Essential Kingston Ontario Weekend Travel Guide

When planning an Ontario staycation, Kingston should definitely be on your list. Located just three hours from both Toronto and Montreal, a mere 90 minutes from Ottawa, and conveniently located on Highway 401, Kingston, Ontario has everything you could possibly hope for in a staycation. The former capital city of Canada is home to a UNESCO World Heritage Site, five national historic sites, four Rembrandt paintings, and more restaurants per capita than most cities in Canada. Kingston has something for everyone.

Kingston Itinerary – 3 Perfect Days

We’ve put together the ultimate itinerary to help you plan your trip to Kingston. If you want to make the most of the long weekend, follow this guide to create the perfect weekend getaway in Ontario. For more information on Kingston Travel, visit the Kingston Tourism Website.

Where to Stay in Kingston

Secret Garden Inn is a beautiful boutique manor home. It is such an iconic Victorian Inn that they even mention it on the Kingston trolley tour! Located within walking distance from the waterfront, Princess Street, and many of Kingston’s top attractions, it is a great choice to stay, and the breakfasts are delicious. Visit their website for reservations and availability.

Day 1 Kingston – Downtown

Day one of Kingston is all about being introduced to Kingston’s top attractions. Make your way downtown to explore the highlights of the city and get acquainted with its rich history.

Trolley Tour

Start your trip on the Kingston Trolley tour. This one-hour guided tour starts in historic downtown Kingston and takes you on a journey through the city’s history and top attractions. An entertaining guide keeps the trip moving while offering insights into Kingston’s storied past. The tour includes stops at various points of interest around Kingston, including Fort Henry, the Kingston Pen, the shopping district, and Queen’s University. Visit theCity Trolley Tours for tickets – $28 for a one-hour guided tour.

Kingston Visitor Information Centre

At the end of your tour, the Trolley lets you off at the Kingston Visitor Information Centre in front of City Hall and Confederation Park. This is a perfect next stop. Here, you can gather information about numerous attractions that interest you. Consider the following sights to enrich your first day in Kingston.

Engine 1051

Grab a snapshot in front of the Kingston Sign and then walk behind it to check out Engine 1051. This locomotive has adorned the area for 40 years, reminding residents and visitors that this was once a bustling train yard. Beautifully restored, it provides one of the best photo opportunities in Kingston.

Confederation Park

From here, take a leisurely stroll along the waterfront to enjoy views of City Hall, the marina, and the nearby fountain. Keep an eye out for the Martello Tower standing proudly at the center of the marina. This location houses one of six Martello Towers in Kingston. While you can’t tour this one, others are open for exploration. For example, the Murney Tower is a 15-minute walk from Confederation Park, and Fort Frederick Tower is free to visit at the Royal Military College.

Spend as long as you like exploring the waterfront, which stretches for 8km, featuring numerous attractions including the Marine Museum and the PumpHouse Museum. Be sure to take in the beautiful scenery.

Lunch on the Patio at Olivea Fine Dining

Now that you’ve worked up an appetite, grab lunch on a patio on Brock Street. Located just a two-minute walk from the Visitor Information Centre, Olivea Fine Dining is renowned for its exquisite Italian cuisine. Every year, the staff travels to Italy to immerse themselves in the culture, gathering inspiration for their recipes. The food is outstanding, situated across the street from City Hall, which features Canada’s oldest public market. Make reservations atOlivea Fine Dining.

Springer Market Square

This square feels like a step back in time, surrounded by historic buildings. Its authentic architecture has even been featured in films and TV shows set in the 1700s and 1800s, including Murdoch Mysteries.

Explore Kingston’s Historic Downtown

To work off some of that delicious food, it’s time to explore downtown Kingston more fully. Beyond Princess and Ontario Streets, start at Kingston City Hall. This National Historic Site is a stunning 19th-century Neo-classical building, prominently featuring Kingston’s skyline. Guided tours are available.

Kingston’s Alleyways

Next, discover two iconic alleyways in Kingston. Walk just two minutes around the corner to find Rocheleau Court, boasting an array of restaurants, shops, and gorgeous courtyards. Here, you’ll find one of Kingston’s beloved eateries, Chez Piggy. This picturesque lane is a lovely stroll through a network of courtyards and shops.

Martello Alley

Another must-visit alley is Martello Alley, located on Wellington Street, just a short walk from Rocheleau Court. This historic alley is one of Kingston’s hidden treasures, with a vibrant courtyard showcasing original art by local artists. Inspired by La Rue du Trésor in Québec City, the friendly atmosphere invites you to explore and perhaps pick up a unique piece of memorabilia. See what events are happening in Martello Alley.

Walking Tour with Arthur Milnes

A walking tour with Arthur Milnes offers a unique experience in Kingston; this leisurely hour is perfect before dinner. Meeting at the Visitor Information Centre, this tour takes you through the waterfront and downtown area. Arthur, a local historian, shares engaging personal stories about life in Kingston while providing insider tips on the best dining spots. One particularly noteworthy moment is his hosting of President Jimmy Carter during a visit to receive an award. Visit Arthur Milnes Walking Tours to learn more.

Dinner at Wooden Heads

With so many culinary options in Kingston, choosing a dining spot can be a delightful challenge. Among our recommendations is Wooden Heads, known for its gourmet wood oven pizzas. We can confirm the food is delectable. Additionally, the menu includes pasta and other Italian favorites sure to please a variety of palates. See theirwebsite for details.

Drinks at Musiikki Cafe & Whiskey Bar

A trip to Kingston wouldn’t be complete without experiencing live music. Musiikki Cafe & Whiskey Bar provides a fantastic ambiance and exceptional cocktails. The outdoor setting creates a relaxed venue to enjoy performances by local artists. Be sure to sample their renowned whiskey cocktails, but note that they can be quite a treat.

