Sleepy Dorset: quieter things to do in the wintertime, free from crowds

The Jurassic Coast is beautiful in winter

It’s no surprise that summer in Dorset can get a bit hectic. Ours is a beautiful, rural region - famous for its Jurassic Coast - so it’s a magnet for those escaping city life (or ‘grockels’ as we affectionately like to call these non-native tourists). 

At this time of year, Dorset’s market towns (like Bridport where Outbuildings is based) come alive with visitors exploring the independent shops and enjoying Dorset’s dog-friendly beaches. Visit us in the summer and you’re sure to love the buzzy happy vibe that fills the air, as much as we love it.

In winter, Dorset has a completely different personality that’s just as captivating.

As October unfolds, a wonderful calm and ease settles on the region: sun-bathing crowds are replaced by chilled-out residents enjoying the coastline and soft sunlight with their dogs or loved ones, whilst the villages and towns empty leaving behind pubs where you can sip a quiet pint chatting to a local then explore the peaceful shops for locally-made treasures. 

So, if you fancy exploring Dorset’s sleepy side (whilst staying cosy with us), let us be your guide. Here are some of our favourite things to do in Dorset in the winter. 

Sleepy Dorset: Things to do in Winter

Explore Dorset's famous fossil beaches for prehistoric treasures 

Only a short drive away from Outbuildings, you’ll find the lovely beaches of Charmouth and Lyme Regis. Not only are they delightful in their own right (this is a UNESCO World Heritage Site after all), they are also among the very best beaches in the UK to go fossil hunting on. 

Both Charmouth and Lyme Regis sit on an incredible stretch of coastline - known as the Jurassic Coast - which holds 185 million years of the Earth’s history in its rocks. In the winter, both beaches are arguably at their best when it comes to finding fossils, thanks to the storms, wind and waves that often wash new prehistoric treasures from the cliffs onto the beaches below. 

Spend time wandering the pebbles and you’re sure to find an ammonite or two to take home with you, even if you’ve no previous fossil-hunting experience. If you’re bringing your four-legged friend with you on your winter break, you’ll be pleased to know that many of the beach restrictions are lifted at this time of year and your pet pooch is welcome to join you on a seaside fossil hunt. 

Sleepy Dorset: Things to do in Winter

Take a countryside walk into Dorset legends and lore

West Dorset is full of myths and legends that seem to draw closer as the crowds of summer abate. Why not use your winter staycation to step into the stories and lore that pepper our region?

A perfect place to start is Colmer’s Hill, rising just outside of Bridport like a lone sentinel above the patchwork landscape. Locals call it the Watchman of West Dorset, and from its summit it’s easy to see why. Stand beneath the silhouette of the pines and you’ll feel as if the hill is keeping its eye on everything. From the distant shimmer of Lyme Bay to the rooftops of Bridport in the distance, and in between the rolling Dorset fields and ancient tracks that weave through them.

Below Colmer’s Hill lie the old Holloways - sunken lanes carved deep into the earth by centuries of footsteps, cartwheels and grazing animals. In winter, when bare roots arch overhead and frost clings to moss and stone, these pathways feel like corridors through time. Folklore tells of smugglers, pilgrims and travellers who once slipped silently along these hidden routes, sheltering from watchful eyes and wild weather.

Sleepy Dorset: Things to do in Winter

Tuck yourself into the county’s fascinating museums or heritage pubs

Winter is one of the best times to explore the cultural side of West Dorset, particularly around Bridport. Without the bustle of peak season, you can discover historic places at a slower, more welcoming pace.

Start with Bridport’s historic pubs, many of which still carry the charm of their past. One of the town’s most notable heritage pubs is The Bull. It dates back to 1535, when it was established as a coaching inn - since then, it has seen a lot of British history pass by its doors. 

For instance, it was part of the route for the famous Battle of Waterloo courier ride. Horses were changed here during the urgent dispatch of Waterloo news, marking it out as a significant stop on what became known as the Trafalgar Way. 

To step deeper into local history, Bridport Museum is also a wonderful winter stop. Housed in a Grade II-listed building, it traces the area’s rope-making, fishing and agricultural past; all woven together with fascinating stories from the Jurassic Coast and its communities.

Whatever time of year you decide to visit Dorset, we’re sure you’re going to love it as much as we do as it swings from spring and summer to autumn and winter. 

Whilst the region varies as the season changes, you can rest assured that here on the farm life is perennially chilled - whether it’s the peak or low season. In the summer you can laze in your room with the floor-to-ceiling windows wide open to let the countryside greenery roll inside; in the winter, you can snuggle by your log-burner with a book or feast quietly in our on-site lounge and bar, The Cart Shed. 

One mood, one indulgent break - whatever time of year you stay.  

Happy exploring,

The Outbuildings Team

The Whitehead Family, Outbuildings Dorset