As the holiday lights begin to twinkle and the fires of the season are crackling, is it just us or does Ontario get a little romantic? All those made-for-TV holiday movies have to be for a reason right?
If you’re looking to tap into the charm of the holiday season and plan the perfect “holidate” (that’s holiday date), look no further than York-Durham-Headwaters and Burlington to do just that! We’ve crafted three perfectly delicious date ideas in each destination to help you make this season an extra magical one.
Don’t feel like reading the whole thing right now? No worries! Skip ahead by section.
- Winter Adventure with Great Eats near Port Perry + Uxbridge
- Winter Dome Dining + Craft Spirits in Caledon
- Culture, Fun + Great Eats in Vaughan
- Festival of Lights + Spencer’s on the Waterfront
- DiMario’s Chef’s Round Table + Joseph Brant Museum
- Visit + Eat at the Botanical Gardens
Romantic Holidates in York Durham Headwaters
Grab your skates, your snow shoes and your hearty appetite for these three date ideas in York-Durham-Headwaters!
Date 1: Winter Adventure with Great Eats near Port Perry + Uxbridge
Let’s dive into a cozy holidate in the charming towns of Port Perry and Uxbridge in Durham Region. From baked goods and holiday shopping to a great lunch and even outdoor adventure, this is the date that has it all.
A Morning Well Spent
Start your date with a kick off at Annina’s Bakeshop where coziness and flavour are king. Depending on timing, grab a few baked goods like their classic cinnamon buns, cheese croissants or peach-ginger-rhubarb streudels and split them so you can try a bit of everything. Of course, during the holiday season, this spot rolls out the red carpet on festive treats to boot!
Once you’re finished up, head down the road to Port Perry for a delightful date at the Port Perry Lakefront Skate and Vendor Village. Strap on those skates and hit the rink. Open daily and absolutely free, this rink is open all the way until mid-March but of course, is extra special during the holiday season.
Once you’re finished, up, it’s time to explore Port Perry’s historic downtown filled with some great date options like grabbing a beer at Old Flame Brewing Company, a sweet treat from Hank’s Pastries or do a wee bit of shopping at That Place On Queen.
Not big on skating? No worries! If you’re a foodie or love a unique field trip of sorts, check out the farm store at Thunder Ridge Bison together. Open Saturdays, you can shop a range of the farm’s high quality, sustainably-minded bison cuts. Chat with the team about the herd as you peruse the products.
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When lunch rolls around, Slabtown Cider makes for the perfect holidate addition. Hit the on-site restaurant for a great menu of locally-inspired items like warm brie topped with local honey from 3 Boyz, crispy brussel sprouts with prosciutto and hearty bison meatballs. Top it all off with one of their Feast On® ciders for the perfect pairing. During the colder months, we recommend trying their Cider House Rules cider served warm with notes of cinnamon and clove.
An Adventure-Packed, Delicious Afternoon
Want to keep this date rolling? Must be going well! Good for you.
If you’re not ready to stop the fun quite yet, we recommend heading over to Trail Hub, just ten minutes away. If the snow has flown, grab your cross country skiis or snowshoes and hit the exttensive trail network. You can check conditions on their website and grab your pass there too. There’s nothing quite like winter in Ontario and Trail Hub offers the best of it.
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Once you’re finished working up an appetite, head to Trail Hub’s on-site Feast On® certified restaurant, Nest. With a full menu of locally-sourced eats, we recommend ordering a bunch to share (how romantic)! Sumac roasted carrots, Morrocan chickpea smash and seared lamb sirloin are just a few of the bites to savour! Once you’re finished, why not split a chocolate molten lava cake or raspberry almond tart for good measure?
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Date 2: Winter Dome Dining + Craft Beverages in Caledon
The wide open spaces and craft beverage scene in Caledon leave very little to be desired. Whether you’re looking for beer or cider, there’s something for everyone and when paired up with some fresh air we can’t think of a better way to spend a fun day together. So, grab your sweetheart and let’s roll.
Feast On®: Lunch at GoodLot’s Oast Barn or Spirit Tree Estate Cidery
There are so many reasons to love our Feast On® friends at GoodLot Farm & Farmstead Brewing Co. and when winter hits, we feel that all the more. This winter, curl up with your partner in GoodLot’s Oast Barn (that’s a barn made for drying hops) where the taps are overflowing with high-quality, sustainably-minded beers and the vibes are warm n’ cozy.
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If the weather is a bit chilly, we recommend grabbing the farmstead ale, touted by the GoodLot team as “sunshine in a can” for its delicate tropical fruit notes given off by Ontario-grown hops. In fact, 100% of the hops that go into GoodLot’s beer are from Ontario. How cool is that?!
Alternatively, sip on their Highfalutin English Style Pale Ale. With notes of raisin and toffee, it’s sort of begging to be paired up with some holiday fruit cake, no? We definitely think you should take a few home with you. Finally, pair your brew up with a sharable charcuterie board and enjoy.
