Myles Goode
Published November 28, 2025 7:00am
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Fall in love with Dorset when the crowds have gone (Picture: Myles Goode)
With the curtains drawing earlier by the day, there’s never been a better time to break for the coast and immerse yourself in Dorset’s cosy charm.
Hugging England’s dramatic southern coast, this lyrical landscape has long been a retreat for those drawn to wilderness, heritage, and quiet luxury.
Here, the Jurassic Coast sweeps past sea-carved bays and fossil-studded cliffs, while Iron Age forts, manor hotels and fairytale castles embroider the hills that inspired Enid Blyton’s beloved stories.
If it sounds romantic, it is, and then some.
With the help of my partner, I explored what Dorset has to offer in winter — in my book, the best time to visit.
Where we went in Dorset
Lyrical landscape (Picture: Myles Goode)
Our first stop is Weymouth, a place that seamlessly blends the best of the British seaside with charming boutiques and an array of cosy coffee shops to stop in.
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When we arrive in mid-October, there are no crowds or tour buses, leaving us free to traipse at leisure.
A must-visit is St Alban Street. What it lacks in length, it makes up for in character, with quirky gift shops and, of course, several quintessential fudge stores.
We highly recommend Roly’s (they’ll give you a free taste).
In winter, this heritage-rich region takes on an added depth. The absence of crowds throws subtle details into sharper relief, from the Georgian terraces to pastel beach huts and peaceful shoreline.
A few minutes walk from Weymouth’s high street is a bracing but beautiful sandy beach, mostly empty and inviting you to wander (Picture: Myles Goode)
Another great place to visit after the crowds have gone is, I’m serious, Sea Life.
Being mostly outdoors and relatively small, it is home to over 2,500 creatures.
The penguins and otters love to be out when it’s cooler and wetter, so you’ll have a clear view of your favourites without standing on tiptoe, peering through crowds of people.
Penguins pausing for a photo during feeding time (Picture: Myles Goode)
A 15-minute drive from Weymouth, we take a romantic stroll, high on the white-brushed clifftops of Portland in the heart of the Jurassic Coast.
With 185 million years of Earth’s history written into the rocks, this spectacular UNESCO-listed landscape leaves us in awe as we wander hand in hand where dinosaurs roamed.
It would be a fantastic way to blow away the cobwebs after Christmas; a great place to breathe.
Wallaby farm in Portland (Picture: Myles Goode)
Wallaby farm in Portland (Picture: Myles Goode)
Verne Quarry High Angle Battery, Portland (Picture: Getty images)
Verne Quarry High Angle Battery, Portland (Picture: Getty images)
Memory stones overlook Tout Quarry and the wider Quarry Park (Picture: Myles Goode)
Memory stones overlook Tout Quarry and the wider Quarry Park (Picture: Myles…
Isle of Portland clifftop walks is an incredible venture to reset and feel the fresh sea air (Picture: Beth Chambers)
Isle of Portland clifftop walks is an incredible venture to reset and feel the…
Portland war memorial (Picture: Myles Goode)
Portland war memorial (Picture: Myles Goode)
Capture gorgeous views from Portland heights beacon (Picture: Myles Goode)
Capture gorgeous views from Portland heights beacon (Picture: Myles Goode)
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We move on for a history lesson at the High Angle Battery.
Visitors are free to wander the abandoned military site at their own pace, exploring its labyrinthine network of tunnels and open battlements that speak to the area’s layered history.
The so-called ‘ghost tunnels’, dimly lit and echoing with footsteps, add a thrilling edge to the experience, making the site as evocative as it is educational.
Here is the map of our adventure so you can do the same yourself.
Where to stay for a winter break in Dorset
Warm up in a cosy, modern clifftop apartment surrounded by rich history and luscious green woodland overlooking soft sandy beaches.
For something special, check into Clifftops, a set of five lodges hewn into the cliffs on the Isle of Portland. Set within the grounds of Pennsylvania Castle and only a 15-minute drive from Weymouth, the minimalist apartments — all slick, stylish furnishings and floor-to-ceiling windows — seem to float above the waves below.
Suites big enough for four guests (two bedrooms, two bathrooms) are £803 for three nights.
For something more reasonable that doesn’t compromise on views, try The Front Rows, also on Pennsylvania Castle Estate. Suite for up to six guests (two bedrooms, one bathroom) are £254 for three nights.
(Picture: Beth Chambers/ Myles Goode)
(Picture: Beth Chambers/ Myles Goode)
(Picture: Beth Chambers)
(Picture: Beth Chambers)
(Picture: Beth Chambers)
(Picture: Beth Chambers)
(Picture: Myles Goode)
(Picture: Myles Goode)
(Picture: Beth Chambers)
(Picture: Beth Chambers)
(Picture: Beth Chambers)
(Picture: Beth Chambers)
Sit and enjoy a glass of Pennsylvania Fordington Gin with tonic whilst watching the moon blanket the dark ocean at night (Picture: Myles Goode)
Sit and enjoy a glass of Pennsylvania Fordington Gin with tonic whilst…
Take a walk around Pennsylvanis castle estates grounds (Myles Goode)
Take a walk around Pennsylvanis castle estates grounds (Myles Goode)
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Where to eat in Dorset
Dorset’s culinary scene comes into its own in winter.
Restaurants lean into hyper-local, seasonal produce — think Dorset crab, Portland lamb, and hearty root vegetables, allowing visitors to experience flavours unique to the colder months.
A standout for us is The Club House in West Bexington, a fantastic eating experience with beautiful sea views and friendly, welcoming staff. It’s also remarkably affordable.
The restaurant has indoor and outdoor seating (heated at this time of year), where you can enjoy a hearty meal and wine with a view of West Bexington beach, which is part of the 18-mile-long Chesil Beach. Lunches range from £15 – £20 while a generously portioned Sunday lunch is modestly priced at two courses for £20 or three for £25.
Don’t leave without trying the cauliflower cheese and buttermilk Panna cotta. Check out the full menu here.
Caption: Orange duck Paté for starter and White chocolate cheesecake for dessert(Picture: Myles Goode/ Beth Chambers)
Another star is The Clockspire in Sherbourne.
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Set inside a grand, palatial building, which is a restored 19th-century school, this Michelin-recognised restaurant is warm and inviting with outstanding service and food to match.
I could talk about it all, but special mention goes to the Glazed pork cheek, with burnt apple and Jerusalem artichoke, and a mouth-watering Blackmore Vale 8oz Sirloin steak served with autumn leaves, beef fat béarnaise, and triple cooked chips.Starters range from £15 – £29 and elegantly curated mains from £37 -£45. Full menu here.
Exquisite starters (scallops left, pork cheek right) at the Clockspire (Picture: Beth Chambers/ Myles Goode)
Travelling to Dorset outside the summer season reveals a wilder, more atmospheric side of the county — one that feels both adventurous and effortlessly romantic.
Quiet beaches, dramatic winter skies and peaceful market towns create a setting where the landscape takes centre stage, inviting long walks, coastal exploration and unhurried moments that might otherwise be lost in the crowd.
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