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13 Romantic Things To Do This Winter In Hamilton

13 Romantic Things To Do This Winter In Hamilton

Hamilton is overflowing with cosy and entertaining romantic activities that’ll keep the love burning bright all season long, even when the temperature drops like nobody’s business. (We’re looking at you, frosty winter days!)

So keep on reading, ’cause we’ve got a special list of romantic things to do in Hamilton this winter that’ll have you both head over heels in no time. It’s time for some lovely, unforgettable memories, don’t you think?

Go ice skating at Pier 8


Address: 47 Discovery Dr, Hamilton, ON 

Contact details: +1 905-523-4498

Operating hours:

  • Monday to Sunday – 10 AM to 9:45 PM

Pier 8 isn’t just your regular ice rink. It’s right on the waterfront, offering you the kind of views that’ll make you say, “This city is awesome!” So, while you’re out there on the ice, you get to enjoy these breathtaking winter scenes around you.

Plus, there’s something pretty endearing about watching your date attempt not to fall down, eh? And when you’re done skating, or, when your legs are screaming for mercy, you’ll find plenty of cosy spots close by to warm up and grab a bite.

Imagine ending your date cuddled up together, sipping hot chocolate, and laughing about the day’s antics. That’s a winter date worth bragging about!

Local tip: The ice conditions at Pier 8 can be fickle, thanks to our crazy Ontario winters. Make sure you check the city’s website or give them a call before planning your skating date!

Explore Dundas Valley Conservation Area 


Address: 650 Governors Rd, Dundas, ON

Contact details: +1 905-627-1233

Operating hours:

  • Monday to Sunday – 8 AM to 7 PM

In Dundas Valley, you can explore over 40 kilometres of nature trails that are simply, well, magical in the winter. Imagine crunching through the snow with a warm gloved hand in your date’s hand—yeah, it’s as romantic as it sounds.

Plus, there are charming waterfalls to discover; nothing says romance like a frozen waterfall, eh? Around every trail bend, you’ll find something new to explore.

We’re talking about heritage sites, gorgeous Carolinian forests, and wildlife (if you’re into that). It’s an outdoor date that’s sure to get your hearts pumping.

Local tip: Always check the weather conditions before heading out on a winter hike, and remember that the trails at Dundas Valley aren’t cleared of snow regularly. So, come prepared with good winter footwear!

Visit the Hamilton Farmers’ Market


Address: 35 York Blvd, Hamilton, ON

Contact details: +1 905-546-2096

Operating hours:

  • Tuesday, Thursday and Friday – 9 AM to 4 PM

Situated smack dab in the heart of Hamilton, Ontario, the Hamilton Farmers’ Market is a warm and bustling hub. It is always buzzing with shoppers from all walks of life.

Hipsters buying vintage records, families picking out colourful produce, fitness buffs shopping for the perfect protein. Oh and the food court! 

Do try the food court with multi-ethnic dishes that hit every spot. You’ll also find the Market’s friendly vendors who’re always up for a chat.

And hey, don’t just wrap your date up after shopping. Stick around for the cooking demos or unwind with a cup of joe at one of the charming little cafes. 

Local tip: For first-timers, don’t forget to check out the famous “Sam’s Cheese and Meats”; their selection is unrivalled and a real treat for foodies!

Catch a performance at the FirstOntario Concert Hall


Address: 1 Summers Ln, Hamilton, ON

Contact details: +1 905-546-4040

Operating hours:

  • Monday to Friday – 10 AM to 2 PM

FirstOntario Concert Hall is a place with pure class and the venue is poppin’ with a massive stage, and a vibe that screams ‘good times’. We’re not messing around here; it’s a stunning spot where you can score major points on a date in the winter. 

This place houses some seriously killer acts—from rock concerts and classical music to stand-up comics and dance performances.

Why not even make an evening out of it? There are plenty of cool places around to get your grub on before the show or for that post-performance debrief.

Basically, you’re in prime location for an unforgettable experience, and watching your date’s face light up with the magic of live entertainment is going to be so worth it!

Local tip: Check out Anchor Bar, a local dive bar just around the corner from the Concert Hall, for some cheap beers and pool after the show. You’ll thank me later.

