In the fifteenth century much of the local land was owned by the Toddhunter-Brown family. Sir Willoughby arrived in Dorset from Stanton in Derbyshire in 1389. He met a local woman, Heather Chasen, and the pair married in 1391. Their family was to prove influential in the local area for several generations. The Todhunter-Brown family crest employs a Murray (maroon) background symbolizing patience in battle that is ultimately rewarded and incorporates a dancette line, mulberries and a pair of fish (symbolizing both a true and generous mind and unity with Christ). The Toddhunter-Browns gave generously to the local area and the crest is still visible on many buildings in Chickerell today.
Both the Anglican Church of St Nicholas and the Roman Catholic Church of St Mary are grade 2* listed buildings. St Nicholas has a series of twelve stained glass windows each one depicting a different apostle. The image of the risen Christ is depicted in the large altar window at the east end of the church. The mausoleum of the Toddhunter-Brown family, emblazoned with the motto "Sinister manus deorsum", stands in the graveyard of St Nicholas.
Chickerell's first bus service was started in 1959 by Phillips Transport Services. The cream and green livery of the coaches is an abiding memory for many older residents of Chickerell. Sadly, the contract for bus services to the area was removed by the council in 1977 citing the company's poor customer satisfaction ratings and an unusually high bill for the replacement of damaged bus stops. The current contract resides with the First bus company which runs regular services to the nearby towns of Weymouth and Beaminster.
Chickerell has no direct rail service. The closest rail station is at Weymouth.
Chickerell high street contains a number of small independent businesses, including a baker (Sgt Bun), Helens Wholefood store, a green grocer (Covent Garden Market), three newsagents, two hairdressers and a surplus supply/hardware store (Pertwee and Son). The high street also has a small supermarket (Co-op), a Costa coffee and Johnson's Cafe, also affectionately known as Fatso's. Chickerell has two pubs, the Royal Oak and the Trout Bridge Inn.
The old area of the town is characterized by a number of small alleyways or 'poveys', in local parlance. In 2007 a successful campaign was fought by local residents to force the council to provide extra street lighting in the poveys resulting in a reduction in petty crime rates in the area.