The town has a long history, dating back to the days of the Gold Rush of the 1850s, when Woodend was a service centre for people on their way to the goldfields of Bendigo and Castlemaine.
The commercial centre of Woodend is located along the tree-lined boulevard of High Street and retains a collection of historic buildings including the soaring clock tower in front of the post office and the Art Gallery building. Woodend's supermarket, at the 19th Hole Shopping Centre, features a collection of large murals depicting the Woodend's history on its outside walls. Other historical buildings include the bluestone St Mary's Anglican church built in Buckland Street in 1864, and the old court house, dating back to 1870 in Forest Street. The Woodend Bridge, located near the visitor information centre, is a bluestone structure built in 1862 that allows High Street to span Five Mile Creek.
The Woodend Golf Course, with its entrance on Davy Street, is built on the slopes of an extinct volcano. Fine views over the town, surrounding countryside and towards Mount Macedon can be enjoyed from many of the fairways.
One of Woodend's major attractions is the Hanging Rock Reserve, located around 8 kilometres to the east of town. The Hanging Rock Reserve features a landmark rocky volcanic formation, around 100 metres in height. Walking tracks lead to the summit, offering commanding views over the surrounding countryside and the opportunity to explore rocky outcrops and formations. The reserve includes a discovery centre, cafe, large picnic and BBQ grounds grounds, and a racecourse. Hanging Rock was the location of Joan Lindsay's mystery novel in which a party of schoolgirls picknicked at the rock on Valentines Day 1900, with several members of the party disappearing without a trace. The novel was adapted into a feature film in 1975, now regarded as an Australian Classic.
The Macedon Ranges boasts a significant collection of wineries around the Woodend, Romsey and Lancefield area. To the north-east of Woodend, in the village of Newham, is the Hanging Rock Winery which is open daily and offers scenic views south towards Hanging Rock and Mount Macedon.