One great street to walk

Everything in Appleby is arranged along Boroughgate, an uncommonly wide main street that has been described as one of the finest in England. It runs from the north end at the Cloisters—elegant arcades designed by Sir Robert Smirke, architect of Lowther Castle, given to the local school by a bishop in 1700 to shelter the butter-sellers—all the way up the hill to the castle gates at the southern end. An avenue of mature lime trees, planted in the 1870s, shades properties from the 17th to 20th centuries.↗↗

The two ends of the street are marked by the High Cross and the Low Cross, which once defined the limits of the market; the High Cross carries the 17th-century motto "Retain your loyalty, preserve your rights," and the market itself has sat here since the early 13th century. Keep an eye out for the town's narrow alleys, known locally as "wiends," which could be sealed off to protect the townspeople in times of trouble.↗↗↗

At the foot of the hill stands the Moot Hall, dated 1596, where the town council still meets and which now houses the Tourist Information Centre and exhibition room. Set into the paving nearby is the Bull Ring, the tethering point where bulls were baited until 1812, when one ran amok through the market. The whole climb up Boroughgate has a real sense of stepping backwards into medieval England.↗↗↗

Castle, church and Lady Anne Clifford

You cannot understand Appleby without meeting Lady Anne Clifford. Born in 1590, she fought a forty-year legal battle to win back her father's estate, finally inheriting it in 1643 at the age of fifty-three. She then devoted the last twenty-five years of her life to putting the north back together, restoring castles, churches and almshouses across Westmorland, and Appleby bears her stamp everywhere.↗↗↗

Overlooking the town from the brow of Boroughgate is Appleby Castle, a largely Norman structure with a keep founded in the early 12th century by Ranulf le Meschin. It passed to the Clifford family in the 13th century and was the home Lady Anne restored. The castle is privately owned and opens to the public on a seasonal basis for tours, weddings and events, so check before you set out.↗↗↗

At the bottom of the hill, the Grade I-listed parish church of St Lawrence grew up alongside the castle. Badly damaged by the Scots in 1388 and rebuilt by Lady Anne in the mid-17th century, it keeps a Norman tower base, a medieval nave and a fine 17th-century organ. In the church lie her splendid tomb and that of her mother, Margaret Countess of Cumberland, with a magnificent marble memorial beside them.↗↗↗

Halfway up Boroughgate, behind a wall around a quiet courtyard, are the Hospital of St Anne—almshouses Lady Anne founded in 1651 to house poor Appleby widows. They are still occupied today, and the courtyard and chapel can be visited during the day if you respect the notice in the entrance porch. Together with the church and castle, they form a gentle Lady Anne Clifford trail through the town.↗↗↗

The Appleby Horse Fair

The biggest date in the calendar is the four-day Appleby Horse Fair, held each year on the first weekend of June on and around Fair Hill. Its origins go back to 1685, when James II granted the town a second charter to hold a fair "for the sale of all manners of goods, cattle, horses, mares and geldings." Since then it has run almost continuously as one of the great surviving gatherings of travellers and Gypsy and Irish families in the world.↗↗↗

The fair's most photographed moment is the washing of the horses: traders bring their animals down to a bend of the River Eden beside The Sands to wash and groom them, a tradition that fills the riverbank with colour and movement. Alongside the sales there are harness races and celebrations, with many families arriving in brightly painted, horse-drawn caravans. If you come for the fair, expect the town to be transformed and book accommodation well ahead.↗↗↗↗

The river and walks from the door

Appleby sits on the looped River Eden, and the riverside is the town's natural breathing space, perfect for a stroll or a picnic. The Appleby Riverside Walk is a circular route of about seven miles over fairly flat ground, following the Eden and the tributary Hoff Beck through woodland trails with fine views across the Eden Valley. A pleasant two-mile town trail links the railway station to the river, the weir at Bongate, the castle precincts and down Boroughgate.↗↗↗

From the Moot Hall you can pick up longer routes through the surrounding fell country. The classic Discover Eden walk runs seven miles from Appleby across to Hoff and Great Ormside, taking in ancient field patterns, drumlin hills and, on a clear day, views to Cross Fell and the conical Pennine pikes of Knock, Dufton and Murton. Along the way, the wooded banks of Hoff Beck lead toward Rutter Falls, a Jekyll-and-Hyde waterfall that turns from a gentle curtain to a raging torrent after rain.↗↗↗

Look out beside the river for The Primrose Stone, one of a series of carved stone benches called the Eden Benchmarks, commissioned for the millennium and set along the length of the river. The clean-flowing Eden is also prized by anglers, holding salmon, sea trout, grayling and brown trout, and birdlife along the banks includes heron, dipper and kingfisher.↗↗↗

Browsing, food and the wider valley

The town is pleasantly unhurried, with a good selection of traditional independent shops—bakers, butchers and delis—set among the honeyed-red sandstone that gives these villages their warm glow at sunset. Appleby's long dairying heritage lives on at the Appleby Creamery, which makes premium hand-crafted cheeses including the local Eden Valley Brie.↗↗↗

For longer days out, the surrounding Eden Valley is rich in discoveries. A couple of miles away, the National Trust garden at Acorn Bank holds the largest collection of culinary and medicinal plants in the north of England and a traditional orchard of regional apple, pear and damson varieties, with panoramic views over the valley to the Lakeland fells. The nearby village of Orton runs one of the northwest's best farmers' markets on the second Saturday of each month, and the ancient towns of Kirkby Stephen and Brougham lie within easy reach.↗

There's a literary and artistic thread here too. The solicitors' firm with roots in Appleby connects the town to Beatrix Potter, who married local man William Heelis and was a regular visitor to Battlebarrow House on the edge of town, while the landscape painter J. M. W. Turner stopped here in 1831 to sketch the view over the castle hill. It adds a quietly cultured layer to a town that is, above all, a place to slow down and walk.↗