Can’t Miss Milton Events for December 2025

December is packed with festive fun to get you into the holiday spirit. From Christmas markets and hands-on workshops to visits with Santa, holiday shows, and community celebrations, there’s no shortage of ways to make the season feel special, whether you’re crossing gifts off your list or treating yourself along the way.

Experience of the Month

• Santa at the Fairgrounds 2025: An annual favourite celebrating its 4th year. Santa is coming to town and will visit with kids every weekend leading up to Christmas from 10 am to 4 pm. Make sure your kids are ready with their wish lists! After your visit and photo, be sure to shop the local vendors and enjoy some roasted marshmallows by one of the outdoor fire pits. Entry is free, but donations are appreciated for the Milton Community Resource Centre’s Fill a Crib campaign.

Ongoing Events

• Pilates Reformer Flow: Stay fit over the holidays with a combination of Pilates and resistance machines. This flow takes place twice a week, Tuesdays and Thursdays, from 5:15 to 6:15.
• Tuesday Night Trivia at Shoeless Joe’s in Milton: Love knowing all the answers to tricky questions? Then Trivial Night is calling your name! Reservations via  Eventbrite are required, but please also call Shoeless Joe’s at (905) 864-9779 to reserve your table.
• Wednesday Night Trivia at St. Louis Bar & Grill in Milton: Milton loves its trivia nights! Join in for fun with questions at St. Louis Bar & Grill. Reservations are required on Eventbrite and a phone call to Louis Bar & Grill to secure your spot at (905) 875-1333. 
• Public Speaking & Leadership Skills- Supporting Women Entrepreneurs: Build your voice in this public speaking and leadership skills series. It runs on Wednesdays at Martindale Gardens Community Centre. The first meeting is FREE.
• City LOVE Scavenger Hunt Date Night for Couples: Love is in the air, and what better way to spread that feeling than going on a scavenger hunt date made just for couples. Choose from a variety of Milton dates for a night of puzzling fun.
• Date Night at The Note: Bring your loved one and enjoy two main dishes, a shared dessert, and some drinks for $59.99. It’s a fun evening out with live music to engage you from 7-10 pm.
• Graceway Baptist Church Kids 4 Truth: Kids 4 Truth gives children, ages 4-12, the opportunity to understand the truth of God’s Word through games, songs, bible lessons, and scripture memory. This gathering takes place every Thursday, from 7-8 pm. Registration is required.
• Live Music @ Marquee Steakhouse & Piano Lounge: Every weekend, the Marquee Steakhouse hosts talented artists with a piano or guitar performance that pairs perfectly with their delicious food. Visit their music calendar for details and dates.
• The Princess and the Pop Tart: It’s your classic tale; a princess and a peasant switch places for a day, but then fairy magic happens, and plans don’t go as…well, planned. Add in the fact that this is a pastry-themed story, and you’re in for a hilarious time. Multiple dates are available.
• Christmas on the Rails: It’s your last chance to ride the rails on vintage streetcars through the woods until the spring. Enjoy Christmas carols, a visit from Santa, and lots of holiday spirit. Each ride takes about 20 minutes, and you can also enjoy some hot chocolate or cider with cookies as you wander the grounds of the Halton County Radial Railway. Multiple weekend days and times available.  
• Cooking Up A Story: The Great Cookie Exchange: Bring on the cookie fun! This event is made for parents, grandparents, or caregivers with young children who want the joy of making Christmas cookies together. The first event is on December 5, the second is on December 19.
• Salsa at Champs: The rhythm is gonna getcha, the Salsa rhythm, that is. Let DJ Gio guide your feet to a night of Salsa beats every third Friday of the month.
• NCIM Saturday Night Racing: If you’ve got a UCI Track Cycling license but have always been curious about testing out your racing ability, now’s your chance. Pick the Saturday that works best for your schedule until March.

Events By Date

Monday, December 1

• Sign Painting Night at The WORKS: Create your very own festive sign with a fun night out with friends. Pricing includes a wooden sign, your choice of appetiser, and a drink.