That’s not all though, GoodLot will be hosting weekly Wednesday events, food pop ups, and live music Fridays and Sundays through out the holiday season so be sure to stay tuned on their socials for all the festivities.
Hot Tip:Need a little extra exercise? Check out GoodLot’s on-site disc golf course for a little friendly competition.
If cider is more your thing, you’re in luck. Run by the Wilsons, a fourth-generation farming family in Caledon, Feast On® certified Spirit Tree Estate Cidery offers up a beautiful collection of noteworthy ciders including dry hopped and pear varieties alongside flagships like their draught cider made from 100% freshly pressed apple juice aged on site.
We recommend enjoying it at the on-site bistro full of delicious menu options like their wood oven pizzas, grilled sausage with apple chutney and their mussels steamed in cider. Ask your server for a great beverage pairing and this spot is sure to be a hit.
Looking for even more reasons to visit? On November 16th, Spirt Tree will be hosting their Holiday Artisans Market so you can wander a great selection of vendors to do a little holiday shopping and pretend you’re in a Hallmark movie (if that’s your thing, no judgement)!
Nature Hike + Farm to Table Dining
If you’re ready to get off your tush and out into nature, head to Hockley Valley Resort for a unique experience. First, take advantage of their trails as you set out on their extensive network. If the conditions are right, you can swap those sneakers for snow shoes and take in the breathtaking vastness of Hockley Valley in style.
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Once you’re done, we recommend booking into a snow globe at Cabin (the on-site restaurant) for a stunning farm to table experience that really dials up the romance. The ambience in these geodesic domes are right on point with twinkle lights and fake fur throws to keep it cozy. You’ll enjoy a chef-curated 5-course dinner complete with wine pairings in an extra-intimate setting (or invite two other couples to make it a group hang) for the ultimate holidate.
Finally, no need to go far. Book yourself for a stay in one of the suites onsite to keep the adventure going!
Date 3: Culture, Fun + Great Eats in Vaughan
Vaughan is home to some world-class attractions: think everything from the McMichael Art Gallery to Canada’s Wonderland but did you know that they’re also home to some pretty epic eats? For a date that packs the culture and the crunch, the fun and the flavour, the daring and the drooling (okay, okay you get it), look no further than Vaughan.
Culture and Crunch: The McMichael Art Gallery
Just minutes from Canada’s Wonderland, The McMichael Art Gallery boasts 6500 works by First Nations, Métis and Inuit artists alongside a massive collection of works by Tom Thomson and the Group of Seven. As Canada’s largest publicly funded art gallery, this spot should be a can’t-miss for any Canadian and it makes for a great holidate.
This season, look forward to a new exhibit of miniatures by the talented artist Clarence Gagnon. Because of the fragility of these pieces, they can only be shown every three years or so, so we highly recommend you don’t miss out!
Once you’re finished, head to the on-site CABIN restaurant (yes, another cabin!). Designed with the inspiration of the art the gallery showcases, you’ll find a rustic setting bursting with natural light and cozy touches. Ready for the best part? We fell head over heels for the truffle grilled cheese- a grownup twist on a childhood classic with cheddar, brie, provolone and sunflower seed pesto served with kettle chips and a salad.
Alternatively, dive into local bites like Georgian Bay trout with spicy remoulade or a prime beef burger. Topped all off with a classic Canadian butter tart, what could be better? The answer of course, is two butter tarts.
Winterfest: Canada’s Wonderland
Once you’re finished skating, enjoying the holiday rides and taking in the extensive light displays, it’s time to warm up with a treat or two. Indulge in creamy hot chocolates, egg nogs topped with gingerbread friends and a slew of other over-the-top beverages.
To pair up, we suggest the ultimate Canada’s Wonderland treat— a funnel cake. With takes across the park like Rudolph’s version with soft serve and strawberry sauce or the Snowflake Funnel Cake with vanilla icing and a cookies n’ cream shell, it’s pretty darn hard to resist.
Looking for something on the savoury side? No worries! Fully loaded baked potatoes are calling your name topped with a lineup of ways to customize. Don’t forge to check out CW’s drink and dining deals to make the most of your time.
Feast On® Fare at Ay Carambah, Eh!
We’d be remiss if we didn’t point you in the direction of Ay Carambah, Eh!, Vaughan’s first Feast On® certified restaurant. This taqueria is all about celebrating the bright flavours of Mexico with a wee Canadian touch. Their menu leaves little to desire with favs like carnitas and quesabirria alongside inventive new dishes like chilaquinachos, chori-taquitos (that’s taquitos with chroizo) and more.
Finish off the meal by splitting an order of warm, cinnamon-sugar-coated churros together and chatting about your day. It’s sure to be the best way to wind down with full bellies and hearts too!
