There's truly no better place to spend autumn than in New England. The quaint towns, historic homes and winding country roads seem extra charming dressed up in colorful leaves and pumpkins. Living in New York City, the New England states are very close by, but I can't remember previously taking a trip there for the purpose of celebrating autumn. Fall is my absolute favorite season and I look forward to it all year long. Unfortunately this fall was a bit of a let down in New York, as the temperatures were unseasonably warm and many of the leaves remained green on their branches. The "fall feeling" didn't arrive until much later than usual.

Being that fall's my favorite time of year, I started to brainstorm ways to get a bit of those traditional autumn vibes. I immediately thought about New England, and specifically the town of Woodstock in Vermont. Woodstock, Vermont is a historic town in the center of the state. It's extremely photogenic and images of the  town, with its colorful rolling hills, fences lined with pumpkins and charming covered bridges, filled my Instagram feed year after year. I knew I wanted to make a pilgrimage up to Woodstock for fall fun, New England style.

Woodstock, Vermont is a historic town in the center of the state that was settled in 1768. It's an incredibly charming small town with preserved 19th century Victorian mansions, covered bridges and picturesque maple and cheese farms. It was named "The Prettiest Small Town in America" by the Ladies Home Journal magazine, and it really lives up to that title. I'm happy to report that Woodstock lived up to my high expectations and really is as gorgeous as it looks in pictures. The whole weekend we were there felt like living in a postcard!

Woodstock is about a five hour drive from New York City. It's the perfect weekend escape because it's close enough to make it an easy drive for a late Friday afternoon, but it feels worlds away from the hustle and bustle of Manhattan's streets. If you're coming from further away you can fly into either Boston or Manchester and continue to drive to Woodstock. A car is necessary in Vermont as we didn't find many taxi options. The center of town is very walkable, but to visit farms and some of the picturesque locations out in the country you'll need to drive.

I stayed at On The River Inn and absolutely loved it. The location is a little out of town, right on the Ottauquechee River with gorgeous country views. The decor throughout the inn is a "country chic" style and rooms are very comfortable with nice amenities. The Inn restaurant is incredibly cozy with many different seating options (tables, couches) and a beautiful fireplace. It was a great spot to unwind with a cocktail after a day of sightseeing! The food was delicious and we enjoyed a breakfast that was included in our room price as well as dinner one night. A highlight of our stay was the nightly bonfire in the Inn's expansive backyard, complete with s'mores to compliment the beautiful stargazing. It was a really special place and I highly recommend it for your stay in Woodstock!


Woodstock is an incredibly picturesque town. Any budding photographer would have a field day there, as every time we turned a corner there was another beautiful photograph to be had. We kept running into groups who were on photography tours, so it's a well known destination to shoot. Some of my favorite spots to take pictures at were Sleepy Hollow Farm, the various covered bridges throughout town and the winding back country roads.

We visited a few farms on our trip to Woodstock. One of our favorites was Sugarbush Farm, a maple syrup and cheese farm located on a beautiful piece of land in the hills. Sugarbush has a large sampling room so you can try all of their products and learn about how their made.  I had no idea there were so many types of syrup!

Walking around the town center of Woodstock, its shopping district, is a blast. There are so many unique clothing stores, local food shops and cafes. We loved the Vermont Flannel Company and had fun trying on their various patterns and picking a souvenir. Another highlight of the town center is seeing the gorgeous Victorian mansions and covered bridges. The architecture adds to Woodstock's charm and truly makes you feel like you're in a charming spot in "small town America."


Despite being a pretty small town Woodstock packs a punch in the food and drink department. Everything we had was so fresh, with many ingredients coming from nearby farms.

Worthy Kitchen- A great spot for lunch or a casual dinner. Worthy Kitchen serves up an inventive menu filled with unique sandwiches, comfort food and an expansive craft beer list

Long Trail Brewery- Perfect for any craft beer aficionado, Long Trail is a great spot for a pint at the end of a day of hiking or sightseeing. The brewery gives tours and also has a menu full of standard bar fare

Bentley's- This spot is in the center of Woodstock Village and serves classic pub food and strong drinks. It's known as the "cheers" of Woodstock and is a fun place to spend the night

Have you been to Vermont? Do you have any favorite spots to visit in autumn?


Post a Comment