Will and I had a really fun weekend exploring Vermont this past weekend and definitely want to make this an annual trip going forward! Next year we’ll try to go a little later in the season to catch more foliage (it seems like mid-October would be ideal) but this was one of our only free weekends this fall so we went for it anyways. There weren’t many changing leaves yet but it was definitely chilly (low 40s in the morning but up to 65 degrees mid-day) and got us in the mood for all things fall. Here’s what we did on day one!

j.crew downtown field jacket and j.crew leather riding boots with white jeans

the equinox manchester vt on design darling

It was a three-and-a-half hour drive from Greenwich to Manchester, Vermont, and we had a hot mess of a morning involving getting Rory to the groomer and dropping off a massive chair to be reupholstered because it was “on the way” (sorry, Will). When we finally got to Vermont we stopped for a late lunch at Marsh Tavern inside the Equinox hotel. It was pretty overcast outside so we had a leisurely lunch inside complete with an insane cheese plate and a glass of rosé (which I insist on drinking year-round because I’m basic and the worst). A couple of our friends said it was a must-stop along our route and a ton of you recommended it as well and it wound up being the perfect way to break up the drive between home and our hotel in Woodstock. The Equinox was absolutely stunning and surrounded by the most beautiful flowers. I can only imagine how incredible it is once the leaves start to change!

j.crew downtown field jacket and polo ralph lauren lennox vachetta wide belt

design darling vermont the equinox hotel manchester vt

After lunch we drove ten minutes to nearby Dorset, a quaint little town with a town green and pretty fall decorations at every door. The clouds magically parted when we pulled up and all of a sudden it looked like a picture-perfect blue sky day so this was a favorite quick stop on our trip. We stopped for coffee from the Dorset Union Store and I snapped a photo of all the pumpkins across the street at the Dorset Inn. So festive!

fall outfit with white jeans and j.crew leather riding boots

the equinox hotel manchester vt in september

With coffee in hand, we drove the remaining hour and a half to the Woodstock Inn and checked in to our room. The hotel was even more beautiful than it looks in pictures with huge lawns in the front and back and a roaring fire in the lobby. The leaves were just barely starting to change and again I can only imagine how magical it must be once there’s full-blown foliage (or a fresh blanket of snow!).

fall outfit with white jeans and polo ralph lauren lennox vachetta wide belt

dorset union store in vermont

We drove a half hour to Hanover, New Hampshire, for dinner at Pine, a spot that several of you had recommended and that totally lived up to the hype. There were so many places we wanted to try from all your recommendations it was hard to narrow it down, so we’ll have to check out more of them on our next visit. Stay tuned for more from days two and three!

j.crew leather riding boots with white jeans on design darling

dorset inn vermont

J.Crew field jacket (similar for less)  //  Polo Ralph Lauren cable-knit cashmere sweater

Celine sunglasses (similar for less)  //  Polo Ralph Lauren leather belt (similar for less)  //  Tory Burch satchel

J Brand jeans  //  J.Crew riding boots

P.S. Shopbop is offering 20-25% off sitewide right now! Shop all my picks here.

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  1. Mid October is definitely the time to go. I drove from Albany to Williamstown to Cambridge last October, and it was the most beautiful time of year to go! I’ve never seen anywhere more beautiful. I was in Burlington in August and I’ve never seen more beautiful sunsets… so between the foliage and the sunsets, I think Vermont would be magical in October!

  2. Looks like an amazing trip, I can’t wait to see more pictures. Also, rosé is delicious and there is nothing wrong with drinking it year-round! What are some of your favorite rosés?

      1. I love AIX and Whispering Angel too! I see Miraval everywhere and can’t believe I haven’t tried it yet – I’ll have to look for it and the others on your list. I would absolutely love to see a post on all your favorites. I’m sure you have a ton of rosé-loving readers who would appreciate it!

  3. I’m so thrilled to see you enjoying Vermont! My husband and I were married in Manchester, lived in Hanover, and hiked the Long Trail in it’s entirety together–it’s easily our favorite place in the world! Also, it’s a myth that rose is a summer drink–a close friend and master somm taught me recently it’s to be drunk year-round. Go for it and don’t feel “basic”!!