Our Fall Trip to Woodstock, Vermont

If you follow along on Instagram, you’ll know Anthony and I spent a few days exploring Woodstock, Vermont in mid-October. (I mentioned it in my Fall Bucket List blog post, too.) We chose the most beautiful time of the year to visit and we planned our trip perfectly for peak foliage season. Since sharing some of our trip, I’ve received a lot of questions as to where to stay, what there is to do, where to eat, and more. Rather than share a long list of recommendations that we may or may not have tried out, I’ve shared a “diary” of our trip below. 

Pro tip: Ahead of our trip, I created a full slideshow with a day-by-day layout of plans because there was so much we wanted to see. While it may seem a little extreme, I’m so glad we had it to refer back to. We didn’t waste any time planning what to do each day as we had set plans for each day. This also forced us to look ahead and book restaurant reservations – most places are NOT taking walk-ins! 

Day 1: October 13th

We left Boston around 8:00am. Our first stop wasn’t very exciting, but needed to get done: Jiffy Lube for an oil change. 😂  Once that was taken care of, we began driving towards the Kancamangus Highway in New Hampshire. We didn’t have any specific destination in mind so we just drove and pulled over when we wanted to take pictures. It may be the highlight of our trip: the foliage was brighter than anywhere else we explored.

After we had seen plenty of colorful trees, we drove towards Woodstock, Vermont to check-in to our Airbnb at 4:00pm. We absolutely loved where we stayed and it had so many perks: a private entrance, less than 10 minute drive into downtown Woodstock, a full kitchen, space to work remotely if needed, plenty of closet and dresser space, and it was such a peaceful location. We booked it in July as many places sell out months before peak foliage season, so if you’re going to book a trip, make sure your stay is booked early!

We quickly dropped off our bags and changed outfits for our 5pm dinner reservation at Worthy Kitchen. At least 5 people recommended we make a reservation here one night. It wasn’t our favorite meal of the trip but the atmosphere was super relaxed and the people working were SO sweet.

Day 2: October 14th

After we woke up, we drove into the town and had breakfast at Soulfully Good Cafe. They don’t take reservations so when we arrived around 9:45, there was a line of about 10 people. Luckily it went quick and we were able to order at the counter and snag a table outside. The breakfast sandwich (The Local) was delicious and I had a Vermont Maple iced coffee which was SO good. We walked around downtown Woodstock, where I was able to get the infamous photo in front of the covered bridge.

We drove around a little bit and then went to Billing’s Farm to spend the day. It’s basically like a museum in the sense that you pay admission which allows you to watch a 30 minute movie showcasing the history of Billing’s Farm and the rest of your time visiting is a self-guided tour. It was fun seeing the goats and the inside of the historic home on the grounds, but both Anthony and I didn’t love seeing all of the cows in small spaces. I don’t think we’ll ever go back and I honestly wouldn’t recommend visiting: there’s plenty of other ways to spend your time.

Once we left the farm, we drove around for a few hours to marvel at the foliage and all of the farms surrounding Woodstock. If you know Ant, you know he’ll go anywhere with animals/farms/large pieces of land. I swear he’s destined to be a farmer. 😂

After driving around for an hour or so, we went back to the Airbnb and got ready for our 5:45pm dinner reservation at Richardson’s Tavern. This was by far our favorite meal of the trip. The restaurant is inside the Woodstock Inn and everything about our reservation was superb: incredible service, tables decorated with flowers, pumpkins, and candles, dim lighting, and the most delicious food. I’m pretty sure they’re now closed for the season but I’m so glad we were able to get in while we were there.

Day 3: October 15th

]We woke up before the sun to get to this highly photographed landmark in Pomfret, VT: Sleepy Hollow Farm. I’ve seen “behind the scenes” videos showing crowds of people lining up waiting to get their turn to snap a photo. But when we arrived, there were less than 5 people there. By the time we left, only one photographer remained. Call it luck, but I think we chose the coziest, foggiest morning to see this landmark.

When we finished gazing at this landmark, we got on the road and headed to Stowe, Vermont for the day. At this point, it was still only around 8:30am, so I was hoping for a coffee. After driving for an hour or so, we finally came across this giant red barn (which turned out to be a coffee bar) and they brew their own coffee! I was thrilled to find something local, and the coffee was delicious.

Shortly after, we arrived at our destination: Stowe Mountain Resort to ride the Gondola. The ride up was absolutely stunning – we both highly recommend this! The ride was around 15ish minutes to the top (I think?) and once you get up the mountain, there are hiking trials, seats to sit and just take in the views, picnic tables, and a restaurant where we had made reservations. The restaurant is reservations-only and the food was incredible.

Pro tip: We made reservations at the Cliff House  2 weeks in advance, and there weren’t many spots left. So, BOOK IN ADVANCE! You’ll also need to purchase Gondola tickets ahead of time. You purchase based on the date, and it’s up to you to get to the top of the mountain on time for your reservation. So, we took the ride up VERY early so we didn’t have to worry about missing it. 

After lunch we were both exhausted, so we drove back to Woodstock. We drove by the Ben and Jerry’s HQ and knew we had to stop.. I’d like to think I’m one of their biggest fans, LOL. They weren’t doing tours due to COVID, but we were able to walk around their “retired flavor graveyard” and get ice cream at the window shoppe. It was such a fun stop on our drive back.

When we got back to the Airbnb, we were both tired from the long day. We decided to order takeout from a local restaurant and stay in for the night where we watched the Red Sox game and played cards. On nights like this, we’re so thankful that we’re both homebodies.

Day 4: October 16th

We had booked one more day at the Airbnb and planned on leaving Sunday, but when we woke up on Saturday we decided that we had seen enough foliage and we were more than content with everything we had already done. So, we packed up our things and headed home… Waking up in Boston on Sunday morning (instead of driving back from Vermont) made a huge difference for the following week.

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This trip was a dream for the both of us, and we’re so glad we made it happen this year. To many more! 🥂