Road trips from Detroit: Charming small-town or big-city getaways

Travel to charming towns or explore Ontario's cities in this road trip from Detroit into Canada.

A bridge crossing the river, leading to a building.

Court House Bridge|Destination Stratford

Visit some of Canada’s prettiest small towns or experience the best of urban adventure just across the border in Ontario this fall. Take in a show at the Stratford Festival, North America’s largest classical repertory theatre company and experience what National Geographic has called “Ontario’s Best Small Town Escape” or head to Windsor, Hamilton and Toronto for big-name entertainment, pro-sports and epic nightlife.

Choose your trip: 

  1. Charming Small-Town Getaway Itinerary: Detroit to Stratford, St. Jacobs and Elora
  2. Getaway to Big City Entertainment Itinerary: Detroit to Windsor, Hamilton and Toronto

Find more road trip itineraries in Ontario, Canada 

Documentation Needed

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.

Charming Small-Town Ontario Getaway

Explore the charm and character of idyllic, walkable small towns of Stratford, St. Jacobs and Elora that are big on the arts, world-class theatre, history, nature, boutique shopping, good food and some of Ontario’s finest micro-breweries.

A massive stone building dominates the landscape with blue flowers in the foreground.
Elora Mill Hotel & Spa | Destination Ontario

Day 1 - 2: Detroit to Stratford

Billed as Ontario’s premier arts town for the annual Stratford Festival theatre, Stratford is also known for Victorian architecture, beautiful gardens, galleries and shops and a burgeoning culinary scene. Plus, it’s the hometown of Justin Bieber.

Route Options

  • Route Option #1: Take the I-94 from Detroit north to the Port Huron-Sarnia Border Crossing across the Blue Water Bridge, follow ON-402 east, north on County Road 81, north on Country Road 19, east on ON-7 to Stratford.
    Approx. distance & travel time: 150 miles (240 kilometres), 3 hours
  • Route Option #2: Cross the border from Detroit to Windsor, Ontario via the Detroit Windsor Tunnel, follow Ouellette Avenue to Dougall Avenue to Highway ON 401 East, exit onto Oxford County Road 119 north, northeast on ON-7 to Stratford.
    Approx. distance & travel time: 160 miles (260 kilometres), 3 hours

Suggested detourSt. Marys, about 20 minutes drive south of Stratford

Where to Stay in Stratford

  • Sister Inns, Edison Inn and Perth Country Inn offer uniquely themed rooms that pay homage to the history of Stratford. Book the Edison suite, where Thomas Edison once lived, or embrace the cult of Beliebers in the Music Room. There’s also a Cuban cocktail bar and taco shop on site. 
    Location: 48 Ontario Street
  • Upscale and elegant, The Bruce Hotel is within walking distance of the Stratford Festival and perks include a gym, pool, spa tub and dining options.
    Location: 89 Parkview Drive
  • The Stone Maiden Inn provides a personal bed and breakfast service in a boutique, Victorian-style inn.
    Location: 123 Church Street

Things to Do in Stratford

The Arts

Nature & Fall Colour 

  • Admire fall colour on natural trails in and around Stratford. The Stratford Side Trail, which is connected to the longer Avon Trail, leads along the Avon River and into the T.J. Dolan Natural Area.
  • Stroll through the Shakespearean Gardens, originally designed to feature plants and flowers mentioned in Shakespeare’s play. The entrance is close to the Huron Street Bridge, one of the oldest double-arched stone bridges in Ontario.
    Location: 5 Huron Street

Foodie Experiences 

  • Taste your way along the self-guided Savour Stratford Chocolate Trail, and enjoy innovative and tasty chocolate-based treats, including beer, ice cream and kettle corn. Pick up six vouchers for $39.55 at the Visitor Welcome Centre, 47 Downie Street.
  • One of Ontario’s oldest markets, the Stratford Farmers’ Market bustles with vendors selling fresh produce as well as baked good, craft beer and handmade arts. It’s held every Saturday morning at the Stratford Agriplex, which is also the location of the 181st Stratford Fall Fair, September 22–25, 2022 (free admission).
    Location: 357 McCarthy Road

Where to Eat & Drink in Stratford

Day 3 - 4: Stratford to St. Jacobs & Elmira

Visitors are drawn to St. Jacobs & Elmira in the heart of Ontario’s Mennonite country for fresh, local food, down-to-earth friendliness and for one of the country’s largest farmers’ markets and Market Country.

Route: Follow Mornington Street/County Road 119 north, east on County Road 56/County Road 7/County Road 5/east on Lobsinger Line to St. Jacobs.
Approx. distance & travel time: 30 miles (50 kilometres), 45 minutes

Suggested detourShakespeare, on Highway 7/8, just east of Stratford.

Where to Stay in St. Jacobs

  • In the heart of St. Jacobs, Hotel 52 is brimming with personality. Add-ons include charcuterie boards, mimosa kits and buckets of craft beer.
    Location: 1430 King Street North
  • Maryhill Inn Bed and Breakfast specializes in romance with elegant rooms that feature fireplaces and soaker tubs, and a two-course breakfast served in a former stagecoach stop. 
    Location: 1302 Maryhill Road, 15 minutes drive east of St. Jacobs

Things to Do in St. Jacobs & Elmira

Market Shopping

Touring & Entertainment

Where to Eat & Drink Around St. Jacobs & Elmira

Huge river travelling in between trees
The Grand River | Explore Waterloo Region

Day 5 - 6: St. Jacobs to Elora & Fergus

Described as “Ontario’s Best Small Town Escape” by National Geographic, the two communities Elora & Fergus define small-town charm.

