Fall is a great time to Visit Kingston, there’s plenty do from live performances by local talent to events to get you in the mood for Halloween. Take a look at this list of 11 things to do this fall in Kingston. We even added a playlist recommendation to get you in the mood for the trip plus “the number 1 fun thing to do in Kingston.”

1. Cruise The Waterway In Style This Fall

Cruises aren’t just for summertime anymore! Both Kingston Destination Group and St. Lawrence Cruises offer a variety of cruises that will show you the beautiful City of Kingston and stunning St. Lawrence River with an Autumn backdrop.

Kingston 1000 Islands Boat Tours

Choose between 90 minute and 3 hour cruises, hear live entertainment and enjoy some gourmet food prepared by their talented culinary team while you learn some interesting facts about the Kingston waterfront including its 19th-century Military Defence Fort (Fort Henry), cottage islands such as Wanderer’s Channel and Bateau Channel, shipwrecks, and other unknown folklore.

St. Lawrence Cruises

If you are looking for a memorable vacation this fall, book a spot on the Fall Harvest and Colour Cruise with St. Lawrence Cruises. You won’t believe the beauty of the colourful shoreline as you travel from Kingston to Montreal (and back) over 8 days and 7 nights. Get your camera ready as you will pass serene shorelines decorated with falling leaves in beautifully rustic colours. Enjoy many excursions that take you off of the boat and onto land to enjoy what we call “Fall Harvest”.

Who doesn’t love food? We know we do! How can you feel guilty if you are walking between bites? The Kingston Food Tour is a walking tour of the Limestone city’s beautiful downtown hub. Blending drool-worthy food with sightseeing and inside secrets about the historic culture and thriving community will have you ramped up for a fun night on the town. With food so delicious, people come from hundreds of miles away to explore their taste buds, you can expect to try some mouthwatering fish tacos, creamy gelato and aromatic sauces at each of the many locally-owned restaurants featured on this tour.

Dress for the weather and keep the kids at home on this tour as you will be given a first-hand glance at one of Canada’s oldest penitentiaries. Follow your knowledgeable tour guide around the inside and outside grounds of the Kingston Pen and hear stories from retired guards who remember the good, the bad and the ugly of this beautiful building’s history. Beyond the incredible story-telling and interesting history, you will be in awe of the beautiful architecture of this timeworn building.

Another great event to enjoy in the Kingston Penitentiary this fall is a movie night! Enjoy a special presentation before a movie at 8:00PM. Choose your night to attend from some great prison classics including The Blues Brothers, O Brother, Where Art Thou?, The Green Mile and The Shawshank Redemption.

Have you ever attended a concert in a prison? Well this may be a first for you! Join KPP Concerts for their Mattress Shop Series hosted in the Kingston Pen where you can enjoy the musical talents of Classified with Reeny Smith and Status/Non-Status with Funeral Lakes and Tiny Horse.

5. Catch Live Performances By Local Talent

Music is a language that everyone speaks, and if you have heard of The Tragically Hip, then you know that Kingston produces incredibly talented musicians. Many of the bars and restaurants feature local talent throughout the week and weekends all year long. We have highlighted some of the top spots for you to hear the Kingston sound on your next trip to the city.

Musiikki Café – Visit this hot spot any night of the week for local music, including Jazz Monday, Open Mic Tuesdays and the Goodnight Irenes every Thursday! The Toucan – A rustic and cool pub that is always looking to share local talent. The Toucan features different local bands from a variety of genres including Ghetto Express, BAG$, Goldwing and Maybelleen. Olivea – If jazz gets you jazzed then you need to check out Olivea on Tuesdays between 6 and 9 pm for their traditional jazz night. No cover required and delicious Italian food available! The weekly jazz nights feature local artists such as Spencer Evans, the Downtown Trio or the Dave Barton Trio.

