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Getaways from Toronto · Winter 2026–27

Winter getaways from Toronto

Eighteen ways out of the city between December and March, from a 90-minute drive to Niagara's Icewine weekends to a short flight into Québec's Carnaval. Each is sorted by how you get there, with the event worth timing it for, where to stay and one thing to know before you go.

  • 18trips
  • 10by car
  • 3by train
  • 5by air
  • Facts checked 20 October 2026

18 winter trips from Toronto, sorted by how you get there: 10 by car, 3 by train and 5 by air. The quickest to reach is New York City, 1 hr 20 min away; the longest trip is Eastern Townships, 6 hr 45 min. Each one lists the travel time, the dates worth timing it for and where to stay.

At a glance

GetawayFrom TorontoBest forTime it for
Blue Mountain & Collingwood 1 hr 30 min Ski, Spa, Family Holiday Magic Light Trail (2027 dates TBA)
Elora & Fergus 1 hr 30 min Spa, Romantic, Outdoors January to March for Elora Mill's winter wellness programme and snowshoeing
Niagara-on-the-Lake 1 hr 30 min Food & wine, Festival, Spa Niagara Icewine Festival (2027 dates TBA)
Buffalo Passport 1 hr 30 min Culture, City break, Food & wine Ragnar Kjartansson at the Buffalo AKG, Until 31 Jan 2027
Stratford 2 hr Food & wine, Festival, Culture Lights On Stratford, 18 Dec 2026 – 10 Jan 2027
Muskoka 2 hr Outdoors, Family, Romantic Fire & Ice Nights at Arrowhead (2027 dates TBA)
Haliburton Highlands 2 hr 30 min Outdoors, Family, Romantic January to March for dog sledding, ice climbing and snowshoeing
Prince Edward County 2 hr 30 min Food & wine, Spa, Romantic Élevage Winter Wine Festival (2027 dates TBA)
Lake Placid & the Adirondacks Passport 6 hr Ski, Outdoors, Romantic Ski Jumping and Nordic Combined World Cup, 5–7 Feb 2027
Mont-Tremblant 6 hr 30 min Ski, Spa, Romantic January to March for the most reliable snow
Ottawa 4 hr 32 min City break, Festival, Spa Winterlude, 29 Jan – 15 Feb 2027
Montréal 5 hr 13 min City break, Festival, Food & wine Montréal en Lumière, 18–28 Feb 2027
Eastern Townships 6 hr 45 min Spa, Ski, Food & wine January and February for skiing and spa weekends
New York City Passport 1 hr 20 min City break, Culture, Food & wine NYC Winter Outing (2027 dates TBA)
Québec City 1 hr 30 min City break, Festival, Culture Carnaval de Québec, 5–14 Feb 2027
Boston Passport 1 hr 30 min City break, Festival, Culture Boston Frostival, 22 Jan – 5 Mar 2027
Chicago Passport 1 hr 55 min City break, Food & wine, Culture Chicago Restaurant Week, 22 Jan – 7 Feb 2027
Charlevoix 2 hr 30 min Ski, Spa, Food & wine January to March for skiing at Le Massif

By car 10 trips

1 hr 30 min
Photograph · Blue Mountain Resort
Southern Georgian Bay, Ontario

Blue Mountain & Collingwood

About 90 minutes by car (Blue Mountain Resort's stated estimate)Blue Mountain lists FlixBus service from Toronto Pearson and Union Station Bus Terminal to the resort, though its page refers to summer rides, so check winter service; no resort shuttles are operating.

Ontario's only year-round mountain resort and spa puts downhill skiing, a pedestrian village and a Nordic spa within a short drive of each other. Scandinave's outdoor baths in a 25-acre hardwood forest make a strong second day after skiing.

Time it for Holiday Magic Light Trail Mid-November to early January; 2026-27 dates still to be confirmed

A free one-kilometre illuminated walking trail through snow-covered trees and lit archways, starting at the Blue Mountain Village Welcome Centre, nightly from dusk to 10 pm.

Do
  • Skiing and snowboarding at Blue Mountain The 2026/27 season is scheduled to open Thursday 10 December 2026 at 8:30 am, with night skiing, a terrain park and Snow School lessons.
  • Scandinave Spa Blue Mountain A thermal journey of hot baths, cold plunges, waterfalls, saunas and a eucalyptus steam room in a 25-acre hardwood forest with Niagara Escarpment views.
  • Scenic Caves snowshoe trails Snowshoe trails in The Blue Mountains, including a suspension bridge crossing.
Stay

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Winter tip Scandinave books massages about four months ahead and often runs a wait list for the baths on weekends and holidays; it recommends midweek or evening visits.

1 hr 30 min
Photograph · Elora & Fergus Tourism
Wellington County, Ontario

Elora & Fergus

About 1 hr 30 min by car (Elora & Fergus Tourism's stated time)Elora & Fergus Tourism lists no rail or intercity bus link from Toronto; driving is the practical option.

