Group at Rendezviews patio Toronto.

RendezViews, Toronto | Destination Ontario

Trendy areas to visit in Ontario

Group at Rendezviews patio Toronto.

RendezViews, Toronto | Destination Ontario

Explore a collection of trendy areas within Ontario’s big cities and small towns. These cool places attract travellers from around the world with their unique charm. In popular destinations like Toronto, Ottawa and Prince Edward County, you’ll find hidden gems with thrilling experiences that celebrate Ontario’s diverse landscape and history. This guide explores why a visit to this province’s most hip cities is a must for culture lovers, foodies and entertainment enthusiasts.

Prince Edward County

Location: Three hours east of Toronto by car

Couple on rocky beach by Drake Devonshire.
Drake Devonshire, Prince Edward County | Destination Ontario

With lush wineries and vineyards, a thriving arts and culture scene, farm-to-table restaurants and picturesque island vibes, Prince Edward County is one of Ontario's best kept secrets. The area has become a magnet for young entrepreneurs and budding artists, fostering a spirit of innovation and creativity in this county’s historic towns.

Feast at delicious restaurants

One of the top hotels in the county, Drake Devonshire has an on-site restaurant where you can enjoy hearty foods like steak frites, French onion soup, County pickerel and more.

If you love trying new cooking styles, stop by La Condesa for authentic Mexican cuisine with mezcal-based cocktails, or Flame + Smith for lamb or steak prepared with sustainable, woodfire cooking.

At night, the new Adega Wine Bar offers tapas-style dishes such as cheese, bread and olives, plus an extensive collection of curated wines from around the world. Alternatively, you can play lawn games and sample tropical-themed cocktails and snacks with pineapple, orange, grapefruit and more at the outdoor Old Salt.

Shop for food from nearby farms and producers at the Picton Town Hall Farmers’ Market, where many restaurants source local ingredients. The market runs every Sunday from May to October. Or eat some of the best foods in the county at the Taste Prince Edward County Food Festival, an annual festival in Ontario held every September.

Embark on a fun weekend getaway

Take a self-guided tour of the Prince Edward County Arts Trail to discover inspiring artworks at unique artist studios and historic galleries like the Oeno Gallery and ANDARA Gallery.

If you’re an aspiring wine connoisseur, travel on a private wine tour through the top wineries in the county with Prince Edward County Wine Tours or Get Corked PEC Tours. You can try creative cocktails at the Kinsip Distillery. Enjoy wine tastings at Closson Chase Vineyards and at wineries all across the county.

Explore over 30 hectares of picturesque farmland at The Eddie Hotel & Farm, a Loyalist architectural site complete with a pond, orchard and expanded gardens. Here, you can listen to live music or browse the local farmers’ market on Saturday mornings. Stay overnight in the main house suites or a private cottage.

Lounge on beautiful beaches

Prince Edward County is known for having some of the most spectacular beaches in the province. Shielded from Lake Ontario by a long ribbon of sand, North Beach Provincial Park is a great place for a quiet picnic or private swim. Visit the popular Outlet Beach at Sandbanks Provincial Park to relax on two kilometres of soft sand sloping into gentle, warm freshwater. Or go for a leisurely stroll along the stony Wellington Beach, a family-friendly boardwalk that draws hundreds of walkers and cyclists every summer.

Access to the beach is on a first-come, first-serve basis, and without a reservation you may be turned away. To visit the beach, you can book a reservation online up to five days in advance. If you’re arriving by bar, be sure to select “Seasonal Vehicle Permit Holder” for free parking.

Stay overnight in hip accommodations

The hotels in Prince Edward County are as trendy as the region itself. Check into the classic roadside motel, Drake Motor Inn—you can’t miss its bright, colourful exterior at the gateway of Wellington. With its retro-designed rooms, contemporary art installations, game room and outdoor terrace with a fire pit, you’re in for a stay that combines vintage flair with modern amenities.

