Autumn in Vermont

I could write a book about my deep love for New England. I suppose many of us long for places that look and feel nothing like home. I have always been drawn to the undeniable comfort and charm of little villages, real seasonal change and the simplicity of quiet. The soothing vibrancy of fall foliage that resets your nervous system. I often dream of picking up and moving into an old farmhouse set amongst the maple trees, but since that may only be a fantasy, a dreamy vacation helps fill the void. I am so happy we were able to make it back to Vermont for a week getaway this fall. Daniel and I went on a roadtrip through Maine, New Hampshire and Vermont years ago and have been longing to get back ever since. This was a quick trip, but the absolute perfect respite and a great chance to visit some old favorites and new stops.

We met my parents in Boston early in the morning and drove about two and a half hours to Stockbridge, Massachusetts. I have always wanted to see the famed Norman Rockwell town and it was on the way to our first stop in Vermont. We had breakfast at the Main Street Cafe and walked around the small town which is essentially Stars Hollow from Gilmore Girls. After breakfast we drove up to Manchester, Vermont stopping at Armstrong Farm outside of Bennington to look at their pumpkin display. If you are looking for the height of leaf peeping I would suggest planning your trip at the end of September – mid October. They have a ton of online trackers, but you are at the mercy of mother nature and never really know what you are doing to get. This was for my birthday at the end of October, so we knew we were going to see the tail end of color. It was still way more than we get at home and we were lucky enough to get a little snow which made the trip even more magical! It was very cold and rainy which added to the coziness and made me so appreciative for this time of year. It felt like a complete reset and a trip I will remember forever.

views at Armstrong Farm

We started in Manchester and stayed at the Reluctant Panther Inn. This small hotel feels like quintessential New England, offering both standard rooms and suites and incredible breakfast baskets delivered to your room. We chose one of the suites so it wasn’t in the main house and it was very comfortable! The first night we had a wonderful dinner at Ye Olde Tavern in Manchester Village. The menu is classic comfort food – highly recommend the chicken pot pie. We also ate at the Copper Grouse inside the Kimpton Taconic, which is a very short walk from the Reluctant Panther and an adorable hotel I had on my list. This place has such a cute interior, a great bar and was packed when we went. Another great spot in Manchester Village is Mystic Restaurant & Bar.

I had never stayed in Manchester, so it was nice to see more of the Southern part of the state. We drove to Dorset to see the old General Store and main street and then Weston to stop at the Vermont Country Store. There are many locations throughout the state, but the one in Weston is my favorite and feels like stepping back in time. When the weather isn’t too cold, Manchester is a wonderful place to hike like Lye Brook Falls trail and to golf.

Apple cider donuts and fresh cider from Cold Hollow Cider Mill

charming exterior of the Woodstock Inn

After Manchester, we drove up to Woodstock where we stayed for the next few days. Well, about 25 minutes outside of town in a stunning Airbnb on 7 acres. I was a little hesitant to stay essentially in the middle of nowhere, but it turned out to be my favorite part of the trip. The property was absolutely beautiful, the wood burning fireplaces were so cozy and it was great to have a full kitchen. There is also a large outdoor fire pit and it is stocked with a ton on boardgames. You just have to plan ahead because there are no nearby grocery stores and you have to drive about 20 minutes to get to any restaurants. If you prefer to stay in town the Woodstock Inn is beautiful or the Kedron Valley Inn in South Woodstock (where we stayed last time). Both of these places have good restaurant options and Richardson’s Tavern at the Woodstock Inn is lovely for dinner by the fireplace.

We had been to Woodstock before, so I knew I wanted to go back to Simon Pearce and Farmhouse Pottery. We also went back to Sugarbush Farm which is a great family owned/operated farm that makes the best maple syrup and cheeses. They let you walk into the forrest to see how they tap the maple trees and run the lines. I love no frills places like this that make you realize how much work goes into something seemingly simple. Plus the drive up to the farm and surrounding views are worth the trip alone.

Woodstock is such a good location for venturing out to other towns in the state. From here, we did a day trip up to Stowe and Burlington and another over to Hanover, New Hampshire to see the Dartmouth campus. On our last trip we stopped in Shelburne just south of Burlington to go to Shelburne Orchards, a pick your own apple orchard. Another beautiful property surrounded by lush green fields next to Lake Champlain. You really can’t go wrong with any itinerary since the countryside drives and little villages you stumble upon make the trip worthwhile.

I lived in this very warm cashmere beanie

What I Packed


We only had a half day in Boston, but this was my third time there so I was ok with not doing a ton of sight seeing. We booked The Whitney at the far end of Beacon Hill which is a beautiful hotel and makes it very easy to get to the airport. I really wanted to stay in Beacon Hill because I find it the most charming and there are a ton of great shops on Charles Street. Beacon Hill Books & Cafe is the dreamiest, straight out of a 90’s rom com. I could have stayed there all day just hanging out by the fireplace with a coffee. A sweet follower reached out to them after I posted a photo of the interior to let me know the paint color is Light Blue by Farrow & Ball. We had an incredible dinner at 75 Chestnut which was a nice short walk from the hotel. I also couldn’t leave Boston without going to Mike’s Pastry in the North End for a Lobster Tail (IYKYK) and the stopping by stunning Rouvalis flower shop.

Interior details at Beacon Hill Books | Views on Acorn Street

  1. Carolyn says:

    What a lovely sounding trip! My husband and I drove through Maine and Vermont on our honeymoon a few years ago and have always wanted to go back. It really looks enchanting in the fall!

  2. Chelsea says:

    Looks like a beautiful trip! And very different from late-Spring here in Sydney. Also, your packing choices are *great* — so chic!

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