A stone-built mill village on the Grand River gorge, close enough for a two-night spa break. Elora Mill pairs gorge views with an outdoor infinity pool and a winter wellness programme, and the surrounding trails stay open for snowshoeing and skiing.

Do
  • Ice climbing with One Axe Pursuits Climb a 20-metre man-made ice wall overlooking the gorge along Irvine Creek, with beginner sessions that teach the basics first.
  • Wellington County Museum trails and rink Snowshoe rentals ($5 a day) for a 53-acre trail network, including the 1.5 km Aboyne Trail along the gorge, plus a toboggan hill and free outdoor rink.
  • Elora Cataract Trailway A 47 km trail from Elora through Fergus to Cataract, open for cross-country skiing and snowshoeing in winter.
Stay
  • Elora Mill Hotel & Spa 30 rooms in three styles, high above the Grand River along the Elora Gorge, with a Wellbeing Circuit of sauna, heated outdoor pool, hot tub, steam room and cold rinse.
  • Inner Joy Getaways Four repurposed shipping-container suites on the Grand River, each with a private patio and hot tub.

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Winter tip Elora Gorge Conservation Area is seasonal (1 May to 15 October), so for winter walks use the Wellington County Museum trails or the Elora Cataract Trailway instead; the tourism centre is open Wednesday to Sunday, 11 am to 4 pm, in January and February.

1 hr 30 min
Photograph · Jeff Speed / Niagara Grape & Wine Festival
Niagara, Ontario

Niagara-on-the-Lake

About 90 minutes by car (about 130 km from downtown Toronto), depending on trafficGO Transit bus service runs year-round with expanded service in peak season, and FlixBus runs direct from Toronto to Fort George, where a local shuttle connects to Queen Street.

The closest wine-country weekend to Toronto, and winter is when Niagara's signature product, Icewine, gets its own festival on Queen Street. The Shaw Festival keeps its stages lit through the holiday season, and the Old Town's historic hotels have full spas for cold days.

Time it for Niagara Icewine Festival Two January weekends (17 and 18, 24 and 25 January in 2026); 2027 dates still to be announced

Queen Street becomes an outdoor Icewine village with tastings, food pairings, fire pits, ice carving and light displays on the Old Courthouse; admission is free, with paid VIP passes.

Do
  • Shaw Festival holiday season Rodgers + Hammerstein's Cinderella plays the Festival Theatre from 8 November to 23 December 2026, and A Year with Frog and Toad plays the Court House Theatre from 5 November to 23 December 2026.
  • Icewine Festival Discovery Pass A self-guided pass of six food and wine pairings at six wineries during the festival, with a Driver's Pass of non-alcoholic pairings for designated drivers.
  • 100 Fountain Spa at Pillar and Post A 13,000-square-foot spa in Niagara-on-the-Lake, with complimentary spa day passes for Pillar and Post hotel guests.
Stay
  • Prince of Wales Hotel Built in 1864 in the heart of Old Town, with the Secret Garden Spa, an indoor pool, whirlpool and sauna, afternoon tea and the Churchill Lounge.
  • Pillar and Post Home to the 13,000-square-foot 100 Fountain Spa, with complimentary spa day passes for hotel guests.

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Winter tip Festival shuttles between wineries are not running, so plan a designated driver (the festival sells a Driver's Pass) or book a tour; Icewine Village VIP tickets are expected to sell out and all sales are final.

1 hr 30 min
Photograph · Frank Lloyd Wright's Martin House
Western New York, USA Passport needed

Buffalo

About 1 hr 30 min by car, depending on traffic in CanadaThe daily Amtrak and VIA Maple Leaf runs from Toronto Union across the Niagara border into New York State (Amtrak timetable).

Buffalo is 90 minutes from Toronto and makes a strong winter architecture weekend, because the best of it is indoors: Frank Lloyd Wright's Martin House complex and the Buffalo AKG Art Museum's new Gundlach Building. Add skating at Canalside, the largest outdoor rink in New York State, and a stay in a restored H.H. Richardson landmark.

Time it for Ragnar Kjartansson at the Buffalo AKG Until 31 Jan 2027

Exhibition by the Icelandic artist in the museum's Jeffrey E. Gundlach Building.

Do
  • Frank Lloyd Wright's Martin House Guided interior tours of the Martin House, Barton House and Gardener's Cottage, Thursday to Monday 9:30 a.m. to 4:30 p.m.; the conservatory and pergola are open daily.
  • Buffalo AKG Art Museum 1285 Elmwood Avenue campus with the Jeffrey E. Gundlach Building, currently showing Ragnar Kjartansson: Politics of the Obvious, and Cornelia dining in the Knox Building.
  • Ice at Canalside The largest outdoor rink in New York State, with skating, curling, ice bikes and ice bumper cars on the waterfront; last season ran 25 November 2025 to 22 February 2026, 2026-27 dates not announced.
Stay
  • The Richardson Hotel Hotel in the restored H.H. Richardson landmark on the Richardson Olmsted Campus, 444 Forest Avenue.

