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Woodstock (Vermont) to Lenox drive

(tap on any row to expand for more details)

  Woodstock (Vermont)
 Grafton (Vermont)
 Brattleboro
 Shelburne Falls
 Northampton (Massachusetts)
 Stockbridge (Massachusetts)
   Lenox 
driving   /   1 day   /   no pets   /   no RV

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Woodstock (Vermont) to Lenox road trip planner

Here's a sample itinerary for a drive from Woodstock (Vermont) to Lenox. If you're planning a road trip to Lenox, you can research locations to stop along the way. Traveling with a dog or cat? View pet-friendly stops between Woodstock (Vermont) and Lenox. Camping along the way? View RV campgrounds between Woodstock (Vermont) and Lenox. Find the best hotels, restaurants, and attractions based on the most talked about places recommended by Trippy members.

customize this trip

10:00 am  start in Woodstock (Vermont)
drive for about 55 minutes

10:55 am  Grafton (Vermont)
stay for about 1 hour
and leave at 11:55 am
drive for about 36 minutes

12:31 pm  Brattleboro
stay for about 1 hour
and leave at 1:31 pm
drive for about 36 minutes

2:07 pm  Shelburne Falls
stay for about 1 hour
and leave at 3:07 pm
drive for about 35 minutes

3:42 pm  Northampton (Massachusetts)
stay for about 1 hour
and leave at 4:42 pm
drive for about 51 minutes

5:33 pm  Stockbridge (Massachusetts)
stay for about 1 hour
and leave at 6:33 pm
drive for about 14 minutes

6:47 pm  arrive in Lenox

driving ≈ 4 hours


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Where should I stop along the way?

Grafton (Vermont)

Brattleboro  (2 answers)
    questions about Brattleboro:
        What are the best restaurants in Brattleboro, VT

Shelburne Falls  (2 answers)

Northampton (Massachusetts)  (3 answers)

Stockbridge (Massachusetts)  (5 answers)


What are some things to do in Lenox?

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!

Click the button below to explore more questions and answers related to Lenox.




Do I really have to go back home?

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 Lenox to Woodstock (Vermont) drive, or go to the main page to plan a new road trip.

Looking for ideas for more destinations within driving distance of Woodstock (Vermont)? Try searching for places within 3 hours of Woodstock (Vermont).

You can also compare the travel time if you're flying or driving by calculating the distance from Woodstock (Vermont) to Lenox. Or get a full Woodstock (Vermont) to Lenox 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 Woodstock (Vermont) well, please help your fellow travelers and answer their questions about Woodstock (Vermont)!





At a Glance
without making any stops
total driving distance is 158 miles
driving time of 2 hours, 49 minutes
3 Woodstock (Vermont) travel answers
1 Grafton (Vermont) travel answer
2 Brattleboro travel answers
2 Shelburne Falls travel answers
3 Northampton (Massachusetts) travel answers
5 Stockbridge (Massachusetts) travel answers
3 Lenox travel answers





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