Go on a coffee date at The Cannon


Address: 180 Ottawa St N, Hamilton, ON 

Contact details: +1 905-545-5565

Operating hours:

  • Monday to Friday – 7 AM to 9 PM

The Cannon is cosy, no doubt about it, decked out in rustic decor with a real down-to-earth vibe perfect for winter relief. It’s the kind of place where you can chat about anything while sipping on some seriously delicious coffee.

Speaking of coffee, let’s talk about the drinks. They serve up the most scrumptious espresso-based drinks along with delightful tea and hot chocolate selections.

And, we all know food can totally make or break a date, eh? The Cannon is filled with delicious treats ranging from hearty breakfast sandwiches to yummy vegan and gluten-free options. 

Plus, they make some of the best waffles in town, which is, like, a total bonus.

Local tip: Wanna make your coffee date even more special? Hit up the amazing Gage Park just a short distance away from The Cannon to explore their winter wonderland of twinkling lights and skating hand-in-hand with your date.

Check out Levity Comedy Club & Lounge


Address: 120 King St W, Hamilton, ON

Contact details: +1 905-308-7888 

Operating hours:

  • Wednesday, Friday and Saturday – 7 PM to 2 AM

Levity Comedy Club & Lounge is the perfect place to forget about the cold weather outside and just enjoy each other’s company. The lineup of comedians here is on fire!

They’ve got local talents and big names too, so you’re in for a treat no matter who hits the stage. Few things bring people together like sharing some genuine, side-splitting laughs.

Before you leave, make sure to explore their drool-worthy food menu. I mean, come on, who doesn’t enjoy munching on some tasty bites while enjoying a comedy show?

Levity has got your cravings covered with their delish selection of eats, so you won’t be leaving with an empty stomach—just a big grin on your face.

Local tip: In the winter months, keep an eye out for holiday-themed comedy shows and events at Levity—they’re always a hit!

Visit Dundurn Castle 


Address: 610 York Blvd, Hamilton, ON

Contact details: +1 905-521-3168

Operating hours:

  • Tuesday to Sunday – 12 PM to 4 PM

Dundurn Castle is an 18th-century mansion that has over 40 rooms—talk about spacious! It also has an awesome tour that’ll take you and your date through its fascinating history.

Aside from the sheer beauty and history of the castle, the surrounding grounds are honestly breathtaking too. 

Don’t miss out on a serene winter stroll through the picturesque garden, admiring the snow-covered flora, and feeling all warm and fuzzy inside.

Oh, and let’s not forget about their delightful seasonal events! From Victorian Christmas-themed tours to candlelit evenings, Dundurn Castle knows how to make a winter date truly magical. 

Trust me, both you and your date will leave with hearts full of warmth, despite the frosty weather outside.

Local tip: Snag some tickets to Dundurn Castle’s Victorian Christmas event; it’s the perfect way to spark that lovely holiday spirit.

Have a pizza date at Shorty’s Pizza


Address: 1099 Cannon St E, Hamilton, ON

Contact details: +1 905-312-9293

Operating hours:

  • Monday to Sunday – 11:30 AM to 10 PM

Let me tell you what makes Shorty’s Pizza such a great pizza joint for your date. First of all, their pizza game is on point, and their crust is the stuff of dreams.

They use quality ingredients that’ll make your taste buds dance with joy, and there’s a pizza flavour to satisfy everyone’s cravings. Sharing a pie with your date will no doubt be the highlight of your day.

And hey, if the date is going particularly well, why not level up by sharing a killer dessert? Go on, treat yourselves.

Oh, and don’t just stop at pizza; their appetisers and salad selections are mind-blowing too. It’s a great opportunity to share a couple of dishes and really have a feast for two because, after all, variety is the spice of life, especially on a winter date night.

Local tip: Swing by on a weekday evening; it’s less crowded, making it the perfect time for a cosy, romantic pizza date.

See the Whitehern Historic House & Garden


Address: 41 Jackson St W, Hamilton, ON

Contact details: +1 905-521-3168

Operating hours:

  • Tuesday to Sunday – 12 PM to 4 PM

Winter is never a drag at Whitehern. During this time, this vibrant garden is neatly blanketed with white snow, creating this romantic, pristine setting. 

Inside the house, you’ll find an exquisite collection of antique furnishings, wallpaper and toys, showcasing the lifestyle of the privileged McQuesten family.

It’s like stepping into a time machine, going waaay back and stepping into a homely yet opulent household. Definitely gonna make your normal, everyday life seem like a snoozer.

