Niagara’s vineyards to Toronto’s downtown views
Travel through the lush vineyards of Niagara to downtown Toronto, Canada on a five-day road trip.
Experience historic small-town charm in the heart of Ontario’s famous wine region and vibrant energy and excitement in the nation’s largest city. Enjoy top cuisine, local culture, boutique shopping and exceptional wine along the way.
And the best part? You’ll love how much further your dollar goes in Ontario, Canada.
Border crossing information
Travellers to Canada must present a valid passport or NEXUS card. Find out what else you’ll need to know to cross the border into Canada.
Before travelling, check border wait times.
Border crossing locations from New York State into the Niagara region in Canada include:
Day 1 - 2: Niagara-on-the-Lake
- Approximate distance and travel time: from Niagara Falls 15 miles (25 kilometres), 25 minutes, from Fort Erie 30 miles (48 kilometres) 40 minutes
Niagara-on-the-Lake lives up to its reputation as “the prettiest town in Ontario” with well-preserved Victorian architecture, scenic waterfront views and lush vineyards nearby.
Where to stay in Niagara-on-the-Lake
Combine the quaint small-town charm and romance of a historic hotel with luxurious, modern amenities and spa services at one of three Vintage Hotels.
Prince of Wales, 6 Picton Street, Niagara-on-the-Lake
Queen’s Landing, 155 Byron Street, Niagara-on-the-Lake
Pillar and Post, 48 John Street West, Niagara-on-the-Lake
Stay at one of Niagara’s Finest Hotels, three deluxe boutique properties in Niagara-on-the-Lake’s romantic Old Town.
The Charles Hotel, 209 Queen Street, Niagara-on-the-Lake
Harbour House Hotel, 85 Melville Street, Niagara-on-the-Lake
The Shaw Club Hotel, 92 Picton Street, Niagara-on-the-Lake
Riverbend Inn & Vineyard is a striking, Georgian-style mansion located along what many consider to be Ontario’s prettiest drive, the Niagara River Parkway, and surrounded by vineyards and gardens.
Location: 16104 Niagara Parkway, Niagara-on-the-Lake
Niagara-on-the-Lake Bed & Breakfast Association features charming and cozy B&B options.
Things to do in Niagara-on-the-Lake
Wine tours and tastings
Niagara-on-the-Lake’s main attraction is the award-winning wine. In fact, this historic town is home to some of Canada’s most established and oldest vineyards, some dating back over four decades.
Wayne Gretzky Estates Winery is a 23,000-square-foot (approximately 2,127 hectares) facility founded by the Great One himself. It also happens to be Ontario’s first combined winery and distillery.
Location: 1219 Niagara Stone Road, Niagara-on-the-Lake
Find more wineries with our wine lover’s guide to Niagara, Canada.
History and culture
In 1792, Niagara-on-the-Lake became the first capital of Upper Canada (later the Province of Ontario), after being settled by British Loyalists. The town’s 19th-century architecture has been carefully preserved and the entire old town, centred around a charming main street complete with a cenotaph clock tower, is a designated National Heritage Site.
Step back in time for a glimpse of military life in the 19th century during the War of 1812 at Fort George, a National Historic Site and former military post.
Location: 51 Queen’s Parade, Niagara-on-the-Lake
Founded in 1962, the Shaw Festival in Niagara-on-the-Lake stages world-class plays in three different theatres. With many productions running through the fall, along with classic holiday performances, the Shaw offers a fun and entertaining theatre experience.
Location: 10 Queen’s Parade, Niagara-on-the-Lake
Sightseeing and shopping
Add a little excitement with a helicopter ride over the falls with Niagara Helicopter Tours. In addition to spectacular views of the falls, on a clear day you’ll see the outline of Toronto to the north, and the shores of Lake Erie to the south.
Location: 3731 Victoria Avenue, Niagara Falls
Parks and gardens
Stroll around Queen’s Royal Beach, located at the foot of King Street, with great views of the Niagara River. While there, don’t miss the Royal Gazebo — a great place to sip a takeout coffee from nearby local favourite Balzac’s Coffee Roasters.
