First Date Ideas in the Hammer

First Date Ideas in the Hammer

Ladies and gents, here’s your guide to Hamilton dating. You’re welcome.

Meeting people can be tough in general, never mind when you’re seeking that special someone. Whether you found a match on Tinder or serendipity brought you into the same elevator (does this happen in real life?), there will be a point where you’ll have to actually go on a date IRL, unlike this couple who chatted for years and never met.

There are some great places in Hamilton to take out that girl or guy you’ve been dreaming of spending time with, so find something that suits the two of you and ask them out already! Here are some of our first date ideas, but feel free to add your own in the comments below.

Art Crawl

Art Crawl is the perfect atmosphere for a first date (it takes place the second Friday of every month on James Street North) and people are more friendly and likely to want to chat. Artists are not only notoriously more stimulating than average non-artsy people, but they usually keep good (or at least interesting) company. A couple of hours on James Street North can lead to something fun and the ever-evolving studios and random after parties are usually worth the wait. Art crawls are always free and great for discussions that can lead to a post crawl beer. Even if your date isn’t an artsy type, art should start a conversation and provides ample opportunity to figure out if you are into someone or not. Any thoughts are better than no thoughts. Your first date may have you working on a cool art project together or falling in love with the same piece.

Supercrawl is another option (coming up in September), although there are way more crowds. Too much to do can make it harder to have a conversation and takes the attention off getting to know each other (maybe that’s a good thing?).

Pier 8

Most activities here are low cost or free, and the city hosts plenty of events in the park during the summer (like Because Beer) as well as Winterfest by the ice rink in the winter — and there’s nothing more romantic than skating while holding hands. The summer is perfect for a casual picnic and watching the sunset. Own a boat? This is where you are going to be taking your date. Don’t own a boat? This is where you can talk about the type of boat you two will own together when you travel the world. You can walk along the pier for a unique view of the waterfront or rent roller skates at William’s Pub (which alternate for ice skate rentals in the colder seasons). If fitness is your preference, this can be a great meeting spot to build a relationship and get in shape together while running the track. If you’re a dancer, or want to get close real quick, try Salsa on the Waterfront and enjoy a lesson, laughs, and some moves together. (Read what was supposed to be a salsa date here.)

Eat, Drink and Be Merry 

The good part about a dinner date is if the date doesn’t go well, at least you’ll have a meal in your belly, so pick somewhere you’ll enjoy. For something elegant and trendy, fit for a professional or mature couple, we like The French. For something more laid back, The Mule has a cool vibe and good drinks. It’s always fun to try new food together, so try somewhere you haven’t been! HAMBRGR is also fun to see your S.O. dig into a massive burger or share a milkshake. Best of luck with the bill awkwardness – we’ve all been there and that’s a whole other blog post.

For drinks:

  • Uno Mas/Mezcal: Who doesn’t love tacos and tequila? Have a bite to eat at Mezcal or sharing plates at Uno Mas. Enjoy great food, cocktails and loud hip hop on James Street South. If it’s going well, have just one more…The good thing is you can switch up the scenery without going far.
  • Augusta Street: Perpendicular to James Street is Augusta Street, lined with casual bars for beer and cocktails. There are also some good patios for summer drinks and people watching. Bar hop and drink as much beer as you can.
  • Two Black Sheep: For something more upscale, this small place serves up a good cocktail and wine menu, plus oysters and charcuterie boards.
  • Bar Sazerac: This place is very small, but has inventive and fun cocktails. It’s good for an in-between drink.
  • The Brain: This place is a hidden gem with comfy couches, dim lighting, and board games in the back.
  • Brux House: This Locke Street restaurant is upscale-casual with a trendy interior and patio. Visit for cocktails and craft beer.

For ice cream, head to Hutches on the Beach and take a romantic stroll or visit AMO Gelato Caffe and people-watch on Locke Street. For coffee shops, Mulberry Coffeehouse and Brown Dog Coffee Shoppe are big enough that not everyone has to hear your convo, plus they are comfortable, trendy, and have good offerings (especially sweets).


Trivia nights bring strangers and friends together to face off against other patrons. You’ll get to see how smart your date really is, how they fare under pressure, and how you work as a team! There is a great trivia night at Lou Dawgs (if your date is vegetarian, maybe rethink this option) and the BBQ is great.

Hamilton Farmers’ Market

Visit the market to browse and talk to the vendors. See how they interact with others, grab a snack, and hope they have an appreciation for local businesses and local food. Better yet, pick out ingredients to make dinner together or have a picnic.

Warplane Heritage Museum

This is a good first date but it needs a coffee or lunch/dinner follow up. If you drive together, you’ll have some car time to chat. While you’re there, you can learn a thing to two during your visit, even if you’re not interested in the company. If all goes well, from there you can hop on over to Upper James for a pizza at Sasso or a more casual, lively atmosphere at State & Main.

Similarly, visiting the Art Gallery of Hamilton is a good date activity assuming you’re into art.


I am so NOT a bowling person but lots of people love it. I don’t see how much conversation you can have between taking turns plus I feel like I’m 10. BUT some people enjoy Splitsville and there’s an arcade too.


Did you know Hamilton has 153 km of on-street cycling lanes and 49 km of city-owned trails? Obviously we have a ton of waterfalls. Put on your running shoes and get in touch with nature. The best dates are the ones where you don’t have to look pretty. You + them + the trees = <3


Pick up a Timmys and head to the Ti-Cats game…you can’t get more Hamilton than that.

Where are your favourite date spots?

How did you first date end up? Good, bad, or ugly, check out our DATING DIARIES & submit your own!

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3 thoughts on “First Date Ideas in the Hammer”

  • Well, we’re well past our first date. But we love Sam Lawrence Park, the Locke Street Boutique shops, ice skating at the Habour-front, sampling all the ethnic restaurants in and around James Street, cycling down to Sulphur Springs Rd towards the Hermitage, hiking the Spencer Gorge to Dundas Peak. There’s lots of things to do. We love finding the hidden jems in nooks and cranny of Hamilton. Hopefully your date is into that kind of thing. I find the best dates are when you don’t have a schedule and you go where ever the wind takes you.

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