For years, I’ve wanted to take a trip with Eddie to go see the fall foliage. We kept putting it off – money was tight, I was pregnant, there was a global pandemic. Finally, this year I told Eddie, “Let’s just go. The timing will never be perfect.” But you know what, it was! We booked this trip fairly last minute, because I wanted to go at JUST the right time. I used this handy predictor to help pick the best weekend to go. The colors were just perfect, and I’m so glad we decided to go. 

We flew into Boston on Friday and we stayed there one night. We stayed at The Langham Hotel, which is absolutely gorgeous. We mostly walked around Boston and enjoyed the weather, but we ate Lobster Rolls at Bell in Hand Tavern, had beers at the Sam Adams Brewery, took a stroll through Boston Common, and had dinner at the beautiful Contessa. 

On Saturday morning we picked up our rental car – we rented it from a Hertz location in the city and it was MUCH less expensive than getting it at the airport. From there we started our drive. Our drive took us from Boston through New Hampshire, where we started to get a peek at the foliage. The drive to Woodstock in Vermont was just about 2.5 hours from Boston. We arrived in Woodstock, a perfectly picturesque town. I had booked us for two nights at The Shire, an Inn located within walking distance of the Main Street in Woodstock. The inn was very clean, check in process was seamless, and we had a huge corner room with a fireplace. 

In Woodstock

Walk Central Street and pop into the shops there. We loved GH Gillingham General Store! And make sure you have a Maple Creemee (pronounced creamy) at Woodstock Scoops. 

Take a drive to Quechee, and park at the bridge to see the River and Quechee Gorge. We did the hiking path down to the bottom and it was very much worthwhile. Afterwards, stop in at Simon Pearce Glass Blowing Factory – they have incredible things here. There is also a restaurant, but you need reservations. We took a break at the Whistle Pig Bourbon Tasting Room (You know we love our bourbon!) and then we headed back to Woodstock and had a late lunch/early dinner at Worthy Kitchen – get reservations, but it was delicious. It’s farm-to-table, American food. We had burgers, fries, Mac & cheese, and a fried chicken sandwich. 

We finished off our evening with some drinks at the bar at The Woodstock Inn. I will say that most of the restaurants, especially during busy season, are absolutely reservation only, and even then, reservations are limited because they are having a big issue with hiring!

On Sunday morning we picked up some breakfast bright and early at Mon Vert Cafe. I had a latte that had maple syrup in it and it was delicious! We headed up to Sleepy Hollow Farm (a 5-minute drive) and got some beautiful views early in the morning. There were already 5 or 6 people there at 8 am so I would definitely recommend getting an early start! From there, we headed to Stowe! 

The drive to Stowe gave us all the colors were were looking for. I barely looked down because every turn was more beautiful than the next. We stopped at Cold Hollow Cider Mill for some cider donuts and we tried a flight of season hard ciders, which were yummy. 

One of my favorite movies of all time is The Sound of Music, and I honestly had NO IDEA that it was based on a real family! When the Trapp family fled Austria before the Second World War, they settled in Vermont and created this beautiful lodge and cabins. 

Our next stop was a quick hike/walk to Moss Glen. The views were gorgeous here, too.

We went to Downtown Stowe and walked around there for a little bit. Then we headed back in the direction of Woodstock. We stopped and drove through Montpelier, the capital of Vermont, and then kept going. We stopped at the Sugarbush Maple farm and sampled some maple syrup and Vermont cheeses before heading to The Woodstock Inn again. There we had dinner at the bar and hung out for a little while. 

Everything closes early in Woodstock, so be prepared for that! We fit a lot into this trip, but it was also a very relaxed trip for us. Activities were not super long, and many things are close to each other. I absolutely loved it – and we can’t wait to come back and bring the kids next time! 

Here’s a map with all the places we got to. 
Did we forget anything? Let me know in the comments below, and we’ll add it to the itinerary for the next trip! 

xoxo