Outfits
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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
Goodnight Macaroon jeans // V-neck sweater // Gucci handbag // Sole Society wedge booties
striped poncho // over-the-knee boots // leggings 
oversized scarf, striped top, OTK boots
stripe crewneck tee // Free People scarf // leggings // over-the-knee boots // similar handbag
AG jeans // Volcom cardigan // blanket scarf // floppy hat

 fall outfit

Sole Society wedge booties // AG jeans // Volcom cardigan // blanket scarf // floppy hat

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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33 Comments

  1. Ev

    As always great photos 🙂

    http://www.evdaily.blogspot.com

    11.3.16Reply
  2. Tess Felber_Sequins are the New Black

    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

    11.3.16Reply
  3. Anne Arnold

    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!

    11.3.16Reply
  4. Erin at Top Knots & Sweatpants

    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.

    Erin
    http://www.topknotsandsweatpants.com

    11.3.16Reply
  5. Carey Spence

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

    xo, Carey
    https://thedaintydetails.wordpress.com

    11.3.16Reply
  6. Olivia DiTomaso

    Loving all your looks!

    Liv

    http://www.livforstyle.net

    11.3.16Reply
  7. Rach DiMare

    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!

    http://www.rdsobsessions.com

    11.3.16Reply
  8. Carrie Khodanian

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

    Carrie | http://carrieelise.com/

    11.3.16Reply
  9. Nina Lacher

    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

    11.3.16Reply
    • Caitlin C.

      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!

      11.3.16Reply
  10. Around Colours

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

    Marta – http://www.aroundcolours.blogspot.com

    11.3.16Reply
  11. Emma Walker

    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

    11.3.16Reply
  12. masha berman

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

    11.3.16Reply
  13. Natali

    Wonderful photos!!!

    https://lartoffashion.com/visit-helsinki-little-paris/

    11.3.16Reply
  14. Morgan Flinchum

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

    -Morgan
    How 2 Wear It [] http://how2wearit.com

    11.3.16Reply
  15. Briana Nicole

    Looks gorgeous! Love your outfits!

    Briana
    http://www.beyoutifulbrunette.blogspot.com

    11.3.16Reply
  16. Sheila Joy

    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

    http://www.insearchofsheila.com

    11.3.16Reply
  17. Sasa Zoe

    Amazing, babe!

    Shall We Sasa

    11.3.16Reply
  18. Jessica H

    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

    alljessedup.com

    11.3.16Reply
  19. Lauren

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

    Lauren,
    http://www.atouchofsoutherngrace.com

    11.3.16Reply
  20. Erin Phillips

    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
    http://www.attentiontodarling.com

    11.3.16Reply
  21. Amy's Fashion Blog

    Thanks for sharing these tips.

    http://www.amysfashionblog.com/blog-home/

    11.3.16Reply
  22. Leeann Bienfang

    Love all the fall colors!!

    http://www.memoriesandmacchiatos.com

    11.3.16Reply
  23. Polly

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

    Polly
    http://gemsandjoy.com

    11.4.16Reply
  24. Janinafran

    Your plaid scarfs are everything! They're my absolute fave 🙂
    XO Janina
    http://janinafran.blogspot.ca

    11.4.16Reply
  25. valerie guesgen

    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

    11.4.16Reply
  26. Brooke Reagan

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

    Brooke du jour
    http://www.brookedujour.com

    11.4.16Reply
  27. Dana Nicola

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

    Dana | fashiondew.co.uk

    11.4.16Reply
  28. Katie M

    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!

    xoxo,
    Katie
    chicincarolina.blogspot.com

    11.5.16Reply
  29. sstraus

    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???

    11.11.16Reply
  30. Leanne Ruderman

    so pretty!!! <3

    11.27.17Reply
  31. Amanda

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

    8.25.19Reply
  32. Amanda

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

    8.25.19Reply