Valentine’s Day Events in Milton Ontario 2026. Dinners, Dates, Family Fun

Flowers Team Real Estate • January 21, 2026

Valentine’s Day Events in Milton Ontario. February 2026

Santa claus is sitting in a sleigh on a city street.

February in Milton is all about connection. Cozy dinners. Live music. Creative nights out. Family friendly fun. Whether you are planning a romantic evening, a date with friends, or an experience everyone will enjoy, this guide brings together the best Valentine’s events happening in and around Milton.

 

Bookmark this page and start planning early.

The Dreamboats Live

Artist: The Dreamboats

Venue: FirstOntario Arts Centre

Date: February 12, 2026

Time: Evening

Location: 1010 Main St E, Milton

 

Step back into the sounds of the ’50s and ’60s with this high energy rock and roll show. A fun and nostalgic night out leading into Valentine’s weekend.


Registration Link


Pickleball Is My Valentine Tournament

Milton Pickleball Association

Date: February 14, 2026

Time: 2:15 PM to 6:00 PM

Location: Mattamy National Cycling Centre, 2015 Pan Am Blvd, Milton

 

Celebrate Valentine’s Day with fun energy and competitive doubles play. This themed tournament is open to 18 plus and 55 plus divisions. A great option for active couples and friends who love a little friendly competition.


Registration Link


Valentine’s Day Dinner and Dance at Ned Devine’s

Valentine's Day menu with pink floral background, appetizers, entrees, and desserts, featuring live music by James Anthony.

Ned Devine’s Irish Pub

Date: February 14, 2026

Time: Live music at 7:30 PM

Location: 575 Ontario St S, Milton ON


Enjoy dinner and dancing with a live performance by the James Anthony Band. The three course Valentine’s menu creates a lively and welcoming night out in the heart of Milton.


Link to Event

Valentine’s Dinner and Dance

Valentine's Day dinner & dance flyer. Red and gold design with champagne, roses, hands holding, and event details.

Milton Conference & Convention Centre

Date: Saturday, February 14, 2026

Time: 6:30pm

Location: 3090 Steeles Ave W, Milton ON


An elegant Valentine’s celebration featuring dining and dancing. Couples planning something extra special can enhance their evening with a VIP romantic experience that includes premium seating, a champagne toast, and a picture perfect atmosphere.


Link to Event

Paint Night: Path of Petals

Paint Nite

Date: February 14th 2026

Time: 2:00 PM

Location: Boston Pizza Milton

 

A relaxed and creative way to celebrate Valentine’s season. Paint together, laugh together, and take home a piece of art you created side by side. Ideal for date night or a fun evening with friends.


Link to Event



Valentine’s Enchanted Evening at Winterlit

Conservation Halton

Date: Saturday, February 14, 2026

Time: 6:00 PM to 10:30 PM

Location: Winterlit, Halton Region

 

Stroll illuminated woodland trails surrounded by art installations. Relax by fireside lounges. Enjoy live music, sweet treats, and fire and light performances. Guests can add candle making and take home handmade souvenirs for a truly memorable Valentine’s experience.


Link to Event



Valentine’s Day at Champs with Otis Wonder

Champs Family Entertainment Centre

Date: February 14, 2026

Time: 9:00 PM to 11:30 PM

Location: 300 Bronte St S, Milton ON

 

A family friendly Valentine’s celebration with dinner and dancing, live music, bowling, arcade games, billiards, and more. Perfect for couples who want a high energy night out that still welcomes all ages.


Link to Event



Valentine’s Day Dinner and Dance Party at Eighth Note

Eighth Note

Date: February 14, 2026

Time: 5:00 PM to 12:30 AM

Location: 243 Main St E, Milton ON

 

Celebrate Valentine’s Day with dinner specials, themed drink features, and a DJ starting the dance party at 10 PM. Two seating options make this an easy choice for both early dinners and late night celebrations.


Link to Event



Live Music Valentine’s Evenings at Marquee Steak House

Marquee Steak House

Date: February 14, 2026

Time: 6:30 PM to 10:30 PM

Location: 204 Main Street East, Milton ON

 

Enjoy an intimate dinner paired with live piano and gypsy jazz performances in both the main and upstairs dining rooms. A great option for couples who enjoy music, atmosphere, and a refined dining experience.


Link to Event


Link to Event



Sushi Making Class at Third Moon Brewery

Third Moon Brewing

Date: February 12, 2026

Time: 7:00 PM to 8:00 PM

Location: 295 Alliance Rd, Unit 3, Milton

 

Learn how to make sushi from scratch in a relaxed brewery setting. This hands on class includes all ingredients and instructions. A fun and interactive idea for date night or a creative evening with friends.


