Long Weekend Fun in Kingston, Ontario

Summer is short. We want to soak up all the adventures we can before fall arrives with our busy schedules and our back-to-work/back-to-school routines. For families with teens looking for a great way to spend the August long week, look no further than Kingston, Ontario. With everything from great food and wineries (for mom and dad) to haunted walks and thrill-seeking attractions, this relatively short drive from Toronto is jam-packed with family fun.

For the Foodie

Bistro on Ontario Street
Over the August long weekend, Ontario street will be closed to traffic, allowing foodies to taste their way through the city and lounge in Muskoka chairs under the sun. With expanded patios and bistro dining, foodies can enjoy a variety of cuisines. Ontario Street is home to several notable restaurants including Feast On-certified Dianne’s Fish Shake and Smokehouse (East Coast meets Mexican), Wooden Heads (gourmet wood-fired pizza), Namaste (fine Indian cuisine), Mio Gelato, and White Mountain Homemade Ice Cream. 

County Sips Wine Tours
This is the ultimate foodie’s day out — enjoying a variety of wineries and a local market. Hosted by sommelier Ian Nicholls, the tours begin with a scenic drive to Prince Edward County along the shores of Lake Ontario. All wine tours will include wine tastings at four selected wineries and a lunch at the Waupoos Market. Expert Ian will explain the terroir of PEC, winemaking and tasting while showcasing the beauty of The County. The tours run on Wednesday, Thursday, Friday and Sundays with different itineraries offered each day. Each tour departs at 9:15am and returns to Kingston by 5:45pm. Check out hotel packages here.

For the Explorer

Kingston Penitentiary 


Closed less than 10 years ago and now open to the public for tours, the explorers in the family can venture into Canada’s oldest maximum security prison. The facility is now offering two new tours for the season: Architecture Tour, where visitors dive into early history of the buildings and the architects and planners responsible for drafting and building the institution; and a Film Tour, where guests visit various areas of the site and learn about how they were used in film, the different productions that filmed there and learn about how these films were made.

For the Thrill-Seeker

Kingston Haunted Walk

For the family thrill seeker, this ghost tour’s spooky stops include haunted hotels, hidden burial grounds, grave robbings, hangings at the old courthouse and Kingston’s famous haunted courtyard. The Ghosts of Fort Henry Walk explores Kingston’s spooky 19th-century fortress and its many dark twists and turns. Not recommended for young children or easily frightened adults!

Kingston Trolley Tours

Anyone who likes a haunted walk would love a haunted trolley. Take a tour through Kingston’s mysterious past on the Ghost and Mystery Trolley. This 90-min evening tour takes guests off the beaten path to notable sites and notorious neighbourhoods that played a ghostly role in Kingston’s early history.

For the Historian

Frontenac County Schools Museum
Featuring a replica one-room school and a display gallery, the Frontenac County Schools Museum collects, preserves and displays artifacts and archival material from the elementary (grades 1– 8) one-room schools of Frontenac County from their earliest establishment to the consolidation of school districts in 1970. Open Tuesday-Saturday from 10am-4pm. Pre-booking is strongly encouraged.

Fort Henry

The historian in the family can enjoy a self-guided tour, along with rifle firing, music and artillery demonstrations taking place every hour. Challenge the talented Fort Henry Guard and inquire about his experiences. 

PumpHouse Museum

To learn about Kingston’s early history, take the 60-minute guided walking tour and explore Ontario Street, a space that helped define and form Kingston as a city. Attendees will learn about intriguing, and impressive people, fires, explosions, industry, transportation, archaeology, and everyday vices.

Museum of Healthcare at Kingston
For historians and those in the medical field, visit one of Canada’s oldest public hospitals, Kingston General Hospital. Walk in the footsteps of some of Kingston’s earliest residents and arrivals as they engage in a quest for health care in the Limestone City. The story of establishment of one of Canada’s oldest public hospitals, Kingston General Hospital, is one full of success and sacrifice, triumph and tragedy. Join them for a fascinating look into the lives of those that lived, arrived and died there, as they unlock the secrets of Kingston’s medical history. Offering tours Wednesday-Saturday at 10:00am, 11:30am, 2:30pm and 3:00pm.

For the Laid-Back Type

Kingston 1000 Island Cruises 

For the laid-back travellers who prefer sipping cocktails under the sun, Kingston 1000 Island Cruises offers sightseeing tours, dinner and lunch cruises and a scenic sunset cruise. Discover where the world-famous 1000 Islands begin in Kingston and enjoy live music and live-hosted commentary about the scenic views of the region.

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