Our New England Road Trip Itinerary

Good morning, friends! I meant to get this post up yesterday, but it ended up taking a really long time to write! I wanted to share our exact itinerary for our recent New England road trip. A ton of planning went into this trip, as we were there for nearly two weeks! The tricky thing with planning a fall foliage trip is making sure that you get the timing right to catch the leaves in their peak. A safe bet is usually going during the first couple weeks of October, and if you can, check out a fall foliage predictor map to help you decide on locations. If you have any questions about our trip that I didn’t answer, leave me a comment and I’ll get back to you there!

similar black dress, also love this one // flannel shirt (almost sold out), also love this one // Converse sneakers // leopard handbag // Delsey luggage // black lanterns // battery-powered candles

First Stop: Harrisburg, PA

The first day of our road trip, we drove six hours from Winston Salem up to Harrisburg, Pennsylvania. There are really two main routes you can take to get to New England, but we go through the Shenandoah Valley every year (it’s a much easier and less trafficked route rather than going through Baltimore). Harrisburg, PA, was a great place to shop for the night; if you can make it an hour further, I would also recommend staying in Allentown because there’s a Whole Foods (buy lots of snacks!!) and a Target.

buffalo plaid pajamas

tan sweater (only $40) // plaid scarf (only $20) // Spanx faux leather leggings // similar booties here and here // Quay mini aviator sunglasses // Gucci handbag

turtleneck sweater ($29), almost identical here // jeans in the “dark wash” color ($14) // snakeskin handbag ($22) // wool hat // suede boots ($49)

Second Stop: Litchfield, CT

Our second stop was Winvian Farm near Litchfield, CT. Winvian Farm is a really cool resort encompassing 113 acres of land and 18 individually-designed cottages. We stayed in the Library Cottage, which was designed to look just like a two-story library – bookshelves filled with books adorned every wall (even in the bedroom), along with heated bathroom floors and a real fireplace. The real winner of Winvian Farm, though, is their restaurant, where they serve farm-to-table meals with fresh ingredients right from their own organic garden. We had breakfast there every morning (it’s included in the cost) and ate there twice for dinner – and they were the best meals we had the entire trip!

While you’re in Litchfield, definitely check out downtown Litchfield and the neighboring town of Bantam. Downtown Litchfield is adorable (as are the nearby houses!) and we loved the restaurant Market Place Tavern, which is the old Litchfield jail. Bantam is another really cute spot – we went to Bantam Pizza one day for lunch, and visited Arethusa Farm Dairy multiple times for ice cream made from fresh milk and cream.

on Jessica: red buffalo check blanket // Spanx leggings // on me: American Eagle buffalo check fleece pullover // Zella leggings // UGG boots

metallic sweater dress // suede boots

on me: Abercrombie plaid fleece pullover // Good American jeans // UGG boots // on Jessica: Abercrombie pullover // Timberland boots

buffalo check flannel shirtdress (comes in four colors!) // cable knit cardigan // similar suede boots, also love these // similar Chanel boy bag

On Jessica: white turtleneck // black and white flannel // Timberland boots // on me: white ribbed tee // similar orange and black flannel // Red Dress Boutique jeans (almost sold out), also love these// booties

Third Stop: Green Mountains, VT

After Litchfield, we drove north through the Green Mountain National Forest headed towards our next cabin. We drove through at exactly the right time: the leaves were all in peak, but they hadn’t started falling yet – to be honest with you guys, it was so beautiful I cried! I had never seen the leaves look so brilliant before. We arrived in Wardsboro, Vermont, to stay in this incredible A-frame cabin with our friends Jessica and Jasmine. The cabin is pretty isolated (not many restaurants or shops nearby), but that was part of the fun! We made our own log fires every night, cooked meals and had lazy mornings drinking coffee and reading novels. One day, we drove to the Vermont Country Store for lunch – it’s SUCH a cool store with so many interesting knick-knacks, I ended up going home with some authentic Vermont maple syrup, cookies, chocolate and a few beauty products.

white lace tank // cable knit cardigan // American Eagle jeans

on Jasmine: Abercrombie camel coat // similar faux leather skirt // black over-the-knee boots // on Jessica: black turtleneck // on me: white tank (almost sold out), also love this one // camel cardigan // similar Chanel bag // similar over-the-knee boots

Fourth Stop: Manchester, VT

After Wardsboro, we drove about an hour north to Manchester, VT, to stay in one of my favorite hotels for the night: the Equinox Resort! A visit to New England simply wouldn’t be complete without a visit to Manchester. This hotel is incredibly peaceful – I got a massage at the Equinox Spa, had room service delivered to the room, and went to bed early the one night we were there. To see my full travel guide on Manchester, check out this blog post from last year.

white ribbed tee // similar Abercrombie scarf // Goodnight Macaroon sweater skirt // similar suede boots, also love these

on Dani: cable knit off-the-shoulder sweater // Express plaid skirt // similar Chanel boy bag // boots // on me: white ribbed tee // Forever 21 plaid skirt // Gucci Marmont handbag // similar suede boots , also love these