Location: 45 Front Street, Niagara-on-the-Lake
The Niagara Region is home to numerous parks and natural experiences.
Visit the Botanical Gardens, a 99-acre (40 hectares) floral oasis and Butterfly Conservatory featuring over 2,000 colourful tropical butterflies floating freely among lush, exotic blossoms and greenery. Hourly parking is available.
Location: 2565 Niagara River Parkway, Niagara-on-the-Lake
Where to eat in Niagara-on-the-Lake
Sunday brunch between 11:00 a.m. and 2:00 p.m. at the Queenston Heights Restaurant includes delicious Belgian waffles and eggs benedict with a breathtaking view of the Niagara River. Make reservations online.
Location: 14184 Niagara River Parkway, Niagara-on-the-Lake
Located in the Shaw Club hotel, Zees Grill is excellent, for breakfast, lunch or dinner.
Location: 92 Picton Street, Niagara-on-the-Lake
The Clubhouse Restaurant at Niagara-on-the-Lake Golf Club has wonderful views of Lake Ontario. Check the calendar of events to see what entertainment is on the patio.
Location: 143 Front Street, Niagara-on-the-Lake
Dinner resembles a work of art at local favourite Masaki Sushi in Niagara. Featuring world-class seafood brought in straight from Japan, this hotspot offers a modern twist on traditional Japanese dining.
Location: 60 Picton Street, Niagara-on-the-Lake
Treadwell Cuisine was hailed as one of Canada’s Top 10 Wine Restaurants by Wine Enthusiast Magazine. For an extra treat, homemade fudge is made daily in small batches next door at Maple Leaf Fudge.
Location: 114 Queen Street, Niagara-on-the-Lake
Meals are paired perfectly with the wine at these Niagara Region winery restaurants.
Day 3: Twenty Valley
- Approximate distance and travel time: 24 miles (40 kilometres) 40 minutes
The Twenty Valley region along the Niagara Escarpment is a sub-appellation of the Niagara Peninsula wine region. Its many quaint villages are home to mostly family-run boutique wineries and vineyards and worth further exploration.
The tiny village of Jordan in Twenty Valley is brimming with charm and a surprising number of wineries and independent boutiques. Cave Spring Cellars is a mainstay of the village. Enjoy a pub lunch at Jordan House or a meal at Inn on the Twenty Restaurant.
Day 3 - 5: Toronto
- Approximate distance and travel time: 70 miles (110 kilometres),1.5 hours
Canada’s largest and most cosmopolitan city, Toronto is a multicultural mosaic of art, heritage, cuisine and entertainment. From renowned art galleries to graffiti culture, haute couture to vintage shopping and fine dining to market food stalls, discover the best of Ontario’s trendiest city.
Where to stay in Toronto
Hotel X is Toronto’s first luxury resort-style hotel that features tennis courts, a movie theatre, rooftop pool and bar and even deluxe picnic packages. Secure parking available onsite.
Location: 111 Princes' Boulevard, Toronto
A mix of hotel and residences in Toronto’s Entertainment District, Bisha Hotel features suites designed by artist Lenny Kravitz, a rooftop patio with infinity pool and the upscale KOST restaurant on the 44th floor. Valet parking is available.
Location: 80 Blue Jays Way, Toronto
1 Hotel Toronto strikes the perfect balance between urban and cottage chic with reclaimed and upcycled materials, natural design elements plus high-end perks like a rooftop pool.
Location: 550 Wellington Street West, Toronto
With its stylish décor, top-notch service and signature cocktails, you won’t want to leave the Shangri-La Toronto, especially if you treat yourself to a visit at the Miraj Hamman Spa.
Location: 188 University Avenue, Toronto
Things to do in Toronto
Art and culture
Explore provocative and powerful exhibitions at the Art Gallery of Ontario (AGO), one of the largest art collections in North America as well as the Museum of Contemporary Art (MOCA).
