(tap on any row to expand for more details)
Here's a sample itinerary for a drive from Portland to Philadelphia. If you're planning a road trip to Philadelphia, you can research locations to stop along the way. Traveling with a dog or cat? View pet-friendly stops between Portland and Interior. Camping along the way? View RV campgrounds between Portland and Interior. Find the best hotels, restaurants, and attractions based on the most talked about places recommended by Trippy members.
11:00 am start in Portland
drive for about 4 hours
2:48 pm Walla Walla
stay overnight and leave the next day around 10:00 am
day 1 driving ≈ 4 hours
find more stops
10:00 am leave from Walla Walla
drive for about 9 hours
6:48 pm Bozeman
stay overnight and leave the next day around 10:00 am
day 2 driving ≈ 9 hours
find more stops
10:00 am leave from Bozeman
drive for about 9 hours
7:06 pm Interior
stay overnight and leave the next day around 9:00 am
day 3 driving ≈ 9 hours
9:00 am leave from Interior
drive for about 4 hours
1:03 pm Sioux Falls
stay for about 1 hour
and leave at 2:03 pm
drive for about 7 hours
8:49 pm Madison (Wisconsin)
stay overnight and leave the next day around 10:00 am
day 4 driving ≈ 11 hours
10:00 am leave from Madison (Wisconsin)
drive for about 7.5 hours
5:32 pm Cleveland
eat at Lola
stay overnight at The Cleveland Hostel
leave the next day around 10:00 am
day 5 driving ≈ 7.5 hours
10:00 am leave from The Cleveland Hostel
drive for about 6.5 hours
4:34 pm arrive in Philadelphia
stay at Loews Hotel Philadelphia
day 6 driving ≈ 6.5 hours
Walla Walla (7 answers)
Bozeman (20 answers)
Interior
Badlands National Park (7 mentions)
Sioux Falls (11 answers)
questions about Sioux Falls:
First timer to Sioux Falls- what are the best outdoor things to do/explore?
Madison (Wisconsin) (29 answers)
Wisconsin State Capitol (3 mentions)
restaurants around Madison (Wisconsin):
The Old Fashioned
Great Dane Pub & Brewing Co
L'Etoile
Ha Long Bay
questions about Madison (Wisconsin):
What is your favorite restaurant in Madison?
Where is there a good Japanese restaurant?
Family-friendly campsites near Madison for large groups
One day trip, looking for a good time under $100
Catholic Easter Vigil Mass with good music in Madison?
Cleveland (54 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
hotels around Cleveland:
The Cleveland Hostel
questions about Cleveland:
What is your favorite restaurant in Cleveland?
Good restaurants for business dinner?
New to the city, friend coming to visit: What should we do?
What's the best neighborhood in Cleveland for a first time visitor?
Fun things to do
Are you going straight to a hotel, or looking for a vacation rental or Airbnb?
The best resource on neighborhoods, areas, and hotels is the Trippy page on where to stay in Philadelphia.
If you're looking for a quick answer, you can check out Loews Hotel Philadelphia, which was mentioned 2 times on Trippy.
Want to research more popular hotels in Philadelphia? Click the blue button below.
Need some recommendations on somewhere to get food?
Trippy members suggest Reading Terminal Market, which was mentioned 24 times.
Here are some more restaurants people talk about:
Want to research more popular restaurants in Philadelphia? Click the blue button below.
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!
For example, here are some questions people have asked about Philadelphia. Click on any question to see answers from the community!
Hannah from Milwaukee asked:
What is there to do in Philly besides eat cheese steaks? (14 answers)
Scott from Chicago asked:
Pat's or Geno's: Which has the better cheesesteak? (13 answers)
Katie from Los Angeles asked:
What is your favorite restaurant in Philadelphia? (12 answers)
Sharon from West Los Angeles asked:
Anybody know of great gems in the city I can dine at during my stay? (9 answers)
teri from Atlanta asked:
Eating out on a budget. (9 answers)
Click the button below to explore more questions and answers related to Philadelphia.
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 Philadelphia to Portland 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 Portland to Philadelphia. Or get a full Portland to Philadelphia 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 Portland well, please help your fellow travelers and answer their questions about Portland!
More info on this route:
road conditions
alternate routes
Google driving directions
