Holding Hands in Winter

The Sweetest Guide to Best Treats & Unique Date Ideas for Valentine’s Day in YDH

Love is in the air, and Valentine’s Day is just around the corner! While classic gestures like chocolates and flowers never go out of style, this year, we’re sharing a few new ideas to elevate your celebration. In this guide you’ll find the best places to find traditional favourites like chocolates and flowers from businesses across York, Durham, and Headwaters. Or are you keen to win their heart with something different? Discover the sweet joy of giving homemade baked goods that add a personal touch to your celebration. Plus, if you’re looking for date night ideas that offer unique memorable experiences, we’ve got those too!

Get ready to infuse your Valentine’s Day with a perfect blend of tradition and creativity, ensuring a celebration as unique as your love story!

Where to Find the Best Chocolates & Flowers

Thornhill Market Florist

In the heart of Thornhill is one of York Region’s best flower shops, Thornhill Market Florist! Stop in to pick up a few fresh flowers for your love this Valentine’s Day. They’ll craft a beautiful bouquet of the best quality flowers, and at a reasonable price.

Old Firehall Confectionery


A classic chocolate shop in York Region is Old Firehall Confectionery. With two locations, in Unionville and Kleinberg, you’ll find an irresistible selection of premium Belgian chocolates. Handcrafted with love, they use locally sourced ingredients. Plus, they offer chocolates that are vegan, sugar-free, kosher, dairy-free, and gluten-free, so there’s something for everyone! For Valentine’s Day you’ll find a variety of collections for the special day. There are gift baskets, heart-shaped truffles, chocolate bombs and so much more!

Branching Out Floral Designs

For those in the Port Perry area looking for fragrant flowers to woo your love, visit Branching Out Floral Designs. This lovely florist masterfully creates everything from iconic bouquets of roses to modern pieces. Choose from one of their many designs that feature romantic names like Cupids Arrow, Loves Journey and Endless Love. Or order a custom design to suit your partner’s style.

The Nutty Chocolatier

Nutty Chocolatier

An institution in downtown Port Perry for over 30 years is the Nutty Chocolatier. With an assortment of handmade truffles, crafted from the finest Belgian chocolate, they cater to everyone’s taste. In addition to their traditional boxes of chocolates, for the special day they have fun chocolate designs in the shape of a heart or spelling out love and more. 

DesBarres Chocolate

For the eco-conscious chocolate lover in your life, give them DesBarres Chocolate. From their factory in Uxbridge, this micro-batch manufacturer crafts single origin bean to bar chocolate made with ethically produced cacao. You can find their stunning chocolate bars at various locations across Durham Region including Passion Cook Essentials and Second Wedge Brewing Co in Uxbridge as well as Nexus Coffee in Port Perry. Plus, for the big V-Day their making caramel filled hearts and raspberry hearts.

Van Belle Flowers

Since 1960, Van Belle Flowers has been putting smiles on people’s faces with their incredible flowers. With locations in Whitby and Bowmanville, this Durham flower shop favourite is the perfect spot to grab a bouquet for your boo. They have everything from roses to hydrangeas, sunflowers and more.

One More Cocoa Gourmet Chocolate


Grab some sweet treats for your sweet at One More Cocoa in Whitby! Inspired by her Jamaican heritage, Kenesha Lewis sprinkles a little of the island flavours into her chocolate. This gourmet chocolate shop got world recognition when it was highlighted in a recent list of Oprah picks. Home to hand-crafted premium chocolate bars and truffles, choose from over 18 flavour, each made with love.

Williams Chocolate

For over 35 years, Williams Chocolate in Whitby has been a beloved family-owned business creating some of the finest chocolates in Durham Region. Using only the finest Belgian chocolate it’s a great place to find unique chocolate gifts for your sweet. Along with a variety of traditional chocolate boxes, they make fun bouquets of chocolate roses, bars that say ‘Love You,’ Be My Valentine heart-shaped chocolates, and more!

Suzanne Gardner Flowers

Florist with Dog

The dreamiest flower shop in Headwaters is Suzanne Gardner Flowers. Located on the main street in Orangeville, this shop sources both locally in Ontario as well as globally for the freshest flowers. At the shop you’ll find traditional flowers to buy for your partner as well as potted plants like orchids. Plus, if your significant other is a plant enthusiast, consider getting them a flower and plant subscription from Suzanne Gardner Flowers as a unique gift.

The Chocolate Shop

Another sweet spot in downtown Orangeville is the Chocolate Shop. For nearly 20 years they’ve been crafting handmade chocolates. Pop into the store to find a wide range of chocolates and truffles that will melt that special person in your life’s heart!

Debora’s Chocolate Shop

For over 17 years, Debora’s Chocolate Shop in downtown Erin has been creating incredible chocolates. Stop by this little gem and you’ll find it stocked with handmade Belgian chocolate truffles. Crafted with fresh ingredients, Debora’s has all the classic chocolates as well as fun Valentine’s Day treats. You can choose from a traditional box of her truffles or opt for a chocolate heart-shaped box to fill with sweets. Another fun item that’s unbearably cute is their chocolate cinnamon heart bears!

