The Most Vermont-y Weekend in Woodstock, Vermont

New England is so beautiful, with so many little towns and gorgeous nature to explore. A few weekends ago, we drove up to Woodstock, Vermont for a weekend trip. Although we stayed only one night, we somehow fit in so many fun things, and ended up driving back down to Boston with a car full of pumpkins, apples, cheddar, maple syrup, and matching flannels for babe and dad (I couldn’t resist). It felt like the most Vermont-y shopping haul ever!

Here are a few highlights if you care to see. The foliage was in full force, but the weather was warmer than expected — such a contrast! It was beautiful to see the sun through the fall colors on the trees.

We stopped at Riverview Farm on the way up to sample some ciders and pick out a few pumpkins. So cute, since Serena loves pumpkins after seeing them everywhere all October! They also have apple orchards and raspberry bushes, and a horse drawn carriage to bring pickers around.

riverview farm

We had lunch at the Simon Pearce Restaurant, where we have been a few times before. It is so so delicious, and way more kid-friendly than one might imagine, and the views of the water are so pretty.


For dinner we decided to pick up some cheese and salads at the Woodstock Farmers’ Market, a great little gourmet grocery. It was delicious and perfect after a busy day, although Serena had snuck a few more cheeses into our basket (!) and so we had some extras to bring home.

Strolling around the town of Woodstock is so pleasant. We stopped into Mon Vert Cafe for breakfast and maple lattes, and I couldn’t resist buying my husband and Serena matching flannels at Vermont Flannel. (If you are strolling around town, Gillingham and Sons is another fun place to browse.) We stopped to pick up a little something at Farmhouse Pottery — so pretty but really pricey! Serena was a big fan of their chickens.


We then took the gorgeous drive to Sugarbush Farm. The dirt back road we were on for most of the drive there was so so beautiful, and we kept marveling at the scenery. Visitors can walk up the hill to see the maple trees, and there are little signs explaining how the taps work. So pretty — we all loved this little chapel among the trees. A huge group of turkeys then came around the bend and startled us! The farm also has a few animals to see, and they make their own cheddar along with all different types of maple syrup. You can do a syrup tasting to see how the flavors concentrate as the season goes on — so interesting and so different from buying maple syrup at a store.


It was so great to go explore and do a few things we hadn’t yet tried in this beautiful area. Vermont is just glorious, and this quick trip made me feel so lucky to have beautiful places like this close by!

Any other favorite spots in New England to share? Especially with the busy toddler in tow, trips that are only a few hours drive away look more and more alluring. ;)

More on Woodstock here and here, plus see more travel in New England and further away here.

Image Credit: Laura Chassaigne

one comment
  1. Molly Galler says:

    Love Serena’s smile at the chicken coop!