Link to Event



Sam Roberts Band Live in Milton

Sam Roberts Band

Venue: FirstOntario Arts Centre

Date: February 14, 2026

Time: 8:00 PM

Location: 1010 Main St E, Milton

 

Celebrate Valentine’s Day with an unforgettable night of Canadian rock. A perfect choice for music lovers looking to turn the holiday into a full experience.


Link to Event



Looking for Even More Things to Do in Milton

 

If you are planning a full Valentine’s weekend or want ideas beyond February 14, there is always something happening locally.

 

For a complete and regularly updated list of local events, visit our Milton events page www.flowersteam.ca/milton-events

 

If you enjoy being outdoors in winter, you might also love our guide to seasonal experiences around town. It is perfect for couples, families, and anyone looking to make the most of winter in Milton www.flowersteam.ca/outdoor-winter-activities-in-milton

 

Check back often. New events are added throughout the season, and there is always something special happening close to home.


Overhead view of a dense forest canopy, varying shades of green, dappled sunlight.
By Flowers Team Real Estate December 19, 2025
Hidden nature gems in Milton include quiet trails, scenic parks, and local outdoor spots. Explore where locals hike, picnic, and unwind year-round.
Christmas tree shape formed by colorful, blurred lights against a dark blue sky.
By Flowers Team Real Estate December 5, 2025
The holiday season is here, and Milton truly lights up with festive cheer. This guide helps you find the best spots to enjoy the lights with your loved ones.
The Ultimate Guide to Splash Pads and Community Pools in Milton, Ontario
By Flowers Team Real Estate June 21, 2025
Discover the top splash pads and community pools in Milton, Ontario for summer fun. Find locations, amenities, and tips for the perfect family outing.
By Flowers Team Real Estate May 23, 2025
Craving a delicious burger in Milton? Discover the top 10 burger joints locals love—from gourmet creations to classic diner favourites. Find addresses, menus, and what makes each spot unique!
A man is riding a bike on a track in a velodrome.
By Flowers Team Real Estate May 21, 2025
Get ready to ride at Milton’s Mattamy National Cycling Centre velodrome. Learn booking steps, resident perks, gear rentals, and track etiquette.
A box of colorful donuts with sprinkles on them
By Flowers Team Real Estate May 15, 2025
Discover the best donut shops in Milton, Ontario! From gourmet treats at Maverick’s Donuts to Italian pastries at La Rose and Portuguese delights at WildFlour Bakery—explore where to find Milton’s most delicious donuts.
By Flowers Team Real Estate May 14, 2025
Discover the best ice cream and gelato spots in Milton, Ontario! From local favourites like Jay’s Ice Cream & Sunshine’s Gelato to artisanal gems like Nani’s Gelato, treat yourself to the sweetest frozen desserts the town has to offer.
An aerial view of a cliff covered in trees on a sunny day.
By Flowers Team Real Estate April 30, 2025
Bike scenic trails, enjoy Niagara Escarpment views, relax in family-friendly parks, and join community events in Harrison, Milton’s outdoor haven.
A woman is standing in the snow in a snowy forest.
By Flowers Team Real Estate January 23, 2025
Winter hiking in Milton, Ontario, is a magical experience. With snow-covered trails, crisp fresh air, and breathtaking landscapes, it's the perfect way to stay active and enjoy nature. Whether you're an experienced hiker or just looking for a scenic winter walk, Milton has several incredible trails to explore. Here’s a guide to the best winter hiking spots in Milton and tips to make the most of your adventure.
A little girl is sitting in a ball pit filled with colorful balls.
By Flowers Team Real Estate January 9, 2025
If you’ve been searching for a “children’s play centre near me,” you’re in luck! Milton boasts a variety of indoor playgrounds where kids can run, climb, and let their imaginations soar. From towering slides to creative workshops, these venues are perfect for keeping little ones entertained, no matter the weather.