Remember the good old days when fun kinda meant something more than just endless scrolls on your screens? Bring those back by getting into some uncanny conversations around history, art and culture. 

Local tip: Don’t forget to grab a hot cup of Joe to go from the nearby cafe, Cherry Birch General. This will surely keep you cosy while exploring the snowy garden.

Visit the Royal Botanical Garden


Address: 680 Plains Road West, Burlington, ON

Contact details: +1 905-527-1158

Operating Hours:

  • Monday to Sunday – 10 AM to 8 PM

The Royal Botanical Gardens in Hamilton aren’t your typical greenhouses filled with common plants and ferns; they’ve got one of the largest botanical collections in the whole of Canada. 

So, it’s kind of like taking your date on a mini-globe trotting trip, but only you’re just strolling around lush gardens.

This place transforms into a magical, ice-covered kingdom that would put even Elsa’s castle to shame (kidding aside). Ice sculptures form naturally on the plant life, creating a spectacle that’s totally worth seeing.

Inside, it’s a warm, tropical paradise filled with the most exotic plants you’ve ever seen. Plus, there’s loads to learn about these plant species from all over the world.

Local tip: The festively lit pathways of the garden are a must-see during the winter months.

Swing by at Ice Flame


Address: 620 Upper James St, Hamilton, ON 

Contact details: +1 289-674-4200

Operating hours:

  • Sunday to Tuesday – 3 PM to 1 AM
  • Wednesday – 4:30 PM to 1 AM
  • Thursday – 4 PM to 1 AM
  • Friday and Saturday – 3 PM to 2 AM

Ice cream is always a good idea, and the perfect spot for that is the Ice Flame. I know it sounds like a contradiction that they’re serving the coldest dessert in the chilliest season, but hey, who can resist the creamy goodness of ice cream?

With so many choices, you’d think it’d be hard to choose, but no! The eclectic mix of flavours is off-the-charts unbelievable, and they serve up everything from classics like vanilla and chocolate to exotic ones like durian!

Plus, you get to watch your ice cream get made from scratch—how cool is that? Putting it simply, an ice cream date at Ice Flame is the kind of sweet, and absolutely fun date.

This will have you both sharing, and maybe even engaging in a playful ice cream feeding challenge. 

Local tip: You’ve gotta try the signature matcha flavour! It’s quite the hit among the locals.

Hike at the Escarpment Rail Trail Lookout


Address: Escarpment Rail Trail, Hamilton, ON

Contact details: +1 289-769-5155

Operating hours:

  • Monday to Sunday – Open 25 hours

Well, let’s talk about taking a hike at the Escarpment Rail Trail Lookout in Hamilton, Ontario. The hike isn’t too strenuous and the trail is pretty well maintained even during winter. 

You’ll meander through beautiful wooded areas and you better believe the views are absolutely stunning! Occasionally there are informational plaques along the way too, so you can learn a bit about the nature and history of the area.

And now, the highlight of the hike, reaching the Lookout. You’d think the Lookout would be pretty amazing considering they named the whole trail after it, eh?

Well, it totally lives up to the hype as standing there, you’ll get panoramic views of the city and the winter wonderland. It’s the perfect spot for a romantic selfie, just in case you need to update your profile pic!

Local tip: After sunset, the Lookout provides a brilliant view of the city lights, so if you are a night owl, this could be a charming winter night experience for you.

Check out Chocolat on James


Address: 123 James St N, Hamilton, ON

Contact details: +1 289-396-5097

Operating hours:

  • Monday to Wednesday – 9 AM to 8 PM
  • Thursday – 9 AM to 9 PM
  • Friday – 9 AM to 10 PM
  • Saturday – 11 AM to 10 PM
  • Sunday – 11 AM to 8 PM

You wouldn’t believe the selection of goodies they got here—everything from hand-painted chocolates, to creamy truffles, to decadent hot chocolate. It’s like being a kid in a candy store, but way more sophisticated.

The shop itself has a very charming and romantic atmosphere with its rustic decor and charming ambience. And after you’ve had your fill of chocolate (if that’s even possible), why not take a stroll in the nearby neighbourhood?

There are plenty of interesting shops and sights, offering more opportunities for quality time and conversation.

Local tip: Want to impress your date? Ask the staff about their chocolate-making process or about the unique flavours they offer; it’ll make you look like the ultimate chocolate connoisseur!

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