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Weymouth And Portland

The best walks and hikes around Weymouth And Portland

4.6

(1639)

12,763

hikers

227

hikes

Hiking around Weymouth And Portland offers diverse landscapes, characterized by the dramatic cliffs and coves of the Jurassic Coast, a UNESCO World Heritage Site. The region includes the rugged Isle of Portland, connected by the distinctive Chesil Beach, an 18-mile-long shingle bank. Inland areas feature former quarries, now nature reserves, and rolling hills. This varied terrain provides a range of hiking experiences from coastal paths to more sheltered routes.

Best hiking trails around Weymouth And Portland

  • The most popular hiking…

Last updated: October 10, 2026

4.6

(193)

1,035

hikers

#1.

A loop of Portland from Chesil Beach

20.3km

05:36

330m

330m

This difficult 12.6-mile (20.3 km) hike loops around the Isle of Portland, offering a challenging experience with 1079 feet (329 metres) of elevation gain. You can expect to complete it…

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Hard

4.7

(24)

138

hikers

Embark on an easy hike along the South West Coast Path: Portland Bill Loop, a route that offers wild, windswept, and ruggedly scenic views. This trail spans 3.5 miles (5.6…

Easy
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Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

Moderate

Hard hike. Very good fitness required. Easily-accessible paths. Suitable for all skill levels.

Hard

This easy 4.3-mile (6.9 km) loop in Weymouth combines the lively Sea Front with the tranquil urban wetlands of Lodmoor Country Park and Radi

Easy

Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

Moderate

4.6

(5)

8

hikers

Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

Moderate

Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

Moderate

Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

Moderate

Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

Moderate
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Popular around Weymouth And Portland

Hiking around Weymouth

Hiking around Portland

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South West Coast Path — Part 4 — Conquer Britain's longest trail

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Running Trails around Weymouth And Portland

Road Cycling Routes around Weymouth And Portland

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E9 Plymouth to Dover — An epic exploration of England's south coast

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Tips from the Community

MCW73
October 11, 2026, Smugglers Inn

The Smugglers Inn is a historic, 13th-century thatched country pub and boutique hotel nestled on the clifftops of Osmington Mills, Dorset. Boasting sweeping views of the English Channel and the Isle of Portland, this Hall & Woodhouse coastal gem sits steps away from the rugged Jurassic Coast and the South West Coast Path. Steeped in local lore, the inn served as a notorious 17th-century smuggling landing site and was once the headquarters for the French smuggler Pierre Latour and the infamous Emmanuel Charles. Inside, the building retains its authentic, centuries-old character with low oak-beamed ceilings, original flagstone floors, and a historic central chimney. Today, it operates as a cozy retreat featuring eight en-suite bedrooms, EV charging bays, and a large tiered outdoor terrace complete with a natural stream. The restaurant serves seasonal British pub classics, hearty Sunday roasts, and locally brewed Badger Beers. Known for its warm hospitality, the inn remains highly popular with hikers, families, and dog owners looking for a scenic countryside escape.

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Cut right into the limestone of Osmington Hill, the Osmington White Horse is a massive, 280-foot-long hill figure that has been watching over the Dorset coast since 1808. Unlike most chalk horses, this one features a rider: King George III on his favorite charger, Adonis. The King loved vacationing in nearby Weymouth, so local residents carved it to honor him. However, local legend says the design backfired. Because the horse is depicted riding away from the town, the King supposedly took it as a passive-aggressive hint that he wasn't welcome and never came back. Over the years, it has been a target for playful pranks—even getting a temporary plastic unicorn horn in 2011. It is a fantastic landmark to spot while driving along the A353 road or while enjoying a breezy hike on East Hill.

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MCW73
October 4, 2026, St Osmund's Church

St Osmund’s Church in Osmington, Dorset, is a historic parish church with origins dating back to around 1170. Dedicated to the 11th-century Bishop of Salisbury, the building forms part of the scenic Ridgeway circuit. While extensively rebuilt between 1845 and 1846 using local stone and Ham Hill dressings, it beautifully incorporates its medieval heritage. Surviving architectural treasures include a Romanesque chancel arch from circa 1200, a restored font of the same era, and a 14th-century north arcade. Its striking two-stage west tower houses four historic bells, including one dating back to the late 14th century. The churchyard features two Grade II listed monuments, including a 1678 table tomb. Famed landscape artist John Constable even captured the church during his 1816 honeymoon in the village, cementing its place in English cultural and architectural history

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MCW73
October 4, 2026, The Springhead Pub

The Springhead is a traditional country pub nestled in Sutton Poyntz near Osmington. It features a large orchard beer garden with scenic views of the Osmington White Horse. Known for its Sunday carvery, log fires, and wood-fired pizzas, this dog-friendly retreat is perfect for walkers exploring the Jurassic Coast.

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Ian
September 15, 2026, Osmington White Horse

The only white horse to have a rider. It is George III, on top of his horse Adonis.

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Gelan
September 10, 2026, Smugglers Inn

Very nice picnic spot with toilets. Not a big detour.

Translated by Google•

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part of the 17 miles of earthworks.

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Stone Tipping bridge - to dispose of spoil

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More Information

The splendour of Portland

Some of the best hiking trails in the Weymouth and Portland area are surely those that enjoy views along Chesil Beach’s incredible 18-mile (29 km) length. Stretching from West Bay to Portland, this exquisite barrier beach provides protection for numerous villages and Weymouth. Shingle is tough-going underfoot but you can certainly explore as much of Chesil Beach as you like. 

Portland itself is a small island making perimeter walks possible over a weekend. There are plenty of traffic-free trails and footpaths criss-crossing it, so you can explore for as long as you like. Hikes along Portland’s west side offer sweeping views across Lyme Bay, whilst the east side offers views to the Isle of Purbeck and, in exceptionally clear weather, the Isle of Wight. The lighthouse on Portland Bill is particularly spectacular. 