Festive Holidates in Burlington
Perched along the shores of Lake Ontario, Burlington’s beautiful waterfront, intimate restaurants and great events make for a fun day or evening date just an hour from Toronto.
Date 1: Festival of Lights + Spencer’s at the Waterfront
Where: Spencer Smith Park, 1400 Lakeshore Rd., Burlington, ON (View Map); Spencer’s at the Waterfront, 1400 Lakeshore Rd., Burlington, ON (View Map)
Starting November 29th, 2024 and running all the way until January 8th, 2025, Burlington’s Festival of Lights is the kick off to the holiday season in Burlington. Open from 4pm until midnight daily, we recommend starting your adventure around 4:30 and grabbing a coffee or hot chocolate from nearby Tamp Coffee before walking or driving down to Spencer Smith Park.
As darkness begins to descend, stroll along the beautiful waterfront trail as you take in a beautiful and fun selection of light displays to put a little pep in your step. The festive cheer in the air is palpable and we can’t think of anything more romantic than a walk along the water, mitten in mitten with your sweetie. Take your time as you stop for photos, catch snowflakes on your tongue (weather pending, of course) and get into the spirit.
Afterwards, grab your table (don’t forget to make a reservation) at Spencer’s at the Waterfront. This Feast On® certified restaurant is home to a stunning glass-walled dining room with jaw-dropping views of Lake Ontario to enjoy as you sip and savour. Take in the moon over the lake and dive into a menu that places craftsmanship at the forefront with confit mushroom flatbread, ricotta gnocchi Bolognese and one bone lamb with butternut squash.
Date 2: DiMario’s Chef’s Round Table + Joseph Brant Museum
Start your day with a visit to the Joseph Brant Museum which celebrates the life and achievement of Mohawk and British Army Captain, Joseph Brant. Wander through exhibits all about him as well as travelling exhibits that call the museum home for just a little while. Starting on November 2nd, the museum will host an exhibition called Refuge Canada from The Canadian Museum of Immigration at Pier 21. This fascinating exhibit traces the lives and stories of refugees who have come to Canada over many, many years.
Starting on November 29th, the museum will also be offering an event called Lights from the Rooftop where visitors are invited to check out the lights in Spencer Park (Burlington Festival of Lights) from a different perspective— the rooftop terrace at the museum. Check here for the schedule.
Also on during the holidays, check out a number of festive workshops and events together like visits with Santa and family drop in activities.
Want to dial up for a special date night? For an intimate dining experience, book the Chef’s Round Table at DiMario’s. Known for their elevated, Italian fare crafted right in the heart of downtown, the menu changes regularly with inventive new takes on Italian classics. Recently ranked one of Canada’s Top 100 Most Romantic Restaurants on OpenTable, we can’t think of a better spot for a holidate.
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If you’re looking to make dinner into a special occasion, we recommend booking the Chef’s Round Table. Up to six guests are welcomed at the intimate, round corner table to savour a chef-curated menu crafted by culinary mastermind and Celebrity Chef Claudio Aprile (yes, the very same from all seven seasons of MasterChef Canada). Each visit offers a unique tasting journey, as the freshest seasonal ingredients unfold in an unforgettable celebration of Italian flavors that will leave taste buds buzzing.
Date 3: Visit + Eat at the Royal Botanical Gardens
Want to keep the date simple and all in one spot? You’ll still dazzle your sweetheart with a visit to and meal at the Royal Botanical Gardens! This spot is part of the Niagara Escarpment UNESCO World Biosphere and its there goal to protect plant life and the environment. Home to 400 acres of nature sanctuaries, 300 acres cultivated gardens and an arboretum, you’ll be dazzled by the many unique plants and natural settings here.
During the holiday season, two events at RBG really stand out as the perfect fit for a date night. Winter Tide is a 19+ event that invites visitors into the rock garden for an indoor-outdoor live jazz lounge experience. Paired up with T.U. Jazz Fest, RBG brings in live performances from award winning and emerging artists alike.
Decked out in twinkling lights and roaring firepits, the Rock Garden provides a stunning backdrop for a fun night out. You can wander through the garden pathways, take in the view from the Rock Garden Greatroom while enjoying the jazz and classic cocktails and grab a delicious meal at the on-site Rock Garden Bistro. This spot is extra special as many of the ingredients found on the menu are sourced straight from the on-site gardens!
Have the kids in toe? No worries! Make it a family date by checking out the fun and festive train display (dates to be announced) in the Mediterranean Gardens on site. Kids and kids at heart will love watching the elaborate displays weave in and out of the flora as you enjoy time together as a family.
Looking for more delightful holidate ideas and inspiration? Be sure to check out Tourism Burlington’s website for more.
Enjoy Your Holidate
Ready to start exploring? Love that for you! We hope you have a romantic and festive holiday season with those you love the most.
Keep exploring more delicious festive trip ideas across Ontario.
