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

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 

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.

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

• The Stratford Festival is an annual, professional theatre event that brings the work of Shakespeare, as well as other classics and contemporary performances, to life on stage. Plus, talks, forums, exhibits and behind-the-scenes tours are offered. This season’s playbill includes Shakespeare’s Hamlet and Richard III, as well as the musical extravaganza, Chicago. Review the 2022 Stratford Festival Visitor Guide and get your tickets in advance. 
  Location: Four main venues include the Festival Theatre, the Avon Theatre, the Tom Patterson Theatre and the Studio Theatre.
   
• For all things Stratford, pay a visit to the Stratford Perth Museum and explore exhibits on local history, including Justin Bieber: Steps to Stardom. Open 10 a.m. to 4 p.m.
  Location: 4275 Huron Street
   
• Each year, Stratford hosts the Stratford Writers Festival, a gathering of readers and writers, including songwriters. If you love to read, browse independent book shops like The Book Stage and Fanfair Books.

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

• For a hearty brunch, head to Old Man or The Planet Diner for a mostly vegan Sunday brunch.
  Locations:
  Old Man, 75 Wellington Street
  The Planet Diner, 118 Downie Street
   
• Housed in a heritage church building, Revival House creates international fusion lunch, brunch and dinner dishes and exceptional cocktails.
  Location: 70 Brunswick Street
   
• Bringing South Africa’s braai culture to Ontario, Braai House will wow you with the level of flavour you can only get from open-fire cooking. Prix fixe and tasting menu options are available plus their own in-house brewed beers on tap.
  Location: 34 Brunswick Street
   
• Enjoy a farm-to-table blackboard prix fixe menu, shareable food flight platters, tasting menus and a thoughtful wine selection at Bijou Restaurant. Open Tuesday to Saturday.
  Location: 74 Wellington Street
• Stratford’s largest craft beer menu is paired with Izakaya-inspired food (Japanese version of Spanish tapas) at Mercer Kitchen & Beer Hall.
• Location: 104-108 Ontario Street
   
• Stratford is home to outstanding local craft breweries, give these a try: 
  Black Swan Brewing Co., 144 Downie Street
  Heritage Hops Brew Co., 21 Market Place
  Jobsite Brewing Co., 45 Cambria Street

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

• The St. Jacobs Market District is easily a full day’s event. Canada’s largest farmers’ market features over 250 vendors, plus an outlet mall and an antique bazaar. 
  Location: 878 Weber Street North, Woolwich

Touring & Entertainment

• Tour the countryside aboard the Waterloo Central Railway, a heritage train providing scenic fall rail rides between the St. Jacobs Farmers’ Market, the village and St. Jacobs and the town of Elmira. Just under two hours, round-trip rides cost between $25–$40 and parking is available.
  Location: St. Jacobs Market Station, 330 Farmers Market Road
   
• Learn about the rich Mennonite history and culture in the area on a guided tour at The Mennonite Story Interpretive Centre.
  Location: 1405 King Street North, St. Jacobs
   
• Explore the history of St. Jacobs on a locally led, guided walking tour with Stroll Walking Tours.
   
• Fall performances at the St. Jacobs Country Playhouse include Driving Miss Daisy, American Son and Wizard of Oz: the Panto. 
  Location: 40 Benjamin Road East
   
• Paddle the Grand River with a canoe or kayak rental from Canoeing The Grand, a shuttle service makes convenient drop-offs and pick-ups.

Where to Eat & Drink Around St. Jacobs & Elmira

• The Village Biergarten features a large outside patio and serves local Block Three Brews along with a seasonal menu of apps, sharables and mains.
  Location: 1381 King Street North, St. Jacobs
   
• In addition to fresh farm produce, there is an abundance of homemade, ready-to-eat treats and eateries at the St. Jacob’s Market. You’ll find everything from Mexican to Middle Eastern, just don’t miss the Mennonite-style apple fritters. 
  Location: 878 Weber Street North, Woolwich
   
• Check out the daily specials like Smoked Wing Night and Smoked Prime Rib Dinner at Crowsfoot Smokehouse, a German-inspired barbeque grill just a few minutes drive east of St Jacobs. Come hungry. 
  Location: 1872 Sawmill Road, Conestogo
   