Tuesday, December 2

• Graceway Baptist Church: Surviving the Holidays (GriefShare): It can be hard for some to get through the holidays, especially when grief keeps you in constant company. Gather together with others who know what you’re going through at Graceway Baptist Church.
• Fresh Greens Centrepiece Making Event: You’ve long dreamed of having a beautiful, fresh green centrepiece for your Christmas dinner with family, but need a bit of guidance. Now’s your chance. Come join Sari Yorke for an engaging evening of centrepiece-making. Registration is required.

Thursday, December 4

• 2025 December Dinner CFUW Milton and District: Dinner and a good cause may be one of the best reasons for a night out. Join CFUW Milton and District for their annual December dinner with cocktails, a silent auction, and, of course, a delicious meal. Registration is required.
• 2 Mediums. 1 Night. Live Audience Mediumship Readings: Come out for a night where mediums Trish Finch and Barbara Quinton will breach into the spirit world with readings to those in the audience seeking connection.
• The Barra MacNeils: An East Coast Christmas: Nothing beats an evening of toe-tapping instruments and singing. Add in music from the holidays featuring the Barra MacNeils, and you’ll be feeling the festive spirit in no time.
• Milton Comedy Show: If you could use a laugh, head on out for a night of comedy filled with four comedic greats: Dylan Gott, Fiona O’Brien, Kerby Darius, and Mr. Lewin. This 19+ event takes place at Ned Devine’s Irish Pub.

Friday, December 5

• Holiday Cheer Celebration & Toy Drive Invitation: Join Exit Realty Connect for an afternoon of holiday cheer from 3-6 pm. Enjoy appetizers and beverages; all that’s required is that you bring a new, unwrapped toy for SickKids donations. RSVP at [email protected].
• Holiday Trivia Night!: It’s trivia with a holiday twist. Join quizmaster and Third Moon Brewery at 7:30 pm for a night of festive facts and some drinks.
• Derek Edwards – Oxy Moron: Come and see the winner of Best Standup Comic, Derek Edwards, for a night of lighthearted comedy. A perfect night to get out with friends, family, or with a date.

Saturday, December 6

• The Golden Spike Trail Race: Cheer on (or run your own race) at the Golden Spike Trail Race at Crawford Lake in Conservation Halton. Runners will race one of three distances, 5k, 10k, or 21k, tackling the trails with winter frost and snow. Winter-themed race swag is available for purchase.
• Track OCup #1: It’s the cycling event of the season, as cyclists of 8 years and older race for their chance to win the OCup. Come cheer on your favourite rider.
• Christmas Craft & Connect: Renew Church presents the Christmas Craft & Connect, a great way to build a gingerbread house and connect with fellow Miltonians. A great event for families with young children.
• Paint-Your-Own Mug + Cocoa Bar: Another great family event where parents and children get to design and paint their own mug and enjoy some hot cocoa at the cocoa bar. Registration is required.
• 3D Archery Shoot: Archers looking for some practice will want to come out to this event. With 40 individual targets, all categories welcome, and a lunch included, you’re in for a great day in the great outdoors.
• Christmas Afternoon Tea: Tea and holiday-inspired treats, count us in! The Lavender Teahouse presents an early afternoon of delicious tea, treats, and, as a bonus, Dalton Malcolm from mycaricaturecreators.com will join, where every guest can take home a custom piece of art.
• Visit Santa at the Tree Farm!: Santa is making another stop, and it’s at Van Dongen’s Garden Centre. Bring the kids, babies, and even fur babies for some fun, free activities, snacks, and warm drinks. A great opportunity to leave with a photo with Santa and a freshly cut Christmas tree.
• Brazilian Christmas Market: Need a little inspiration with your Christmas shopping? The Brazilian Christmas Market is a great way to spend the day looking for the perfect gift at St. Paul United Church, with a special visit from Santa
• Jingle Jam: If the weight of the world has got you feeling a little down, come on out for the Jingle Jam, a great afternoon event that runs from 1 pm to 3 pm, helping families focus on the true meaning of Christmas. Enjoy a fun and interactive Christmas show at the Connect Centre.  
• Miracle on Main Street: This is one of Milton’s favourite ways to get into the spirit of Christmas and join in the community fun. Kids love the free amusement rides, enjoy the live entertainment, petting zoo, pony rides, and so much more. It’s free to attend with a new unwrapped toy donation.
• Christmasfest Sale: Perfect for when you’re looking for that special something they haven’t already gotten for Christmas. Held from 1 pm to 5 pm at the Historic Waldie Blacksmith shop, come and select from a wide range of gifts for the loved one who is a die-hard Milton fan.
• Family Paint Party: Join local artist Aswini for a night of festive painting at Shoeless Joe’s. Come paint, eat, and connect with family.
• Colin James Trio: Sit back and relax for a night of musical talent with the Colin James Trio, a Canadian blues-rock band.  
• The Loonie Tunes (half of The 2 Dollar Bills) at The Ivy Arms: Enjoy some acoustic renditions of hits from the 70s, 80s, 90s, and early 2000s alongside some great food and drinks at The Ivy Arms.