For a relaxing, laid-back vacation, The June Motel offers good vibes and good wine in the quaint town of Picton. Sleep in a tiny cabin close to the beautiful shores of the Bay of Quinte at the Lil Crow Cabin. Some other trendy places to stay in Prince Edward County include Angeline’s Inn in Bloomfield, The Royal Hotel in Picton and The Lakeside Motel in Wellington.


Location: 3.5 hours east of Toronto by car

The exterior of the Rosemount Inn
Kingston | The Rosemount Inn

A rich blend of historic charm, diverse restaurants and other eclectic hotspots make Kingston a trendy city that appeals to a wide range of tastes. 

Discover local culture and heritage

Walk behind the walls of Canada’s oldest and most notorious maximum security prison, the Kingston Penitentiary. Jam out at the Kingston Music Festival, the largest outdoor Reggae and Dancehall music festival in the Greater Toronto Area. If you’re an art lover, check out Martello Alley, a twisting, historic alleyway lined with colourful local art, or Modern Fuel, a contemporary art gallery situated by the water. Alternatively, admire historic and contemporary Canadian and Indigenous art at the Agnes Etherington Art Centre.

Enjoy a memorable night

Seek solace on your own private patio and deep soaker tub in the sleek Frontenac Club, which also features unique curated artwork within its historic limestone walls. The majestic Smith Hotel was formerly a church located in Kingston’s historic centre, close to the city’s shops and restaurants, and the hotel retained many of its industrial accents like its steel beams and concrete floors. Or enjoy an enchanting stay at the Victorian house turned boutique hotel, The Rosemount Inn, which offers gourmet breakfast, romantic fireplace rooms and one of the best spas in Ontario.

These are just a few of the best places to stay in Kingston, Ontario—explore other great accommodations in the city.


Location: Two hours southwest of Toronto by car

Known as “The Hammer” and “The Waterfall Capital of the World,” Hamilton boasts natural beauty, a burgeoning food culture and bustling nighttime entertainment.

Navigate scenic waterfalls

Hamilton is known for its incredible waterfalls. View the stunning 21-metre cascade of the Tiffany Falls, which is particularly breathtaking during the spring melt and when it’s frozen in the winter. The classic ribbon waterfall, the Devil’s Punchbowl, was formed by melt-water rivers at the end of the last ice age over the Stoney Creek Escarpment. Ontario’s famous Waterfront Trail cuts through Hamilton and provides a dense network of pedestrian and cycling paths along the bluffside parks, shops and restaurants.

Indulge in a culinary experience

Dive into the morning with brunch plates at Undefined, where you’ll enjoy comfort foods like waffles, benedicts and burgers. For dinner, dine on French cuisine in a fashionable setting at The French or sample gluten-free tacos and tequilas at The Mule Hamilton.

Experience Hamilton’s exciting nightlife and sip on premium craft beers at Collective Arts Brewing—make sure you keep the limited edition cans as a souvenir. Or try hard cider made from Ontario heritage apples at West Avenue Cider.

For more delicious food options, check out the restaurants on Hamilton’s popular James Street.

Make your night special in a stylish hotel

Situated on the bustling Augusta Street in Hamilton’s downtown core, The Laundry Room is a boutique hotel with a funky rooftop bar and modern rooms with retro decor.

Alternatively, experience a rejuvenating retreat at The High Acre Hotel. With its private ensuite, infrared sauna, steam shower and fresh breakfasts, you’ll find the perfect oasis to unwind and recharge for the next day.


One of the most culturally diverse cities in the world, Toronto’s neighbourhoods feature a rich tapestry of ethnicities and cultures. Explore hip eateries, boutique shops and colourful markets.