Final Stop: Woodstock, VT

Our final stop on our road trip was Woodstock, Vermont, about an hour north of Manchester (so we slowly made our way north the entire time!). My mom flew in and we met up with my friend Dani and her mom for a girls trip, and this time we stayed at the Woodstock Inn, which we absolutely loved! Unfortunately, it rained almost the entire time we were in Woodstock, but that didn’t stop us. One night we ventured out to Simon Pearce Restaurant for an amazing meal made with fresh, local ingredients. Another day, we headed to the Woodstock Inn spa and spent almost an entire day there, even having lunch and wine delivered to us. πŸ™‚ I really wish the weather had been better, because I really wanted to go back to Sugarbush Farm to sample their maple syrup and cheese like we did last year!

Like I said, if you have any questions about our trip let me know in the comment section! xoxo and HAPPY HALLOWEEN!

Leave a Comment


  1. Anne Arnold

    Hi Caitlin, love all these pretty fall photos you took! Couple of questions please: is the jumper in the first photo really the Shein jumper? I noticed it has 3 rather awkward “lines” of material and I wondered if you kept them on as I can’t see how this would work if you wear them at the front? Also, where is the exact white beanie from in your latest Insta photo with Chris? The one linked in Liketoknowit seems different? Thanks so much in advance for your time and help, and have a great rest of the week and weekend!

    • Hey Anne,

      Yes it is really the Shein jumper! I’m wearing it backwards, so the three lines were in the front. It doesn’t look bad, but you could always cut them out if you decided you didn’t like them πŸ™‚ Here is the real hat that I’m wearing in my latest Instagram photo: https://rstyle.me/+ND5y10xTd2BrEkr_WNjBzg Let me know if you think of anything else!

      • Anne Arnold

        Good morning Caitlin, thanks so much for your reply and the tip with the jumper.
        Is your hat an old one though as I still find it looks slightly different (sorry for being a pain), and the one on Nordstrom looks more cream than white as in your photo? Have a great day πŸ™‚ Anne

  2. You literally have the best pictures in the blogging community. I always love seeing what content you have next. This place looks amazing, I never get to see stuff like this because I live in LA. I need to escape the city one day! Happy Halloween (:

    Erika Marie | https://imerikamarie.com

    • Nichole Magliocco

      Hi! I was wondering which bedroom you had for the picture looking out the huge window? With the white bedding and you with a book. I might go with some couples and I want that room lol!!! Is it with the king bed? Queen bed? Or one of the doubles? Your pictures are just dreamy😍

  3. OMG!!! In love with your trips, the place you stayed in and the amazing outfits that you and your friends were wearing: so matchy!! Love them all!
    have a wonderful halloween πŸ™‚



  4. Patty

    Love the Simon Pearce restaurant!! So beautiful!

    • Emma Jones

      I love this so much! Can you link the cabin you stayed at in Harrisburg, PA?! I’m getting married next month and would love to plan a trip for my parents to give as a gift at the wedding. This place looks like somewhere they would love and being from TX, they would love to go somewhere like this!!! Thanks for all your content.. seriously love everything you post!

      • Hey Emma, Sorry if this post was a little confusing – we spent the night in Harrisburg, PA, on our way up to Connecticut, and the cabin is actually in Connecticut, not Harrisburg! We stayed at a hotel in downtown Harrisburg and it was okay, but not anything special. Sorry about that!!

  5. Laura Leigh

    Looks and sounds like the most incredible trip! Definitely resulted in some absolutely beautiful photos!

    xo Laura Leigh

  6. Deanna

    Wow, this was very time consuming with planning of the trip too setting up the info in the blog. Thank you for all your time and effort. The pictures are beautiful and so much wonderful info. We are planning a trip next year.

  7. love the pics on this post so fall-ish….

  8. I have been dying to take a road trip through NE for fall so this was actually so helpful! thank you!!!

  9. Jenny

    I love all your photos! Could you possibly share the link to the Airbnb you stayed at in Woodstock, VT? You have a picture on your IG of you sitting by a window next to a pillow that says “The Cabin is my Happy Place” and the window view is a road lined with trees – it’s so beautiful. I would greatly appreciate it!!

  10. Maria

    Hi Caitlin, thanks so much for all the info! We are planning a trip to VT this year and I wanted to ask you what dates did you end up going last year? My dates are looking like 10/12-10/16 and I’m worried it might be too late for the fall foliage.

  11. Ali Graham

    Where did u stay in Harrisburg PA?

    • I can’t remember the name of the hotel, but we did not like it so I wouldn’t recommend it anyways!

      • Alison Graham

        Thank you!

  12. Megan M

    Hi there! Planning a fall trip up north! What was the name of the cabin you stayed at that was in the middle of the woods? Would LOVE TO STAY THERE!