Here's a sample itinerary for a drive from Portland (Maine) 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.
11:00 am start in Portland (Maine)
drive for about 1.5 hours
12:35 pm Salem (Massachusetts)
stay for about 1 hour
and leave at 1:35 pm
drive for about 1.5 hours
3:05 pm Old Sturbridge Village (Massachusetts)
stay overnight and leave the next day around 10:00 am
day 1 driving ≈ 3 hours
10:00 am leave from Old Sturbridge Village (Massachusetts)
drive for about 54 minutes
10:54 am Hartford
stay for about 1 hour
and leave at 11:54 am
drive for about 2.5 hours
2:21 pm Bethel (New York)
stay for about 1 hour
and leave at 3:21 pm
drive for about 1.5 hours
4:57 pm arrive in Woodstock (New York)
day 2 driving ≈ 5 hours
Salem (Massachusetts) (26 answers)
Salem Witch Museum (2 mentions)
The House of the Seven Gables (2 mentions)
questions about Salem (Massachusetts):
What is your favorite restaurant in Salem (Massachusetts)?
witch
What is a good nighttime tour
Old Sturbridge Village (Massachusetts) (4 mentions)
Hartford (15 answers)
The Mark Twain House & Museum (4 mentions)
Wadsworth Atheneum Museum of Art (2 mentions)
questions about Hartford:
What is your favorite restaurant in Hartford?
Bethel (New York)
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 Portland (Maine) 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 (Maine) to Woodstock (New York). Or get a full Portland (Maine) 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 Portland (Maine) well, please help your fellow travelers and answer their questions about Portland (Maine)!