Windsor: quirky and curious - the alternative tourist trail

By Karen Bowerman, a Travel Professional

Read more on Windsor.

Overall rating:4.5 out of 5 (based on 2 votes)
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Windsor in Berkshire is famous for its castle - but few know of its hidden tunnels, crooked house and odd postbox. Discover the town's quirky and amusing sites with this alternative tourist guide

If you're planning a trip to Windsor the castle is bound to be top of your list. But this historic riverside town has a lot to offer too...

Beyond the castle walls, hidden among boutiques, wine bars and cafes are some quirky and often amusing points of interest.

If you know where to look, you can enjoy a very alternative tourist trail....

The house that was "given a shove"

Start your walking tour on High Street where, next to the statue of Queen Victoria,  you'll find Market Cross house - more commonly known as The Crooked House; it's easy to see why. 

There are several explanations as to why the building tilts; the most likely being that it was built with unseasoned wood which from 1718 onwards caused it to lean sideways

My favourite (though least plausible) story is that builders, working on an extension to the Guildhall next door, thought the house too close so leant over and gave it a good shove!

Market Cross House was built in 1687 and is now a tea room. Enjoy delicious scones and jam in a building where there isn't a right angle in sight! (The Crooked House: 51 High Street, Windsor, SL4 1LR; 01753 857534;

Sir Christopher Wren's revenge

Next to the Crooked House is Windsor Guildhall (High Street, Windsor, SL 1LR; 01628 79603; best known as the place where in 2005 Prince Charles and Camilla Parker-Bowles got married and Elton John and David Furnish celebrated their civil partnership.

But its alternative claim to fame rests with its pillars which stop short of the first floor (the one they’re supposed to support), giving the impression the top of the building is floating in thin air.

Legend has it that Sir Christopher Wren was forced to add the pillars because councillors thought the original design (without them) was unsafe. Wren, annoyed at their interference, purposely left a gap to prove a point.

Contrary to common belief Wren didn't design the Guildhall although he did oversee its completion. The building was actually designed by Sir Thomas Fiddes, who died in 1685, two years before the Guildhall was finished.  

The UK’s shortest street

Close to the Guildhall is Charlotte Street - which has put Windsor into the records books.

It's officially the shortest street in the UK with a length of just 16 metres (51 feet, 10 inches). It took me a lot longer to find than to walk down!

If you can’t find it either it runs (almost hidden) alongside the Crooked House...

Mail anyone? The UK's only blue pillar box

Windsor's also home to the UK's only blue pillar box. If you want to take a look, keep the Crooked House on your left, walk down High Street and you'll find it among the trees as the road curves round to the right.

The box was erected in 1911 to mark the first UK airmail flight which took place between London and Windsor.

The haunted house

Staying with the colour theme, retrace your steps to Church Street and you'll find the (now incredibly bright blue) home of Nell Gwynn, Charles I's mistress, who was once an orange seller at Drury Lane Threatre in London. 

The bottom floor of Nell's house has been turned into a Chinese restaurant (Nell Gwynn Chinese Restaurant, 6 Church Street; 01753 850929;

Have a meal and you might hear Nell's footsteps pacing the floorboards above! Locals say she still waits for Charles to visit.

A few streets down is Peascod street (pronounced Pes-cod) so named because in medieval times it led to the pea fields. It's now full of shops - some of which are also thought to be haunted. 

Windsor's hidden passageways

Strange sounds have been said to emanate from behind the bricked up arch of one of Windsor's secret tunnels too - tunnels I knew nothing about until I started chatting with some of the locals at the Horse and Groom pub (4 Castle Hill, Windsor, SL4 1PD; 01753 30172;

The pub's known locally for its homemade pies but it wasn't the kitchen that the barman wanted to show me....

He led me down steep, uneven steps into the pub's cellar where at the far end he pointed out a bricked-up archway, spanning a width of about 5 metres - once the entrance to one of the tunnels.

He went on to list a whole number of secret passageways linking the castle with various buildings, including the basement of the Crooked House and Nell Gwynn's House.

The tunnel where "spooky noises" have been heard can be found at the Carpenter’s Arms pub (4 Market Stree,t Windsor, SL4 1PB; 01753 863739;

Order a drink, sit in the lower bar and listen hard....! 

Tunnelling to safety

It's thought the tunnels were built so the royal household could escape if the castle was under seige.

One, running under High Street, is so big it's referred to as a Sally Port - a tunnel large enough to accommodate hundreds of soldiers. It was built so the royal garrison could leave the castle undetected and attack the enemy from behind

Jump on board

If, after all this, you're still hankering for more titbits and trivia take a 40-minute bus tour round Windsor and the surrounding areas and enjoy a commentary packed with information and amusing anecdotes.

The route (from outside Windsor Castle) takes you round the edge of  Windsor Great Park, into the countryside, through Datchet - famous in 1895 for the first car journey on an English road - and on to Eton, with stories of the town's old stocks and  Princess Beatrice and Eugenie's first ballet lessons.

If you're lucky enough to be driven by "Gorgeous Gordon" or so he calls himself, he'll even stop for photos! (City Sightseeing tours;; adults £8, children £4. Tickets are valid for a day).  

Somewhere to sleep?

The Christopher can be found just over Windsor bridge at 110 High Street, Eton. This former coaching inn is ideal if you want to stay locally. Prices are around £100 a night.

Radisson¬†Edwardian on Bath Road, Middlesex is perfect if you want a midway point between Windsor and London. The hotel has free WiFi, a spa (sauna, steam room, plunge pool and relaxation room) and gym. Prices start from £100 per night.

Getting to Windsor

Windsor is 30 miles west of London, one mile from junction 6 of the M4. The town has two train stations, Windsor & Eton Central and Windsor & Eton Riverside.

General visitor information:; 01753 743907.

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Karen Bowerman
Traveller type:
Travel Professional
Guide rating:
Average: 4.5 (2 votes)
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First uploaded:
23 February 2011
Last updated:
4 years 39 weeks 4 days 10 hours 46 min 36 sec ago
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Budget level:
Free, Budget, Mid-range, Expensive

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Community comments (2)

0 of 0 people found the following comment helpful.

Fascinating! I thought this was a brilliant guide written in an entertaining and informative style. A unique take on a destination.
I learned a lot of things I knew nothing about and I have been inspired to consider visiting Windsor.
The guide is laid out very nicely with the subheadings and short paragraphs making it a joy to read.

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0 of 0 people found the following comment helpful.

Thanks Karen- enjoyed this interesting take on Windsor. On my last visit there were so many tourists about that I didn't linger, but you have some nice suggestions. No food prices I note, but then it's London- you pay what you have to.

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