Kingston, Ontario is one of my favorite cities in the province and I’m so excited to share my Kingston itinerary with you. There’s no shortage of amazing things to do in Kingston for the weekend. It’s one of the best road trip destinations in Ontario whether you’re traveling from the Toronto area, Hamilton, Ottawa, Montreal, or essentially anywhere else in Ontario or the northeastern USA.
I recommend spending three days in Kingston as it’s the perfect city for a long weekend getaway in Ontario, though it’s easy to spend a whole week in the region (especially if you include the Thousand Islands region as well!). I’ve visited the “Limestone City” numerous times and fall in love with the city more and more. After several trips to Kingston, I’ve developed the ultimate three day Kingston itinerary that I know you’ll love.
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Kingston Ontario Itinerary: Day 1
It’s your first day in Kingston, Ontario, and my itinerary starts with learning some history about the city. You’ll be able to see some famous Kingston landmarks and visit some iconic attractions. There’s also a couple of ways to explore the waterfront and admire views of Lake Ontario.
Get a Photo with the Kingston Sign
When you first arrive in Kingston, you must get a photo with the Kingston sign! Become the letter “I” in Kingston and pose for an Instagram-worthy photo.
The Kingston sign is beside the Kingston Visitor Centre and near the Confederation Arch / Confederation Park Fountain. It’s right at the trolley stop where you’ll begin your Kingston Trolley tour, too.
Hop-On Hop-Off Trolley Tour
The Kingston Trolley Tour is an iconic activity that you must do in Kingston. It’s a great place to start whether you’re visiting Kingston for the first time or you’ve been here many times in the past. They offer city tours, ghost and mystery tours, and a hop-on hop-off tour.
I usually recommend walking tours when you first arrive in a new place. The Kingston Hop-On Hop-Off Trolley Tour is much like a walking tour because you’ll learn about the history of the city and its important landmarks from your guide. The main difference is that you’ll get around town in a more relaxed setting and you’ll get around town quicker.
The Hop-On Hop-Off Trolley Tour is available in three passes: 24 hours, 48 hours and 72 hours. You can choose to stay on board for the full 75 minute tour or hop off the trolley at any location you’d like. The trolley offers roundtrip service from 9:30am to 4:30pm and stops at each location every half hour. When you book your ticket, you’ll receive a schedule for the stops so you can time your day accordingly.
The trolley stops around the historic downtown shopping area, Fort Henry, Queen’s University, the Kingston Penitentiary, and several museums on the way. It’s a great way to immerse yourself in Kingston’s history and heritage, enjoying the journey from Kingston’s vibrant red trolley.
Fort Henry and the Kingston Fortifications National Historic Site
From the hop-on hop-off trolley, get off the trolley at Fort Henry to explore at your own pace. Fort Henry is a National Historic Site of Canada and a UNESCO World Heritage Site along with the Rideau Canal. From Fort Henry, you can soak up scenic views of Kingston, watch military demonstrations, and listen to riveting musical performances.
Visit this museum and historic site to learn more about 19th century military roles, watch demonstrations by the Fort Henry Guard and embark on guided tours. There are special events at Fort Henry throughout the year, like craft beer festivals and performances by the Fort Henry Tattoo. It’s also possible to book a ghost tour of Fort Henry in the evening, too.
The Kingston Fortifications National Historic Site includes Fort Henry, the Shoal Tower, the Murney Tower, and Fort Frederick. Fort Henry is just one of many stops on the Kingston Trolley Tour. Hop off here to visit Fort Henry and hop back on the trolley to continue your tour of Kingston.
Walk Along the Waterfront
Kingston is a city where the St. Lawrence River, Rideau Canal, and Lake Ontario meet, so you can imagine that it’s a magnificent place to go for a walk along the shoreline. The Great Lakes Waterfront Trail is an expansive path on the shores of the Great Lakes and you can experience a portion of it in Kingston.
Kingston’s Waterfront Pathway is an 8km walk from Lake Ontario Park to downtown Kingston. Kingston has six beaches in total, including the award-winning Gord Edgar Downie Pier and Breakwater Park Beach. I also recommend stopping for a coffee at Juniper Cafe during your scenic walk on the waterfront.
Would you rather go cycling than walking? This small group bike tour of Kingston takes you along the waterfront and visits key historic sites around town. Over the course of a few hours, you’ll cover a lot of ground and learn about the city from your guides on the way. No matter how you experience it, walking, cycling or paddling on the waterfront is a must on any Kingston Ontario itinerary.