Sunday, December 7

• Family Jingle & Mingle 2025: The perfect way to get your shopping done without the kids seeing what you buy. Activities for the kids include a ball pit, glow-in-the-dark rides, karaoke, and more. Add-on experiences include holiday shopping with local vendors, a silent auction, and pictures with Santa and Mrs. Claus. All proceeds go to Million Dollar Smiles. Tickets can be purchased here.  
• XXXmas Drag Brunch: The Eightnote presents XXXMas Drag Brunch from 12 – 2 pm with Kenadie St. James as she puts on a dirty drag show. Don’t forget to book your table and wear your ugly Christmas sweater for a chance to win a prize.
• A Swingin’ Christmas with Toronto All-Star Big Band: Celebrate the season with Toronto All-Star Big Band as they blend swing music with classic Christmas tunes.

Monday, December 9

• Chocolate Sale: If you’ve got a chocolate lover in your life, then this is the sale you won’t want to miss. From December 9 to December 12, 9 am to 5 pm, at Milton District Hospital Food Court, come and stock up on chocolate gifts for loved ones, and maybe get some for yourself too. You deserve it!

Wednesday, December 10

• Church Planters Round Table Christmas Lunch: Milton Bible Church hosts the Christmas Round Table for the whole family. It’s a time to reflect, worship, and celebrate Christ.
• Mindful Meetup @ Sherwood: Rediscover yourself and gain some inner peace in this meetup where you’ll learn techniques to cultivate moment awareness, enhance your well-being, and reduce stress. Please register beforehand.

Thursday, December 11

• Celebrate the Season – Opening Reception: Celebrating the creativity of FASM members during the holidays, join us for an evening. Light refreshments will be served.
• Tartan Terrors: A Celtic Christmas: It’s the Tartan Terrors, a rock show with humour and stepdance, but Christmas-themed! Get your tickets now for a great evening of Celtic Christmas music fun.

Friday, December 12

• Scott Woods presents “Christmas Hoedown”: Get your hoedown on Christmas-style, with Scott Woods, Canadian Fiddle champion. Music will feature traditional country and gospel songs, and accompanying vocals of Nadine Boles.

Saturday, December 13

• Milton Christmas Market: A fun way to find the special gift you’re looking for and show support for local businesses and artisans. Join in the festive spirit at the Royal Legion 135 from 10 am to 3 pm and enjoy some warm, yummy treats, handcrafted holiday décor, and of course, gifts.
• The Believer’s Journey – Full Day Seminar!: Engage your beliefs with a full-day seminar from 12 pm to 5:30 pm. Lunch is included, and childcare is available.
• MYTP Extended Holiday Showcase: Come show your support for the youth who participate in a variety of activities, including drama club, musical theatre dance, stunts and stage combat, vocal ensembles, and more. Tickets may be purchased here for one of two time slots.
• Christmas Cheer: Come and experience some Christmas Cheer at the hands of the Milton Concert Band. Tickets can be purchased here for this evening’s event.
• Ned Devine’s – Last time for 2025: It’s the last of the year! Come on out to Ned Devine’s for some rocking music from Station 31, playing a mix of top 40 rock, pop, retro, country, and hip hop. Don’t forget to wear your best Christmas sweater.

