Are these the 50 most important buildings in Ipswich?

Here's a challenge: Pick 50 buildings that tell the story of Ipswich over the centuries. And don't be cheeky by suggesting the town can't even manage five! Actually, Caleb Howgego did think he might struggle to fulfil the brief when he started writing his latest book. That fear soon vanished…

"In fact," he says in his introduction to Ipswich in 50 Buildings, "the real challenge was not so much finding buildings with interesting histories, but deciding which ones I would have to leave out."

His book aims to celebrate the town's architectural heritage in an easily-digested way as he guides readers around its historic and modern buildings - from the wealth of medieval churches to the internationally-lauded black-glass beauty of Willis Towers Watson. (Or Willis Faber, as it will forever remain in the hearts of a couple of generations of locals.)

We could, it seems, do with a bit of help.

"For a town that claims to be the oldest continually inhabited in England, precious few truly ancient buildings are obvious to the casual observer," suggests the author and historian.

"This is mainly thanks to the cycles of decline and prosperity that Ipswich has seen over the centuries. In times of prosperity, those who could afford to made their mark on the town - often at the expense of older constructions. Consequently, small fragments from each century remain scattered around the town in an intriguing hotchpotch of old and new."

He cites the area around Cromwell Square car park as an example. Stand there, turn around, and we can see the liquid black of that modern Willis building. Reflected in it is the Unitarian Meeting House chapel (opened in 1700) and St Nicholas Church, with its "jumble of fine medieval and Victorian flint and stone architecture".

Caleb reckons: "When you start looking closer, you find pockets of remarkable architecture like this the whole town over.

"It is a shame that the town has not done a better job of holding on to some of its finest architectural treasures, but it could equally be said that a long-held spirit of embracing change is as much a part of the heritage of Ipswich as any building may be said to be."

Those historic yo-yos between economic good days and bad have changed the fabric of the town.

The twisty River Orwell and the silting-up of the docks at Ipswich led to a slump in the 18th Century, for example. So, in the 1800s, the authorities altered the shape of parts of the river and formed what was then the country's biggest wet dock. Happy days were soon here again.

It heralded a mushrooming of industry during the Victorian age, and large parts of the town were redeveloped as the population rocketed. "This helps explain why so much of the important architecture left to us today was either built or altered during the Victorian era."

Caleb recognises: "The downside of sweeping changes like this is that some of Ipswich's most fascinating architecture has been masked or demolished, but get below the surface…and you'll see that Ipswich is crammed with architectural treasures from across many centuries."

* Ipswich in 50 Buildings is from Amberley Publishing at £14.99

We asked Caleb - born and bred in the town - to pick just five of his favourite Ipswich buildings (not 50!) and explain why he likes them.

The Sailors' Rest, St Peter's Street

"I like this one because the history of the building, which is an interesting one, seems to have been almost forgotten and I'm glad to be able to shine a little light on it.

"A lot of people fought hard in the 1960s to save this building from demolition and I'm so glad they did - the plan was to knock it down and replace it with an office block because it had become run down from years as a hostelry for sailors.

"Unfortunately, in the past, Ipswich has allowed far too many of its architectural treasures to be destroyed, so I like the fact that on this occasion the building was restored and the streetscape was saved."

The Old Neptune, Fore Street

"One of the great things about doing the book was getting to see inside some of the buildings and one of my favourite opportunities to do this was with the Old Neptune, which was once a merchant's house and later an inn. It's like a Tardis. I had no idea it was so huge and impressively restored inside."

Christchurch Mansion

"I think Christchurch Mansion is going to be in most people's list of favourite buildings in the town - it's a beautiful building with a fascinating history and we're so fortunate that it is open as a free museum, with so much to see and do there."

Willis building, Friars Street

"The Willis building wasn't to everyone's taste when it was built but I think it's fair to say it's very well thought of in the town today.

"It was a truly ground-breaking design and it's good to think that Ipswich has, even in recent times, attracted the best in design - and there's no reason why it shouldn't continue to do so in the future."

St Margaret's Church, Soane Street

"There are so many beautiful medieval churches in Ipswich that it's difficult to pick one out in particular, but if I had to I'd probably go with St Margaret's - it recently completed a project to make the church's heritage more accessible to visitors, so go and have a look for yourself!"

Ones that didn't make the cut

"There are a few others I might have included if there had been space. The old Cliff Brewery was one that only just didn't make it in, for example.

"Maybe the R.&W. Paul building on the waterfront, or the former Odeon cinema building that is currently being refurbished and turned into a church, would have been interesting too."

The fantastic 50

The buildings featured in Caleb Howgego's book are: 1 Ipswich Town Hall; 2 The Old Post Office (opened 1881 and now empty); 3 The Corn Exchange; 4 Ipswich County Library (1924); 5 County Hall (once the site of a jail; now redundant); 6 Ipswich Institute (main entrance in Tavern Street); 7 Arlingtons (original home of Ipswich Museum, it's been a dance hall and now a restaurant); 8 Ipswich Museum; 9 Christchurch Mansion; 10 Ipswich Art Gallery, High Street; 11 New Wolsey Theatre; 12 Gippeswyk Hall, Gippeswyk Avenue (home of Red Rose Chain theatre company); 13 Regent Theatre; 14 Portman Road football stadium; 15 Freemasons Hall, Soane Street; 16 Willis building; 17 Old Custom House; 18 Tooley's Court, Foundation Street; 19 Ipswich and East Suffolk Hospital, Anglesea Road; 20 Sailors' Rest, St Peter's Street; 21 Curson Lodge, corner St Nicholas Street and Silent Street; 22 Pykenham's Gatehouse, Northgate Street; 23 Ancient House, Buttermarket; 24 Manor House, St Margaret's Green; 25 St Helen's Church, St Helen's Street; 26 St Mary-le-Tower Church; 27 St Mary at the Elms Church, Elm Street; 28 St Mary at the Quay Church (dates from 15th Century); 29 St Mary at Stoke Church (only one of Ipswich's 12 medieval churches south of the river); 30 St Lawrence Church, Dial Lane; 31 St Margaret's Church, Soane Street; 32 St Clement's Church, Star Lane; 33 St Stephen's Church, St Stephen's Lane; 34 St Peter's Church, College Street; 35 St Matthew's Church, Portman Road; 36 St Nicholas Church, Cutler Street; 37 Bethesda Baptist Church, St Margaret's Street; 38 Unitarian Meeting House, Friars Street; 39 Blackfriars ruins, Foundation Street (former Dominican friary); 40 Ipswich School, Henley Road; 41 University of Suffolk Waterfront Building; 42 Ipswich Ragged School, Waterworks Street; 43 The Spread Eagle (oldest inn still open as a pub in Ipswich); 44 The Sun Inn, St Stephen's Lane; 45 Old Packhorse Inn, corner of St Margaret's Street and Soane Street); 46 Isaacs on the Quay, complex of buildings on the waterfront; 47 Old Neptune Inn, Fore Street; 48 Great White Horse Hotel, Tavern Street (represented Britain at 1893 World's Fair in Chicago and now closed); 49 Crown and Anchor Hotel, Westgate Street (now WHSmith); 50 Royal Oak, corner Oak Lane and Northgate Street (oldest parts probably date from late 15th or early 16th centuries).