Route: Take Sawmill Road/County Road 17 east out of St. Jacobs, turn north on Northfield Drive East/County Road 18 to Elora.
Approx. distance & travel time: 16 miles (25 kilometres), 25 minutes

Suggested detourWest Montrose Covered Bridge, about 10 minutes drive north of St. Jacobs and east of Elmira.

  • Also called the Kissing Bridge, 60 metres (198 foot) rustic oak and pine-covered bridge crosses the Grand River in the village of West Montrose. Constructed in the 19th century, it’s the only one of its kind left in Ontario.

Where to Stay in Elora & Fergus

Things to Do in Elora & Fergus

Outdoor Fun

Local Heritage & Entertainment

Where to Eat & Drink in Elora & Fergus

Getaway to Big City Entertainment

Embark on a road trip of a lifetime with the very best sports, theatre and musical entertainment, food and nightlife and next-level accommodations in three of Ontario’s top cities, Windsor, Hamilton and Toronto.

 Personnes debout devant la façade avant du bâtiment du Temple de la renommée du hockey
Temple de la Renommée du Hockey | Destination Toronto

Day 1 - 2: Detroit to Windsor

From the casino entertainment to unique whisky tours, you’re guaranteed good food, drinks and fun in Windsor, Canada’s southernmost city.

Route: Cross the border from Detroit to Windsor, Ontario via the Ambassador Bridge or the Detroit Windsor Tunnel.

Where to Stay in Windsor

Things to Do in Windsor

Sample Local History

Shopping & Entertainment

Where to Eat & Drink in Windsor




CFL players on a football field.
Hamilton | John Sokolowski/Hamilton Tiger-Cats


Day 3 - 4: Windsor to Hamilton

No longer a hidden gem, Hamilton, the ‘City of 100 Waterfalls’ also boasts art, culture and cuisine.

Route: Follow Ouellette Avenue, Dougall Avenue & Dougall Parkway to ON Highway 401 East/Macdonald-Cartier Freeway, exit onto Highway 403/Alexander Graham Bell Parkway, exit onto Highway 8/Main Street East into Hamilton
Approx. distance & travel time: 185 miles (300 kilometres), 3 hours

Where to Stay in & Around Hamilton

Things to Do in Hamilton

Sports, Events & Entertainment

Theatre & Culture

Where to Eat & Drink in Hamilton

Day 5 - 6: Hamilton to Toronto

Revel in Canada’s most multi-cultural and vibrant city. Experience top theatre, pro-sports, entertainment and accommodations in Toronto.

Route: Take ON 403 East/Queen Elizabeth Way (QEW) east to the Gardiner Expressway East, exit for Bay Street via Harbour Street, follow Bay Street north into downtown Toronto
Approx. distance & travel time: 45 miles (70 kilometres), 1 hour & 15 minutes

Travel option : Take ON 403 East/Queen Elizabeth Way (QEW) east to the Gardiner Expressway East, exit at one of four GO Train stations west of Toronto for overnight GO parking and take the GO train into and out of the city, stations include:

Where to Stay in Toronto

  • Hotel X is Toronto’s first luxury resort-style hotel that features tennis courts, a movie theatre and rooftop pool and bar. Secure parking available onsite.
    Location: 111 Princes' Boulevard, Toronto
  • Le Germain Hotel Maple Leaf Square is just steps away from the Scotiabank Arena and the Rogers Centre, which is convenient if you are seeing a show or catching a game. Indoor valet parking available. 
    Location: 75 Bremner Boulevard, Toronto
  • Toronto’s landmark heritage hotel, Fairmount Royal York is within walking distance of most downtown sports and nightlife. Valet parking at the east entrance, self-parking options nearby are also available. 
    Location: 100 Front Street West, Toronto
  • Recently renovated, the Park Hyatt Toronto sits opposite the Royal Ontario Museum and a short walk to Yorkville, one of Toronto’s trendiest neighborhoods. The cityscape view from the rooftop lounge is outstanding. Valet parking offered.
    Location: 4 Avenue Road, Toronto
  • The St. Regis Toronto is a five-star property with all the luxury services and amenities you’d expect and then some like the white-glove butler service and the daily Champagne sabering ritual. Valet parking and electric car charging station provided.
    Location: 325 Bay Street, Toronto

Things to Do in Toronto

Attractions, Museums & Galleries

Theatre & Stage 

Sports & Comedy

Where to Eat & Drink in Toronto

Day 7: Extend Your Trip

Experience more urban adventure on your way home. 

Kitchener and Waterloo: Home of the largest Oktoberfest outside of Germany, running September 23 to October 15, 2022.
London: For more theatre, live music and food.

Enjoy your visit!

Remember, this is only a sampling of the many hotels and attractions available. Find more road trip itineraries in Ontario, Canada.

Last updated: September 12, 2023

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