Woodstock, Vermont Travel Guide

Disclaimer: We loved Vermont — as much, if not more than anywhere we’ve traveled so far. We’d move there today if we could. And because we loved it so much, I wanted to share with you how we spent our little getaway in Woodstock, Vermont. Although, this town and the surrounding area were all we explored of Vermont, I feel we had the quintessential Vermont experience.

Where we stayed

The Jackson House Inn

I cannot say enough good things about this bed and breakfast or the innkeepers, Matt & Chris. Craziest thing — they were actually from Asheville and had moved to Vermont 18 months prior to try their hand at innkeeping. Seriously the nicest guys ever! They warmly greeted us on the lawn, helped us with our bags, showed us around the B&B and truly made us feel at home. The rooms were so cozy, part of me just wanted to stay inside and watch the snow fall softly outside the window. But there was too much to explore! Also, did I mention these guys made us some of the best breakfasts we have ever had?! — homemade muffins, poached apples and pears, polenta with local cheese and bacon, apple stuffed bread pudding — I dream about those breakfasts. We would go back to them in a heartbeat.

Where We Ate

Like I mentioned earlier, we ate breakfast at our B&B, which I do not regret. I read that Eat Woodstock and Mon Vert Cafe have great breakfasts. We did eat lunch at Mon Vert Cafe and they had quite the sandwich selection which was great for us (especially Bobby :)) The local Farmer’s Market has excellent grilled cheeses, too. We had lunch on our last day at Simon Pearce overlooking the river when we explored Quechee.

Our dinners were at Mangalitsa — one of my most favorite restaurants, ever! you will definitely need to make reservations for this one — and at Worthy Kitchen — casual and no reservations needed, but also excellent food!

Worthy Kitchen

What we did

When we arrived we spent our day exploring the quaint little town of Woodstock, seeing the covered bridges and New England architecture. Each new corner of this place was just as warm and inviting as the other. No billboards, no big box stores, everything was local and everyone there was beyond polite.


On our second day it snowedddddd! But later in the afternoon turned to rain, which made for a lazy afternoon. But that morning we explored a bit more of the town, visited the farmers market and drove to a tiny town called Pomfret, where we got to see Sleepy Hollow Farm.


Our last day, we visited Sugarbrush farm, where we tasted homemade cheese and maple Syrup. I mean isn’t that what you’re supposed to do when you visit Vermont? Afterwards, we traveled to the town of Quechee and hiked the Quechee gorge, visited the antique mall and an alpaca farm in the town! Bobby had never fed goats before (crazy, I know) and neither of us had fed alpacas before!


On our way out of Vermont we drove through New Hampshire back to Boston and our way we saw the most beautiful mirrored lake with brilliant foliage and had to stop. It was the perfect way to end our trip and we cannot wait until we get to visit again. We would love to make it an annual trip!



  1. Katherine
    November 9, 2018 / 1:44 am

    DYING! I’m obsessed with all of your pictures! This is so picturesque and perfect. Woodstock is definitely on our bucket list and we’re hoping for a fall New England trip in the next year!

    Katherine | http://www.oneswainkycouple.com

    • awesomeonoccasion
      November 17, 2018 / 1:03 am

      Thank you so much, Katherine!! I want to go back sooooo bad!

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