Wander Around Queen’s University
From the waterfront, I suggest taking a self-guided walking tour of Queen’s University. This stunning campus was established in 1841 and contains many buildings dating back to the 1800s and early 1900s. Be sure to check out Grant Hall, Ontario Hall and the Theological Building to admire some magnificent architectural works.
I also loved seeing the public art, murals and sculptures around Queen’s University. Some of the buildings are decorated with colorful and thought-provoking works of art. There’s also a large collection of outdoor art that you can see any time of day, free of charge. Take a self-guided tour of the sculptures and learn more about them on this outdoor campus art tour.
Heart of the Islands Cruise: 1000 Islands Cruise at Sunset
The Heart of the Islands Cruise aboard the Island Queen takes you on a tour from Kingston to the spectacular 1000 Islands. This sunset cruise is the perfect way to end your first day in Kingston. Depart on a three hour sailing from the Crawford Wharf around some of these picturesque islands, and you may have the opportunity to experience a pretty sunset, too.
While you may have already learned some interesting facts and history about Kingston, this sunset cruise is another opportunity learn to more about the region. The knowledgeable tour operators on the boat will tell you some intriguing stories and details as you drift on Lake Ontario towards the St. Lawrence River. There’s also live music on the Island Queen, as well as indoor and outdoor seating, a bar, and a dining deck.
Kingston Ontario Itinerary: Day 2
It’s day two of this Kingston Ontario itinerary and we’re going to spend most of the day in downtown Kingston. If you’re visiting Kingston over a weekend (Saturday/Sunday/Monday), this is the perfect opportunity to check out the weekly farmers market on Sunday.
If you aren’t visiting Kingston on a Sunday, you may be able to experience another weekly market. The Kingston Public Market takes place every Tuesday, Thursday and Saturday, and it’s the oldest market in Ontario. You can substitute the Memorial Centre Farmers Market for the Kingston Public Market in this case.
Memorial Centre Farmers Market
Memorial Centre Farmers Market is a 100% producer-run, year round market that takes place every Sunday at the Kingston Memorial Centre. In the spring and summer months, you’ll find the market outdoors on the lawn with over thirty top local food and craft producers.
Shop for fresh produce from within 100 km of Kingston, hot comfort foods, coffee, takeout meals, health foods, vegan and gluten free vendors and handmade crafts. In order to reduce waste, the market offers reusable plates and cutlery that you can return once you’ve finished eating your meal. It’s also possible to borrow a picnic blanket to enjoy your meal on the grass while listening to live music.
While there are numerous vendors and I suggest browsing as many booths as you can, definitely check out Knifey Spooney for delicious vegan eats, including breakfast sandwiches and baked goods. Get to the market early to snag one of their decadent cinnamon buns (they sell out fast!).
Collective Joy Farm has an urban farm location within Kingston and they also have a booth at the market. They grow microgreens, edible flowers and lettuce, and you can also purchase cold-pressed juice and plant-based meals, too.
Kayaking on Lake Ontario
For adventures on Lake Ontario, Ahoy Rentals has got you covered! They have kayaking, SUP, canoeing, cycling and sailing rentals all in one place. Walk over to their little hut on the shores of Lake Ontario to choose your own adventure. Exploring Lake Ontario by water deserves a worthy place on any Kingston Ontario itinerary.
I took a kayak out for about an hour on the water, paddling on the shores down to Confederation Park and back. It was quite breezy when I visited, which makes it a little more challenging, especially if you’re looking to kayak across to the nearby Wolfe Island. The staff at Ahoy Rentals will assist you with your route planning according to the weather conditions and the length of time that you’re looking to be out on the water.
In addition to kayaking, I also rented a stand-up paddleboard from Ahoy Rentals on a past trip to Kingston. No matter whether you choose to take a SUP, kayak or canoe out on the water, it’s always such a fun time. If you prefer a more relaxed journey on the water, you can also book a skippered sailing charter for groups up to five people aboard a 26′ sailboat.
Go Shopping in Downtown Kingston
Downtown Kingston is home to many wonderful shops and boutiques with something for every taste. The main city street in Kingston’s downtown core is Princess Street. There are unique shops on Princess Street, but don’t miss the establishments on the surrounding side streets, too.
There’s truly something for everyone in downtown Kingston, and it’s the perfect place to find the perfect gift. A few of my favorite shops include Minotaur (gift shop with board games, crafts and more), The Keep Refillery (zero waste shop), Midori Gifts (cute gifts from Japan), Black Dog Pottery, Closett Candyy Consignment and the Antique Emporium.
