others reveal centuries of history or end at one of our favourite pubs. Every walk has become part of our own Dorset story.
If you’re staying in one of our dog-friendly or luxury holiday cottages in Dorset, we hope it becomes part of yours too.
And if you’re looking for even more inspiration, don’t miss our curated guides to dog-friendly beaches, pubs and attractions in Dorset, along with our wider collection of Dorset holiday cottages, all carefully chosen to help you experience Dorset beyond the guidebooks.