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Fun Events in Ancaster This Fall/Winter: 2024 Edition

As fall slowly ushers in winter, there’s a lot going on in our bustling village. Follow this guide to plan your next day trip to Ancaster and top it off with a stay at our boutique hotel, The Barracks Inn.

This November and December, there’s a lot to be excited for as Ancaster becomes a festive wonderland with a calendar stuffed with fun events. From early-bird holiday shopping at the Christmas Village to a fun night with your family at the Hamilton Santa Claus Parade, there’s plenty to see and do.

Read on to get the scoop on all that’s going on in our part of the Niagara Escarpment. We hope you’ll consider booking a stay at The Barracks Inn, where we’re ready to host you in one of our boutique rooms or suites for the full Ancaster experience.

November 2024

4th Annual Trivia Night Fundraiser—November 15

Gather up your smartest pals and head straight to the Ancaster Fairgrounds for a night of trivia fun! This trivia night is a fundraiser supporting Juravinski Hospital and Cancer Centre and local food banks, so you can do good while enjoying some brain twisters. Bring teams of 2 to 6 people and compete for bragging rights and prizes. Enjoy complimentary food and a cash bar.

Ancaster Christmas Village—November 16th

If you’re ready for some early holiday shopping, head to the Ancaster Fairgrounds for the annual Ancaster Christmas Village. Find one-of-a-kind handcrafted gifts and unique treasures, sip on some festive drinks, and enjoy some delicious food. If you can get all your holiday shopping before December, it’s a bonus!

Hamilton Santa Claus Parade—November 16th 

This beloved Hamilton tradition is a short hop away from Ancaster. Bundle up, brew some hot tea, and go watch the festive floats, marching bands, and, of course, jolly St. Nick himself!

Annual Jingle & Mingle—November 17th

If you’re a beer lover or just love the holidays, join Shawn & Ed Brewery for their Annual Jingle & Mingle. Drink some festive pours, enjoy live music, and chat with good company as you ring in the beginning of the holiday season. It’s the perfect opportunity to unwind and get into the spirit by December.

Ancaster Toy And Collectibles Expo—November 17th

Whether you’re a collector, toy enthusiast, or simply love to check out great collectibles, the Toy and Collectibles Expo is coming to town! The Ancaster Fairgrounds hosts this exciting expo, where you can find your favourite vintage toys, rare collectibles, and unique treasures from the past and present. It’s a great event to discover hidden gems and add to your collection.

Christmas in Ancaster Craft Show—November 23rd & 24th

This holiday-themed craft show features one-of-a-kind gifts and supports local artisans. The Christmas in Ancaster Craft Show is held at the Ancaster Fairgrounds, featuring various handcrafted items, from jewelry and pottery to home decor and artwork.

Bad Apples Comedy Show—November 26th

If you love live comedy, the Bad Apples Comedy Show is for you. Enjoy a showcase of talented local comedians at Pub Fiction in Ancaster and unwind with laughter before holiday stresses get to you. 

December 2024

Hamilton Military Collector Show—December 8th 

Our village brings in all the history buffs and collectors with the Hamilton Military Collector Show hosted at the Ancaster Fairgrounds. Discover fascinating military artifacts, memorabilia, and historical items from various eras, and enjoy a blast from the past. 

Ancaster Christmas Craft Show—December 14th 

Another opportunity to find unique and handcrafted gifts and finish up your holiday shopping! This Christmas Craft Show at the Ancaster Fairgrounds offers a diverse selection of artisan creations, perfect for those last-minute holiday shopping needs.

Ancaster Toy & Collectibles Expo—December 15th

If you miss the December session, the Ancaster Fairgrounds once again welcomes toy and collectible enthusiasts with this exciting expo. Browse through a wide array of vintage toys, comics, games, and other treasures.

Ancaster Collectibles Extravaganza—December 16th

Calling all collectors! This extravaganza at the Ancaster Fairgrounds is a must-visit for those seeking rare and unique collectibles. Discover hidden gems and add them to your collection.

The Barracks Inn—Boutique Hotel Hamilton Ontario

Let this guide inspire you to discover the charm and excitement of Ancaster this fall. Whether you’re seeking festive cheer, outdoor adventures, or cultural experiences, our village has a little something to offer everyone.

After a day of exploring Ancaster’s fall events and activities, retreat to the comfort and luxury of The Barracks Inn. Our historic century-stone building offers a cozy and elegant atmosphere, with 18 luxuriously appointed suites featuring modern amenities and personalized service. Relax by our wood-burning fireplace, enjoy a glass of scotch from our whiskey cart, and savour a delicious breakfast to start your day.

Book your stay today to join in on these fun events and create some unforgettable holiday memories.

Book Your Room Today!