One of the most picturesque approaches to Bakewell is to drive into the town on the A619, crossing the 14th century bridge with its string of five gothic arches, which has coped for almost 700 years with the ever-increasing flow of traffic. This then leads you directly to Bridge Street where a one-way system operates, taking you to the heart of the town at Rutland Square.
Standing guard over the bridge on the western side is a huge horse chestnut tree, which in spring has a wonderful display of blossom.
Leading off Bridge Street is Castle Street, a reminder that Bakewell was a fortified town way back in 924, when Edward the Elder, son of Alfred the Great built a military post after he had succeeded in his campaigns against the Danish invaders. It is thought that the site of this fortification was in a riverside meadow just south of the town, but any remains have long since disappeared. All that exist now are the references such as Castle Street and nearby Castle Hill.
At the head of Castle Street is the impressive Castle Hotel which was formerly the Commercial & Castle. Regular horse fairs were held in front of the hotel right up until the onset of World War I, with horses and ponies being paraded up and down Bridge Street, prior to their auction.
There are many interesting Victorian and Georgian properties to be found on Bridge Street including Bridge House, which is on the left after having crossed over the bridge, but the most impressive building of all is the Old Market Hall dating from the 17th century which was restored between 1968-1971, and is now home to the Tourist Information Centre.
Just before Bridge Street opens out into Rutland Square, you will find The Old Original Bakewell Pudding Shop with its quaint façade and bulls eye glass windows. The Bakewell Pudding is famous throughout the world, with the ‘secret recipe’ being created by mistake in the kitchen of The White Horse Inn (now known as The Rutland Arms). Take note however that the Bakewell Tart is a poor modern imitation concocted by Mr Kipling!
Bridge Street contains several shops selling distinctive and high quality goods ranging from clothing, hardware, tools and toys to a local butchers and an ice cream parlour. There is a trendy café, a wine bar and no less than three public houses – close enough for a pub crawl! Also on Bridge Street are the offices of Goodwin, Cockerton and Colhoun, being a long standing firm of Solicitors in the town, together with the National Westminster Bank.