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Winter tip At the Peace Bridge, tolls are collected Canada-bound only (card accepted in all toll lanes; E-ZPass saves 50 percent), and live lane-by-lane wait times are on peacebridge.com and the Peace Bridge app.

2 hr
Photograph · Destination Stratford
Perth County, Ontario

Stratford

About 2 hours by car (Destination Stratford's stated driving time)VIA Rail serves Stratford from Toronto; Destination Stratford notes some weekend trains are replaced by buses in autumn 2026, so check the VIA schedule.

Out of theatre season, Stratford turns to food and light: self-guided chocolate and bacon-and-ale trails run all year, and the free Lights On Stratford festival fills downtown with light art over the holidays. Boutique hotels in Victorian buildings keep it walkable.

Time it for Lights On Stratford 18 Dec 2026 – 10 Jan 2027

The seventh annual free winter festival of light art across downtown and its parks, featuring Canadian artists, with a free hop-on hop-off shuttle and free hot chocolate.

Do
  • Chocolate Trail A year-round self-guided pass ($39.55 including HST) with six vouchers for chocolatiers, bakeries and shops; vouchers never expire.
  • Bacon & Ale Trail A year-round self-guided pass ($39.55 including HST) with five vouchers for bacon and ale tastings around town.
  • Farm tours at The Bruce The Bruce Hotel offers farm tours with Chef Nick Benninger and a culinary stay package built on local flavours.
Stay
  • The Bruce Hotel A luxury boutique hotel offering elegant suites, fine dining and refined service, pairing polished modernity with vintage charm.
  • The Stratford Hotel An intimate 12-room boutique hotel in an 1875 Victorian landmark on Erie Street, in the downtown core.

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Winter tip Lights On Stratford runs Thursday to Sunday evenings only, and trail vouchers are sold at Destination Stratford (47 Downie St, Mon to Sat 9 am to 5 pm); check each trail stop's winter hours before going.

2 hr
Photograph · Discover Muskoka
Muskoka, Ontario

Muskoka

About 2 hours by car to Deerhurst Resort near Huntsville (245 km), per the resortSeasonal flights from Billy Bishop to Muskoka run in summer, not winter.

Muskoka in winter means a forest skating trail, groomed Nordic skiing in Algonquin Park and lakeside resorts built for snow days. Deerhurst runs snowshoeing, kick sledding, fat biking and skating on site, and Arrowhead Provincial Park is about 10 minutes away.

Time it for Fire & Ice Nights at Arrowhead Friday and Saturday evenings, 6 to 9 pm, from late January, weather permitting; 2027 dates still to be announced

Evening skating on the Arrowhead ice trail lit by torches and lanterns.

Do
  • Arrowhead Provincial Park ice trail A 1.3 km skating trail through pine forest, open roughly mid-January to mid-March depending on weather.
  • Algonquin Park cross-country skiing 85 km of groomed and 32 km of ungroomed ski trails off Highway 60, typically December to March, plus snowshoeing and a rink at Mew Lake.
  • Deerhurst winter activities Snowshoeing, skating on the Maple Lawn rink, kick sledding, fat biking and downhill skiing next door at Hidden Valley Highlands.
Stay
  • Deerhurst Resort Spread across 760 acres on Peninsula Lake, welcoming vacationers since 1896, with snowshoeing, skating and kick sledding from December to March.
  • JW Marriott The Rosseau Muskoka Resort & Spa On Lake Rosseau in Minett, about 2.5 hours north of Toronto, with HydroSpa Muskoka, a year-round indoor/outdoor pool and winter-only Muskoka Ice Caves rooftop dining.

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Winter tip Arrowhead needs a daily vehicle permit; Ontario Parks advises reserving online ahead (up to five days in advance) to guarantee access, and Fire & Ice Nights sell out.

2 hr 30 min
Photograph · Haliburton Highlands Tourism
Haliburton County, Ontario

Haliburton Highlands

About 2 hr 30 min by car (Haliburton Highlands tourism's stated time)No scheduled rail or air service is listed by Haliburton Highlands tourism; driving is the practical option.

The most hands-on winter on this list: husky sledding on private wilderness near Algonquin, a wolf centre, ice climbing and snowmobiling in a 100,000-acre private forest. An adults-only lakeside inn with a WaterSpa balances the cold days.

