Here's a sample itinerary for a drive from Cleveland to Woodstock (New York). If you're planning a road trip to Woodstock (New York), 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 Cleveland
drive for about 1 hour
11:14 am Youngstown (Ohio)
stay for about 1 hour
and leave at 12:14 pm
drive for about 1 hour
1:20 pm Pittsburgh
stay for about 1.5 hours
and leave at 2:50 pm
drive for about 1 hour
4:00 pm Fallingwater
stay for about 1 hour
and leave at 5:00 pm
drive for about 1.5 hours
6:26 pm Breezewood
stay overnight and leave the next day around 10:00 am
day 1 driving ≈ 5 hours
find more stops
10:00 am leave from Breezewood
drive for about 2 hours
12:11 pm Lancaster (Pennsylvania)
stay for about 1 hour
and leave at 1:11 pm
drive for about 3 hours
4:00 pm The Cloisters
stay for about 1 hour
and leave at 5:00 pm
drive for about 2 hours
6:45 pm arrive in Woodstock (New York)
day 2 driving ≈ 7 hours
find more stops
Youngstown (Ohio) (9 answers)
questions about Youngstown (Ohio):
Where to stay near Youngstown
Pittsburgh (61 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.
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?
Fallingwater (7 mentions)
Breezewood (3 answers)
Lancaster (Pennsylvania) (20 answers)
The Cloisters (23 mentions)
This section could be endless, so rather than trying to suggest every local activity or attraction, we'll leave it open-ended.
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!
For example, here are some questions people have asked about Woodstock (New York). Click on any question to see answers from the community!
Stacey from asked:
attractions (1 answer)
Click the button below to explore more questions and answers related to Woodstock (New York).
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 Woodstock (New York) to Cleveland 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 Cleveland to Woodstock (New York). Or get a full Cleveland to Woodstock (New York) 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. Maybe try typing in a faraway location like London, Hong Kong, or Sydney, and get inspired for your dream trip around the world.
And if you know Cleveland well, please help your fellow travelers and answer their questions about Cleveland!