• Anna Mae’s Bakery and Restaurant serves homemade Mennonite food and seriously delicious pies, baked goods and sweet treats. You can even sit in a buggy booth.
  Location: 4060 Line 72, Millbank

Where to Stay in Elora & Fergus

• The Ayrshire House offers comfortable guestrooms in two downtown Elora properties with extra add-ons like bike rentals, picnic baskets and sunset charcuterie and wine. 
  Location: 249 Geddes Street, Elora
   
• Providing the ultimate mix of country hospitality and modern luxury, the Elora Mill Hotel & Spa sits perched above the fast-moving Grand River and offers spa, dining and a variety of rooms and suites. 
  Location: 77 Mill Street West, Elora
   
• Choose from deluxe and vintage suites at the Breadalbane Inn Boutique Hotel and enjoy the onsite gastro pub and Italian restaurant.
  Location: 487 St. Andrew Street West, Fergus

Things to Do in Elora & Fergus

Outdoor Fun

• Explore the Elora Gorge, a stunning natural area with massive cliffs towering the shoreline of the rushing Grand River. Park of the Elora Gorge Conservation Area, hike the three kilometres of trails to lookouts or even go tubing down the white water rapids (weather permitting).
   
• Follow the boardwalk in Bissel Park to a small waterfall or hike a portion of the Elora Cataract Trailway.
   
• Cruise the Grand River in style. Elora Raft Rides offers guided outings in a custom punt-style rowing boat, similar to Venetian gondolas.
  Location: 38 Mill Street West
   
• Visit the Templin Gardens, a downtown garden and heritage site atop limestone cliffs overlooking the Grand River in Fergus. 
  Location: Between Tower Street South and St. Andrew Street West
   
• Try your hand at fly fishing with Grand River Troutfitters. Based in Fergus, they offer guided ‘walk-n-wade’ and drift-boat excursions. 
  Location: Fergus
   
• Take your relationship to a whole new level, sign up for a private, guided zip-lining, rock-climbing or urban rappelling adventure with One Axe Pursuits.
  Location: 24 Henderson Street, Elora

Local Heritage & Entertainment

• Two floors of permanent and visiting exhibits showcase a range of local history and beyond at the Wellington Country Museum and Archives. The building itself is a significant heritage site, built in 1877, it’s the oldest example of a ‘poor house’ or shelter for those in need in Canada. If These Walls Could Speak: The House of Industry and Refuge 1877–1947 is an awarding-winning exhibit that explores this era. 
  Location: 0526 Wellington County Road 18, Fergus
   
• The Elora Centre for the Arts features regional artists in the gallery and an artisan market shop selling local, handmade crafts and gifts.
  Location: 75 Melville Street, Elora
   
• Play the slots and tables at Elements Casino Grand River.
  Location: 7445 Wellington County Road 21, Elora
   
• Catch Little House on the Prairie: the Musical in late October at the Fergus Grand Theatre, a heritage performing arts venue.
  Location: 244 St. Andrew Street West, Fergus
   
• Home to the annual summer Fergus Scottish Festival and Highland Games, Scottish roots run deep in Fergus. Stock up on all things Scottish including tartan kilts, tweed caps and bagpipes at the Fergus Scottish Corner Shop.
  Location: 181 St. Andrew Street West, Fergus

Where to Eat & Drink in Elora & Fergus

• Plan something extra special and arrange an afternoon or sunset picnic in a scenic farm setting at Fieldstone Barn.
  Location: 7450 Middlebrook Road, Elora
   
• For elevated French-inspired fare, The Evelyn in downtown Elora is a must for lunch or dinner.
  Location: 130 Metcalfe Street, Elora
   
• Sweet and savoury crepes are on the menu at Café Crêperie Of Elora, as well as coffees and wines, so it’s perfect for breakfast or lunch. 
  Location: 40 Mill Street West, Elora
   
• Tea lovers will enjoy the upscale afternoon tea served at The Wild Tart and the selection of loose leaf teas and French pastries at Ambiances Gourmandes.
  Locations:
  The Wild Tar, 61 Metcalfe Street, Elora
  Ambiances Gourmandes, 240 St. Andrew Street West, Fergus
   
• Locally owned, The Brewhouse on the Grand is a local favourite for great pub food and brews in Fergus while the Elora Brewing Company pairs classic comfort dishes with house drafts.
  Locations:
  The Brewhouse 170 St. David Street South, Fergus 
  Elora Brewing Co. 107 Geddes Street, Elora

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.