Do
  • Winterdance Dogsled Tours Tours from two hours to multi-day, plus moonlit runs, on 2,200 acres between Haliburton Lake and the edge of Algonquin Park, with a kennel of 150 Siberian Huskies.
  • Haliburton Forest Wolf Centre An indoor centre with one-way glass overlooking a 7-acre wolf enclosure, plus over 13 km of snowshoe trails from the parking lot; winter hours run to 18 June 2027.
  • Ice climbing and skijoring with Yours Outdoors A half-day beginner ice-climbing introduction, and skijoring, where a dog pulls a cross-country skier.
Stay
  • Sir Sam's Inn & Spa An adults-only, four-season historic inn on Eagle Lake with a WaterSpa circuit, lakeside rooms and private cottages with wood-burning fireplaces.
  • Haliburton Forest & Wild Life Reserve Wilderness accommodation in the forest reserve, with winter bookings from late November or early December to late March or early April.

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Winter tip Winterdance tours fill quickly, especially weekends, and late arrivals are charged in full; cancellations made a month or more ahead are fully refunded, and holiday dates (14 to 16 February) cost more.

2 hr 30 min
Photograph · Visit The County
Bay of Quinte, Ontario

Prince Edward County

About 2 hr 30 min by car (213 km from Toronto)Destination Ontario notes public transit is available from Belleville, and the free, year-round Glenora Ferry links Adolphustown to Glenora for drivers coming from the east.

Wineries, craft breweries and cideries in The County stay open twelve months a year, so a winter trip trades summer crowds for quiet tasting rooms. Design-led stays like Wander the Resort and the Drake Devonshire add saunas, cold plunges and lakefront dining.

Time it for Élevage Winter Wine Festival Usually the first weekend of March Break (14 and 15 March in 2026); 2027 dates still to be announced

The Prince Edward County Winegrowers Association's winter festival on how wines age between fermentation and bottling, with a self-guided Tasting Passport and Elevated Tastings.

Do
  • Winter winery and cidery visits Visit The County says its wineries, craft breweries and cideries are open all year, though some adjust hours after summer.
  • Wander the Resort Nordic spa A lakefront Nordic spa on West Lake that takes day guests for dining, lounging or spa visits any time of the year.
  • Sugarbush Vineyards trail A two-kilometre snowshoe or hiking trail at the Hillier winery.
Stay
  • Wander the Resort A modern lakefront resort in Bloomfield with ten cabins, a destination restaurant and a lakefront Nordic spa on West Lake.
  • Drake Devonshire A boutique lakeside retreat on Lake Ontario in Wellington, with a sauna, cold plunge, original artwork and seasonal, locally sourced dining.

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Winter tip Some County businesses cut hours after summer, so Visit The County advises calling ahead before driving to a winery or restaurant in winter.

6 hr
Photograph · Cody Updike / Lake Placid ROOST
Adirondacks, New York, USA Passport needed

Lake Placid & the Adirondacks

About 6 hours (531 km) by carOr fly to Montréal and drive about two hours, or connect to Saranac Lake (SLK), where Cape Air flies from Boston and New York JFK.

Two-time Winter Olympic host Lake Placid lets visitors use the actual venues: skate the 1980 speed skating oval, ride the skeleton track at Mt Van Hoevenberg and ski Whiteface's 3,430-foot vertical. Mirror Lake becomes a free two-mile ice track once it freezes, and the Mirror Lake Inn sits right on it.

Time it for Ski Jumping and Nordic Combined World Cup 5–7 Feb 2027

World Cup ski jumping and Nordic combined on the Olympic venues, the same weekend the Saranac Lake Winter Carnival begins (5 to 14 February).

Do
  • James C. Sheffield Speed Skating Oval Public skating on the outdoor Olympic oval at the Olympic Center, with rentals; adult tickets $15.
  • Whiteface Mountain 3,430-foot vertical drop, 94 trails and 299 skiable acres, plus the Cloudsplitter Gondola to Little Whiteface.
  • Mt Van Hoevenberg 55 km of groomed cross-country trails (5 km with snowmaking) and the Skeleton Experience, a solo head-first run down the Olympic sliding track at about 30 mph for $75.
Stay
  • Mirror Lake Inn Resort and Spa AAA Four-Diamond lakefront resort with a spa, heated pools, a seasonal skating rink on the lake and free snowshoes in winter.
  • The Whiteface Lodge "Whiteface Lodge is tucked away in the serene woodlands of the High Peaks region"; I LOVE NY notes cabin-style suites, heated indoor and outdoor pools, a cinema and its own skating rink.

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Winter tip Mirror Lake typically freezes in January or February and the toboggan chute onto the lake usually opens around Presidents' Day week, weather permitting, so plan lake activities for February rather than December.

6 hr 30 min
Photograph · Tremblant
Laurentides, Québec

Mont-Tremblant

About 6 hr 30 min by car (655 km), per TremblantTremblant says Porter flies from Billy Bishop to Mont-Tremblant International in 65 minutes, with a 38-minute shuttle to the resort, but Porter has not published 2026-27 dates yet. Montréal-Trudeau is 90 minutes away by shuttle.