Discover the Historic Homes of Kingston
If you love old homes and architecture, you need to go for a wander around Kingston’s old Sydenham ward. The Old Sydenham Heritage Area is a neighborhood in Kingston with fine examples of 19th century architecture. There are about 550 properties in total, including a castle.
How do you find the Old Sydenham Heritage Area in Kingston? Walk around the streets bordered by Johnson Street, Barrie Street, King Street East and Lake Ontario. There’s a seemingly endless amount of charming homes, pretty gardens, and colorful front doors.
Haunted Walk of Kingston: Kingston Ghost Tour
After you’ve seen the Sydenham ward by day, why not explore its spookier side by night? The Original Haunted Walk of Kingston takes you on an evening journey around downtown Kingston and the old Sydenham ward. Your costumed guide/storyteller will show you some of the city’s key landmarks with a new macabre perspective.
Learn about spooky tales, scary stories, and unexplained events that have happened in Kingston over hte years. The city has many haunted and supernatural sightings at hotels, local pubs and homes. There are tales of hangings at the old courthouse, hidden burial grounds, and grave robbings that all took place in Kingston.
There are numerous tour times throughout the evening to suit your schedule. Our guide was fantastic and shared so many creepy tales. Book your ghost tour of Kingston for a fun evening activity in the city.
Kingston Ontario Itinerary: Day 3
It’s the last day of this Kingston Ontario itinerary. I’ve kept the itinerary to a couple of activities that will easily occupy more than half a day in Kingston. It’s likely that you’ll be driving home for a portion of this day. You’ll start the day with a beautiful hike at Lemoine Point Conservation Area and end with one of the best things to do in Kingston, the Kingston Penitentiary Tour.
Go Hiking at Lemoine Point Conservation Area
Lemoine Point Conservation Area is a peaceful natural space to explore within the city limits of Kingston. It’s amazing that there are such beautiful trails and you don’t even need to leave the city. The property Lemoine Point was a family farmstead for decades before the land was transferred to Cataraqui Conservation and transformed into a park for everyone to enjoy.
Lemoine Point amasses 136 hectares of forest, field and marsh, including 2500 metres of shoreline. Go for a walk on the 11km of trails here to discover an abundance of flora and fauna. I managed to spot ducks, geese, squirrels, chipmunks, and even owls while hiking here. You may also spot many species of migratory birds in the deciduous woods here, as well as pretty wildflowers in the spring.
Kingston Penitentiary Tour
The Kingston Penitentiary is the oldest penitentiary and maximum security prison in Canada. It was home to Canada’s most notorious criminals until it closed in 2013. Nowadays, the old penitentiary is open to the public for guided tours and it is one of the most unique things to do in Kingston. Touring the Kingston Pen is an absolute must for history buffs on this Kingston Ontario itinerary.
Kingston Pen is a National Historic Site of Canada that opened in the 1830s, predating Canada’s confederation in 1867. There are three different types of tours that you can book. We chose the in-depth 2.5 hour guided tour (the extended tour), and I highly recommend it. You’ll visit the jail cells, outdoor areas, the hospital, the gymnasium, and many other places around the property. It’s truly unlike any other tour I’ve ever taken.
Your tour guide will share intense tales of prison riots and elaborate escapes. You’ll also meet former staff members and discover their personal accounts of what it was like to work there. Be sure to book your tour of the Kingston Pen in advance because there are only a limited amount of tickets available and it tends to sell out daily.
Kingston Ontario Itinerary: Food and Drink
Kingston has the most restaurants per capita in Ontario and it’s an awesome city for foodies. If you’re looking for a specific kind of cuisine or you follow a certain diet, there’s a good chance that several restaurants in Kingston will cater to your wishes or dietary requirements.
For instance, I follow a vegan diet and I’ve found so many vegan-friendly restaurants in Kingston. On my most recent trip to Kingston, I had the opportunity to try some new eateries in the city. Every time I travel to Kingston, there are always more restaurants to try, which is one reason why I recommend visiting Kingston again and again.
Miss Bao
Miss Bao is a restaurant and cocktail bar serving sustainable and local cuisine. Not only have they created a zero waste operation, but their food is divine. You must try the Burmese Fermented Tea Salad and the Szechuan Tofu Bao, two delicious plant-based dishes.
Tango Nuevo
Tango Nuevo is a globally-inspired tapas restaurant in Kingston. Share several small plates with your pals for a variety of yummy eats. If you follow a vegan diet like I do, ask your server for a vegan menu. It isn’t advertised, but they do have a separate vegan menu with many tasty dishes. I recommend trying the sauteed green beans and the patatas bravas.
