Having explored the Lower Town, you will want to press on uphill. Start with a gentle stroll, leaving the Stonebow behind you and disregarding the shops (there’ll be time for shopping later), begin the gradual incline toward the Cardinal's Hat. This is a half-timbered 15th-century building located at the top of the pedestrianised High Street. It was originally an inn named after Sir Thomas Wolsey, Bishop of Lincoln from 1514 to 1515, and was restored to its present glory in the 1950s.
Keep walking to the right, and you’ll begin to see the interesting shops of Lincoln. You’ll pass a plethora of antique shops (and if these give you an appetite, I’d recommend that you reserve a day to visit the antique centre at nearby Hemswell). You’re walking on the cobbled road at the bottom of Steep Hill, and you will soon understand how it got its name and be wishing that you’d worn some sensible shoes!). The houses now have some real age to them, and I’d particularly point out the Jew’s House on your left, and next door to it, the old Jewish Synagogue. These houses were built in the 12th century, when the Normans were encouraging Jews to settle in Lincoln to help finance the further development of this prosperous city. The Jew’s House, which has an extremely fine decorated Norman arch, is believed to be England’s oldest domestic residence. And you can grab a decent cup of coffee here.
Before tackling the walk to the top, I’d recommend that you make a detour to The Usher Art Gallery. The Usher Gallery was opened in 1927 by the Prince of Wales and made possible by James Ward Usher, a successful entrepreneur and collector of decorative art. Usher once had a local jewellery- and watch-making business and was honoured with the position of Sheriff of Lincoln in 1916. When he died at the age of 76, he bequeathed his amazingly large collection of artworks to the City of Lincoln. This included impressive freestanding clocks and ornate watches, porcelain, silver, enamels, miniatures, and coins, and remains the core of the gallery's collection. The collection has grown substantially and now includes a range of artwork, from neoclassical sculpture to contemporary portraits and craftwork. There is a superb collection of portraits, photographs, and personal items associated with Tennyson, including his distinctive cloak, hat, and walking sticks, and even a drawing of the Tennyson family home by the poet Edward Lear.
The walk up Steep Hill will burn off a few calories, and you may need to hang on to the handrail and make an excuse to visit the numerous quality shops that you’ll see en route. Examine the Black and White building at the corner of Michaelgate (one to photograph, I reckon). You may need a rest here after your climb, and the nearby old antique book shop will beckon you indoors. I love this shop.
Now is the final leg of your walk up to Castle Square.