Where to Stay in Windsor

• Caesars Windsor is a luxury casino resort with chic suites fitted with whirlpool tubs, stellar river and city views. Resort amenities include a spa, fitness area, pool, restaurants, bar and entertainment. 
  Location: 377 Riverside Drive East, Windsor
   
• Overlooking the Detroit River, Best Western Plus Waterfront Hotel is another great option for accommodations in the heart of downtown Windsor.
  Location: 277 Riverside Drive West, Windsor

Things to Do in Windsor

Sample Local History

• Whisky played a significant role in Windsor’s history. Visit the Hiram Walker & Sons Distillery for whisky tasting followed by an informative tour of Walkerville and a flight of craft beer at Walkerville Brewery on the Drinks of Walkerville Walking Tour (with Windsor Eats on select weekends). 
  Location: 2072 Riverside Drive East, Windsor
   
• The historic distillery is now home to J.P. Wiser’s Canadian Whisky, among other renowned labels and offers a 90-minute J.P.Wiser’s Experience tour that explores the storied history of Canadian whisky along with a tasting session.
  Location: 2072 Riverside Drive East, Windsor

Shopping & Entertainment

• Try your luck at Caesars Windsor Casino, from tables games like Blackjack, Roulette and Poker to over 2,000 slot machines the excitement is palpable. 
  Location: 377 Riverside Drive East, Windsor
   
• The Colosseum is Caesars Windsor’s state-of-the-art entertainment venue for top live music, comedy and more. Alice Cooper, Tom Jones, Bill Burr and Sebastian Maniscalco are just some of the performers scheduled this fall.
  Location: 377 Riverside Drive East, Windsor
   
• For live rock & roll and a fun, friendly vibe, check out The Backstage at Players Sports Club.
  Location: 1530 Langlois Avenue, Windsor
   
• Shop W.E. Made It for locally made apparel, jewellery, home accessories and art and crafts.
   
• Designed by the renowned Thomas McBroom, Ambassador Golf Club is an 18-hole, 71 par championship golf course and driving range.
  Location: 1025 Sprucewood Avenue, Windsor
   
• Windsor ComiCon 2022 will take place across three levels of the St. Clair College Centre for the Arts from October 29–30.
  Location: 201 Riverside Drive West, Windsor

Where to Eat & Drink in Windsor

• Tuck into French toast, waffles and omelettes at The Twisted Apron in the Walkerville neighbourhood or kick start your day with coffee and a pastry at Anchor Coffee House. 
  Locations:
  The Twisted Apron at 1833 Wyandotte Street East, Windsor
  Anchor Coffee House at 543 Lincoln Road, Windsor
   
• Mezzo Ristorante & Lounge has been voted the best restaurant as well as most romantic dining in Windsor, for its food, atmosphere and entertainment. Plus, they make great gourmet take-out boxes.
  Location: 804 Erie Street East, Windsor
   
• Enjoy upscale dining with an elevated view at Fourteen Restaurant Sky & Lounge overlooking the city and river. Be sure to make reservations well in advance, this is a very popular spot.
  Location: 100 Ouellette Avenue, Windsor
   
• Discover Windsor’s passion for pizza, including Windsor-style pizza with shredded pepperoni, local Galati mozzarella and canned mushrooms at Terra Cotta Pizzeria.
  Location: 318 Pelissier Street, Windsor
   
• For local, small-batch craft brews, choose from Walkerville Brewery, Craft Heads Brewing Company, Frank Brewing Company, Chapter Two Brewing and Sandwich Brewing Company.
  Locations: Walkerville Brewery at 525 Argyle Road, Windsor
  Craft Heads at 89 University Avenue West, Windsor
  Frank Brewing at 12000 Tecumseh Road East, Windsor
  Chapter Two at 2345 Edna Street, Windsor
  Sandwich Brewing at 3232 Sandwich Street, Windsor