Namaste Kingston
Namaste Kingston serves fine Indian cuisine from an award-winning chef on Ontario Street in Kingston. I loved dining out on the patio, which isn’t too loud but still great for people watching. There’s a whole page of vegetarian dishes that you can easily ask to be made vegan. I ordered the daal tadka (red lentil puree with onion and garlic), onion bhaji to start, and some tandoori roti to go with the daal.
Harper’s Burger Bar
Harper’s Burger Bar is a longtime favorite in downtown Kingston, and they’ve served vegan-friendly fare for many years. There’s a burger for every taste and they’re all fully customizable. Choose your patty, burger bun, side and drink. I ordered a Beyond burger on a pretzel bun with waffle fries, and it was a very delicious choice.
Mio Gelato Kingston
Craving a sweet treat? Pop over to Mio Gelato Kingston for a scoop of gelato or sorbet that’s homemade right on site. The flavors are always changing depending on what’s in season at the time. I love the large selection of vegan gelato and sorbet, which are marked by red scoops (it was one entire section!). I couldn’t resist trying the chocolate pudding sorbet and the chocolate mint gelato.
Kingston Brewing Company
Kingston Brewing Company is Ontario’s oldest brew pub, dating back to 1986, and it’s also Canada’s oldest wine-producing pub. You can order beers, ciders and soda pops made on the premises. They also have a menu of standard pub fare, as well as a large collection of beer memorabilia across every inch of wallspace.
I enjoyed a refreshing pint on their street front patio, and they also have a second courtyard patio out back. This is a great space to meet your friends for beer and appetizers after work or in the evening. I savored a pint here after an afternoon of shopping before heading out for dinner.
If you love coffee shops and cafes, it shouldn’t come as a surprise that Kingston has an amazing coffee culture, too. Check out these top Kingston coffee shops if you’re craving an espresso bevvie or a rich cup of coffee.
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Kingston Ontario Itinerary: Where to Stay
On my most recent trip to Kingston, Ontario, I spent two nights at the luxurious Frontenac Club. Located in the heart of downtown Kingston, Frontenac Club has 20 uniquely decorated and themed rooms for a new experience each time you visit.
I stayed in the Backstage Room, which celebrates Kingston’s talented musicians and the local arts scene. The walls are adorned with photos from live concerts and music memorabilia. There’s also a small collection of LPs and a record player to enjoy, too.
Overall, this room is fabulous. There’s a 4-piece bath with a massive shower and soaker tub, as well as a fireplace and king bed. This “smart room” enables you to have control over the thermostat and TV with a remote control, and you can shut off all the lights in the room with the click of a button.
The Bank Gastrobar is an upscale lounge and named after the fact that this building used to be the former bank building in town. You can even dine inside one of the old vaults. I enjoyed breakfast here and the staff are very accommodating to any dietary needs, especially vegetarian and vegan. My avocado toast tasted delicious and each meal starts with a bowl of fresh fruit.
This hotel has many special touches, like a rooftop patio, the candy bar and even an old arcade machine. It is an exceptional hotel and I’m pleased to include it on this Kingston Ontario itinerary. Here’s where you can read more reviews about the Frontenac Club.
More Places to Stay in Kingston
Looking for more places to stay in Kingston? Here’s a handy map that showcases all available accommodations in the city. Enter your travel dates for more precise information. See the location of each property and click each one to learn more, as well as book your stay.
More Things to Do in South Eastern Ontario
Looking for even more things to do in South Eastern Ontario? I’ve got many travel blog posts and travel guides for you.
- Best Things to Do in Napanee, Ontario
- Town of Greater Napanee Weekend Itinerary
- Things to do in Brighton
- Best Things to do in Belleville
- Things to do in Cornwall
- Vegan Restaurants in Cornwall
- Pumpkinferno: Pumpkin Lantern Festival
- Things to do in Kingston
- Coffee shops in Kingston
- Kingston Vegan Guide
- Standup Paddleboarding in Kingston
- Hotel Belvedere in Kingston
- Things to do in the Thousand Islands
- Kayaking in the Thousand Islands
- Hiking at the Thousand Islands National Park
- 3 Day Itinerary for Lennox and Addington County (Amherst Island, Stone Mills Township, Loyalist Township, Bath, Sheffield Conservation Area and more)
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Lauren is the full-time travel blogger and content creator behind Justin Plus Lauren. She started Justin Plus Lauren in 2013 and has travelled to 50+ countries around the world. Lauren is an expert on vegan travel as one of the very first vegan travel bloggers. She also focuses on outdoor adventure travel, eco and sustainable travel, and creating amazing travel itineraries for cities and small towns.