Tremblant is the biggest ski village in reach of Toronto, with 102 runs over 715 acres and a car-free pedestrian village at the base. Pair skiing with the Scandinave Spa on the Diable River and it works as both a family trip and a couple's weekend.

Do
  • Ski Tremblant 102 runs across 715 acres, with ski-in, ski-out access from the village.
  • First Tracks Paid early access to the north slope 45 minutes before public opening, booked through Fairmont Tremblant.
  • Scandinave Spa Mont-Tremblant Silent outdoor thermal circuit on the Diable River; the basic Thermal Journey takes walk-ins, with reservations for priority access.
Stay
  • Fairmont Tremblant Billed as the only ski-in, ski-out resort in Mont-Tremblant, at the base of the mountain in the village centre, with ski valet and in-room rental delivery.
  • Hôtel Quintessence Thirty-suite boutique hotel on the shore of Lake Tremblant, with a Michelin Key (2024), heated marble floors and private balconies.

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Winter tip Scandinave can reach capacity on busy days; book a time slot and check in within 30 minutes of it to keep priority entry.

On Not An Atlas: Club Med Tremblant Is Now Real

By train 3 trips

4 hr 32 min
Photograph · James Peltzer / Ottawa Tourism
National Capital Region, Ontario

Ottawa

About 4 hr 32 min by VIA Rail, Union Station to Ottawa (VIA average; scheduled trips range from 4 hr 8 min to 4 hr 35 min)VIA lists 54 Toronto to Ottawa departures a week over a 444 km route, so a Friday afternoon train works for a two-night weekend.

The train lands downtown, a short walk from the Rideau Canal Skateway, which the NCC calls the world's largest skating rink at 7.8 km. Winterlude adds Snowflake Kingdom across the river in Gatineau, and Nordik Spa-Nature in Chelsea is about 10 minutes north of downtown, so skating, festival and a spa day fit in one weekend without a car.

Time it for Winterlude 29 Jan – 15 Feb 2027

Canadian Heritage's winter festival with main sites at Confederation Park in Ottawa and Jacques-Cartier Park in Gatineau.

Do
  • Rideau Canal Skateway Skate a 7.8 km stretch of the UNESCO-listed canal for free, open 24 hours a day when ice allows, usually January to early March.
  • Snowflake Kingdom, Jacques-Cartier Park Winterlude's snow-slide and Ferris wheel site in Gatineau, with Afterslide evenings on select nights.
  • Nordik Spa-Nature Hot and cold pools, saunas and Källa, a salt-water floating pool, in Chelsea about 10 minutes north of downtown Ottawa.
Stay
  • Fairmont Château Laurier A historic château downtown between the ByWard Market and the Rideau Canal locks, with rooms looking onto Parliament Hill or Major's Hill Park.

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Winter tip Skateway season depends on the weather, so check the NCC ice conditions page the day before travelling and plan Winterlude activities as a backup.

On Not An Atlas: Remembrance Day 2026: Where Canada Closes · Air Canada and United Add Summer 2027 Routes

5 hr 13 min
Photograph · Victor Diaz Lamich / Montréal en Lumière
Montréal, Québec

Montréal

About 5 hr 13 min by VIA Rail, Union Station to Montréal (VIA average)VIA lists 40 Toronto to Montréal departures a week on the 538 km route.

Montréal runs two winter festivals back to back: Igloofest's outdoor electronic music nights in January and Montréal en Lumière in late February, which closes with a free all-night Nuit blanche. The train arrives downtown and Bota Bota, a floating spa in the Old Port, gives a warm counterweight to the cold.

Time it for Montréal en Lumière 18–28 Feb 2027

Late-winter festival of food, performance and outdoor light installations, ending with Nuit blanche on 27 February.

Do
  • Igloofest Outdoor winter electronic music festival, listed by Bonjour Québec for 14 January to 6 February 2027.
  • Nuit blanche Free all-night program centred on the Quartier des spectacles near Place des Arts, on 27 February 2027.
  • Bota Bota, spa-sur-l'eau Floating spa moored in the Old Port since 2010, adding a second boat designed by Sid Lee Architecture for its 15th anniversary.
Stay
  • Hôtel William Gray Old Montréal hotel overlooking Place Jacques-Cartier, with the Perché rooftop terrace.
  • Ritz-Carlton Montréal On Sherbrooke Street West in the Golden Square Mile since 1912, with 129 rooms including 31 suites.

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Winter tip Nuit blanche falls on Saturday 27 February 2027 inside the Montréal en Lumière window, so book hotels for that weekend early; entry to the main program is free.

