Winter is prime time for quick escapes to the small towns just beyond Toronto where crisp air, cozy streets and bold flavours steal the show. For big taste without the long drive, the Niagara Benchlands and York Durham Headwaters deliver.
In the Niagara Benchlands, vineyard views and orchard roads lead to Beamsville’s wineries and gin makers, Vineland’s craft wine and brunch spots, Lincoln’s heritage gems and Jordan Station’s beloved bakers, growers and cheesemakers.
York Durham Headwaters brings the adventure. Caledon’s saunas, hot springs and globe dining feel like a winter retreat; Uxbridge mixes ski hills and hot cider with a rising food scene; and Stouffville shines with winter trails, treetop thrills, skating and standout restaurants and brews.
Short trip, huge flavour. Two delightful winter road trips unlocked.
Want to skip ahead by destination? No problem!
Niagara Benchlands: Small Towns with Big Flavour All Winter Long
Winter in the Niagara Benchlands hits differently. Snow settles on vineyard rows. Tasting rooms glow a little warmer. Small towns feel friendlier. Food tastes better. Everything slows in the best possible way. This is a region that knows how to make winter feel delicious and cozy as heck.
Beamsville
We recommend finding a designated driver for this one because exploring award-winning, family-owned wineries is the name of the game in Beamsville. Consider it your winter soft landing. It’s calm, cozy and full of flavour.
With no shortage of wineries to explore, we recommend starting at Peninsula Ridge Estate Winery, a Feast On® certified gem with a drive-worthy restaurant tucked into a Queen Anne Revival Victorian Mansion.
From there, move on to Redstone Winery for bold pours and a sleek tasting room that deserves its own slow moment or hit Back 10 Cellars for small batch wines with big personality. This time of year, we love any reason to celebrate with their Smitten Sparkling 2024.
Spirits more your thing? We recommend checking out Dillon’s Small Batch Distillers (book a tasting in their small but cozy tap room) and discover a wide variety of products from gin cocktails to DIY cocktail kits to bring warmth all season long. Really into gin? Craft your own by booking their make-your-own gin experience!
Before you roll out of town, grab a bite at The Good Earth for a welcoming and comforting meal sure to warm you from the outside in as you look out from the glassed dining room onto their snow vineyard. You could also pop by nearby Littlefoot Farm for gourmet finds like jams, seasonings, pickles, farm fresh meats and eggs to remember your trip by!
Vineland
Vineland feels like a winter postcard you can walk into. Snow covered vines stretch across the hills. The quiet is soft. The wine is not.
Feast On® certified Vineland Estates Winery brings the drama with sweeping vineyard views that look even better with a glass in hand, food crafted by the talented Chef George Ward and unique experiences to keep things cozy all winter long. Indulge in an outdoor fireside tasting and snack, taking a pairing class or just grab a great meal!
Those needing a little vitamin D will appreciate a winter warm up at the Watering Can Flower Market. This greenhouse and cafe is where flowers, herbs, pastries and steaming drinks all share the same cozy space. It is impossible to be stressed here. Please do not try.
For brunch, head to Penny’s Kitchen Diner and Coffee House or Revalee Brunch Café. Both deliver comfort on a plate. Eggs. Fresh breads. Coffee. Maybe a cocktail. Winter calls for it and you won’t be disappointed. Looking for recommendations? We’ve got ’em. At Penny’s, try the breakfast croissandwich for savoury, flaky goodness and at Revalee, dive into the Full Monte challah French toast with a mimosa!
Before hitting the road to home, check out Grand Oak Culinary Market. You’ll be tempted with shelves of local goods and snacks that somehow leap into your basket on their own and even meals to go. This is a judgment free zone.
Vineland feels easy in winter. It is all about soft light, slow meals, cozy corners and the simple joy of discovering treats you did not know you needed.
