Here's a sample itinerary for a drive from Washington, DC to Windsor (Ontario). If you're planning a road trip to Windsor (Ontario), you can research locations to stop along the way. Make sure you check road conditions to double check the weather. Traveling with a dog or cat? Find pet-friendly stops. Camping along the way? Search for RV campgrounds. Find the best hotels, restaurants, and attractions based on the most talked about places recommended by Trippy members.
10:00 am start in Washington, DC
drive for about 1.5 hours
11:27 am Gettysburg
eat at Dobbin House
stay for about 1 hour
and leave at 12:27 pm
drive for about 1.5 hours
1:43 pm Sideling Hill
stay for about 1 hour
and leave at 2:43 pm
drive for about 1.5 hours
4:08 pm Fallingwater
stay for about 1 hour
and leave at 5:08 pm
drive for about 1 hour
6:18 pm Pittsburgh
eat at Primanti Brothers
stay overnight at Fairmont Pittsburgh Hotel
leave the next day around 9:00 am
day 1 driving ≈ 5.5 hours
find more stops
9:00 am leave from Fairmont Pittsburgh Hotel
drive for about 1 hour
10:06 am Youngstown (Ohio)
stay for about 1 hour
and leave at 11:06 am
drive for about 1 hour
12:18 pm Cleveland
eat at Lola
stay for about 1.5 hours
and leave at 1:48 pm
drive for about 1 hour
2:58 pm Cedar Point (Ohio)
stay for about 1 hour
and leave at 3:58 pm
drive for about 1 hour
5:02 pm Toledo (Ohio)
stay for about 1 hour
and leave at 6:02 pm
drive for about 1 hour
7:08 pm arrive in Windsor (Ontario)
eat at Slows Bar-B-Q
day 2 driving ≈ 5.5 hours
find more stops
Gettysburg (9 answers)
Gettysburg National Military Park (2 mentions)
restaurants around Gettysburg:
Dobbin House
questions about Gettysburg:
What shouldn't I miss with 24 hours in Gettysburg?
good campsite in gettysburg pa
Sideling Hill (3 mentions)
Fallingwater (7 mentions)
Pittsburgh (50 answers)
Andy Warhol Museum (9 mentions)
Carnegie Museum of Natural History (8 mentions)
National Aviary (6 mentions)
Carnegie Museum of Art (6 mentions)
Phipps Conservatory (5 mentions)
restaurants around Pittsburgh:
Primanti Brothers
Primanti Bros.
hotels around Pittsburgh:
Fairmont Pittsburgh Hotel
questions about Pittsburgh:
First timer to Pittsburgh, what should I explore?
First time to Pittsburgh, what are things a first time visitor has to do?
What's the best neighborhood in Pittsburgh for a first time visitor?
Parking spots for a 45' motorcoach in or near downtown Pittsburgh
Pittsburgh on a budget?
Youngstown (Ohio) (5 answers)
questions about Youngstown (Ohio):
Where to stay near Youngstown
Cleveland (69 answers)
Rock and Roll Hall of Fame and Museum (13 mentions)
The Cleveland Museum of Art (12 mentions)
Rock and Roll Hall of Fame and Museum (6 mentions)
West Side Market (6 mentions)
Great Lakes Brewing Company (5 mentions)
restaurants around Cleveland:
Lola
Lolita
The Greenhouse Tavern
Melt Bar & Grilled
L'Albatros
questions about Cleveland:
Good restaurants for business dinner?
What is your favorite restaurant in Cleveland?
What's the best neighborhood in Cleveland for a first time visitor?
New to the city, friend coming to visit: What should we do?
Fun things to do
Cedar Point (Ohio) (5 mentions)
Toledo (Ohio) (8 answers)
Toledo Zoo (2 mentions)
questions about Toledo (Ohio):
Where's a fun place for breakfast in Toledo Ohio?
Need some recommendations on somewhere to get food?
Trippy members suggest Slows Bar-B-Q, which was mentioned 3 times.
Here are some more restaurants people talk about:
This section could be endless, so rather than trying to suggest every local activity or attraction, we'll leave it open-ended.
These are some of the places people talk about on Trippy:
Of course, Trippy is the perfect place to ask questions because there's an entire community of travelers talking to each other and sharing tips and advice. Trippy is where you can get answers personalized for your tastes, budgets, trip dates & more!
Click the button below to explore more questions and answers related to Windsor (Ontario).
Yes, even this step is optional, because if you're on vacation who wants the trip to end? It's okay, you can start planning your next trip!
Want to plan the trip back? Get the reverse directions for a Windsor (Ontario) to Washington, DC drive, or go to the main page to plan a new road trip.
You can also compare the travel time if you're flying or driving by calculating the distance from Washington, DC to Windsor (Ontario). Or get a full Washington, DC to Windsor (Ontario) flight plan.
Don't forget about exploring your own hometown with a staycation. You can also find some cool day trips or get away for a weekend.
And if you know Washington, DC well, please help your fellow travelers and answer their questions about Washington, DC!