Visit the Musiikki Cafe website for the latest music lineup and menu. It also serves as a fair-trade coffee shop throughout the day.

Day 2 in Kingston – Art and Academics

After a delightful breakfast at the Secret Garden Inn, set out to explore day two of your Kingston itinerary. Everything is accessible by walking, but if you prefer a quicker journey, consider calling an Uber, or since you’re likely on a road trip, simply hop in your car to head to Queen’s University campus.

Queen’s University Campus

Today presents an excellent chance to admire Kingston’s historic architecture. Queen’s University, founded in 1831, showcases the city’s beautiful heritage.

Agnes Etherington Art Centre

While exploring the campus, make sure to visit the Agnes Etherington Art Centre to view four of Rembrandt’s masterpieces. This art gallery is free to enter (donations welcome) and ranks among our favorite destinations in Kingston. The collection offers a mix of traditional, contemporary, Indigenous, African, and regional art, making it a must-see while in Kingston. Visit their website for exhibits and opening times.

Lunch and Afternoon – River Cruise

After a morning of exploration, it’s time to board the Island Queen for the Heart of the Islands cruise. This three-hour lunch cruise facilitates an adventure on the St. Lawrence River, showcasing the world-famous Thousand Islands. This archipelago consists of approximately 1800 islands and islets lining the Canada-U.S. border. You’ll enjoy views of Fort Henry, the Martello Towers, and the Kingston skyline while indulging in a delectable three-course meal. Be sure to upgrade to a window seat for an optimal view of the Thousand Islands, and feel free to roam for great perspectives on the cruise.

• Purchase your tickets for the lunch cruise at Heart of the Islands.

Murney Tower National Historic Site

Although it’s been a full day already, a stroll to Murney Tower is worthwhile. This is one of two Martello Towers open for tours in Kingston. Just a 15-minute walk from Confederation Park (your cruise disembarkation point), this scenic site offers a perfect opportunity to work up an appetite after being seated for hours. Even if you opt not to tour inside, walking around the tower to appreciate its architecture is a must. Visit theMurney Tower Website for hours.

On your way, stop by the PumpHouse Museum, home to Kingston’s original waterworks, operational from 1851 to 1952. Discover more here.

Dinner – Union Kitchen and Cocktails

After a day of historical tours, head to Princess Street for dinner at Union Kitchen and Cocktails. This stylish urban lounge serves fantastic dishes, notably their steak frites, a personal favorite. Check here for reservations at Union Kitchen.

Drinks and Arcade Games at Barcadia

For a unique evening entertainment option, visit Barcadia. This beer hall combines a classic video arcade atmosphere, perfectly evoking nostalgia. Enjoy a refreshing beer or cocktail while playing your favorite arcade games. Check out Barcadia for more information.

Day 3 – History and Heritage

Kingston Mills Locks

A visit to Kingston wouldn’t be complete without experiencing the UNESCO World Heritage Site of the Rideau Canal. Located just outside of town, you’ll find the picturesque Kingston Mills Locks. This fascinating set of four locks dates back to 1784, serving as the site of the first mill on the Rideau Canal. A short drive is necessary to visit this remarkable feat of engineering. If you time it well, you might witness a boat navigating through the locks. Check out: Amazing Rideau Canal Cruise – A Unique Cruise Holiday with Le Boat

Morning tour of Kingston Penitentiary

Don’t miss the chance to explore the notorious Kingston Penitentiary, recognized as the number one attraction in Kingston. A selection of tours ranging from 60 to 90 minutes are available. The Kingston Pen closed its doors in 2013, but today offers thrilling tours of a facility that housed some of Canada’s most infamous criminals. Not far from here lies the former Women’s prison. A variety of tours are available, including standard, extended, and architectural options. Interestingly, a Hollywood film was in production during our visit. Kingston Pen movie tours are also available. Select your tour here.

Lunch at Juniper Cafe

Perched along the waterfront, Juniper Cafe boasts one of the best settings for lunch in Kingston. Nestled between the Tett Centre for Creativity and Learning and The Isabel Bader Centre for the Performing Arts, this area harmoniously blends historic charm with modern architectural beauty. Make sure to stroll through the Tett to see the artisans at work. Check out Juniper Cafe for more information.

Make Your Way to Fort Henry

Following lunch, visiting Fort Henry—another national historic site—is essential. This fort provides one of Kingston’s finest viewpoints, ideal for watching the sun set over the city. Fort Henry, constructed during the War of 1812, occupies a strategically significant location. Kingston, being the first capital of Canada, faced potential threats during the war but thankfully, the fort wasn’t invaded, remaining in superb condition since its 1936 restoration. It’s now a top site for discovering Canada’s military history. Visit their website for opening hours and exhibits.

On Your Way Home Bonus…

Kingston has a long history of beer brewing that dates back to 1790, with connections to Canada’s oldest brewery, Molson. In 1824, the son of John Molson established his own brewery and distillery in Kingston. Today, Kingston is home to eight breweries and one cidery, with Daft Brewing Company being a standout visit. This unique brewery, designed in a converted five-car garage, offers a Key West vibe. Be sure to order a tasting flight to savor their distinct flavors, and consider picking up a six-pack to enjoy at home after your extended getaway. Visit Daft Brewery for details.

There are so many activities in Kingston that a long weekend barely scratches the surface. However, with proper planning, you’ll be able to maximize your experience in this surprising city. Kingston has evolved significantly since its days as Canada’s first capital, and planning a getaway here is sure to be fulfilling.