Welcome to my web site which contains maps, stories, history, advice and over 800 photographs to help you explore Portland, Dorset - The Jewel of the Jurassic Coast

Fortuneswell South

Portland, Dorset

Back to Portland Home Page


Back to Portland Map Index page


All the pictures on this page showing a thick border are thumbnails. Clicking on the picture will produce a larger version. Use your browser BACK button to return to this page.

The above image is copyright Dorset County Council 2000 and is reproduced here with permission.

This area of Fortuneswell is characterised by the main shopping centre, Tilleycombe and the steep hill up to New Ground.

We start high up on New Ground overlooking one of the finest views in Britain.

Please see the next page north for more pictures of Fortuneswell.

Please click here for a detailed street map. Click the BACK button on your browser to return to this page.

Please click here to visit the satellite image of this area on Google Maps. Click the BACK button on your browser to return to this page.

This area can be viewed on Google Street View by clicking here.

On this page we start at New Ground by the Portland Heights Motel and travel north, down the steep road to the southern end of Fortuneswell's busy shopping area. Further pictures of Fortuneswell are in the square to the north.

This enlarged area of the above aerial photograph centres on the Portland Heights Motel, "A". 

The War Memorial is immediately north of the motel "C" and Dowsett's Garage is to the south at "D".


The above image is copyright Dorset County Council 2000 and is reproduced here with permission.

At the top of Portland lies New Ground with its views towards the Mainland and along Chesil Beach.

The War Memorial stands silhouetted against a mid-summer sunset.

Typically, Underhillers and Tophillers vehemently argued that there should be two war memorials to remember the dead of World War 2. A compromise to this feud was reached by placing the memorial where it could be seen by both communities.

It was unveiled on 11th November 1926 in torrential rain by ex-Private Crispin who had lost three brothers in the war. The memorial recorded the names of 223  Portlanders who had died in the Great War.

The pictures below show the names displayed on the War Memorial.

In 2005 the memorial below was erected nearby for the men who died in the explosion of a torpedo onboard the submarine SIDON whilst docked alongside Portland Harbour. 

Please click here and here for websites relating this tragedy. The dead from this accident are buried in the nearby Naval Cemetery, please click here.


1989                                                                           2010

This mound of brambles is passed by thousands of visitors and locals as they go to New Ground to admire the view. It stands at the back of the Portland Height Motel where the arrow marked "B" is in the above aerial picture.

So, what wonders are hidden beneath the foliage?

A surprisingly well preserved lime kiln. The oven can just be seen if the effort is made to step into the central area and peer into the brambles.

Another limekiln stood nearby where the Portland Heights Motel now stands.

This dilapidated building stands opposite the lime kiln at the top of the Old Hill footpath close to the Portland Heights Motel. The left-hand pictures shows it in 1990 and the right-hand in 2003. Yes! It really is still there now but you might never know.

 What was this building?

The Spirit of Portland

by artist and sculptor

Joanna Szuwalska

This magnificent carving stands near the point where stone was loaded onto trucks to start their journey down the Merchants' Railway to Castletown.


Old Hill

This a very steep footpath that goes straight from New Ground to near the Council Offices in Fortuneswell .

On the way it crosses the track of the Merchants' Railway that used to take stone blocks from Tophill to Castletown where they would be loaded onto boats.

This path used to be the main route for getting between Tophill and the rest of the world.

The famous Dickey Hoskins had a Pets' Cemetery on Old Hill. He was paid to dispose of unwanted pets and promised to give them a burial on Old Hill. However, he took the pets to Weymouth and sold them so he made two sources of income in return for appearing to dig a few 'graves' and a journey to the Mainland!

Here we have views of 'Old Hill' which - amazingly - was once the main route between Tophill and Underhill.


This view shows the remains of the tramway that took stone blocks to the docks in Castletown. 

The tramway was once much wider as it went off into the middle of the picture.



Descending down to the Council Offices we enter the main shopping area of Fortuneswell. Fortune's Well itself is now hidden under the public toilets at the top of the High Street but it once was exposed and provided water for this community.

For many old pictures of this area please click here.