Sunday, December 14

• Christmas in Milton Market: Another fantastic way to get some amazing gifts for loved ones for holiday gift exchanges and support local artists and businesses. Entry is PWYC donations to Cool Aunt Jr to help send kids to crafts and nature camp for free; every donation will be matched, so be prepared to donate generously.
• Family Paint Party: Join local artist Disha Sharma at Boston Pizza Milton for a fun night of painting an engaging holiday-themed image you can bring home and hang proudly.

Tuesday, December 16

• Metal Stamping Workshop: A wonderful way to give a personalized gift made by you for that special someone. Hosted by Lovely Creations at The Barn Door Studio from 6:30 to 8:30 pm. Register in advance here.
• Milton Speed Dating and Comedy Show (Age 28-42): Come meet new people and potentially click with that special someone, plus get your laugh on at the same time. Each “date” is 4 minutes, where you decide if you think there could be something more.
• Milton Comedy Showcase – Free Admission!: Laugh your way through your next meal at the Eighth Note Eatery as you join them for this free comedy event. Please get a free ticket beforehand to help them track numbers.

Wednesday, December 17

• Holding Space for Connections: Gazal Lounge hosts this free event for females in the Milton community to meet and connect with other females. Tickets may be booked here.

Friday, December 19

• Family Paint Party: There’s still time to get in your festive painting before Christmas comes at Shoeless Joes with local artist Disha. It’s a great time for laughter, food, and painting creations you can proudly take home.

Saturday, December 20

• Milton Naija Christmas Party 2025: It’s a night full of delicious food, joyful music, and connecting with others at Connect Centre, a Christmas event you won’t want to miss.
• MPO Winterlude XII: Returning for their 12^th season, the Milton Philharmonic Orchestra invites you to come out and listen to musicians from and around Milton play. Tickets may be purchased here.
• Ned Devine’s Presents: ACME Hi-Fi’s Holiday Christmas Show!: Join friends at Ned Devine’s for an electrifying night of the best Rock, pop, and Top 40 music by ACME Hi-Fi. 8:30 pm start time. Come early to reserve your spots and get a delicious meal beforehand.

Sunday, December 21

• Elvis’ Wonderful World of Christmas: Graceland Edition: With hits like Blue Christmas and Silent Night, if you’re a fan of the King of Rock and Roll, then you won’t want to miss this special holiday event. Get your tickets here.

Tuesday, December 23

• Family Paint Party: Paint a Christmas scene and get 25% off while you eat some delicious food and chat with friends and family. Sign up for this no-experience-needed painting event at Keenan’s Irish Pub.  

Saturday, December 27

• The Wizard of Oz: Youth Edition: Help Dorothy find her way back home as Milton Community Theatre presents an engaging theatrical experience, creating fun for the whole family. Tickets for this two-day event may be purchased here.

Sunday, December 28

• James Anthony Band @ Ned Devine’s Irish Pub: Gather your friends for an afternoon of blues, soul, and old-school music vibes. Reserve your spot and come thirsty.
• Family Paint Party: Need something to do over the holiday school break with the teens? Why not take them to a family paint party? Let artist Disha Sharma guide you with your painting at Boston Pizza, while you can also get a great dinner out and reconnect.
• Fairy & Iron Yuletide Ball: The Battle of Two Kings: Christmas may be over, but celebrating the spirit is still going strong. Experience an evening of historic fantasy and epic storytelling combined with holiday magic. Tickets include a three-course royal feast.

Monday, December 29

• Paint Night at East Side Mario’s, Milton: Paint a “Snowy Snuggle” pic that will make you feel cosy inside. Come early to East Side’s to order your food before the event begins.

New events are continually being added to our event calendar, so make sure to stay tuned for all the latest festivals and community connections! For more Milton experiences, check out these activities.