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This Charming Ontario City Is Just 3 Hours From Montreal & It’s The Perfect Fall Road Trip

Thrift stores, art galleries, hidden alleyways and more!

Contributing writer
This Charming Ontario City Is Just 3 Hours From Montreal & It’s The Perfect Fall Road Trip

It's that time of year again where you can wave goodbye to Montreal's construction and look forward to nothing but beautiful foliage and the calming sounds of nature on the open road.

If you're seeking relaxing vibes, good food and the opportunity to immerse yourself in local culture, consider putting Ontario's picturesque towns — and one in particular — on your fall road-trip list.

Kingston is a small, vibrant city that's just a three-hour drive from Montreal and a stone's throw from Thousand Islands National Park. Here, you'll find historic sites, unique dining experiences, art galleries, charming boutiques and even hidden alleyways containing antique markets and delightful patios. And because everything is within just a few blocks of each other, it's all walkable.

When it comes to finding a place to rest your head for the night, Kingston has plenty to offer, from endearing historic inns to classic hotels. There are various packages available, and you have the option to enhance your visit with culinary or outdoor experiences, vineyard or brewery tours and shopping excursions.

Right now, Kingston is offering travellers a $100 VISA gift card when they book a qualifying two-night package. If you're ready to start planning your trip, check out this three-day itinerary designed to help you make the most of your visit to Kingston.

Day 1: Out & About

Grab A Bite To Eat

Price: Various

Address: 203 Wellington St., Kingston, ON (Sally's); 326 King St E., Kingston, ON (Harmony Flavours)

Why You Need To Go: Fuel up for your big day with a delicious lunch at Sally's Roti Shop. This local favourite is known for its authentic Caribbean roti wraps, made by Sally herself. Inspired by her mum's recipes from her childhood in Trinidad, Sally offers fillings like jerk chicken and curry eggplant and spinach.

Alternatively, head to Harmony Flavours to pick up a sandwich made on fresh focaccia or a charcuterie tray. This gourmet food store offers local Ontario and Quebec artisanal foods (perfect for picnics!).

Take A Tour Through The City On E-Bike

Photo by Erik Mclean from Pexels

Price: $19.95 per hour (cheaper rates for longer rentals available)

Address: 25 Fort Henry Dr., Kingston, ON

Why You Need To Go: Why walk when you can e-bike? Enjoy the thrill of exploring a brand-new area while doing good for the environment too. Locally owned i-Cycle Electric Bike Co offers e-bike rentals starting around $20 for the first hour, and the longer you rent, the more you save (full-day rentals are $69.95).

Once you're set up with your ride, head off on a self-guided tour of Kingston — from the downtown waterfront trail to the Barriefield Village and Fort Henry area.

Take A Trolley Tour & Learn About Kingston's History

Price: $28

Address: 248 Ontario St., Kingston, ON

Why You Need To Go: The best way to see Kingston in a short amount of time is by booking a tour with the Kingston Trolley. You can get a great overview of the city while taking in historic sites and visitor attractions in the downtown core and along the waterfront. Just sit back, relax and let the tour guide fill you in on over 300 years of Kingston's history.

Face masks are required on the trolley and reservations are required (the hop-on hop-off service isn't available in 2021 but is returning in 2022).

Enjoy Some Spooky Fall Activities

Price: Up to $24.99

Address: 200 Ontario St., Kingston, ON

Why You Need To Go: If you're in for a scare, you can join the Haunted Walk of Kingston for a tour through the city's historic (and possibly haunted) buildings and alleyways. Follow the light of your guide's lantern as they lead you on your ghostly walk and tell stories about Kingston's famously haunted courtyard, hidden burial grounds, grave robbing and more.

Not everything has to be scary if you're not up for it though. With impressive light displays, Pumpkinferno is the perfect Halloween activity for those who prefer to steer clear of the creepier side of Halloween.