Where to Stay in & Around Hamilton

• The Pearle Hotel & Spa is an elegant waterfront property with luxurious spa, earth to table farm cuisine at the onsite Isabelle Restaurant + Lounge and endless, serene lake views.
  Location: 3 Elizabeth Street, Burlington
   
• Hamilton’s C Hotel by Carmen’s offers a European-inspired boutique experience with themed room décor and an onsite Italian restaurant.
  Location: 1530 Stone Church Road East, Hamilton

Things to Do in Hamilton

Sports, Events & Entertainment

• Big-ticket names like Pearl Jam (September), Iron Maiden (October) and Michael Bublé (October) are billed to perform at FirstOntario Centre, Hamilton’s largest live music and entertainment venue.
  Location: 101 York Boulevard, Hamilton
   
• Ontario’s Hockey League season drops the puck in September, catch a Hamilton Bulldogs home game at FirstOntario Centre on October 8 or 16.
  Location: 101 York Boulevard, Hamilton


• The Canadian Football League season runs into October, with Hamilton’s pro team Hamilton Tiger-Cats playing at the Tim Hortons Field stadium. 
  Location: 64 Melrose Avenue North, Hamilton
   
• If you’re in Hamilton September 9 to 11, you’re in for a treat. Supercrawl is an annual arts and indie music event with amazing live music, visual arts performances, art exhibits and more.
  Location: James Street North, Hamilton
   
• Have a laugh at Levity Comedy Club & Lounge with regular local and renowned stand-up comedians scheduled, amateur open mic nights and great drinks and sharable food menu.
  Location: 120 King Street West, Hamilton
   
• Attention pop-culture and comic book fans, Hamilton Comic Con will take place September 24–25 at the Canadian Warplane Heritage Museum.
  Location: 9280 Airport Road, Mount Hope, Hamilton

Theatre & Culture

• Contemporary and thought-provoking stage performances at Theatre Aquarius this fall include Salt Baby and Serving Elizabeth. 
  Location: 190 King William Street, Hamilton
   
• Dundurn Castle (a National Historic Site) is an impressive heritage home and garden of a former premier built in the 1830s that’s been carefully restored and is open for tours and events.
  Location: 610 York Boulevard, Hamilton

Where to Eat & Drink in Hamilton

• The breakfast and coffee at Saint James Espresso Bar and Eatery will fuel your day.
  Location: 170 James Street North, Hamilton
   
• If you’re in the mood for a leisurely brunch, check out The Electric Diner in Hess Village, the weekend brunch at The French Bistro or experience the ultimate, chef-curated Sunday brunch spread at the Ancaster Mill (reservations strongly recommended).
  Locations:
  The Electric Diner at 96 George Street, Hamilton
  The French at 37 King William Street, Hamilton
  Ancaster Mill at 548 Old Dundas Road, Ancaster
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• Satisfy your cravings for tacos and tequila at The Mule.
  Location: 41 King William Street, Hamilton
   
• A seasonal, west coast-inspired small plate menu is perfect for sharing at Berkley North. Closed on Tuesday.
  Location: 31 King William Street, Hamilton
   
• The chef’s Italian roots and love of local shine at Born & Raised, open Thursdays to Saturdays, with a late-night menu including $2 oysters at 10:30 p.m.
  Location: 224 James Street North, Hamilton
   
• Award-wining Quatrefoil Restaurant in nearby Dundas is a must for foodies. Refined, contemporary cuisine is paired with a beautiful wine menu from Wednesdays to Saturdays. 
  Location: 16 Sydenham Street, Dundas
   
• One of Hamilton’s flagship brewhouses, Collective Arts Brewing serves craft beer, cider and sparkling hard tea, along with a full calendar of arts and cultural events. 
  Location: 207 Burlington Street East, Hamilton

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

• Visit the CN Tower, Toronto’s must iconic attraction, and take in unmatched city views from observation platforms, the revolving 360 Restaurant or along EdgeWalk, an exciting daredevil walk around the outside of the top needle of the tower.
  Location: 290 Bremner Boulevard, Toronto
   
