The Coldwater Museum is a living museum, located on a beautiful 2.6-hectare (6.5-acre) historical site with the aptly named Coldwater River running through the property. It is a truly fun, community-run museum that celebrates the heritage of the original Woodrow Homestead, a beautifully preserved log cabin built in the early 1840s on a former stagecoach route.

In 1962, the Orillia Fish and Game Conservation Club acquired this 24-hectare (60-acre) property with a commitment to operate it as a wildlife sanctuary. Comprising primarily wetlands and popular nature trails, the property features an aviary, swan enclosure, pollination gardens and an education building. The sanctuary is ideal for learning about the value of wetlands and conservation.

Nestled on the shores of Lake Couchiching, the Leacock Museum National Historic Site is housed in the summer cottage, boathouse and gardens of famous Canadian humorist and economist, Stephen Leacock (1869-1944). Leacock was known for his witty and satirical works (particularly Sunshine Sketches of a Little Town). His legacy is honoured annually through the Stephen Leacock Memorial Medal for Humour.

This museum has been an art, culture and heritage hub in the heart of Orillia for over 25 years. Located in downtown Orillia, the clocktower of the Sir Samuel Steele Memorial Building is a beacon for the museum. The museum’s mission is to provide inclusive space to engage community, inspire creativity and celebrate culture, by exploring art and history.

The Oro African Methodist Episcopal Church, built in 1846-49, is a designated National Historic Site. This historical site is one of the few remaining "pioneer-built" log cabin churches constructed by persons of African ancestry in North America. Come and visit, feel, touch and be moved by its history.

Discover the Peter Dušek Gallery, housed in the historical Creemore Meat Market building, built in 1881. Showcasing award-winning minimalist and Zen-inspired photography, this premier contemporary art space features Peter Dušek’s serene landscapes of Ontario. Experience cultural elegance in a historical setting, perfect for art lovers and visitors seeking inspiration.

Doors Open will offer visitors the opportunity to visit a typical Masonic Lodge (normally not open to the public) and learn about the history and ideals of Freemasonry — the world's oldest fraternity. The original charter for Seven Star Lodge was granted in 1872 and is on display along with other historical artifacts. Meetings have been held here since 1917.