Day 2: History & Art

Brunch It Up

Price: Various

Address: 44 Princess St., Kingston, ON

Why You Need To Go: Downtown Kingston has a bunch of breakfast and brunch spots to stop for a bite to eat. Pan Chancho Bakery and Café caters to both early birds and late risers, serving brunch from 8 a.m. to 3 p.m. every day.

A popular dish is the El Chancho, which features chorizo, two kinds of bacon, eggs, roasted corn salad, potatoes and brioche. Is your mouth watering yet? Many of the dishes here can be made gluten free, vegetarian or vegan.

Explore A  Former Maximum-Security Prison

Price: From $40

Address: 560 King St. W., Kingston, ON

Why You Need To Go: The Kingston Penitentiary opened in the 1830s and is Canada's oldest maximum-security prison. If the stories behind the forbidden walls intrigue you, you won't want to miss a guided tour. Your tour guide will walk you through the prison and tell the tales of prison breaks, infamous inmates and more.

If you love movie and TV trivia, you can sign up for the 90-minute Film Tour that explores the history of filmmaking at the penitentiary — TV shows like Murdoch Mysteries and Alias Grace have been filmed here.

Visit The Agnes Etherington Art Centre

Price: Free

Address: 36 University Ave., Kingston, ON

Why You Need To Go: Art aficionados will love this stop on the Kingston itinerary. Better known as just "Agnes," the Art Centre at Queen's University has collections spanning Indigenous art, contemporary art, and historical art from Canada, Africa and Europe (including four Rembrandts).

New works are being exhibited all the time at Agnes, so don't miss your chance to see some great artwork from Canada and around the world.

Day 3: Unique Finds 

Explore Kingston's Thrift Shops

Price: Prices vary

Address: 338 Princess St., Kingston, ON (What'll I Wear); 165 Princess St., Kingston, ON (YGK Thrift); 39 Montreal St., Kingston, ON (Montreal Street Collective)

Why You Need To Go: Thrifting during autumn is an opportunity to start switching up your wardrobe for the seasons to come. Plus, you might find a few hidden treasures you can take home with you to Montreal.

What'll I Wear is the ideal place to find vintage clothing and accessories in Kingston. You can also score some awesome wigs just in time for Halloween. Other notable mentions include YGK Thrift and Montreal Street Collective.

Explore The Local Arts Scene At Martello Alley

Price: Prices vary

Address: 203B Wellington St., Kingston, ON

Why You Need To Go: Step up your thrifting and head over to Martello Alley. Here, at Ontario's only alleyway art gallery, you'll come across tons of locally made arts and crafts to admire and purchase.

Nearby, there is also Antique Alley, which features antique furniture, clothing, toys, books, vintage jewelry and memorabilia.

Wrap Up Your Road Trip With Local, Organic & Sustainable Nibbles

Price: Various

Address: 103/171 Wellington St., Kingston, ON (The Everly); 286 Princess St., Kingston, ON (Miss Bao)

Why You Need To Go: To finish off your short-but-sweet getaway, grab dinner at one of many Kingston restaurants. Sustainable and stylish, The Everly works with farmers and producers to create a rotating menu of seasonal dishes made with locally sourced ingredients.

Another great place to eat is Miss Bao Restaurant + Cocktail Bar, an Asian fusion restaurant that's committed to being Kingston's first zero-waste restaurant.

Before you head off on your trip, it's important to note that, as of September 22, Ontario's vaccine passport regulations require you to show proof of vaccination when eating indoors. This doesn't apply to takeout or patio services.

Kingston has a little something for everyone, from exciting outdoor experiences and delicious dining to thrift shopping and fun fall activities (spooky or not). If you're looking for a not-too-far escape from Montreal, you'll be pleased to discover what Kingston has to offer.

For more information on planning your trip to Kingston, check out the city's official website or follow them on Facebook, Instagram, Twitter or YouTube.

Before you get going, check our Responsible Travel Guide so you can be informed, be safe, be smart, and most of all, be respectful on your trip.

In Ontario, a vaccine passport is required to access some events, services and businesses, including restaurants and bars.