Jordan Station + Jordan Village
Jordan is tiny but mighty. It delivers more flavour per block than seems logical, local art galleries, boutique hotels and more. Start in the village at RPM Bakehouse where pastries crackle warm from the oven and sourdough loaves never last long. Grab one. Actually grab two. Thank yourself later.
Small town shopping shines in Jordan Village as well with everything from art galleries and vintage stores to old school hat makers lining the main street. Take your time and wander! Those wanting to stay nearby can book the night (and perhaps a winter spa treatment) at Inn on the Twenty, right next door to RPM Bakehouse!
Next, it’s time to head into neighbouring Jordan Station. Two bakeries, one trip? No problem. Stroll to Plant No 1 for plant-based baked goods with flair. Each treat feels handcrafted for maximum joy. Winter diets do not apply here. We recommend grabbing a salted maple bourbon donut for one hand and a salted ube pistachio cookie for the other. Life is about balance.
Small town shopping shines at Upper Canada Cheese Company where you can sample your way through creamy delights from their herd of Jersey cows. Avant-Guarde Emporium adds art and vintage charm to the mix. If you need a sweet payoff visit Moyer’s Apples for a classic treat— gourmet candy apples.
Prefer a little culture or outdoor time? Check out The Lincoln Museum and Cultural Centre to learn the unique history of the area from the formation of Indigenous communities to the War of 1812 or go for a wintery stroll at Balls Falls Conservation Area! Alternatively, check out the brand new Sho’aríshon Park to discover the legacy of Indigenous peoples in Niagara Benchlands and honour the land on which you’re wandering.
Finally wind down with a guided tasting at Feast On® certified Westcott Vineyards. What a lovely way to cheers to a trip well made!
Why Winter Works Here
The Niagara Benchlands thrive when the temperature drops. Crowds thin. Fires crackle. Tastings feel slower, richer and more personal. Food tastes bolder. Wine feels deeper. Time stretches in a way summer rarely allows.
This is winter made for wandering. A patchwork of pretty towns and vineyard roads. A place where brunch counts as an adventure and a tasting flight counts as therapy. It is close enough for a quick trip yet far enough to feel like a real escape.
York Durham Headwaters: Where Winter Gets Local
Winter turns York Durham Headwaters into a playground of trails, fireside sips, comfort foods and cozy stays. Skip the city noise, breathe deep country air and lace up those boots! You’ll be sipping a warm drink and embracing small town charm in no time. Wondering where to start? We can help!
Caledon
Caledon was built for winter. Snowy hills. Quiet roads. Steam rising from every mug. It feels calm here in a way that you tend to forget about in day to day city life.
For a truly unforgettable experience, check out the winter activities at Osprey Valley! Want to get a little active? Enjoy the on-site skating rink or night-lit snow shoe trail before warming up at The Kettle with a gooey Ontario cheddar grilled cheese sandwich. Fancy a pint? Two Brothers also calls Osprey Valley home with smash burgers, mac n’ cheese and other cozy fare also on deck. When you wrap up, you can even stay the night at their new on-site accommodations!
If you’re still craving movement, Albion Hills Conservation Park delivers. Ski through tall pines. Snowshoe along rolling ridges. Trails twist through the forest like they were made for winter wanderers. Your boots crunch. Your breath fogs. Your mind clears. Need equipment? No worries! You can rent fat bikes and cross country skiis. If you want to keep the wintery fun going, there is winter disk golf and a designated tobogganing hill too!
Once you are back in town, you will want something in your hand. GoodLot Farm & Farmstead Brewing pours fresh farm-brewed ales that taste bright and earthy. This time of year, we love enjoying their Top o’ the Morning Dry Irish Stout made with hops grown on site for a truly delicious warm up!
Feeling hungry? Gather Cafe brings comfort in sandwich form. Soft bread. Hot soups. The kind of food that fuels you without fuss. Feast On® certified Spirit Tree serves wood-fired pizza that melts any lingering chill. Crisp crust. Rich toppings. Winter perfection. Paired up with their made-on-site ciders and baked goods, it’s a match made in heaven. Whichever one you choose, you can’t really go wrong!