On Not An Atlas: Air Canada Keeps Copenhagen and Manchester Flying All Winter · Air Canada Adds Montréal–Seville

6 hr 45 min
Photograph · Mont Sutton
Cantons-de-l'Est, Québec

Eastern Townships

About 5 hr 13 min by VIA Rail to Montréal, then 80 to 90 minutes by car to Lake Massawippi (VIA average plus Manoir Hovey's stated drive)Driving the whole way from Toronto is possible via Montréal and Highway 10 East; no official Toronto drive time was found.

The Townships put four ski hills within 30 minutes of each other (Bromont, Owl's Head, Mont Sutton and Mont Orford) next to lakeside inns and serious spas, so a winter weekend can split cleanly between skiing and doing nothing. It is the snowy version of the same lake villages in our fall weekend plan.

Do
  • Mont Sutton 60 trails and 24 glades, with about 45 per cent of the terrain in tree runs.
  • Spa Eastman Wellness retreat in Eastman that the regional tourism office describes as Canada's first certified forest-bathing (Shinrin Yoku) centre.
  • L'Est GO ski pass A reduced-price pass for unlimited skiing at Bromont, Owl's Head, Mont Sutton and Mont Orford; check the current season's price.
Stay
  • Ripplecove Hôtel & Spa CAA Four Diamond lakeside spa hotel in Ayer's Cliff, steps from Lake Massawippi.
  • Manoir Hovey Relais & Châteaux manor in English gardens on Lake Massawippi in North Hatley, 80 to 90 minutes from Montréal.

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Winter tip Without a car, take VIA to Montréal and arrange a rental or inn transfer there; Manoir Hovey notes Montréal train access is about 140 km away.

On Not An Atlas: The Townships in Colour: A Fall Weekend Plan · Five Townships Towns, One Must-Do Each

A short flight 5 trips

1 hr 20 min
Photograph · Brittany Petronella / NYC Tourism + Conventions
New York, USA Passport needed

New York City

1 hr 21 min nonstop from Billy Bishop to LaGuardia (Air Canada's published schedule); Pearson has nonstops tooAir Canada and Porter fly from both Toronto airports (Porter to Newark from Billy Bishop). The Maple Leaf train takes a scheduled 12 hr 56 min from Union Station to Penn Station (Amtrak timetable).

New York's slow season is when NYC Tourism + Conventions runs its Winter Outing programme: half-price Broadway tickets, prix-fixe restaurant menus and hotel offers. Add free skating at Bryant Park and a January jazz festival and a three-night trip fills easily, and US preclearance at both Toronto airports means you land as a domestic arrival.

Time it for NYC Winter Outing January and February; 2027 dates still to be announced (Restaurant Week ran 20 January to 12 February in 2026)

NYC Tourism + Conventions bundles seasonal deals on hotels, dining, Broadway, tours and museums; Restaurant Week offers two-course lunches and three-course dinners at $30, $45 and $60.

Do
  • The Rink at Winter Village, Bryant Park A 17,000-square-foot outdoor rink beside an open-air holiday market, with free admission (skate rental extra), open 28 October 2026 to 28 February 2027.
  • NYC Broadway Week Twice-yearly programme with 50 per cent off each ticket when you buy two or more; the winter 2027 dates are still to be announced.
  • Winter Jazzfest More than 100 sets across venues such as Le Poisson Rouge, City Winery and Music Hall of Williamsburg, in January; 2027 dates still to be announced.
Stay
  • The Beekman, A Thompson Hotel A historic Lower Manhattan building the hotel calls a "treasure of downtown New York", built around a nine-story atrium, with Temple Court among its restaurants.
  • The Whitby Hotel Firmdale's Midtown hotel on West 56th Street, with a 30-foot pewter bar and a skylit orangery.

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Winter tip US customs is cleared at Pearson before boarding (Terminals 1 and 3; CBP processing runs 3:30 a.m. to 9 p.m.); submit details in CBP's Mobile Passport Control app beforehand, and NEXUS holders can use a dedicated line.

On Not An Atlas: Royal Sonesta Crowns Its Youngest Guests · Hutton Brickyards Hires a Farm-Resort Veteran

1 hr 30 min
Photograph · Audet Photo / Carnaval de Québec
Capitale-Nationale, Québec

Québec City

1 hr 30 min nonstop from Pearson (Porter's published schedule; Air Canada flies the route too)Porter flies Pearson to Québec City 12 times a week on new Embraer E195-E2 jets, leaving Toronto at 8:30 a.m. and 8:45 p.m.

Old Québec in snow is the most complete winter city weekend within reach of Toronto: Carnaval de Québec in February, the Dufferin Terrace toboggan slide below the Château Frontenac, and North America's only ice hotel 20 minutes away. Morning and evening Porter departures from Pearson make a Friday-to-Sunday trip workable.