Chalk street art spelling Kensington Market in front of a brightly coloured green car.
Kensington Market, Toronto | Destination Ontario

Visit the trendiest neighbourhoods in Toronto

Queen West

Toronto’s Queen West neighbourhood boasts an impressive culinary scene with a variety of local and international restaurants, cafes and bars. Treat yourself to classic Italian fare like homemade pasta and thin-crust pizzas at Terroni or enjoy a traditional Chinese “dim sum” meal made with 100% plant-based ingredients at PLANTA Queen.

Filled with vintage stores and high-end fashion outlets, Queen West is also considered the fashion district of Toronto. To keep up with the latest fashion trends, you’ll want to go boutique shopping in Toronto’s Queen West and find high-end clothing, accessories and footwear.

Ossington Avenue

Popular with the city’s young and creative crowd, the Ossington Avenue strip in Toronto is recognized for its distinct hipster vibe.

Start your day with a steaming coffee roast and flaky baked goods from the Bohemian coffee shop Sam James. For main courses, there are tons of great restaurant options—vegetarians will love Mandy’s for its fresh gourmet salads and power bowls, while meat lovers will enjoy the locally sourced beef butchered in-house at Côte de Boeuf.

Check out Ossington’s famous nightlife scene with a visit to Bar Bowie. Hidden underneath a laundromat, the place offers classic cocktails and martinis in a speakeasy-like atmosphere with great music and dancing. If you prefer creative beers and seasonal dishes, head to The Bellwoods Brewery, also known for its array of tasty non-alcoholic beverages.

If you’re a fashionista, shop at upscale stores like Tiger of Sweden and other great local boutiques.

King Street West

Dine on Canadian specialty dishes at the members-only Soho House Toronto, which also showcases breathtaking city views and the chance to walk through the restaurant’s curated art collection. Snack on light bites and wellness cocktails at Harriet’s Rooftop at 1 Hotel Toronto, one of the top rooftop bars in Toronto. Sit in a cabana beside the outdoor pool at Lavelle, where you’ll enjoy Brazilian and Japanese dining. Or get a taste of the Californian lifestyle with seafood and vegetarian dishes at KŌST, located atop the Bisha Hotel’s 44th-floor rooftop.

Kensington Market

With delicious foods, lively festivals, local services and one-of-a-kind wares, Kensington Market in Toronto is a vibrant and diverse neighbourhood, showcasing shops, grocers,art and culture centres, grocers, restaurants, bars and more.

Pair your delicious seafood dish at Grey Gardens with a drink from this quality restaurant’s extensive wine list. A recent winner of Toronto’s MICHELIN Bib Gourmand guide, you’re sure to have an exceptional culinary experience at one of the best restaurants in Toronto. If you’re looking for something more casual, try Fresco’s Fish and Chips or Jumbo Empanadas, where you can eat and chat with the area’s close-knit community.

There are many fantastic bars with live music in Toronto where you can party all night long. Handlebar has a quirky, hip atmosphere where you can join the dance floor and sing on open mic nights. Savour cocktails and Armenian dishes on the cozy outdoor patio at The Oud & the Fuzz.

Book a room at an upscale locale

There are tons of cool hotels to choose from in Toronto. Check out this list of top places to stay in Toronto to find the right fit for you.


As Canada’s capital city, Ottawa is a popular destination for its iconic landmarks, incredible culinary scene, regular cultural events and modern attractions.

Make a trip to Ottawa’s coolest neighbourhoods like Wellington West and Hintonburg. Immerse yourself in creative vibes at numerous art galleries, public art installations and specialty clothing shops.

Whenever you’re hungry, check out this list of where to eat in Ottawa for the best breakfast, lunch, dinner and late-night eateries around the city.

Later, catch a dynamic concert or dance party at Live on Elgin or spend a quiet night at Flora Hall Brewing, a favourite among locals for its full bar, chill vibe and signature drinks list.

Spend the night in a trendy room at boutique hotels in downtown Ottawa, such as ARC The Hotel, Le Germain and Alt Hotel. With their close proximity to the city centre, it’s easy for you to walk to the city’s top restaurants, bars and event spaces.

Last updated: June 6, 2024

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