First occupied by the Calvary Church, this building has housed the synagogue since 1946. Named for Ezekiel Cadesky, a Russian immigrant who settled here in the early 1900s, the structure draws from the tradition of simple, turn-of-the-20th-century Georgian meeting halls. Intricate stained-glass windows tell the story of many member families. Designated under the Ontario Heritage Act in 1990.

The Billy Bishop Museum remains an Owen Sound landmark. Boyhood home of the eponymous First World War flying ace, this museum invites you to explore the Bishop family and to honour the contributions of service men and women, past and present. Dedicated as a museum in 1987, this site became a National Historic Site in 2002.

This church was built in 1889 for the West Side Methodists. They soon outgrew this little chapel and, in 1911, they sold it and it became the British Methodist Episcopal Church (originally known as “the coloured people's church”). Today, this diverse congregation continues to carry on the legacy of the original Black families who settled in Grey County.

The Marine Rail Heritage Centre, housed inside the Community Waterfront Heritage Centre, was established in 1978 by a volunteer group of enthusiasts to showcase Owen Sound’s history as a thriving port. Located inside the historical railway station, this museum preserves the area’s marine, rail and industrial history with artifacts, scale models, archival photos, interactive stations and railway memorabilia.

This school is a 600-square-metre (6,500-square-foot) maker space that complements the expanding arts scene in Owen Sound. With classes in pottery, jewelry, printmaking, stained glass and more, the school is steadily growing — offering new classes and open studios and acquiring new equipment regularly. Come and explore this creative space and see how they foster collaboration and skills development.

Originally a church, this dynamic cultural institution is dedicated to providing the community with accessible and affordable spaces to share, create, educate and perform. With a 700-seat auditorium, a commons area, kitchen/banquet facilities, and numerous smaller lofts and studios, the Harmony Centre is an example of the value of retrofitting an existing community asset to respond to changing times.

Designated under the Ontario Heritage Act, Kennedy Terrace was built around 1900 by J.C. Kennedy, after a previous industrial building burned down. The site originally held Heap’s Furniture Factory, and a fanning mill that separated grain from chaff. Victorian design features include a decorative cornice and large windows. It is considered one of Owen Sound’s best-preserved examples of residential terraces from the era. 

Once a railway station, the Mudtown Station Brewery and Restaurant (now designated) offers a meeting place in Owen Sound’s Mudtown neighbourhood that celebrates both the history of the city and the talents of its present-day residents. Stop by for a tour or enjoy some of their scratch-made food produced with local ingredients and paired with local craft beer.

Lawn bowling has been a popular summer sport in Owen Sound for more than 100 years. The club, originally called Owen Sound North (Brooke) Lawnbowling Club, purchased this property for $200 in 1948. After a fire in the 1990s destroyed the St. George’s Lawnbowling Club facility, Roselawn welcomed its members. Come and visit and try your hand at lawn bowling!

The Roxy Theatre building, which was originally the Grand Opera House, was constructed in 1913 and has long been a landmark in Owen Sound. The Owen Sound Little Theatre, a not-for-profit charitable organization, now uses the building for community theatrical productions as well as many stage performances and musical events. Free parking on Saturdays in the lot behind the theatre.

This church is an active community member — with bi-monthly neighbourhood dinners, the O’Share program for those with food and housing insecurity, the annual Great Lakes Sailors Blessing of the Fleet, community concerts, the weekly Shoreline Chorus and a weekly youth karate group in the parish hall. Doors Open Owen Sound is a wonderful opportunity to explore this heritage building.

The former Sydenham Community School, built in 1967, was an elementary school until 2017. In 2018, Grey County purchased the 4,200-square-metre (45,000-square-foot) building and turned it into a regional hub now called Sydenham Campus. The partners and tenants form a collection of trainers and businesses that support workers, entrepreneurs and local organizations by providing access to education and training.

Established in 1967 as a memorial to iconic Canadian landscape artist Tom Thomson, this gallery houses a nationally significant collection of the artist’s works and artifacts. It develops exhibitions and programs that enrich the region and contribute to a national visual arts discourse. Completely renovated in 1988, the gallery features exhibition halls, collection storage, an educational studio and atrium.