The 420 Wing Oshawa was established to train pilots during the Second World War. After the war, the building was used by the 420 Wing, formerly known as the 420 (City of Oshawa) Wing RCAFA. The building has been in operation since 1948, when returning veterans formed a "Wing," a practice that was common in many Canadian cities and towns.

The Oshawa and Durham Region Métis Council Community Garden, established in 2016, offers free vegetables, berries and herbs during the summer months to Métis citizens and members of the community in need. The garden also honours the memory of murdered and missing women and children through a display of red dresses. Explore the gardens to experience this uniquely designed space.

Originally constructed for the General Motors United Auto Workers Union Local 222, this site is now — following recent renovations — a thriving event centre. The unique venue provides multiple spaces, including the Mainstage music venue, TwoTwoTwo, the Local Lounge, Café and Snack|Bar. During Doors Open Oshawa, BOND|ST will be open for self-guided tours.

The Canadian Automotive Museum was established in 1962 to promote the history of the automotive industry and local tourism. It currently showcases the most significant collection of Canadian automotive history worldwide. Located in a former 1920s auto dealership across from Memorial Park in downtown Oshawa, there are more than 70 vehicles on display, including Lightning McQueen from Disney/Pixar’s Cars.

This site is home to North America's largest collection of operational historical military vehicles and the museum of the Ontario Regiment (Royal Canadian Armoured Corps). The museum is located on the grounds of an original Second World War airfield. Rides in their M548 “Battle Bus” and M113 armoured personnel carriers will be available but at an additional cost.

Explore the City’s greenhouse, one of the few remaining city-run glass greenhouses in Ontario. It is dedicated to housing tropical collections and producing annual bedding plants for city parks, gardens, City Hall, the Oshawa Valley Botanical Garden, and downtown planters/hanging baskets. After sowing over 5,000 seeds and planted 2,000 cuttings, they have 60,000 plants ready for planting by May.

Club Carib, founded in January 1966, houses the Hummingbird Dancers and Oshawa Sounds of Steel. It also serves as a community banquet hall for weddings and conferences. During Doors Open, enjoy a 30-minute steel pan performance. The Caribbean Café will also offer food and refreshments (while supplies last). You can also try your hand at playing the steel pan!

This downtown armoury, built on a stone foundation, features a spacious drill hall. The square towers flanking the façade of the drill hall enhance its fortress-like appearance. It is a recognized federal heritage building due to its historical significance, architectural design and environmental value. Come and explore its military equipment, as well as visit the main floor and officers' mess.

The Hamilton-Oshawa Port Authority offers port/marine assets to support Ontario industries and to facilitate trade. The Port of Oshawa is Durham Region's gateway to the world, handling more than 500 vessels over the past decade. Oshawa is one of the few cities that can boast an airport, rail lines, a deep-sea port, and 400-series highway — giving industry a competitive edge.

Join this fascinating walking tour of the famous top-secret spy camp. Camp X was a Second World War training facility for agents operating behind enemy lines. It was also North America’s largest communication centre. Join one of two guided tours or stay and engage with guest speakers about the site's history. Uneven terrain. Parking across the street from the monument.

This art deco-inspired bandshell was a gift from R.S. McLaughlin, founder of General Motors Canada, to the City of Oshawa. It was constructed in 1942 to give the Oshawa Civic Band a place to perform and practise. Before this, they practised in the Orange Hall over a grocery store near the four corners and the armouries on Simcoe Street North. 

This museum features restored Victorian-era homes, situated on their original foundations. Henry House showcases a traditional Victorian home, depicting family life in the 1870s. In contrast, Guy House features a gallery and gift shop. Each home belonged to prominent harbourmasters from the area. Visitors can enjoy self-guided tours of Henry House, where costumed hosts are available to answer questions.

Forming part of Oshawa's Civic Centre, this library was a gift of Col. R.S. McLaughlin in 1954. Architect Arthur Eadie was influenced by Frank Lloyd Wright in his design of the McLaughlin Public Library, now the central branch. Explore captivating videos, photographs and memorabilia or attend a guided tour showcasing the library’s evolution over the past 70 years.

The Regent Theatre was constructed in 1919, and its King Street façade features symmetrical Georgian architectural lines. It stands as one of the few remaining examples of this classically inspired architectural style in Oshawa. Originally built for Famous Players theatres, it was closed for several years before being reopened in 2010 as a lecture theatre for Ontario Tech University.

This artist-centred and community-oriented public art gallery in the heart of downtown Oshawa was founded in 1967 and expanded to add 3,300 square metres (36,000 square feet) in 1987. Arthur Erickson built the gallery around the existing structure, using dramatic skylights. This is the largest public art gallery in Durham Region, with a collection of over 4,700 works.

The Friends of Second Marsh is a charitable organization dedicated to connecting people with nature through interpretation, education and stewardship services. This site features approximately 7 kilometers (4 miles) of hiking trails. The McLaughlin Bay Wildlife Reserve offers self-guided tours of its naturalized areas and trail system. Leashed dogs only allowed on the Waterfront Trail and in Darlington Provincial Park.

This new temporary public artwork was installed in September 2024. Commissioned at the site of the former John Borlase Warren Flour Mill, it reflects the history and legacy of the historical mill and its relationship to the Oshawa Creek. For Doors Open, join artist Dani Crosby for a talk at 11 a.m., followed by a walk along Oshawa Creek.