Flowers Team News

By Flowers Team Real Estate January 21, 2026
A Year of Market Reset and Renewed Opportunity The Milton housing market in 2025 told a story of shifting tides, cautious optimism, and improving affordability. As interest rate pressures and economic uncertainty reshaped the real estate landscape across the GTA, Milton followed suit with a cooling in sales activity, a modest price correction, and signs of a more balanced market ahead. Here’s a full look back at how real estate in Milton unfolded through the year — and what it could mean for buyers and sellers as we move into 2026. Home Prices Ease But Remain Resilient Milton’s average home price across all property types in 2025 was $1,019,297, down 4.77% from the $1,070,342 recorded in 2024. This dip marks a reset from pandemic-era price surges, bringing more affordability back into the market — a trend echoed across the Greater Toronto Area. Detached homes saw the highest average of the year at $1,257,060, while semis averaged $970,490, and townhomes came in at $862,104. Condo apartments and condo townhouses remained the most accessible options, averaging $593,200 and $686,507, respectively. Sales Activity Slows in a High-Inventory Environment In total, 1,580 homes were sold in Milton in 2025, with activity peaking in July and tapering off significantly by December — which recorded just 55 sales. This marked a clear slowdown from 2024, when consumer confidence was still relatively strong in the earlier part of the year. By housing type: Detached sales totalled 718 Semi-detached sales: 168 Townhouses: 474 Condo apartments: 146 Condo townhouses: 61 The cooling in demand was not unexpected. As TRREB President Daniel Steinfeld put it: “The GTA housing market became more affordable in 2025... Once households are convinced that the economy and labour market are on a solid footing, sales will increase as pent-up demand is satisfied.” Inventory Rises, Shifting the Balance of Power Milton saw a significant boost in listing activity in 2025, with 6,246 new listings, up 45.8% from 4,285 in 2024. Detached homes led the surge, accounting for 2,141 new listings throughout the year. This influx gave buyers more selection and negotiating power. With the sales-to-new-listing ratio hovering near 0.5 , the market leaned toward balanced to buyer-friendly conditions , especially in the latter half of the year. TRREB’s Jason Mercer emphasized the broader implications: “GTA households must be confident in their employment situation before committing to long-term monthly mortgage payments, even in this more affordable market.”
By Flowers Team Real Estate January 8, 2026
Home Prices Hold Steady While Sales Cool to End the Year As 2025 wrapped up, Milton’s housing market mirrored broader trends across the Greater Toronto Area (GTA), where economic uncertainty and interest rate pressures continued to shape buyer and seller behaviour. However, improved affordability and stabilized pricing in Milton may be setting the stage for a more active market in 2026. Affordability Improves as Prices Dip Annually The average sale price in Milton for December 2025 settled at $973,454 , marking a modest 0.92% increase month-over-month from November’s $964,583. While prices held steady to close out the year, we saw an 8.93% decline compared to December 2024 , when the average price stood at $1,068,920. This softening in prices aligns with what Toronto Regional Real Estate Board (TRREB) President Daniel Steinfeld observed across the GTA: “The GTA housing market became more affordable in 2025 as selling prices and mortgage rates trended lower... Once households are convinced that the economy and labour market are on a solid footing, sales will increase as pent-up demand is satisfied.”
Shadows of sunlight on a white wall and carpet, creating shapes.
By Flowers Team Real Estate December 19, 2025
Milton housing styles range from century homes to modern suburbs and condos. Learn how each neighbourhood’s architecture reflects its era.
Overhead view of a dense forest canopy, varying shades of green, dappled sunlight.
By Flowers Team Real Estate December 19, 2025
Hidden nature gems in Milton include quiet trails, scenic parks, and local outdoor spots. Explore where locals hike, picnic, and unwind year-round.
By Flowers Team Real Estate December 16, 2025
Learn how divorcing homeowners in Ontario can manage mortgages, equity, refinancing, and future housing decisions. Get clear financial strategies and expert guidance for a stable future.
By Flowers Team Real Estate December 15, 2025
Selling a home during a divorce is one of the most emotional and complex experiences a family can face. Your home carries history, memories, and meaning. At the same time, the financial stakes are high, and decisions need to be made with care. For couples in Milton, finding the right real estate agent brings clarity, fairness, and support when life feels unsettled. The agent you choose plays a major role in the experience you have during this transition. The right professional helps protect your equity, keeps communication steady, and guides both parties with empathy and neutrality.
By Flowers Team Real Estate December 5, 2025
Understand the difference between legal separation and divorce in Ontario. Learn how each affects your property rights, matrimonial home, and financial future. Includes guidance and resources for families navigating this transition.
Christmas tree shape formed by colorful, blurred lights against a dark blue sky.
By Flowers Team Real Estate December 5, 2025
The holiday season is here, and Milton truly lights up with festive cheer. This guide helps you find the best spots to enjoy the lights with your loved ones.
Real Estate Market Statistics, November 2025. Text over a staircase photo.
By Flowers Team Real Estate December 4, 2025
Milton home prices fell 13.87% in November 2025. See market trends, inventory stats & expert insights from the Flowers Team. Learn what it means for you.
Aerial view of a suburban neighborhood with houses, roads, and some green spaces.
By Flowers Team Real Estate November 28, 2025
Explore Milton’s projected growth from 2026–2031, including infrastructure, housing, and development trends. Learn what buyers and investors should watch for.