• Showcasing art, culture and natural history from around the world, the Royal Ontario Museum (ROM) is the largest in Canada.
  Location: 100 Queen’s Park, Toronto
   
• Explore the Art Gallery of Ontario (AGO), one of the largest art collections in North America as well as the Museum of Contemporary Art (MOCA). 
  Locations:
  AGO at 317 Dundas Street West, Toronto
  MOCA at 158 Sterling Road, #100, Toronto

Theatre & Stage 

• Check what’s on stage during your visit. From Harry Potter and Cursed Child at the Ed Mirvish Theatre to Singing in the Rain and Mean Girls at the Princess of Wales Theatre, Mirvish brings some of the best theatre productions to Toronto.
   
• If you like live music, get your tickets in advance for top crowd pleasers like the Eagles Hotel California Tour, Kid Cudi, Post Malone, GORILLAZ, Lizzo and more at the Scotiabank Arena and New Order & The Pet Shop Boys Unity Tour or Wu-Tang Clan & Nas: NY State of Mind Tour at the Ontario Place Budweiser Stage. Catch Echo and the Bunnymen or Lykke Li performing at the Queen Elizabeth Theatre in the Exhibition Place Grounds. 
  Locations:
  Scotiabank Arena, 40 Bay Street, Toronto
  Ontario Place, 955 Lake Shore Boulevard West, Toronto
  Queen Elizabeth Theatre, 190 Princes’ Boulevard, Toronto
   
• The Toronto Symphony Orchestra will be performing Star Wars: The Force Awakens (October 6–8) and Tim Burton’s The Nightmare Before Christmas (October 28–29) in concert at the Roy Thomson Hall or enjoy the National Ballet of Canada’s world premiere of MADDADDAM (November 23–30), based on Margaret Atwood novels at the Four Seasons Centre for the Performing Arts. 
  Locations:
  Roy Thomson Hall, 60 Simcoe Street, Toronto
  Four Seasons Centre for the Performing Arts, 145 Queen Street West, Toronto

Sports & Comedy

• Pro sports fans will not be disappointed in Toronto. NBA basketball season with Toronto Raptors and NHL hockey season with the Toronto Maple Leafs both get underway in October while the Canadian Football League season with the Toronto Argonauts runs until October.
   
• Visit the Hockey Hall of Fame, a celebration of Canada’s national winter sport and tribute to its greatest players. 
  Location: 30 Yonge Street, Toronto
   
• Various comics including John Mulaney, Trevor Noah and Amy Schumer are scheduled to perform at various venues in the city during Toronto Comedy Festival, Just For Laughs 2022 (September 22–October 1).
   
• Catch local comedians and rising comic stars at YukYuks Comedy Club or a comedy show at Comedy Bar or Second City (the club that launched the careers of countless comedy treasures, including Bill Murray, John Candy, Eugene Levy and Catherine O’Hara).
  Locations:
  YukYuks, 224 Richmond Street West, Toronto
  Comedy Bar, 945 Bloor Street West, Toronto
  Second City, 2800 Danforth Avenue, Toronto
   
• 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.
   
• For what to do after dark, check out Toronto’s nightlife.

Where to Eat & Drink in Toronto

• As one of the world’s most multicultural cities, Toronto is also one of the best places on the planet for people who love good food and drink. Follow your appetite to flavours from around the world in Toronto’s Greektown, Chinatown, Little India or Little Italy.
   
• There are also pockets of the city that have flourished into foodie destinations like the Distillery District, the Ossington Strip and Yorkville neighbourhood. 
   
• Get the inside scoop from local experts at Culinary Adventure Co. or Tasty Tours Toronto on a themed culinary tour.
   
• If it’s a view you’re after, you can’t beat the revolving dining room experience 350 metre (1,150 feet) up the CN Tower at 360 The Restaurant. 
  Location: 290 Bremner Boulevard, Toronto
   
• With over 7,500 restaurants and over a dozen craft breweries, you’ll never run out of great food and drink options in this city.

Enjoy your visit!

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