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The Tissington Trail is one of Ashbourne’s major tourist attractions. This recreational trail starts by the leisure center in the town center, heads through a 353m tunnel, and continues for more than 13 miles up onto the high moorlands, following the route of the former Ashbourne to Buxton railway line. The former stations of Mapleton, Thorpe, Tissington, Alsop, Hartington, and Parsley Hay are now converted into car parks, some also with a cafe & toilets. The route is suitable for cyclists and walkers of all abilities and is also wheelchair and pushchair friendly. The first couple of miles between Ashbourne and Thorpe are often thronged with families, so walkers and cyclists need to take special care in this area. Please see the directory for bike hire information.

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Bordering the countryside east of Ashbourne, the recreation grounds are a place to play and relax without straying too far from the town center. On the corner of Cokayne Avenue and Park Road, you will find the impressive sandstone gateway to the park, comprising a classical arch with pillars and fluted columns, welcoming visitors to the ornate formal gardens planted in memory of Ashbourne’s war casualties. To the north of the gardens, there is a statue of the Salvation Army co-founder, Catherine Booth, who was born in the town. There is a bandstand in the middle(currently closed for refurbishment) and an adventure playground for children. The Henmore Brook flows through the park giving lots of opportunities to spot wildlife on Fishpond Meadow.‍

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The Gingerbread shop was built around 1492, the building is believed to have been an Inn until the period of the Napoleonic Wars when it became a bakery. It is the spiritual home of Ashbourne Gingerbread. Local legend is that the recipe for this gingerbread was given to an Ashbourne baker by a French prisoner of war, billeted in Ashbourne during the Napoleonic Wars; and you can still buy local gingerbread in the bakery to this day.

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The church is named after Oswald of Northumbria with a brass plaque in the chapel on the south side of the church commemorating its dedication on 24 April 1241. Its 212-foot spire presides over the town and was referred to by George Eliot as the "finest single spire in England". It replaced an earlier Saxon church and construction is believed to have started in 1240, probably lasting until the early 14th century. The church is listed as a Grade I building. Impressive stained glass windows adorn the church including a Christopher Whall window dated 1905 with chapels containing historic funerary & monuments which have contributed greatly to the church's renown.

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Ashbourne’s Queen Elizabeth Grammar School is believed to be one of the oldest schools in the country. It was established under a Royal Charter granted by Queen Elizabeth I following a 1583 petition by Sir Thomas Cokayne (1520-1592) for a free school in Ashbourne, on the grounds that the lack of education meant people were“given over to wickedness and vices”. Construction started in 1585 on Church Street, as close to St. Oswald’s Church as possible, and was finally completed in 1608 with Sir Thomas Cokayne as one of the governors. The original building is now a grade 1 listed private residence, with the school moving to its current site on Green Road in 1909. For much of the 20th century, the school was a selective mixed grammar but has now morphed into an Academy, open to all abilities. It continues to expand and develop, providing ever more impressive opportunities for today's students.