How to Plan a Fall Foliage Road Trip

For two years now my family has road-tripped to New England in the fall to see the foliage. These are kind-of difficult trips to plan… how do you know when the leaves will be at peak? And which towns in particular should you visit? Although sitting in the car for a long time can be brutal, it is COMPLETELY worth it when you arrive and see the stunning views – gorgeous mountain ranges, bright yellow, red and orange leaves, and the most charming little towns. First up I’m sharing some photos from my trip… scroll down to the bottom of this post to see how to plan one for yourself!
How to plan a fall foliage road trip
oversized scarf, striped top, OTK boots

 fall outfit

Louis Vuitton Neverfull MM

Tip One: The first step when planning a road trip is figuring out which state (or states) you want to visit. Different states will have different fall foliage peaks! For example, if you want to visit northern Maine, the leaves will peak there sooner than in Connecticut. On our recent trip, I knew I wanted to visit both Vermont and southern New Hampshire, so the next step was figuring out which dates to go.

Tip Two: Use a fall foliage map to see when the leaves will be at peak. You obviously want to plan the trip for when the leaves are at peak! We visited Vermont and NH from October 15-20 and it was the PERFECT time to be there… the leaves were brilliant.

Tip Three: Figuring out the details. Once you have specific states and your dates planned, the next step is figuring out all of the small details. I knew of specific towns and hotels that I wanted to visit, so I added those to our list and then mapped out how long it would take each day to get to the next location. Looking at a map is really helpful so that you can physically see the route you’ll be taking. My mom and I stayed in a different hotel every night which was really fun, but was honestly pretty difficult (especially packing, unpacking and carrying our stuff to/from the car each day). Looking back, we wish that we had stayed two nights at each hotel.

Tip Four: Be Spontaneous! New England is so charming… we would be driving along a highway and then come across cute country stores, pumpkin patches and apple cider mills. Make sure there’s room in your schedule to explore. You may see a pretty road and want to drive down it for a photograph… or you may see a sign for apple cinnamon donuts and get a craving. The best part of being on a road trip is making spontaneous decisions to just explore.

Here are some of my recommendations for towns to visit in New England:
*Burlington, VT (lots of great restaurants and shopping, right on the water. Check out my Burlington Guide here)
*Stowe, VT (stay at Stowe Mountain Lodge)
*Manchester, VT (stay at Equinox Resort)
*Grafton, VT (stay at the Grafton Inn)
*Hanover, NH (stay at the Hanover Inn)
*New Paltz, NY (stay at Mohonk Mountain House)

If you have any additional questions, let me know in the comments! 🙂


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  1. As always great photos 🙂

  2. I feel so blessed to live in New England, especially in the fall- it's an absolute wonderland! I am actually heading to Burlington this weekend for a girls trip and could not be more excited!! Love all your outfits!! Happy Thursday <3
    xx Tess | Sequins are the New Black

  3. Hi Caitlin, you look lovely in these pics!! Could you let me know what size you bought in the burgundy J. Crew hat? They do it in S/M and M/L and I am unsure…
    Thanks so much! Have a good day!

  4. This is my favorite time of year in New England. If you are looking for some new places to visit try Mount Washington in New Hampshire. You can do driving or train tours up the mountain and there are some great places to stay. If you want something different, try Newport, Rhode Island. It's an old money beach town with tons of history and beautiful mansions that you can tour! Hotel Viking & Ocean Cliff are two great hotels to try.


  5. Great tips! And I'm obsessed with your fall style, so cute!

    xo, Carey

  6. Loving all your looks!


  7. It is on my bucket list to head to the Northeast to see the fall foliage! That map is so helpful, thanks for sharing! Love all your outfits!

  8. I've always wanted to go on a fall foliage road trip! Thank you for sharing your tips!

    Carrie |

  9. These pictures are so pretty! I'm definitely going to have to visit Vermont next year for my birthday. Which airport did you fly into to start the trip?

    Xo, Nina
    Law of Fashion Blog

    • This past trip we road tripped all the way from North Carolina! In the past I have flown into Burlington and it's a great place to begin the trip!

  10. The photos look beautiful! Fall is such a gorgeous season!

    Marta –

  11. You are hands down my style icon – you just nail it every time! I would love to road trip like that soon!

    Emma | With A City Dream

  12. Looks beautiful! You've definitely inspired me to plan a road trip soon. Also, all your fall outfits are on point.

  13. I absolutely want to do a trip like this in the future! Thanks for sharing your tips!

    How 2 Wear It []

  14. Looks gorgeous! Love your outfits!


  15. Ahhh, in love with all the fall vibes! I went to Maine October 15-21 and although this was past their peak foliage time, it (and the drive up) were still incredible. x

  16. Amazing, babe!

    Shall We Sasa

  17. So beautiful!! Being from Canada it wasnt a thing to travel to see fall foliage because it was just pretty much everywhere BUT now that I live in California I totally wish I had done this this year! Do you think its too late? I MISS FALL tremendously!

    xo, jess

  18. I love all of these outfits especially that last one! And a foliage trip sounds like so much fun!


  19. Looking at all your beautiful photos so far this fall, I've been craving a trip to see the leaves! Love living in Charleston, but I'm missing being in the Virginia mountains and having changing leaves all around!

    Erin, Attention to Darling

  20. Love all the fall colors!!

  21. I love fall foliage! You need to come to Seattle! It's so gorgeous here during this time of year!


  22. Your plaid scarfs are everything! They're my absolute fave 🙂
    XO Janina

  23. You look gorgeous in every single picture. I could copy all your looks 😊
    Have I mentioned your hair is a dream? 😉 I have been to several places in the United States but never went to New England. Your pics and descriptions are lovely. Think I should go there next time. Greetings from Germany! xo Valerie

  24. Your fall outfits are always on point! I was just in New York and Boston and the fall leaves were beautiful!!

    Brooke du jour

  25. I would love to do this and see all the pretty sights, maybe one day!

    Dana |

  26. This sounds like such a fun road trip! My family has a lake house in Upstate New York that we visit every summer but I unfortunately have never been there to see the changing leaves, definitely on my bucket list!


  27. I love your Victoria Slouch boots!! I am worried about the fit though, the reviews seem to sound they are for people with larger "athletic" calves! I have chicken legs, how do they fit you???

  28. so pretty!!! <3

  29. Amanda

    Where did u drive to to see the foliage ? Could you list the areas you went to in your pictures ?

  30. Amanda

    Where did you drive to to see the foliage ? Do you have a trail you took? Could you please list !