Start a New Tradition with Baked Goods



In the charming Markham Village is one of the best dessert cafes in York Region, Cho-Kwok-Lat! Walking in you’ll be greeted with the sweet aroma of chocolate and fresh pastries. This patisserie & chocolaterie is the perfect spot to pick up a few unique baked goods. With everything crafted in house, their selection is always fresh and includes a variety of sweet and savoury flavours. One of their best is the delectable Crème Brûlée Cruffin. Or try one of their limited time Valentines Day cakes or pastries!

Underground Bakeshop

A beloved bakery in Beaverton is the Underground Bakeshop. This Durham Region gem crafts fresh homemade baked goods with recipes that have stood the test of time. You’ll find an assortment of bakery items that include everything from the classics, like croissants, to unusual treats like their famous Love Child. This flakey pastry is like a croissant masquerading as a muffin and wrapped in sugar and salt, for a mouth-watering creation. Or you could pick up a cinnamon or Nutella bun for your hun!

The Shortiss Café

Shortiss Table Food

In the heart of downtown Beaverton is another cherished café, The Shortiss Café. Set in a historic building that dates to the 1800’s, you’ll find all the perfect pastries to show your significant other how much you care. Your sweetheart will love their adorable Valentine’s Day inspired cookies. They come in all sorts of fun forms like a bouquet of roses and love letters. Plus, the Shortiss Café makes the cutest macarons with sweet sayings like Be Mine and Kiss Me.

Bistro Du Pain

Get your French fix in the small town of Erin at Bistro Du Pain. This French bakery and café makes some of the finest fresh breads and baked goods in Headwaters! If your darling has dietary restrictions, Bistro Du Pain has you covered, with vegan and gluten-free breads available. Bring Paris to your partner with their delightful Raspberry Basket. This sweet pastry is made with croissant dough, cream and fresh raspberries.

Celebrate with These Unique Date Ideas

Fire & Stars Hike

Torch on Trail

Enjoy a wonderful evening embracing your partner and the wonders of the outdoors at Sibbald Point Provincial Park. This York Region gem is offering a truly magical experience this winter. As day turns to night the park’s Maidenhair Fern Trail transforms for their Fire and Stars Hike, where the trail is lined by torchlight. Bundle up this February 14th and hit the trails for a memorable and unique date night!

Food Lovers Valentine’s Day Tasting Menu

One of the utmost distinct date ideas in the GTA is in York Region! At the Chef Upstairs, in Vaughan, you’ll find the most unique cooking venue. Running from February 14-17, is a Food Lovers Valentine’s Day Tasting Menu. You and your partner will be greeted with a glass of Prosecco and then guided through a multi-course meal of your own creation led by a chef. The meal features everything from salad to soup and seafood to a decadent dessert.

Valentine’s Tea or Cookie Decorating

Parkwood Dining

Two of the sweetest date night ideas in Durham Region can be found at Parkwood Estates. This grand mansion in Oshawa is both a National Historic Site and wonderful place to celebrate the special day. On February 10th, Parkwood Estates is hosting two special experiences for you and your love. Enjoy a Valentine’s Tea that features all the classics including scones and sandwiches as well as sweet treats like Meringue kisses and plenty of chocolate. Or try your hand at sugar cookie decorating.

Trivia Night at the Old Flame

Valentine’s Day falls on a Wednesday this year which means it’s Trivia Night at Old Flame Brewery. With two locations, in Port Perry and Newmarket, Old Flame is known for being Canada’s most awarded craft lager brewery. Old Flame Brewery makes for a fun date night out to test you and your partner’s knowledge while enjoy a pint of beer.

Galentine’s Day Dinner Cheese & Cider Pairing

Ladies, we’ve got you covered with a fun Galentine’s Day experience for you and your girlfriends too! At Two Blokes Cider, just north of Port Perry, they are celebrating Galentine’s Day, February 13th. Grab your gal pals and enjoy a cheese and cider pairing led by their head cider maker. Afterwards, this award-winning cidery will be treating you and the girls to a screening of Barbie

Snow Globe Dining

Snow Globes

Northeast of Orangeville are two incredible dining experiences that are ideal for a romantic dinner out. At Hockley Valley Resort you’ll find the region’s most popular snow globes. Outfitted with twinkling lights, faux fur throws and heaters, they are the perfect place to snuggle up with your sweetheart. Dinner is a 5-course farm to table meal with wine pairings. Just down the road is Adamo Estate Winery. Here you and your partner can dine in snow globes overlooking their vineyards. Dinner is an Italian tapas-style meal with a flight of three wines.

Romantic Winter Glamping

Forget about a boring weekend away in a hotel to celebrate Valentine’s Day. Surprise your spouse with an unconventional romantic escape that includes winter glamping at Alabaster Acres. This picturesque farm in Caledon offers luxury glamping experiences, even through the winter! Enjoy luxurious king beds with heated mattress under the canopy of frontier-style tents. Your little oasis comes outfitted with everything you’ll need including cozy chairs, a fire pit, and dreamy twinkling lights.

Alabaster Acres

Whether you choose classic chocolates and flowers or opt for unique delights like homemade baked goods and unconventional dates, this Valentine’s Day is all about celebrating love in personalized style. Embrace tradition with a modern twist, ensuring a day filled with cherished moments and heartfelt connections in York Durham Headwaters.

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