Finally, pick a place to cozy up for the night! When you want deep relaxation, head to Millcroft Inn and Spa. The hot springs sit beside a rushing winter creek. Steam lifts into the trees. Slip into a robe then drift between hot springs, pools and treatments. Your stress does not stand a chance.
Alternatively, Liberty Inn offers another cozy place to land. This boutique country inn features five luxury suites and a whole lot of peace and quiet. Based on Nordic spa traditions, you’ll have the opportunity to rotate between a cedar-fired hottub, Finnish sauna and an exhilarating cold plunge as you feel your troubles melt away.
Uxbridge
Welcome to Uxbridge! This quiet destination is a winter hub of trails, hills and good-vibe après-ski and cider. Locals call it the “Trail Capital,” thanks to 240 km of trails winding forests, meadows, streams and wetlands.
Start with fresh air and movement at Trail Hub. Hike, snowshoe (available for rent) or cross-country ski beneath snow-laden branches. The trails wind and bend making working up an appetite is easy. Once you’ve done just that, head to their on-site, Feast On® certified restaurant, Nest, for farm-to-table fare rooted in local ingredients. Think everything from roasted King Cole duck breast to frites and aioli and a drink menu that really puts Ontario at the forefront.
If you want something with more speed, hit the slopes at Ski Lakeridge or Dagmar Ski Resort. Slalom runs await at both and at Liakeridge you can also take to the tubing hills! Feel the wind in your hair and let out your inner child as you zip down the hill, old school style. You’ll enjoy snowy hills, cold air and thrill before returning to warmth.
After the trails or slopes, retreat with a warm drink at Slabtown Cider. Try their “Cider House Rules” — crisp, orchard-fresh cider that can be be served warm on the patio with marshmallows and a fire. It pairs well with their cozy vibe and good company. We also recommend trying the Thunder Ridge Bison Burger if you’re feeling ambitious.
Need bakery fuel? Little Thief Bakery serves up flaky pastries and warming bread — the kind of decadent baked goods that taste like winter should. We’re talkin’ salted caramel crullers, sour cherry Basque-style cheesecakes and warm cinnamon buns with cream cheese frosting to name just a few past favs. Their house-made loaves and sweets pair perfectly with a hot drink before heading back out or settling in.
If you’re hungry for more than snacks, wind down at Sundays. This brand new, Michelin-recommended Bib Gourmand spot delivers seasonal dishes done with care. Dishes change regularly with the seasons but past favourites have included everything from schnitzels served with sunny-side-up eggs to black cod with leeks, muscles and potatoes. The dishes are approachable, unpretentious and damn delicious.
Stouffville
Last stop: Stouffville — where winter gets playful yet grounded.
Start with a little snow-filled action at tree-top trekking. Nothing beats climbing your way through dusted tree tops on a chilly winter day to put things in a new perspective. Skating more your thing? Stouffville Memorial Park boasts a local skating trail lit to perfection. This might just be the river Joni Mitchell was hoping to skate away on. Ok, it’s not a river but it’s still romantic.
When you’re done gallivanting, it’s time to warm up with a little liquid comfort! Pick your perk- beer or wine? If it’s vino you crave, head to Willow Springs Winery for a glass of local wine that feels like sunshine on a cold day. Known for their award winning ice wines, we recommend sipping on their Cab Franc Ice Wine alongside a hearty dish of pork rillettes.
Beer more your thing? Bounce over to Muddy York Brewing Co. for craft beer, a laid-back vibe and the kind of brew that tastes like community and elbow grease. We recommend grabbing a pint of the Diving Horse Pale Ale for an IPA that celebrates a legendary local story (ask about it) with notes of white grape, grapefruit and pine.
Get Your Winter On
You know what they say! There’s no such thing as bad weather, just bad clothing. So bundle up and discover the deliciousness of Niagara Benchlands and York Durham Headwaters this winter. Want to keep exploring? Check out the trip inspiration below!
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