Day Trip to Woodstock, VT

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This was our longest day trip to date. It took over two hours to get to Woodstock from Rye Beach, NH. It was a lot of driving for one day and the trip did feel a little long (perhaps 30-minutes too long). Nonetheless, we got to experience the idyllic town of Woodstock in person. Nestled in the mountains, and with an adorable historic downtown, we could easily see why people folk to Woodstock and why it’s so often captured on Instagram. 



Sugarbush Farm


We heard that Sugarbush Farm offers cheese and maple syrup samplings so this was on our “must-see” list. The farm is on the way into town, up a steep mountain with multiple yellow signs pointing the way. It’s a working farm with barns, animals, sugar house, a big store, ample parking, etc. Inside, several workers were packaging cheeses in foil and colorful wax. We sampled a few delicious cheeses (the mellow yellow and sharp cheddar as well as the sage and bacon-flavored cheeses). We also sampled 4 maple syrups. It was a truly unique experience that we enjoyed.



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Taftville Covered Bridge & Sleepy Hollow Farm



Both of these landmarks were on our “must-see” list. First we visited the Taftville Covered Bridge. Vermont is well-known for having the most covered bridges of any state and this one is quite impressive with its red color. After stopping to take pictures, we drove along River Road and onto Old River Road for a scenic drive of Vermont’s countryside. 




Sleepy Hollow Farm.jpg

We turned up Cloudlane Road to visit the often photographed Sleepy Hollow Farm. Cloudlane is a charming, uphill road with several working farms (imagine rolling green pastures and big red barns). We stopped to snap a picture at Sleepy Hollow and it’s incredible how great the photo came out with very little effort from the photographer. It’s truly a photogenic spot!





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Shopping in Downtown Woodstock






This was the highlight of the trip. Woodstock’s downtown is sizable with quite a few stores. There is a quaint bookstore, modern cafe, fun toy shop, impressive general store, a village butcher, clothing boutiques and much more! The shopping is plentiful and varied. The other great thing about the downtown area is the historic homes that surround it. Venture off any street and you are met with a variety of colonial homes dating back to the early 1800s. Imagine black shutters, front porches, windowboxes, stacked firewood, white fences, greek columns, red brick chimneys, and so on. Each home is a little different from the next but all have a true New England flare to them.


Looking for more day trips ideas? Check out Newburyport and Rockport in Massachusetts.



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