As we descend into Fortuneswell we see these relatively new flats at the foot of Tillycoombe opposite the Council Offices.

At this point used to stand huge advertising hoardings. When I cycled down the steep hill from Tophill I would imagine that if my bike brakes failed I would be hurled at very high speed off my bike and go head first into those hoardings.

Apart from this certainly being fatal, I also worried about the indignity of being embedded in the advertisements with just my legs sticking out.

Compare the Victorian view at left* of the top Fortuneswell looking north with the view in 1995 taken from the same point. All the buildings on the left were cleared to produce - yes, you guessed it - a car-park! 

Only a solitary stone pillar has survived between the two photographs. This is shown in close-up below and needs preserving as a reminder of Victorian Portland.

A stone pillar standing in Fortuneswell - a lone survivor from Victorian times.


"Isle of Portland Statues" in High Street makes excellent figures. I was given a beautiful clock set in Portland Stone for my 65th birthday from here.

The seller has now (2008) moved a short way down High Street.

An elaborately carved stone ornament in a front garden.


A lone example of industry in the back streets of Fortuneswell.

Originally a Victorian steam laundry and still shown as such on the 1925 Ordnance Survey map, this building has survived into the 21st Century as a home for a Defence Industry Contractor.

The company left and the building was turned into an Art Community Centre - please click here.

The Britannia Inn pictured here in 1990 stands near the junction of Hambro Road and Fortuneswell High Street.

Hambro Road was named in the late 1890s after Colonel Hambro, a much-admired local MP whilst the pub was named after a Royal navy ship which frequently visited the dockyard.

Above left we see Brymer's Avenue - probably the steepest inhabited road in Portland. The Council had to put special road surfacing down to stop cars from sliding to the bottom. Above right we see one of the many narrow alleyways that run along the backs of houses in Fortuneswell.

Some shops in Fortuneswell have changed hands frequently - indeed, in the 1990s it was impossible to keep up to date with the changes. However, some shops lasted a long time but eventually submitted to change.

Here we see one typical shop - The Selection Box pictured closed and up for sale in 1989.

Nearby is a chemist shop which, until very recently, had a wonderful traditional display of large glass containers filled with brightly coloured water.

A few yards to the left in this picture is the original Fortune's Well - now enclosed.


Above left - closed up shops in Fortuneswell show this to be a rather depressed and depressing area in which to shop amidst a general air of decay and abandonment. The these empty shops is an abandoned house - above right - adding to the dismal atmosphere.  

In the foreground is the brightly painted Royal Portland Arms. 

King George III loved to visit this hostelry and particularly praised the Portland Mutton which he rated the best in England. He also enjoyed eating wheatears  - locally called 'snalters' - which were trapped by young boys and sold for 3 d per dozen.

This short row of shops extends from the top of High Street along towards Queen Anne House which is a little beyond the position of the red car. Some of these shops have changed hands many times over the past couple of decades.

The Red House Bakery was first painted this bright colour by Mr. Dunkley in 1897 to celebrate Queen Victoria's Diamond Jubilee. Sadly, it closed in October 2003 and the shop stands here forlorn awaiting a new owner. Eventually it was taken over by an Estate Agency.


The Underhill Methodist Church stands close to the shopping area and almost opposite the Council offices.

It was built in 1900.


One of many typical old houses in Fortuneswell High Street which will, no doubt, eventually be demolished thereby robbing the area of much of its character.

This house faces the junction of High Street and Clovens Road.

Reg Paveley's tailoring shop in the High Street photographed early in 2010.

Underhill Junior School was built almost a century ago and stands close to the edge of the cliffs of West Weares.

Fortuneswell stands on an ancient landslip and this whole area is geologically unstable as seen by earth movements that occurred in the 20th Century on the cliff edge. 

The shopping area of Fortuneswell continues in the next area to the north whilst the area of Chiswell lying at the foot of High Street can be reached by travelling west and then north.

* Picture reproduced by kind permission of Stuart Morris from his book "Portland In Old Picture Postcards"  - see links for publication details.

Back to Portland Home Page


Back to Portland Map Index page