Time it for Carnaval de Québec 5–14 Feb 2027

Québec City's winter carnival with Bonhomme, parades, a night parade and canoe racing on the St. Lawrence.

Do
  • Hôtel de Glace North America's only ice hotel, built from 3,000 blocks of ice at Village Vacances Valcartier, 20 minutes from downtown; open for visits and overnight stays in winter.
  • Dufferin Terrace Toboggan Slide A slide built in 1884 beside the Château Frontenac, open December to March, up to four riders per toboggan.
  • Chez Muffy Four-diamond restaurant in an 1822 maritime warehouse at Auberge Saint-Antoine, cooking with produce from the hotel's own garden on Île d'Orléans.
Stay
  • Fairmont Le Château Frontenac The castle hotel above Dufferin Terrace, which runs the winter toboggan slide and a shuttle to the Hôtel de Glace restaurant (returning January 2027).
  • Auberge Saint-Antoine Relais & Châteaux museum hotel at the foot of the old city walls, with archaeological artefacts displayed in rooms and public spaces.

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Winter tip The Hôtel de Glace ice restaurant served Thursday to Saturday from mid-January last season, and reservations included a round-trip shuttle from the Château Frontenac; book that dinner when booking flights.

On Not An Atlas: Air Canada and United Add Summer 2027 Routes · Globus and Cosmos Tell Clients to Unpack

1 hr 30 min
Photograph · Kyle Klein / Meet Boston
Massachusetts, USA Passport needed

Boston

1 hr 29 min nonstop from Billy Bishop to Logan (Air Canada's published schedule); Pearson has nonstops tooPorter flies from Pearson (from 14 May 2026) and Air Canada from both Toronto airports; Air Canada's Billy Bishop service runs three times a day.

Meet Boston's Frostival turns late winter into a reason to go: a free lodge of firepits, curling and hot chocolate in Copley Square, plus a Ferris wheel in February. The Isabella Stewart Gardner Museum's courtyard runs its Midwinter Tropics and orchid displays through the same weeks, and both Toronto airports have nonstops.

Time it for Boston Frostival 22 Jan – 5 Mar 2027

Meet Boston's citywide winter festival, anchored by a free lodge in Copley Square with curling, firepits, trivia nights and silent-headphone cinema.

Do
  • Frostival Lodge, Copley Square Free outdoor lodge with six furnished living rooms, glass-enclosed firepits, curling and weekly free activities, open daily 11 a.m. to 9 p.m.
  • Isabella Stewart Gardner Museum courtyard The courtyard rotates seasonal plantings: A Holiday Garden (December to January), Midwinter Tropics (January to February) and Orchids (February to March).
  • Boston Common Frog Pond City-owned year-round facility on Boston Common that becomes a skating rink in winter, managed by The Skating Club of Boston; 2026-27 dates not posted as of 19 Oct 2026.
Stay
  • Fairmont Copley Plaza Opened in 1912 on Copley Square, steps from the Frostival Lodge, with Oak Long Bar + Kitchen and a resident hotel dog since 2004.
  • The Newbury Boston Set "within a 1927 Back Bay landmark" with salons overlooking the Public Garden.

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Winter tip US Preclearance opened at Billy Bishop in March 2026, so downtown travellers can clear US customs at YTZ before flying Porter or Air Canada to Logan; at Pearson, use CBP's Mobile Passport Control app before arriving.

On Not An Atlas: Boston's Frostival: Drones, a Lodge and a 75-Foot Wheel · Delta Adds Daily Boston–Reykjavík for 2027 · Four Seasons Boston Now Rents Suites by the Month

1 hr 55 min
Photograph · Choose Chicago
Illinois, USA Passport needed

Chicago

1 hr 55 min nonstop from Billy Bishop to O'Hare (Air Canada's published schedule); Pearson has nonstops tooPorter moved its Billy Bishop Chicago service to O'Hare on 1 September 2026 with three daily flights, and Air Canada flies both YYZ and YTZ to O'Hare.

Two Toronto airports and two airlines fly nonstop to O'Hare, and Chicago leans into winter rather than hiding from it: Choose Chicago lists the Maggie Daley Park Skating Ribbon, a rooftop rink at The Peninsula and free indoor escapes like the Lincoln Park Conservatory. Chicago Restaurant Week, with $30 lunches and $45 or $60 dinners, lands in the coldest stretch of the season.

Time it for Chicago Restaurant Week 22 Jan – 7 Feb 2027

Prix-fixe brunch and lunch at $30 and dinner at $45 or $60 across more than 500 restaurants, opening with the First Bites Bash at the Field Museum. Dates as posted by Choose Chicago; confirm before booking.

