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Uckfield has a long history and many historical buildings. Holy Cross Church has records going back about 8 centuries, although the church building itself was rebuilt during the 19th century. The Churchyard is well preserved with old brick walls in which grows abundant yellow corydalis, and a pigeon coop made from the timber of a giant cedar of Lebanon that fell in the 1987 hurricane force winds. The Church Centre was the Parochial School, and still retains the Victorian school character.

Further information regarding the history of Uckfield and its buildings is well documented in the many publications about Uckfield and can be found in the library or from the Uckfield and District Preservation Society at Bridge Cottage

Due to its location Uckfield was a central point for many trade routes across the South and as far back as1637 coach carriers linked Uckfield and London on what until 1752 was the main Lewes-London road. By 1805 a daily route to London was established and by 1828 a route twice a week to Maidstone.

In and around the town many buildings conceal medieval timber frames beneath later bricks and tiles and await study. From tree-ring analysis, Bridge Cottage dates from 1436 and several High Street shops may be of similar age. Around the entrance to Church Street were hostelries named the Red Lion (now Just So Bar formerly The Maiden’s Head), King’s Head and Spread Eagle. These were likely venues for local administration, including magistrates’ sessions by 1594 and inquests by 1608.

The Upper Ouse Navigation river improvement reached Shortbridge only in 1793, but proved uneconomic for transporting goods as Uckfield was two miles away and the venture lost to the cheaper, faster railway. The advent of the railway brought more development to the lower half of the High Street with new properties and detached villas built along London Road and New Town and a variety of housing around Framfield Road, Ridgewood and Ringles Cross. The corn market grew and another for livestock started. The new cemetery, with twin chapels, on Snatts Road opened in 1884.

Some of the historical buildings were provided by local benefactors, the late Anthony Saunders, rector of Buxted endowed the school, which in 1718 evolved into the Grammar School (closed 1930) and National (later Parochial) School, sited next to the church for over a century from 1850. The Streatfeild family also had great influence for nearly two centuries. From 1865 until death in 1931, Richard James Streatfeild chaired the Urban District Council (to last forty years) from 1895, made up of many prominent Uckfield figures such as the postmaster Samuel Avis, the famous solicitor Charles Dawson, the draper and grocer William Dendy and Edwin Kenward the miller. Streatfeild provided the Cottage Hospital (lately redeveloped as Hughes Way) and, with others, the Public Hall used for council and court business before its conversion to the library.

The Streatfeild Family again assisted by establishing the Victoria Pleasure Ground and a temperance club. In Victorian times, bands, the carnival and horticultural shows rose to the prominence they maintain to this day.

The Uckfield Picture House survived into the twentieth century after overcoming early competition from the 1930s Playhouse.

Council housing appeared pre-war around Framfield Road and post-war at Church Coombe. Development on Manor Park in the 1960s, Rocks Park in the 1970s, and more recently on West Park and Harlands Farm has transformed Uckfield into a thriving town. New development has seen the cattle market close; the Agricultural College give way to the convent. The Union Workhouse (later High View House sheltered accommodation) and Uckfield House have been demolished and shops replace landmarks like the Bell Hotel, White Rails cottages and the original bus station.

Hempstead Mill, the Water Tower and parish poorhouse have new lives as dwellings, while the Roller Mill was converted to offices. Many of Uckfield’s older buildings retain nameplates, dates and initials to catch the notice of thoughtful strollers.