Appleby-in-Westmorland — an ancient market town at the southeastern gateway to the Lake District, nestled at the foot of the Pennine Mountains. Since the Norman Conquest of 1092, it has been the heart of Westmorland. A castle guards nine centuries of secrets, Britain's finest and widest main street, Boroughgate, strings together architectural gems from medieval to Georgian times, and one legendary woman, Lady Anne Clifford, reclaimed her lands through forty years of litigation, then restored the castle, church and almshouses. It is the jewel of the Settle-Carlisle steam railway, Europe's largest Gypsy horse fair erupts every June, and the U-shaped precipice of High Cup Nick — "England's Grand Canyon" — takes your breath away. This 2-day, 1-night classic tour includes castle exploration, a medieval town stroll, canyon hiking, steam train journey and River Eden fishing.
Explore a nearly 1000-year-old Norman castle and the legend of Lady Anne Clifford, stroll along Britain's finest main street Boroughgate, climb England's Grand Canyon High Cup Nick, ride a steam train across the Pennine Mountains.
Arrive at Appleby station in the morning (you can take the Settle-Carlisle railway, crossing the Pennine Mountains en route), then walk 10 minutes to the castle entrance. Appleby Castle was founded in 1092 and is one of only three surviving complete Norman square keeps in England. It has weathered Scottish sieges, Henry II's expansion, and Lady Anne Clifford's restoration, remaining continuously inhabited for nine centuries. Join the guided tour and climb the 11th-century square keep — 3-metre-thick stone walls conceal a ghost audio interactive guide, offering sweeping views over the entire Eden Valley. The castle gardens exemplify Norman military engineering, with the Round Tower (1250) and the 15th-century Great Hall perfectly preserved. Pass through the medieval arch beside the castle entrance and descend Boroughgate — at 30 metres wide, one of Britain's most impressive main streets, lined with lime trees planted in the 1870s and flanked by fine 17th- to 20th-century buildings. The High Cross and Low Cross mark the medieval market boundaries. Visit St Lawrence's Church — a Grade I listed building begun in the 12th century, containing the magnificent monuments of Lady Anne Clifford and her mother Margaret, Countess of Cumberland. Lady Anne personally restored the church in 1654 after it had been twice burned by the Scots. Continue uphill to St Anne's Hospital — 13 cottages built by Lady Anne in 1653 for poor elderly women, still occupied by single older ladies living under the trust deed. In the evening, stroll along the River Eden, watching the stone bridge reflect in the water, swans playing in the shallows, and the distant castle silhouette bathed in golden light.
Drive or take the bus 20 minutes to Dufton village (in the North Pennines AONB) in the early morning to begin climbing High Cup Nick — described by Wainwright as "a great moment in any journey" and named by Lonely Planet as one of England's best hikes, "England's Grand Canyon". Follow the Pennine Way gently uphill for 6 miles (about 10 km), passing Bow Hall and Peeping Hill, the views gradually opening up: the Eden Valley spread out like a green carpet, the Lake District peaks appearing on the horizon. When you reach the top of High Cup Nick, the U-shaped glacial valley drops 200 metres in sheer cliffs, the cleft cutting like a knife through the Pennine ridge. Wainwright praised it in his Pennine Way Companion as "a great moment in any journey". Descend via Middle Tongue back to Dufton, the whole loop taking about 5.5 hours. Return to Appleby in the afternoon and board the Settle-Carlisle Railway — named by Lonely Planet as one of the ten most beautiful railways in Europe. This 72-mile line has 21 viaducts and 14 tunnels, with the crossing of Ribblehead Viaduct (24 arches, 32 metres high) particularly spectacular. Take a steam train charter (2026 marks the 150th anniversary of the line, with many special services), departing from Appleby station south to Settle or north to Carlisle, with sweeping views of the Pennines and the Eden Valley. If time permits, alight at Penrith and explore Brougham Castle — a 13th-century riverside ruin also restored by Lady Anne Clifford, entry just £3.80. In the evening, return to Appleby for a farewell dinner by the River Eden.
A unique restaurant located in the castle's Great Hall, with oak panelling dating from the late 17th century, candlelight reflecting off medieval stone walls. The head chef has thirty years of international experience, signature dishes include Cumberland lamb, local venison steak and Lake District grilled trout, with a global wine list. Breakfast and dinner included for residents; non-residents must book in advance. Budget £25-£45 per person.
A relaxed bistro within Appleby Manor Hotel, awarded an AA Rosette, overlooking the gardens and distant hills. Modern interpretations of local Lake District ingredients: Cumberland sausage roll, slow-braised lamb shoulder, herb-roasted chicken and handmade desserts. Wine list features Cumbrian whiskies and local craft ales. Budget £18-£35 per person.
A traditional pub in a 17th-century coaching inn in the town centre, with original oak beams and fireplace creating an authentic Cumbrian atmosphere. Signature fish and chips, shepherd's pie and Cumberland beef burger, paired with local Keswick Brewing bitter ales. Live folk music at weekends, the most comforting British dinner after a hike. Budget £12-£22 per person.
A cosy tearoom in the town centre overlooking the River Eden. Signature handmade scones with clotted cream, cucumber sandwiches and seasonal fruit cake, plus homemade apple pie and Lake District tea. Summer garden terrace with views of swans on the river, winter fireside seating warm and inviting. Budget £8-£15 per person.
A community pub and craft beer bar in the heart of Appleby, serving hand-pulled ales from several small Cumbrian breweries and local cider. Signature Appleby Ale is a crisp and refreshing amber bitter, paired with handmade beef pie and local cheese platters. Dog-friendly, the best place to chat with locals. Budget £10-£18 per person.