Do
  • Maggie Daley Park Ice Skating Ribbon A winding outdoor skating path with skyline views; timed two-hour sessions run 13 November 2026 to 7 March 2027.
  • The Peninsula Sky Rink A 2,100-square-foot rink on The Terrace above Michigan Avenue, with a chalet serving hot drinks; skate rental proceeds go to children's charities.
  • Garfield Park and Lincoln Park conservatories Free glasshouses for a warm-up; Choose Chicago describes Garfield Park's two acres of greenhouse space as one of the largest conservatories in the nation.
Stay
  • The Peninsula Chicago Michigan Avenue hotel at 108 East Superior Street whose seasonal Sky Rink on The Terrace is billed as the city's only hotel skating rink.
  • Chicago Athletic Association An 1893 Venetian-Gothic former private club on Michigan Avenue, restored as a 240-room hotel with several bars and restaurants.

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Winter tip Skating Ribbon tickets are sold for specific sessions with no waitlist; reservations are released in blocks starting 2 November 2026, so book weekend sessions as soon as they drop.

On Not An Atlas: Chicago, Ten Years Running: A Winter City Break · Royal Sonesta Crowns Its Youngest Guests

2 hr 30 min
Photograph · Jean-Sébastien Chartier-Plante / Le Massif de Charlevoix
Charlevoix, Québec

Charlevoix

About 2 hr 30 min: a 1 hr 30 min flight to Québec City, then about an hour by car (Le Massif)Porter flies Pearson to Québec City 12 times a week; from there, Le Massif and Baie-Saint-Paul are about an hour's drive along Route 138.

Charlevoix gives skiing with a view of the St. Lawrence: Le Massif bills itself as the highest vertical drop east of the Rockies, with runs that seem to drop into the river. Baie-Saint-Paul adds a design-led farm-estate hotel with a Nordic spa, so it reads as a slower, more rural follow-on to a Québec City weekend.

Do
  • Le Massif de Charlevoix Ski resort with the highest vertical drop east of the Rocky Mountains and views over the St. Lawrence River.
  • Spa Nordique Le Germain Outdoor Nordic spa at Le Germain Charlevoix on the edge of Baie-Saint-Paul.
  • Snowmobile from La Malbaie Fairmont Le Manoir Richelieu sells winter snowmobile packages on Charlevoix trails between the mountains and the river.
Stay

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Winter tip The Train de Charlevoix does not run in winter (its 2026 season is 5 June to 1 November), so plan on a rental car or hotel transfer from Québec City.

The season

The winter calendar

The dates that make a winter trip, as the organisers have announced them. Events still waiting on 2027 dates are listed with their trip, not here.

December 2026

  • 18 Dec 2026 – 10 Jan 2027Lights On StratfordStratford

January 2027

February 2027

Ontario's Family Day is Monday 15 February 2027 (with a PA day on the Friday in Toronto public schools) and March Break runs 15 to 19 March. Trains, Québec flights and spa bookings go early for both. School holidays in Ontario →

Questions

Quick answers

What is the best winter weekend getaway from Toronto?

For two nights without a long drive, Niagara-on-the-Lake, Blue Mountain and Elora are each about 90 minutes by car. Québec City and Boston are about an hour and a half by air, and Ottawa is about four and a half hours by train, which lands you a short walk from the Rideau Canal Skateway.

What is a romantic winter getaway near Toronto?

Elora Mill Hotel & Spa (about 90 minutes away) pairs a gorge-side setting with a spa; Prince Edward County has Wander the Resort and the Drake Devonshire; Niagara-on-the-Lake has the Prince of Wales and Pillar and Post with its 100 Fountain Spa; and Sir Sam's Inn in Haliburton is adults-only.

When are Winterlude, Carnaval de Québec and Montréal en Lumière in 2027?

Winterlude runs 29 January to 15 February 2027 in Ottawa and Gatineau. Carnaval de Québec runs 5 to 14 February 2027. Montréal en Lumière runs 18 to 28 February 2027, with Nuit blanche on Saturday 27 February.

What are the best winter getaways from Toronto by car?

The closest are Blue Mountain & Collingwood (1 hr 30 min), Elora & Fergus (1 hr 30 min), Niagara-on-the-Lake (1 hr 30 min), Stratford (2 hr). Times are the tourism boards' own figures from downtown in normal conditions; allow more in snow.

Where can you go from Toronto by train in winter?

VIA Rail runs from Union Station to Ottawa (4 hr 32 min), Montréal (5 hr 13 min), Eastern Townships (6 hr 45 min), which skips winter driving entirely. Book early for Family Day weekend and March Break, when trains sell out.

Do I need a passport for these trips?

Only for the US picks: Boston, Chicago, New York City, Lake Placid & the Adirondacks, Buffalo. Canadians need a passport or NEXUS card to fly to the US; by land, a passport or NEXUS card also works. Everything else on this list is in Canada.

Sources (124)

Checked 20 October 2026. Dates change: confirm with the event or hotel before you book. Spot something out of date? Tell us via our corrections policy.

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