Blu Martini – With live music every Thursday, Friday and Saturday night, the Blu Martini features local talents including Chris Jackson and The Great Unwashed, all while offering some of the best cocktails in town. The Mansion – Not only does the mansion offer some great eats and fabulous drinks, but you can also find new local bands playing on their upstairs stage on most nights of the week. Check out their events page on Facebook to get all the details. The Merchant – Another one of Kingstons hot-spots on the weekend. You are bound to make new friends and find a new favourite band at The Merchant any weekend of the year. Hit up the pub around 10:00 pm on Fridays and Saturdays to hear the sounds of Smitty, Kings of the Cold and many more.

Turn It Up!

In case you are looking to expand your playlist with more Kingstonian musicians, we have put together a list of some of our favourite local artists. You can also check out more on the Visit Kingstons’ Soundcloud.

Beta 58 – If you are feeling the loud and proud Rock ‘n Roll. Golfwing – For those who don’t like to stick to one genre. Jimbo – Get dizzy with this psychedelic rock group. Huraches – Twist it up with this Instrumental Surf Punk party. Deux Trois – Inspire yourself with this 80’s style, dark pop musical talent. The Meriunges – A little indie/punk for you punks and punkettes. Sweet Talk Jackie – A beloved local rock band to get your party started. Savannah Shea – Feel it in your soul with this jazz, blues and pop trio. Relatively Minor – Check your feet. Are you wearing your jazz shoes?. Ghetto Xpress – Because it wouldn’t be a complete list without a little bit of Funk and R&B!

Celebrate fall on stage at this cultural hub known lovingly as the “The Grand”.  The Grand Theatre in downtown Kingston lives and breathes history and the arts, with more than 250 professional and amateur events held each year. This fall live music is where it’s at with big names like musicians Matt Mays and The Jim Cuddy Band joining comedians Derek Edwards and Red Green on the bill, in addition to ballet, classical artists, musicals and more. Make autumn one to remember and see a live performance unfold on stage in a historic setting!

Improbable Escapes is the perfect way to get your fill of adventure. If you and your pals have a thing for mystery, puzzles and creative-thinking, then this is your jam! Book a private adventure with your favourite people and get locked in a room for 60 minutes, then put your heads together to escape before the buzzer goes off. Choose between the creepy and the cute from their many experiences including “Coroners Report”, “The Cure for the Common Zombie” and “Love Letter Lockdown.”

Who doesn’t like to be a little judgy now and then? You can be the judge this November as you join friends to blind-taste some of Prince Edward County’s best wines versus other famous wines from regions all around the world. This not-for-profit event shares all its proceeds with local charities as well.

Get your ghost on by hopping on a trolley tour through Kingston’s mysterious past on the Ghost and Mystery Trolley. This 90-minute evening tour takes visitors off the beaten path to notable spooky sites and notorious neighborhoods like Rockwood Asylum, Fort Henry, Kingston Penitentiary and more that played a ghostly role in Kingston’s early history. As one of the oldest cities in Ontario, Kingston has numerous hauntings to uncover!

10. Taste Test some Sweet Sips

There’s no better time to discover Kingston’s breweries! Tasty sips are around every corner in the city and some even have new brews dropping for fall. Hit the ground running and do a little research before you go by meeting the brewers of Kingston here. From distinct venues (can you say 1800s telegraph office?!) to one-of-a-kind brew (enter the ruby red Ramboozle at Hard Way Cider Co. or the 12 Star Session Ale at Stone City Brewing), Kingston’s breweries are creating new memories in every pint. Have a blast touring locations, finding your brew style and maybe even meeting a brewmaster!

Guided winery tours with County Sips offer a relaxing day of touring through Prince Edward County, with a pick up start in Kingston or PEC. With Sommelier, Ian Nicholls, participants will learn about the County’s terroir, as well as enjoy local lunch and discover award-winning wines. Get your family or friends together and book a spot this fall!

11. Celebrate and Support Local

Celebrate fall the right way by attending the annual Open Farms Harvest. Kingston, Frontenac County and Tourism Kingston join together to celebrate local farmers, chefs and vendors by sharing everyone’s favourite thing – food. Try craft beer from local breweries, Prince Edward County wines, fresh food grown locally and plenty of great storytelling.

Edited & Updated By Rosanne Lake and Lindsay Medeiros