Exploring the mainland

Walks in Weymouth will fascinate any maritime historian as well as lovers of boats in general. With major breakwaters, Nothe Fort and pretty marinas on the River Wey in the heart of the town, there’s plenty to see on your explorations. Hiking west, seek out the Osmington White Horse, one of southern England’s numerous chalk hill figures; it features King George III astride his horse. 

You can ramble further, adventuring across the downs and reaching Durdle Door and Lulworth Cove, both exceptional natural wonders. North of Weymouth, a vast chalk ridge runs east–west and makes for a brilliant place to hike, providing soaring views across the town and over Portland. You can walk to Bincombe Hill, Chalbury hillfort, Friar Waddon Hill amongst others, all with footpaths and viewpoints. To the north west of Weymouth lies the gorgeous village of Abbotsbury, looking like it’s wandered out of a photograph. An Iron Age hillfort, a swannery, two pretty churches and a subtropical garden all call this their home. 

No matter what time of year you explore, there are fantastic hiking routes waiting in the Weymouth and Portland Area. You’ll never be too far from a pub or a cafe and in the summer, you can always cool off with a dip in the sea: it’s almost everywhere you look.


Frequently Asked Questions

How many hiking trails are available in Weymouth And Portland?

There are over 230 hiking routes available in Weymouth And Portland, catering to various skill levels. This includes 148 easy routes, 76 moderate routes, and 10 difficult routes, ensuring options for everyone from casual strollers to experienced trekkers.

What kind of terrain can I expect on hikes around Weymouth And Portland?

The terrain is incredibly diverse. You'll find dramatic coastal paths along the UNESCO World Heritage Jurassic Coast, rugged landscapes on the Isle of Portland, and the unique shingle bank of Chesil Beach. Inland, routes may take you through former quarries, now nature reserves, and rolling hills. Expect a mix of paved paths, gravel tracks, and natural earth trails, often with some elevation changes, especially on coastal sections.

What do other hikers say about the trails in Weymouth And Portland?

The routes in Weymouth And Portland are highly rated by the komoot community, with an average score of 4.6 stars from over 630 reviews. Hikers frequently praise the stunning coastal views, the unique geological features, and the variety of trails available for different abilities.

Are there any notable landmarks or attractions to see while hiking in Weymouth And Portland?

Absolutely. Many trails offer access to significant landmarks. On the Isle of Portland, you can visit the iconic Portland Bill Lighthouse and the striking natural monument Pulpit Rock. Near Weymouth, the Jubilee Clock Tower is a prominent feature. The region also boasts geological wonders like Chesil Beach and historical sites such as Sandsfoot Castle and Gardens.

Are there family-friendly hiking options in Weymouth And Portland?

Yes, there are many family-friendly options. Easy routes like the South West Coast Path: Portland Bill Loop (5.6 km) offer manageable distances with rewarding views. The Weymouth Sea Front, Lodmoor Country Park & Radipole Lake Nature Reserve loop (6.9 km) is another excellent choice, combining coastal promenades with nature exploration, suitable for all ages.

Are dogs allowed on the hiking trails in Weymouth And Portland?

Many trails in Weymouth And Portland are dog-friendly, especially coastal paths and countryside routes. It's always best to keep dogs on a lead, particularly near livestock, cliffs, or nature reserves, and to check local signage for any specific restrictions. The Rodwell Trail, for instance, is a popular choice for dog walkers.

Is parking available for hikers in Weymouth And Portland?

Yes, parking is generally available at various trailheads and popular starting points, especially around Weymouth town centre and on the Isle of Portland. Specific car parks can be found near attractions like Portland Bill and along the coast. Some may require payment, so it's advisable to carry change or check for app-based payment options.

How can I reach the trailheads in Weymouth And Portland using public transport?

Weymouth is well-served by public transport, including a train station and bus services that connect to various parts of the town and the Isle of Portland. Local bus routes can take you close to many trailheads, particularly for routes starting in Weymouth or on Portland. For detailed schedules and routes, it's best to consult local transport providers or visit the Dorset Council website for walking information: dorsetcouncil.gov.uk.

Are there many circular walks available in Weymouth And Portland?

Yes, the region offers a good selection of circular walks. Many routes are designed as loops, allowing you to start and finish in the same location. Examples include the challenging A loop of Portland from Chesil Beach and the easier Weymouth Sea Front, Lodmoor Country Park & Radipole Lake Nature Reserve loop.

What is the best time of year for hiking in Weymouth And Portland?

Spring and autumn are often considered ideal for hiking, with milder temperatures and fewer crowds. Spring brings wildflowers, while autumn offers beautiful colours. Summer is popular but can be busy, especially on coastal paths. Winter walks are also possible, particularly on the Isle of Portland, but be prepared for potentially strong winds and wet conditions, and always check weather forecasts.

Can I find pubs or cafes along the hiking routes?

Yes, you'll find various pubs and cafes, especially in Weymouth town centre and in villages on the Isle of Portland. Many coastal routes pass through or near settlements where you can stop for refreshments. For example, the Portland Bill Loop has facilities near the lighthouse.

Are there any hidden gem walks in the Weymouth And Portland area?

Beyond the well-known coastal paths, consider exploring the unique landscapes shaped by quarrying history. The Tout Quarry Sculpture Park on Portland, for instance, offers a blend of geological interest, art, and nature trails. The Legacy Trail, connecting important wildlife sites, also provides a deeper dive into the area's heritage and natural beauty away from the busiest spots.

Most popular routes around Weymouth And Portland

Family-friendly hikes around Weymouth And Portland

Most popular attractions around Weymouth And Portland

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