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AOS Travel Guide: Woodstock, Vermont

AOS Travel Guide: Woodstock, Vermont


Woodstock, Vermont was hands down the best part of the New England road trip that we took back in October (Boston - Woodstock - Bar Harbor). It is the quintessential New England town and could not have been more charming. All of the restaurants, attractions and activities below contributed to us having the best stay in Woodstock:

S T A Y.

This Airbnb - This is the most unique Airbnb I've ever stayed in. It's located twenty minutes outside Woodstock in Hartland, but the scenic drive into town was one of the highlights of our trip. I won't go into too much detail here because this place deserves a post to itself (coming very soon!).

E A T / D R I N K.

The Red Rooster at Woodstock Inn -  We decided to try the breakfast buffet at The Red Rooster on our first morning in Woodstock and it definitely started our day out on the right foot. Breakfast is my favorite meal of the day so my standards are fairly high. I'm still dreaming about all of the delicious options available on their buffet. Both the setting and service were impeccable as well. This place is not to be missed!

Bentleys Restaurant - We headed to Bentleys for a late lunch after we finished our hike up Mount Tom. The restaurant, established in 1976, offers simple, American fare that does not disappoint. I ordered the Elm Street Wrap + a hot apple cider and couldn't have been more pleased. 

D O.

Riverview Farm - Visiting an apple orchard was high on my bucket list for our New England trip. When I came across Riverview Farm via a Google search, I knew it would be the perfect spot. With over 1,600 apple trees, acres of blueberries, fall raspberries, pumpkins, homemade cider and a corn maze, this place is the real deal. We spent the afternoon wandering through the corn maze (which is the best I've ever seen) before picking a variety of different apples. 

Hike Mount Tom - Hiking Faulkner Trail to top of Mount Tom was another highlight of our trip. I knew I wanted to hike while we were in Vermont, but I didn't want to do anything too vigorous since I was six months pregnant. A good friend recommended Faulkner Trail, which turned out to be the perfect difficulty level and length. The top of Mount Tom provided us with a beautiful view of the town of Woodstock and all of the vibrant fall foliage that our hearts desired.


Shop at F.H. Gillingham & Sons - Opened in 1886, F.H. Gillingham & Sons is an authentic general store with a lot of history. We thoroughly enjoyed wandering down the aisles and left with quite a few souvenirs. If we had more time in Woodstock, I would definitely plan on doing some grocery shopping here and cooking a New England style meal in our Airbnb. 

Explore Woodstock Inn - After we finished breakfast at The Red Rooster, we took some time to explore the rest of the beautiful Woodstock Inn. I'm usually more of an Airbnb/private home traveler, but I would love to go back and stay here. The roaring fireplace in the lobby is just the beginning of the charm that the Woodstock Inn has to offer. This place looks like it is straight out of "Holiday Inn", the classic Christmas movie starring Bing Crosby. Both the inn and grounds are meticulously maintained. We ended our tour down in their game room where we played a few rounds on their antique arcade games. 

The Middle Covered Bridge - This bridge is one of the most iconic spots in Woodstock. It is definitely worth checking out, if only for a quick photograph. 

Baby Shower Style + Third Trimester Styling Tips

Baby Shower Style + Third Trimester Styling Tips