AGO, 317 Dundas Street West, Toronto
MOCA, 158 Sterling Road, #100, Toronto
One of Toronto’s more unusual attractions, the Bata Shoe Museum explores the history of shoes with a unique collection of more than 13,000 exhibits spanning 4,500 years.
Location: 327 Bloor Street West, Toronto
Showcasing the range and significance of Islamic arts, the Aga Khan Museum and gardens is a one-of-a-kind experience. It’s about a 15-minute drive north of downtown, parking is available.
Location: 77 Wynford Drive, Toronto
Sightseeing and shopping
From high fashion to vintage markets, there’s a shopping experience for just about every whim and fancy. Chart your shopping course with the Toronto Neighborhood Shopping Guide.
Take in the sights of the city from above on a helicopter tour with Toronto Heli Rides.
Location: Billy Bishop Toronto City Airport Hangar 1, 2 Eireann Quay, Toronto
Explore the city’s culinary scene on a walking tour with local foodies like Culinary Adventure Co. or Tasty Tours Toronto.
Culinary Adventures, 92 Front Street East, Toronto
Tasty Tours, 30 St Andrew Street, Toronto
Festivals and celebrations
North by Northeast (NXNE): Canada’s answer to NXNW showcasing the best new and emerging talent (June 13-17).
Pride Toronto: The largest Pride event in Canada celebrating the 2SLGBTQ+ community (June 25).
Toronto Fringe Festival: Alternative, unconventional and entertaining theatre (July 5-16).
Honda Indy: A premier motorsports event at Exhibition Place (July 14-16).
Toronto Caribbean Carnival: An epic event showcasing the best of Caribbean culture, music and food (August 3-7).
Where to eat and drink in Toronto
Local favourites to start your day, whether that’s breakfast or brunch, include Café Boulud in Yorkville, Union on Ossington, Bonjour Brioche Bakery and Café and Lady Marmalade in Toronto’s east end.
Café Boulud, 60 Yorkville Avenue, Toronto
Union, 72 Ossington Avenue, Toronto
Bonjour Brioche, 812 Queen Street East, Toronto
Lady Marmalade, 265 Broadview Avenue, Toronto
Toronto is the first Canadian city to be recognized in the MICHELIN Guide, book reservations at one of Toronto’s recently awarded MICHELIN starred restaurants. Several restaurants were also awarded with the MICHELIN Bib Gourmand Award for menu items at great value.
The Distillery District is a pedestrian-only entertainment neighborhood that’s home to a cluster of bars, cafés, restaurants, bakeries, brewpubs and a chocolate-maker. Naturally, there’s also a distillery in the district, enjoy a tour and tasting at Spirit of York Distillery.
Location: The Distillery District extends from Parliament Street to Cherry Street, south of Front Street East, Toronto
Once a bohemian hub, Yorkville is now known for its high-end retail shopping and some of Toronto’s finest eateries and restaurants, such as Sassafraz, Buca Osteria & Bar, Café Boulud and Alobar. Modern and upscale, the menu at W Hotel reflects Toronto’s multicultural culinary scene.
Location: East of Avenue Road and north of Bloor Street East, Toronto
The St. Lawrence Market is located in a large, historic brick building that bustles with organic groceries, bakeries, cheese and olive vendors, restaurants and food stalls. Try the famous peameal bacon sandwich from Carousel Bakery or Paddington’s Pump.
Location: 93 Front Street East, Toronto
One of the city’s most eclectic, colorful and fiercely local neighborhoods, Kensington Market is a mix of boho, vintage shops, fresh vegetable stalls, cheese and spice shops, bakeries, trendy bars and an array of fusion restaurants tucked into the historic Victorian architecture. You’ll find everything from Jamaican patties to Chilean empanadas.
Location: Bordered by Spadina Avenue, Dundas Street, Bathurst Street and College Street, Toronto
Extend your trip to Ontario with more road trip itineraries.
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Last updated: August 22, 2023