Tucked away in the rolling countryside of Caledon, the charming village of Alton is the kind of winter getaway that feels like a well-kept secret. With vibrant arts, scenic outdoors, craft beer and rich cuisine, Alton brings a mix of energy with undeniable small-town charm. This itinerary will walk you through a perfect two day escape in Alton. If you’ve been looking for an Ontario adventure, blending cozy relaxation with outdoor fun, this is the winter retreat you’ve been looking for.

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*Disclaimer: this itinerary features the Fire and Ice Winter Festival, which is taking place January 31 and February 1, 2026. The festival will not be taking place other weekends, but you can still enjoy fun at the Alton Mill and all other stops of this itinerary at any time.

Cozy Up in Gather Cafe

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Kick off your weekend with a cozy first stop that sets the tone for the days ahead. Insert Gather Cafe, the village of Alton’s renowned coffee hub. This charming shop is stocked with comforting menu items for you to fuel up before your busy day. Offering friendly service and small-town charm, Gather makes everyone feel like they’re a local. Here, you can sip on a winter-themed latte next to the fire, or order from the food menu, with items ranging all the way from breakfast to wood-fired pizzas. It’s the perfect place to slow down, warm up and ease into your Caledon weekend.

Attend the Fire and Ice Festival

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After leaving Gather Cafe, make your way to the Alton Mill Arts Centre and buckle up for what’s in store. A true Caledon staple, the Alton Mill is known for its vibrant arts scene, strong sense of community, one-of-a-kind shops and stunning grounds. The Fire and Ice Festival is an iconic event that takes place every winter at the Alton Mill. Like the name suggests, this festival combines elements of both fire and ice to keep you toasty warm, while enjoying the wintery outdoors. For this itinerary, you’ll pop in during the day, then return after dark when the festival really turns up the heat. When you arrive, one of the first things to capture your eye will be live ice carvers in action. These sculptors begin with a solid block of ice and throughout the day carve out their magnificent ice sculptures right before your eyes. If you’re lucky, you might even find a sculptor that will let you help and teach you a few techniques! Other notable highlights include ice skating on Mill Pond, live music and fire performers, food trucks, snowy treats, cozy fire pits and more. If you need a little break from the cold, wander into the rustic doors of the mill for an escape. Inside you’ll find an artisan market to shop unique items and gifts. When you walk upstairs, take a peak into the open artist studios. Tip from a local: many of the artists host classes and workshops, so be on the lookout for an art style that sparks your interest. Next time you come back to Caledon, you’ll already have an activity to look forward to! After soaking up the day time activities of the festival, it’s time to check in to your comfy abode for the night.

Check-in at Osprey Valley and Dinner at Fescue

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Just a quick 5 minute drive from the Alton Mill, you’ll find TPC Toronto at Osprey Valley. Known for being a top-ranked golf course in Canada during the warm months, Osprey Valley has transformed itself into an all seasons destination. With icy outdoor activities, luxury suites, restaurants, a gym, and indoor golf simulator, there’s no shortage of ways you can enjoy Osprey Valley during the shoulder-season. Booking the all-new Winter Escape Package includes your one night stay in the stunning Villas or Clubhouse Suites, alongside two meals and unlimited skating. After settling into your modern, luxurious suite, it’s time to head out for an early three-course dinner at Fescue Restaurant and Lounge, included as part of your stay. Fescue is Osprey Valley’s newest dining addition. This upscale restaurant promises an elevated dining experience with locally sourced ingredients and offers a selection of global wines. It’s the perfect setting to warm up and enjoy a cozy meal before heading back out for the night’s finale.

Watch The Big Burn

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Back at the Fire and Ice Festival, it’s time for the most anticipated moment of the night. “The Big Burn” is the fiery finale that lights up the evening and leaves the crowd in awe. Each year, local artist Paul Morin creates a grande fire sculpture that gets lit at dusk, drawing crowds from all over. Unlike anything you’ve ever seen before, this sculpture comes to life after one hundred hours of welding, and will typically burn for up to 45 minutes. Paul describes the big burn as a tribal experience, bringing a unique connection and meaning to all who attend. Optional after The Big Burn, attend the Hot Mic Comedy Show and Concert, where music meets laughter all in one night. This is a ticketed event at the festival.

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End the evening with a little more adventure back at Osprey Valley. The Kettle Links Light Trail is a new winter edition that will add a joyful, feel-good activity to your evening. The trail follows twinkling lights through the trees, adding a warm touch to Mother Nature’s winter wonderland. Located just behind the Golf Academy and ice rink, you have the option to walk the trail or rent snowshoes for a small fee. It’s a charming way to experience the beauty of Osprey Valley after dark. Warm up afterwards with a boozy hot drink from the take out window. With your Villa just a few steps away, cozy up inside and let the rich warmth of your drink add a final, indulgent touch to the evening before slipping into sleep.

Breakfast at Two Brothers and Ice Skating

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Rise and shine! It’s time for breaky. Included in your Winter Escape Package is breakfast for two at Two Brothers. This restaurant located in the Main Clubhouse offers elevated comfort food and Caledon’s best selection of craft beverages. It’s the ultimate approach to a slow morning, and fuelling up before another exciting day. Once your bellies are satisfied, journey over to the ice rink and lace up your skates! Also included for you is unlimited skating at Osprey Valley’s brand new rink that opened just this winter. Take a spin after breakfast for a little bit of icy fun. The rink is surrounded by scenic views, making it the perfect way to soak up the crisp winter air before continuing on with your day.

Drinks at GoodLot Farm and Farmstead Brewing Co.

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Your last stop for this weekend brings you to a Caledon classic, GoodLot Farm and Farmstead Brewing Co. This brewery is a unique hop farm and solar-powered brewery that blends sustainability with great craft beer and a laid-back atmosphere. Step inside the Oast Barn, an intimate and warm setting, for your last hoorah before heading back home. The glow of the crackling fireplace mixed with a crisp beer in hand will make it easy to slow down and savour the moment. February 1st at GoodLot features live music from Justin McDonald and an Oyster Pop Up, so you can enjoy the oceanic snack as Justin’s live tunes play in the background. It’s a laid-back, feel-good finale to a weekend well spent in Caledon.

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While Alton shines bright in winter, it’s only one small corner of Caledon. From quiet country roads to vibrant villages, there’s so much more to discover. Be sure to check back for more local guides, itineraries and seasonal inspiration! 

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