Popularly referred to as the "Cathedral of the Dales" , the parish church of St Stephen is the major landmark of the town. There have been three churches on the spot where the present church stands now. The first was constructed in Saxon times, and followed by a Norman church in the year 1170. It was then replaced by the present building in 1240 but has been considerably modified in the centuries since then. Within the church is a relief of the Norse god Loki, which is shown bound and chained. Located on the southern edge of Kirkby Stephen is site magnificent site of Croglam Castle, which is a brilliant example of prehistoric earthworks. The ruins of Pendragon Castle, famed for its connection with King Arthur, lie deep in the picturesque Mallerstang Valley. Legend goes that Uther Pendragon, father of King Arthur, was poisoned in the castle. If you need a break from your historic tour then take a leisurely walk or go cycling along the tree canopied serpentine roads, which command spectacular vistas of the scenic landscape. The Coast to Coast Walk, devised by Alfred Wainwright, passes through the town, which has many facilities to offer to visitors including a large number of places to eat and stay. If you have ample time then you can hire a cab from Kirkby Stephen cottage rentals and homes and go for an exciting day excursion to Ravenstonedale, Windermere, and Mallerstang where you can tee off on the greens at the excellent golf courses and indulge in thrilling adventurous sports and activities.

Windermere is renowned for its bustling market and the annual fairs, which draw thousands of visitors from all parts of the country. It is held on every Monday in the Market square surrounded by an ancient collar of cobble-stones and many old well preserved historic buildings. Though you can find everything in a variety of shops in the town but this market is one of the best places for shopping, especially for good hagglers. Here you can find everything fresh fruits and vegetables, hand knitted sweaters and shawls, wooden furniture, homemade breads and cheeses, trendy clothing, artworks, handicrafts and livestock as well. Enjoy a delightful stay in one of the holiday homes Kirkby Stephen during st Luke's Fair or Charter's Day, which is celebrated every year at then end of October. If you are a true gourmets, Kirkby Stephens will amaze with its good selection of wonderful dining establishments including small cafes, restaurants, bars, and pubs where you sample out finest delicacies and wash them down with soul enriching wines and other world famous alcoholic beverages.