When is the May Long Weekend in 2021? (and Victoria Day Trip Ideas from West to East)

Though Whistler is in the midst of slush season (with rock-bottom hotel discounts to match), we’re looking for a wine country escape this May Long Weekend to the Okanagan Valley. Pull over to admire the fruit orchards in bloom with rosy red cherries, golden apricots and indigo plums. A stay on the water at Cove Lakeside Resort or up on the hill at Chez Nicole may fit the bill.

Heading westwards through the Rockies for the Victoria Day Long Weekend can go two ways. Depending on the weather conditions, it could mean some high-elevation skiing at Sunshine Village or Marmot Basin, or some tranquil Spring hiking at lower elevations in K-Country. As the shoulder season (valley?) between summer and winter visitor peaks, you can expect some top hotel deals at spots like the Rimrock Resort in Banff.

As Manitoba’s cultural oasis, Winnipeg is a top contender this Victoria Day for a city break from Alberta or Ontario. Pack your DSLR and follow our Photographic Winnipeg guide around the city. From the Canadian Museum for Human Rights to the Assiniboine Forest, we’ll show you the best sides of The Peg. Make it a historic stay with a room at the Fort Garry Hotel, made all the loveable by a morning tea and cookie service. Macro lenses at the ready!

Celebrate the “May 2-4” in its truest form and pack a case of your favourite brew on your trip to the lake. With Manitoba fishing season opening right in time for Victoria Day, load up your roads, lures and nets to snag a few of the season’s first catfish. A round of golf or a sail on Lake Winnipeg may also figure into your Interlake road trip stops. trivago users are big fans of the smart rooms at the Canalta Selkirk, which puts you close to the city’s historic churches.

Strategically situated between Toronto and Niagara Falls, for less than $200 roundtrip you could be in Southern Ontario over the May Long Weekend. From the airport, it’s only an hour’s drive to charming Niagara-on-the-Lake and its wineries. Then, another half-hour due south to the heart of Niagara Falls. You’ll arrive right in time for the region’s famous tulips in bloom as well — all that’s left to do is snag a hotel deal!

Isn’t it about time we all gave Ottawa another chance? Drive up to Trudeautown this May weekend and divide your time between the city’s essential sights and sliding across to Quebec’s Gatineau Park (just ten minutes from Downtown). In case you stay later in the week (May 23-27) check out the buzz around The Happening in Wellington West, otherwise strolling Bank Street in The Glebe will do the trick!

There’s no escaping the majesty of Charlevoix’s beauty even on the most basic drive following the Saint-Lawrence on Highway 138. Bring along your hiking boots to Hautes-Gorges-de-la-Rivière-Malbaie National Park or sit back and leave it to the captain of your bateau-mouche to steer you down the Malbaie River. If it’s not the Fairmont Manoir Richelieu you’re after, then it has got to be an auberge. An overnight stay, hosted by Odile and Arnaud, at La Châtelaine in Pointe-au-Pic will give you a real taste of the Belle Province.

Fly over to New Brunswick this May Long Weekend and take it slow as you pass from St. Andrews along the Bay of Fundy through Saint John to Moncton. Then double-back through the province’s Acadian communities along the Gulf of St. Lawrence before checking into Fredericton. See for yourself that this Gateway to the Maritimes is more than just its Flowerpots!

All Haligonians (and Nova Scotians) know that a Victoria Day by the water is a question of Where rather than How. Whether you’re more the type to take it easy in Annapolis Royal or the type to savour the thrill of the Cabot Trail’s hair-raising curves, you’ve got all that you need this May Long Weekend within driving distance of Halifax.

You may know NYC from previous visits, but for a city of this scale, you can easily spend a three- to four-day weekend just taking in one of its boroughs. You’ve heard the hype around Brooklyn, but now it’s your time to go incognito with the cool kids this May Long Weekend. Take a look at our top affordable hotel picks and a shortlist of things to do in Brooklyn.